“I do believe that if you want to level up your leadership skills, if you want to contribute at a higher level... everybody should have some form of assistance.” — Casey Putschoegl

In this episode of Outliers, I sit down with Casey Putschoegl (@caseyputschoegl), Co-Founder and CEO of 33Vincent, to talk about when and how to bring on an incredible executive assistant. We discuss how she’s built a successful executive assistant agency with a focus on quality relationships, a rigorous selection process, and true partnerships between assistants and executives. Her insight on self-reflection and honest feedback can be helpful to leaders in all business areas. Casey describes what it’s like to work with a leadership coach, integrating work with real life, and what to look for in a great assistant (it’s more nuanced than you might think.)

After working for 7 years in Planning & Operations at General Mills, Casey and her longtime friend, Paige McPheely, decided there had to be another way to work flexibly, raise a family, and give the same opportunity to others. They started 33Vincent, an agency that matches executives with stellar executive assistants, and the company has grown to a team of 60+ with assistants supporting executives all around the world. As CEO of the company, and a mother of three young boys, Casey is continuously pauses to reflect and realign herself with her goals — making sure she carries out the original goals of her business.

Topics Discussed

• 00:04:51 – Types of assistants and the work they perform
• 00:09:56 – Why leaders come to 33Vincent searching for an assistant
• 00:13:26 – The importance of the quality of assistant/executive relationships
• 00:15:31 – When an executive is not a good fit for a strategic executive assistant
• 00:20:04 – The EA/Executive matching process
• 00:24:41 – The benefits of using an EA agency like 33Vincent
• 00:28:20 – Core traits of a great executive assistant
• 00:34:13 – Using personality tests to match assistants and executives
• 00:38:35 – How Casey works with her EA
• 00:41:56 – Glows and Grows (feedback)
• 00:45:27 – Stepbacks and reflection time for leaders
• 00:52:05 – Working with a leadership coach
• 00:53:35 – Integrating work with life
• 00:56:11 – Recommended books
• 00:59:41 – Advice for those who want to create their own businesses
• 01:02:08 – Casey’s routines and rituals
• 01:10:02 – Advice for parents raising boys

‍SCROLL BELOW FOR LINKS AND SHOW NOTES…

‍

‍

Links from the Episode

• Connect with Casey: LinkedIn | Twitter | 33Vincent
• Kolbe A Index | Strengths and attributes assessment test sometimes used by 33Vincent
• Base | Software for Executive Assistants
• KISS Process (Keep, Improve, Start, Stop)
• 5 Levels of Leadership by John C. Maxwell
• Essentialism: The Disciplined Pursuit of Less by Greg McKeown
• The One Thing: The Surprisingly Simple Truth Behind Extraordinary Results by Gary Keller and Jay Papasan
• The Big Leap by Gay Hendricks
• Workday Shutdown Ritual and Workday Startup Ritual from Michael Hyatt
• Todoist | To-do list app
• Plant-based diet
• Mushroom coffee
• Peloton app | Digital workout classes
• Apple Fitness+ | Fitness experience for Apple Watch
• Slack | Team communication tool
• Salesforce | CRM tool

Key Insight

It's important to admit that everyone needs assistance; for leaders to be truly successful and ensure they are focused on the highest-leverage activities in their businesses, hiring an executive assistant is key. Seeing an assistant as a business partner and gatekeeper, investing time and energy in the relationship, and building trust with each other will greatly increase productivity and alignment with strategic goals.

Actionable Ideas

• Things to think about before starting work with an assistant: "And so what we do is a complete deep dive with our clients in terms of what are your preferences? What do you think about in terms of your time and your boundaries? And let's unpack all of those details. Who are your VIPs? What are your top priorities this quarter? And we'll unpack all of those things so that the executive doesn't have to think through, 'Okay, where do I want my EA to start? And what kind of preferences do I have?'"
• "If you're someone out there looking for an assistant on your own, use a real business example that's happened to you and see how they'll respond, find something complex that might require them to dig a little bit, not just produce an answer but dig a little bit, and be open to having them ask some questions so that you can see what their thought process is.”
• “I come ready to give feedback. We call them glows and grows in our organization. So what's going well and where can we continue to refine our processes together. And I also want feedback. So where can I better help you help me? And when we're communicating, are there ways that I can do things differently in order for us to work together best. And that feedback flow, and I think that mutual invitation, has been really beneficial for our relationship.”
• "I do weekly step backs, professionally, and monthly step backs from a leadership level. So personal leadership reflection step backs. And I look back to all the goals that I set for the month. How did I do on those? Where did I show up in alignment with my core values and where did I not? And what can I do differently this coming month? What can I keep doing this coming month in order to contribute at my highest level?"
• "One thing that I do every day... is my shutdown ritual at work...that is the process of, for me, having a 30 minutes, sometimes 20 or 15, depending on how busy the day was, but a little period of time at the end of the day where I take that breath in a sense and look back at the day, capture anything that's still bouncing around in my mind and get it down, get it out of my head, and into my to do list or into my project tracker with my EA and make sure I get those notes captured, because if I try to remember them tomorrow, they're not going to be as clear. So I'll get them out today and then I focus on closing out. So what do I need to address before I wrap up? What's coming up for tomorrow? One practice I love, which is so simple, is closing out all the tabs I have open. Right now, I look at my screen, I've got probably 10, 15 tabs open. I don't need all of these. So let's do honestly like a refresh and shut down what I don't need, open up the agendas I need for tomorrow, and have my computer teed up, then literally put my computer to sleep, turn off my office lights, close the doors.
  

On Outliers, Daniel Scrivner explores the tactics, routines, and habits of world-class performers working at the edge—in business, investing, entertainment, and more. In each episode, he decodes what they've mastered and what they've learned along the way. Start learning from the world’s best today.

Explore all episodes of Outliers, be the first to hear about new episodes, and subscribe on your favorite podcast platform.

Daniel Scrivner (00:00:01):

Casey Putschoegl, thank you so much for coming on the show. I'm super excited to chat with you.

Casey Putschoegl (00:00:06):

Thanks for having me, Daniel.

Daniel Scrivner (00:00:07):

So we're going to cover a bunch of stuff today. And my hope for this conversation is that, one, it'll be a great way for anyone that's curious, or interested, or that struggled with whether they should hire an assistant to help them think through that, what that looks like. And you have a wealth of experience here, but before we get into any of that, I just wanted to start by going a little bit back into your career and talking about what you did before founding 33Vincent, because I'm guessing there was some inklings or ideas or something in there that led to it. So can you start a little bit of just your career before 33Vincent and what that looked like?

Casey Putschoegl (00:00:42):

Yeah, absolutely. I started my career in corporate America and really looked forward to accelerating in that career. I started out in sales operations and moved into sales, loved connecting with people. Relationships have always been my biggest driver. And so I set into that path and really loved the operational side of my work and simultaneously did not love the fact that the path ahead of me was very scripted and had a lot of prerequisites to get to the next level and not a lot of flexibility in how to progress or lean into my own skills and interests, and not a lot of location or time flexibility built into that. So I developed a career in about seven years in one company thinking I'll stay the course and go the distance and then I had a child and really sat down and asked myself, "What am I willing to trade off in order to have more flexibility? And what might that mean?" And that really led into a revelation for me around what my career would look like from there.

Daniel Scrivner (00:01:43):

That's incredible. Was it always just like, "I know what I want to do, and it's going to be to found a firm that helps just marry assistants with great executives," or what was the idea or that insight that led to 33Vincent?

Casey Putschoegl (00:01:56):

Quite honestly, it was not in the plan. I knew I wanted to start something. I wanted to be an entrepreneur. I wanted to self-manage and not report to anyone else other than myself and build something new. I didn't know what I wanted to do with that but when I had my first child, I got together with a longtime friend, Paige McPheely, and she was working in the ad space at the time and I was still in my corporate job. We both had young children and said, "There's got to be a better way. We have to find a way to bring our services and skills into the market on a flexible basis," because a lot of the positions and opportunities we were finding were, I would say, like errands type jobs and things that I knew I could do, but probably wouldn't stimulate and challenge me in the way that I wanted, and she felt the same.

Casey Putschoegl (00:02:43):

And so we put our heads together and said, "How can we leverage our skills, find other like-minded people looking for flexibility and challenge at the same time, and create a team to bring that to small businesses?" At the time we were working together, working with one freelance client and loving it, loving the team, loving the impact that we were having and the ability to transcend the details and level up into the strategy side and thought, "We could do this with more companies. We just need a team because we are at capacity." And so that's really where we started off, found our niche in executive assistants, finding those core pillars of email, calendar, managing someone's time and inputs, as well as event and project management. Those really became the evident needs and we built our business around it.

Daniel Scrivner (00:03:32):

And so it started just the two of you. And can you give us a sense for what that looks like today and how much time has passed?

Casey Putschoegl (00:03:40):

Yeah, it's been, I call it my third, excuse me, fourth baby. 33Vincent is my fourth baby. It has been around for seven years. We started in 2013. And we started off the two of us, built slowly but steadily. In the time that we grew the business, we had six collective children, so we took it slow to start. And now we are at a team of 65 people, coast to coast, supporting hundreds of clients over our lifetime, but a variety of different types which we can get into, and really leveraging kind of the same core quality that we stood for in the beginning. It's always been our number one tenet.

Daniel Scrivner (00:04:18):

Amazing job. That's incredible. It's scaled so much. The tentpole of what you do at 33Vincent is, it revolves around executive assistants, but that you have assistants that do a wide variety of things, and then add on top of that some of the confusion between is the chief of staff the same thing as an executive assistant. I thought it might be helpful if we just spend a little bit of time grounding what does that mean? What are all the different things that an executive assistant could do? What are the different types of projects or responsibilities that your team takes on? And how does that look like in different ways, just in your business?

Casey Putschoegl (00:04:51):

It's a great question and one that we do answer quite a bit because there are so many support options available. And I think when you look at an assistant, you can get an assistant almost for every flavor of ice cream. There are so many different options and types from very part-time to full-time, fractional and shared to completely dedicated, and then different levels of support within all of that as well. So breaking down the different types of assistants and then chief of staff to your point, really looking at who can support a leader and what are those different roles, to me, well, let me segment out chief of staff, because I do see that as a bit of a shift from typical assistants, executive assistants. Chief of staff roles... and we have a great partner in the industry, so we've been able to work alongside chiefs of staff, really serve as that direct right-hand to the leader, leaning in on strategy, on key business decisions, sometimes managing the team and supporting business on a high level and coming in as that strategic partner.

Casey Putschoegl (00:05:50):

Where we look to the range of assistants, and I think that the two roles compliment well, a chief of staff and an assistant, in the breadth of assistants, you can find an assistant that's a great task taker, can help manage moving pieces and get projects and tasks done and checked off the list, all the way up to what I would say, edges into chief of staff territory, where you can have an EA that does serve as a strategic partner and is able to see your time, Daniel, through the lens of how does the allotment of time align with your priorities? How am I creating systems around your workflow that help all of us optimize our work and make sure that your time is truly dedicated to your highest leverage activities and work?

Casey Putschoegl (00:06:31):

So there is a breadth there. And when I look at your question, what are the different things than an assistant can do, I think if you were to take a VA and look at an executive assistant on that higher end, the core buckets are the same, but there are different layers to each, and different levels to each. So one example of the layers would be in managing someone's time and calendar. We see kind of the basic layer or level of that being someone who can stand in and help triage and set up times for meetings. Pretty simple.

Casey Putschoegl (00:07:02):

On the higher end of that, somebody who can audit time, make sure time aligns with priorities, that the right people are landing on your calendar and that things are shifting as they need to, and being able to look at both historically and forward glance, do your commitments align with your priorities and are you sticking to the exercise we love to tie in is your ideal week. In an ideal setting, how does your week flow? And are we sticking to that? When are we violating boundaries? And what does that mean for your productivity and personal life in addition to your professional output? So looking at that through two different layers, that's kind of the spectrum.

Casey Putschoegl (00:07:38):

And another example I would share would be project and process management. You can find an assistant who can execute some research and details for you, and you can also find a stellar executive assistant who helps manage soup to nuts in terms of all your processes, creating systems, standard operating procedures, even enlisting other assistants to help execute and optimize the workflow. And that includes tech tools and systems, it includes helping to automate where possible so that we're not losing time or having bottlenecks in terms of your execution. And then also I think pulling together multiple parties. A lot of our executive assistants will serve as the gatekeeper for all of the parties on a project. Instead of just executing, they're then taking that turnkey process and owning it. And so again, you get layers in between these different levels and it comes down to what you need and what you're looking for in each of those.

Daniel Scrivner (00:08:32):

Yeah, it's super interesting. And some of the things that you touched on there is almost an assistant as an accountability partner, someone to help keep you accountable, almost like guardrails to help you stay headed in the direction that you've said you want to, then there's a third partner. And then it sounds like part of what you described as kind of they can work on, maybe one way to frame it would be lower leverage tasks where they can do it but it's likely other people could do it, and then higher leverage tasks where they are truly not just making sure stuff gets done, but trying to improve things as you go forward. Is there somewhere in that spectrum that you guys really like to work and that you like to try to find assistants and partner them?

Casey Putschoegl (00:09:10):

We do. We like to work into that strategic gatekeeper space. I love the word gatekeeper because it does speak to the value and the role itself, looking out for your best interests and being there to help ensure that you're protected against any of the distractions, any of the potential sideline things that come in, ensuring that those are handled for you and you can stay out of the weeds and in the strategy, that's really where we aim to be as an organization. And we find that it is a niche. It is a niche and it's not for everybody. There is an assistant out there for everybody, and I do believe that if you want to level up your leadership skills, if you want to contribute at a higher level, I think everybody should have some form of assistants. And we're really aiming to be that leader's right-hand, that strategic gatekeeper.

Daniel Scrivner (00:09:56):

Yeah, it's fascinating. And I want to spend a lot more time on what you just discussed, this idea that... I know in my experience, it took me a long time to finally get comfortable and finally get to a point where I was like, "I need this and I think I finally really need to do this." So I'm curious, do people come to you in a pretty similar state? Are people coming to you before things are kind of on fire, or is it typically people are showing up but it's like, "Everything's bad. I really need your help pulling this all back together."

Casey Putschoegl (00:10:26):

I love that. A lot of, "Everything's bad. I need help." And not surprisingly, those are the hardest folks to get in contact with. I think once we have a relationship formed, it becomes more routine and much easier to build from there, but it is hard for those folks who come in and say, "I am swamped. I'm underwater. I can't keep up. I need someone. I needed someone two weeks ago."

Daniel Scrivner (00:10:52):

Yeah. I have no time for them, but I need them.

Casey Putschoegl (00:10:52):

I keep forgetting to reach out to you because I'm so busy and that's how much I need you. And that's how we know that the value will be there and that the process of, I guess, the lift and impact will be there because we can see immediately some places we can make gains. The other common thing that we hear is, "I had an assistant. It hasn't been working all that well for me. I spend a lot of time managing my assistant, which is counterintuitive because I want to free up my time and I'm looking for that next level." So that's another common one. And then the third that I hear is someone told me, "It's time. It's time for me to have an assistant." So a coach, a strategic advisor, someone nudged them to say, "This was all great and good, but we need to free you up in order to focus on all of this stuff that we've been working on."

Casey Putschoegl (00:11:38):

And so they'll come and say, "I've been told it's time." And that's a process of... and we'll talk about the value of mindset in the relationship. That one is a little bit trickier because if you're hungry for that support, if you come to the table saying, "I need this, I need somebody who just gets it," you are going to value that at every turn. And I think the other side will too, the ones who are being told it's time, but it is a different journey in the relationship.

Daniel Scrivner (00:12:05):

So if that's what it looks like when people come to you and you talked about it, and this was true in my experience of working with your team is really is about, maybe we can just talk about that for a second is how 33Vincent is very different from the space that you're in. Because just to share a little bit, I've struggled with this for a long, long time. I have that voice in my head that's like, "You don't need help. You just need to figure this out. You're managing your time poorly." Always giving me all the excuses why maybe I don't need that. And so it took me quite a few years to finally get to the point where I was like, "No, I need to do this. And I know how I'm going to approach it. I want to find a true partner, someone that can help me not just get stuff done, but help me figure out what we should be doing, how to improve that over time."

Daniel Scrivner (00:12:46):

So then I looked at it, and there's no shortage as I'm sure you know, you can just Google search virtual assistants and there's a ton of services, but what was very different about 33Vincent is, from the very first phone call, it was warm, it was very curious on how my work was, what I was really looking for. And with all the other services, it felt more like checking a box and just like we have this person that can start tomorrow, or just like a nameless, faceless website that I was like, "Does that email I send even get in anyone's inbox?" So how have you... you've clearly approached things very differently. What is that? And what do you see as being really special and different about 33Vincent?

Casey Putschoegl (00:13:26):

There's one fundamental thing I think of immediately when you ask that, and it's quality of relationships. We are always focused on delivering quality and building relationships. Even if it's somebody who we're not a fit for, we would love to make, or have a great conversation and understand, can we help identify the right type of solution for you, even if it's not us. So we approach every conversation with that in mind, how do we build a relationship and how do we serve others, even in our early discovery processes. So from point A through Z, it's really about that balance of let's build a replicable process around a really customized relationship and serve by creating a very high touch relationship.

Casey Putschoegl (00:14:11):

And that goes from point A all the way through kickoff, getting to know your executive assistant, maintaining a tie to our organization. There's always a human that's behind the process and behind the outreach and not just a bot or a box that's being checked. We want to ensure, the core thing I mentioned in the beginning is quality, that our quality is there and that clients feel our quality, prospects feel our quality, people in the network feel the quality even if they never engage with us, but we want that to be transparent throughout everything we do. And I'm glad to hear you felt that way.

Daniel Scrivner (00:14:45):

No, I definitely did. And I think clearly even just hearing your answer there, it was very clear that obviously by focusing on quality, that's going to be a good strategy in a space with a lot of players, but typically people are... they're focused on speed, and they're focused more on cost, and they're not focused on quality. And part of your answer there, it sounds like, clearly I'm guessing part of your processes, you have the executives and you have assistants here, at the end of the day, almost like a marketplace helping match these two together, but just again, on the executive side, clearly part of that is you're trying to understand when someone reaches out to you what they're looking for, but I'm guessing you're also seeing if it's a good fit and you're probably trying to disqualify some people, what disqualifies someone or what kind of suggests as probably isn't the right fit, but maybe we can help you in other ways.

Casey Putschoegl (00:15:31):

It definitely is apparent when it comes through. A couple things that we see that are clearly not a fit are, one has to do with mindset. So if they come in saying, "I need somebody who can be there to do X, Y, and Z for me, I don't want to have phone calls with this person, I don't want to check in with this person. I just want them to make things happen behind the scenes and don't indicate," we ask questions always around how do you view this relationship? And we are looking for folks to say, "I'm looking for a partner. I'm looking for someone who I can bring in, who I can elevate, who I can build trust with." Because as you mentioned earlier, it is about trust. And we don't expect someone to hand over the keys to their personal life and all of their details on day one, but we want to earn that over time with the mindset that this person is a partner. So that's one disqualifier, in a sense.

Casey Putschoegl (00:16:21):

And the other, I would say, is the type of tasks. So if somebody really is looking for a task taker, an executer, somebody who can get things done, I need to schedule my kids' doctor's appointments, in addition to making sure my meetings land, I will always say to those people, "We would love to work with you. Let's pause a second and think about, is this the highest value for you in terms of ROI and in terms of our cost versus output. We're geared to be a high level strategic partner for you in addition to doing some of those other things. But if you aren't going to tap into that higher level, then we may not be the best fit for you." And we find that by identifying that early, we can clarify expectations and make sure they get the right fit. Because inevitably those people will come back and say, "I don't think I'm leveraging my assistant as best as I could," and we attempt to increase that relationship and that trust and that level of performance, but it is difficult if it's lower level tasks or executional tasks.

Daniel Scrivner (00:17:22):

Okay. So I'm curious then if you have somebody that comes to you, you think generally this is a good fit, but maybe their mindset needs a little bit of shifting or you want to try to help them. Even just in that example you just gave of scheduling the doctor's appointments. Is that really it? How do you work with those executives or those people to try to shift their mindset? And what are some of the principles you try to have them keep in mind or the rules of thumb, or just, is there anything there that is helpful to grab onto for someone that might be struggling with that?

Casey Putschoegl (00:17:52):

Yeah, absolutely. There's two different types of mindset that I see coming through. The one that I just shared around, "I don't know if I need a partner yet. I don't know if I need this." And then there's another one around, "I don't feel ready to relinquish this level of detail." So I can speak to each of those, the first being, "I'm not sure I'm ready for a partner level executive assistant." That's a hard one to shift because that partnership mindset sets the foundation for how you onboard that person, how you build a relationship with that person, the type of feedback flow that you have with that person.

Casey Putschoegl (00:18:27):

And so quite honestly, if somebody says, "I'm not looking for a partner," I will refer to another agency, because that partnership is what helps relationships flourish. In the most successful relationships we've seen, that mindset is already there or they're open-minded to developing that perspective. And so we will begin, and always in terms of building trust, we will begin small and scale up from there and prove we can carve out a need and identify ways to continue to take things off the leader's plate. And so I think we shift the mindset by doing, and by acting, and by proving that quality.

Casey Putschoegl (00:19:06):

The other perspective, which is that, "I have some trust issues," or, "I've had an assistant that didn't work out and I want to build up trust, but I don't know if I'm quite ready to do that yet." That is one that we approach similarly, but with a strategic approach. So let's start with those tasks and those projects that can be easy wins, that can show you exactly how this relationship can function, and then set up a plan 30, 60, 90 days in to begin to take off more. So we typically do find that email is one of the last things to come. Sometimes calendaring and interfacing with clients comes a little later as well, because you want to have that trust in someone, you want them to... I think for a lot of leaders, know that they will communicate professionally. They will be there on a dime to execute and follow up really well. And so we do typically recommend if you're uncertain, if you can trust an EA with your work and with your partnership, then let's start there and build into email and calendar and other things.

Daniel Scrivner (00:20:04):

Yeah. And that makes a lot of sense that obviously ties into your focus on quality. You made a great point there, which is, I think one reason which is entirely practical is just that if everything goes well, you're going to share basically everything, all the kind of password details, access to all the accounts. So there is a very high bar for trust. And like with anything, it definitely takes time working with somebody to build that. So we talked about what it looks like when people come to you, how you vet those people. So now I want to explore and talk a little bit about how do you guys approach kicking off work and kind of hearing, I guess, an executive assistant with an executive, what does that look like? And how do you think about that? And then I'd love to start getting into and exploring ways that goes wrong, ways that goes right, ways executives can set themselves up for more success. But just to start there, how do you guys go through that pairing process?

Casey Putschoegl (00:20:53):

This is one of my favorite topics. And it's so important. A lot of folks looking for their own direct hire will struggle with, "Where do I start, and how do I equip this relationship? How do I find someone?" And we have spent seven years refining this process to identify how do we filter out those who will be exceptional executive assistants based on our core criteria. And as we find those fits and bring them in and give them resources and development, we are always looking to that match. How do we make really good matches and prepare those relationships to flourish? And in that process, you'll love this because many of our team members are executive assistants by background, and so we are very information-heavy and detail oriented behind the scenes with the attempt to be as streamlined as possible on the front lines with our clients.

Casey Putschoegl (00:21:42):

And so what we do is a complete deep dive with our clients in terms of what are your preferences? What do you think about in terms of your time and your boundaries? And let's unpack all of those details. Who are your VIPs? What are your top priorities this quarter? And we'll unpack all of those things so that the executive doesn't have to think through, "Okay, where do I want my EA to start? And what kind of preferences do I have?" We'll really pull those out and create a robust, what we call a dossier on the executive, that the EA will ultimately receive and be able to immediately put to work. So instead of starting off the relationship with all of those logistical details and preferences, frequent flyer numbers, all of those things, we prepare all of that and set the foundation so the EA and the executive can build the trusting relationship and have those immediate wins in order to continue to build momentum.

Casey Putschoegl (00:22:37):

And so we find that in the relationship, setting the stage is really important and thinking of it as a partnership is part of this because coming in and saying, "Here are my preferences," is one thing. The next layer is, "What are my expectations for this relationship? And what are our key touch points going to be to ensure we're meeting those expectations?" More than most other work relationships, this one, this partnership in particular, is really important with your assistant because feedback flow, tweaks, all of those things are going to help you refine and build momentum with this person. So we set the stage strong and then ensure that we have the right fit, which we can talk more about, but ensure we have the right fit between the executive and the executive assistant.

Casey Putschoegl (00:23:16):

And you asked another question about where do we see that go wrong? And one key area where we see that go wrong is not getting enough information from the executive about their needs, or maybe they haven't gotten clear about their needs, they haven't quite thought through how to leverage an assistant. And so we have limited information to go off of and we try to draw out more. And when we can, it definitely makes for a more robust match and a more robust kickoff to that relationship. But when we have little detail and little clarity around the why behind the assistant and the what we can do to really wow them, the less likely we will be to achieve those expectations. So where we have seen it go wrong is a client kicking off with an executive assistant and realizing their needs are actually far out in left field where they thought they'd be in right field, and that person doesn't have the capacity or background to meet the needs that they've now articulated.

Casey Putschoegl (00:24:08):

So again, I think going back to leveraging an assistant, it's important whether you're going through an agency or finding an assistant directly to spend a little time, it'll be a time upfront but time very well spent, to identify what are those things that I ultimately want on that ideal wishlist. Like if I could expand the list and think of all of the things I want to hand off with someone, where do I start but know that scope and also know what you expect to get out of that relationship. And by doing that, you set the stage for an ongoing and successful partnership.

Daniel Scrivner (00:24:41):

I want to touch on one thing you've said a couple of times, which is just the recognition that a lot of people, I'm sure, are open to going through an agency but they maybe want to try to find somebody directly, but clearly I never even seriously consider trying to find somebody directly just because I thought of all the ways that that could go wrong. Not only are you doing an incredible amount of vetting on the EAs that you bring on, you're also doing a lot of training and I know there's other things like since you have an entire team, if an EA needs to leave or go on leave of some sort, somebody else can step in and it can be really seamless. Can you talk a little bit about all of the pros going through an agency like 33Vincent versus trying to go direct.

Casey Putschoegl (00:25:21):

You mentioned a couple and seamless coverage is one of them. We have one of our longtime EAs who is out on parental leave right now with her third child. And in that process, we were able to find the right fit for her client to fill in for the time that she's been away and ensure that they have plenty of crossover to train and pick up the ball right where they left off and help adapt to potential changes in capacity or availability as well. So when you go direct, you have... obviously there's benefits to having access to somebody that you've found accustomed to yourself, a little bit more legwork on the front end there, and that person might have capacity constraints that you can't get around and they might need to take some time off or take a leave, as you mentioned. So that's one really great example.

Casey Putschoegl (00:26:04):

The other, I would say, is capacity flexibility. So if you have bursts of needs or a time when business might be slower and you might need to scale back your support, but especially scaling up for we've had a couple of clients do large scale virtual events that have required more hands on deck. So the ability through an agency to say, "I've got this on the horizon, I'm going to need more capacity," or, the EA will bring forward and say, "This is how much time we're going to need. I need some backup," and we'll bring in a team of VAs to support that lead EA and help execute seamlessly. So you get access to that flex capacity on both sides.

Casey Putschoegl (00:26:40):

And also just general flexibility. I think a couple of clients have said to us, "I want to be able to work remotely from my EA. I don't want them sitting next to me every day. And that separation helps me, I think, feel less risk around the relationship." And if they've said, one in particular has said, "If I want to let my EA go, I can do that." He has kept his EA for like six years, so that didn't have to happen, but it was that peace of mind to say, "I've got the flexibility here and the low risk to toggle as I need to, to make decisions as I need to." And especially we've found lately during COVID that flexibility is paramount. And as budgets shift, as needs shift, as travel needs, especially, we've seen a lot of our clients scale back on travel, but scale up in other areas. And so the ability to flex into that is helpful.

Casey Putschoegl (00:27:29):

And then the last thing I will mention is just access to expertise. So with an EA through an agency, you have that EA's experience and their direct support for you. And you also have them backed by a ton of other experience. So an example of that, we have a lot of sharing happening daily on our Slack channel, "Who has Salesforce experience?" or, "Has anybody tried this approach or process? Can you hop on the phone with me and work this through?" And so bringing forward those years of experience in different areas helps to uplift that EA and give them some more resources that a simple blog or a tutorial on a website can't give. And so you get that EA backed by a lot of other expertise.

Daniel Scrivner (00:28:06):

And as a client, of course, as soon as you said that, I'm like, "Well, yeah, of course you should have an internal Slack channel, but I had never even considered that." But yeah, that'd be a huge benefit.

Casey Putschoegl (00:28:15):

We have some 30,000 messages exchanged here. It's a lot of back and forth.

Daniel Scrivner (00:28:20):

Okay. So we've focused on the executive side, we talked a little bit about what that process looks like. I'd love to shift and focus in a little bit on how you vet, and find, and train, and develop just these incredible leaders. And the one thing I would just say really quickly on a couple of your last points is, again, I struggled with this for a long time, reached out to 33Vincent after one person recommended it. I can't remember the name off the top of my head, which makes me feel slightly bad, but someone recommended it. I reached out and ended up getting paired with Crystal Esquivel, and she is incredible. And literally from the first time I started working with her, I just continued to tell her, like, "I love working with you. I just want to find more stuff that we can keep doing together." And it's like, that's clearly what you're going for and why that trust is important and why that fits really important.

Daniel Scrivner (00:29:04):

So clearly there's something special there because I think the downside of I'm guessing when some people think of an agency, I don't know, maybe they think of that in a negative way as you have a bunch of people, but potentially they're not that trained. That nothing could be farther from the truth. So can you talk a little bit about how you find, how you vet, how you train and develop these assistants.

Casey Putschoegl (00:29:25):

I can, yeah. And let me first say that Crystal is incredible and we've loved working with her for several years. So you're in great hands. And yeah, finding the right fit is one of the main things we focus on. Of course, making great matches and filtering to find those great partnerships is one, but it comes down to finding the right talent. And we've spent a lot of years refining our approach and ensuring that we are filtering the best talent. Because one thing I will tell you is that not every exceptional executive assistant has direct executive assistant background. And so we've had some EAs just rise to the top who come from account management, or customer service, or other backgrounds where their skills lends so well to the role, they need a little context and a little support around, "Exactly how do I frame up my skills in the right way to leverage this executive to the best of my ability."

Casey Putschoegl (00:30:18):

So in short, we are looking for the skill sets. We are looking for the skill set experience as part of that, but it's not the only part of that. And so what we look for, there are some core traits, of course, that won't come as a surprise, but we do have metrics based on each of these and it's proactivity, attention to detail, level of thoroughness, ability to manage up, ability to communicate well and think on their feet, and then also to be consultative in their approach. So some of those easier to measure, some a little harder.

Casey Putschoegl (00:30:48):

And when we approach finding the right fit, we've got a few different, I would say, hoops to jump through to prove that you have the right skillset, because for us again, and I'm going to sound like a broken record here, but going back to quality is key for us. So it may not surprise you based on what I've told you about our client side and building those relationships. Every executive assistant candidate who applies gets a high touch relationship with our team. And so we are nurturing those relationships. If somebody is an exceptional talent but actually says, "You know what? I need to hit pause because my commitments and capacity has changed temporarily," we stay in touch and we make sure that we are cultivating that talent over time.

Daniel Scrivner (00:31:29):

I think part of it's too, just on the training and development side and just the context there is part of this, I asked Crystal like, "I'd love your thoughts if you have any questions to ask." But clearly from her perspective, it's just been an incredible experience. I'm sure there's some unique things you're doing there.

Casey Putschoegl (00:31:44):

So in our process, we are looking for those core skills through an initial application geared toward identifying... I love asking people, "What are you listening to? What is your favorite book or podcast?" And you can kind of unpack how they think and then get into some examples. And we use what we call a sample project, but really drawing out real life examples of what could happen in an executive support relationship. So unpacking that and seeing how they respond. As you can imagine, there's quite a variety of answers. And for us, we look for those common threads. Are they thinking beyond the situation at hand?

Casey Putschoegl (00:32:20):

They're not just answering, "Okay, I see this problem that you've presented. Here's the solution," or, "Here are the steps I will take to check the boxes and execute to fix this," but they're thinking of, "What's the root issue? Why is this happening in the first place? And how can we get to the bottom of that? Here are the questions I would ask? Here are the people I would want bring into that conversation and make sure we fix the issue, but we also address why it is happening and showing ownership over taking lead on that." And so we're looking for that level, that X factor.

Casey Putschoegl (00:32:52):

And I think in terms of finding an assistant, if you're someone out there looking for an assistant on your own, use a real business example that's happened to you and see how they'll respond, find something complex that might require them to dig a little bit, not just produce an answer but dig a little bit, and be open to having them ask some questions so that you can see what their thought process is. But ultimately that gets us to and through selection.

Casey Putschoegl (00:33:16):

And for us, we have a simulated two week period where all executive assistants who are coming into our community manage a four executive, they manage a calendar, they manage an inbox, they're going back and forth. And it's fueled by our talent team who is seeing their work in action. So not just have they answered well or are they good task takers, but how are they in the moment? And that really gives us a good diagnostic for fit as well as one of the other key metrics I did not mention to you is level of assertiveness. And can they manage up in a way? For some clients, they come in and say, "I want someone to manage me. I want someone to tell me, Daniel, this is overdue. I need it from you. I'm going to keep calling you until you get it to me."

Daniel Scrivner (00:33:58):

Like a lot of leaders need that.

Casey Putschoegl (00:34:01):

Yeah, exactly. I will be as persistent as possible. And so there are varying degrees of that, and we look for that as well. And so that process helps us unpack that and make the right matches based on the clients that we have coming in.

Daniel Scrivner (00:34:13):

Yeah. It's an incredibly thorough process. I'm curious, just because this is used sometime in interview processes, and I know there's a bunch of different points of view on it, but do you guys... have you looked at using personality assessments at all and matching people in that access?

Casey Putschoegl (00:34:29):

We have, yes. We have. Most recently, we've experimented with five or six different types of personality assessments and issued them to our team to understand what results are we getting. And then is this indicative to what we're hearing from clients on performance? And we've had mixed results. Some assessments are better than others. One that we've tried recently, which we really liked was the Kolbe assessments, Kolbe A Fit Assessment. And so having the executive take an assessment in terms of their needs and then having the executive assistant take the assessment and then pairing those results for a fit grade, giving an A through F fit grade gives us a good benchmark to say of the EAs who have available capacity and the matches we're making, we can pair those up and find the best fit.

Casey Putschoegl (00:35:15):

Now, the challenge is in tapping a busy executive to take that assessment. And so we've found we use it when we can. And sometimes we also find our intuition is really strong having done this for awhile. And a result can give us an A through F and we often find we make the same conclusion, and can do that even without an executive giving their survey results. But yeah, there are many assessments which are great indicators.

Daniel Scrivner (00:35:40):

I don't know if I've heard that one that you mentioned, so I'll make sure to include that in the show notes so people can find that. Okay. One of the things that I wanted to spend a little bit of time on is just around do's and don'ts for once you've matched an executive and an assistant... and just to share a little bit of context like one of the things that Crystal and I have experimented with since we've started working together is something as simple, which I've found invaluable of just doing a weekly call. That was one of the first rules of thumb that I've heard, and a lot of people share as well too, is you definitely need to have some time in person every single week where you're sinking. So maybe we can start there, but what are some do's and don'ts that help executives and their assistants stay on the same page and work as effectively and as frictionless as possible.

Casey Putschoegl (00:36:26):

What you mentioned about weekly meetings is so important because we do have clients who have not shown up for those meetings or say, "I don't need a weekly meeting. As I said earlier, I don't have that time to spend." However, that time spent you get back in spades, because if you can equip your assistant, your executive assistant, with what they need to run forward and accomplish what they need to accomplish, then you freed yourself up. And a lot in that time helps to do a couple of things. Number one, it helps you level set on priorities and what's coming up. One of the do's that I immediately thought of is ensuring that you give your EA context into what is happening around a larger ask.

Casey Putschoegl (00:37:05):

And so if they have the context, if they know that you are setting up these meetings, you've got a variety of moving pieces happening because you're considering an acquisition, there are some levels of sensitivity there but you want your EA to have enough information to know, "I'm going to orchestrate this because it's contributing to this larger initiative," versus saying, "Can you land X, Y, and Z. Let's move on." And so ensuring that you give context into your asks and having that weekly time together helps surface questions, it helps move the dial. And what I recommend for anybody who has that weekly call is, spend that on the high leverage conversation where a lot of the other details can happen offline.

Casey Putschoegl (00:37:43):

So whether you use a project management tool, Slack, we use Base at 33Vincent, which gives executive assistants the ability to store all of their questions that they have in one spot and push a decision stream to the executive to say, "Here are five questions I need you to answer, and I've already clicked in answers for you. So do you want to catch the red eye home? Do you want to catch the 9:00 AM? Here are a few different options. You click one and move on." And so those more logistical, lower level tasks can be accomplished quickly. And then your time together can be maximized. So if you are somebody who has an assistant and you're spending your time on the minutia while you're talking, I would recommend exploring a project management tool or a weekly digest of questions, maybe daily, depending on your workflow, where you can knock out those quick things and then maybe cut back your time together, but definitely spend that rich time together.

Daniel Scrivner (00:38:35):

And I want to now flip the script a little bit, because I know that you yourself have an assistant, which makes a lot of sense. And I would also guess that you're super thoughtful and you're applying all these best principles to how you work together. So can you talk a little bit about that? What your assistant focuses on, what you try to focus on, and how you keep that relationship a great partnership over time?

Casey Putschoegl (00:39:00):

Getting the chance to work with an EA was an aha for me, because I had already been leading 33Vincent for several years before getting my own EA. So similar to your mindset conversation, I had thought, "I can do all of this myself. I'm a very detail oriented person." And bringing in my EA completely shifted my perspective. It definitely increased, I think, the value of what we do in my mind and helped me establish what are the ins and outs of managing this important relationship firsthand. And my EA's name is Leah. And one of the things that Leah and I do that we've recently started doing with more cadence, but we definitely always have a quarterly step back where she and I sit down, we do two-way feedback and I ask her for feedback.

Casey Putschoegl (00:39:44):

Of course, I come ready to give feedback. We call them glows and grows in our organization. So what's going well and where can we continue to refine our processes together. And I also want feedback. So where can I better help you help me? And when we're communicating, are there ways that I can do things differently in order for us to work together best. And that feedback flow, and I think that mutual invitation, has been really beneficial for our relationship.

Casey Putschoegl (00:40:11):

The other thing is a set of questions, and I think the KISS principle, Keep-Improve-Start-Stop, is a really effective one. I like to ask simply what's working and what's not working and come up with creative solutions for what's not working. Typically, what's not working is more just how can we be better and how can we even more refine those little nuances? But it's a great opportunity for us to step back and look at the whole picture and say, "Actually, there's something I've been doing habitually that I could have you do. And you could lean in to support me in ways that I haven't." Or if I just shared a little bit more context around what I'm working on, or maybe the board that I'm using for annual planning or other things, she can have the context to help me even increase her involvement. So those step backs have been hugely helpful.

Casey Putschoegl (00:40:58):

The other thing is our communication cadence has changed over time. And I really like where we've settled in. So she is sending me... and she has access to all of my boards, and to do lists, and initiatives, and goals, and all of those things. So she is able to lean in and hold me accountable in a lot of ways, but say, "You said you were going to do X on Friday, and I actually see you scheduled something on top of that. So I'm going to go ahead and move that for you." But through this process of communicating regularly and having her well involved, she's able to see all of those pieces. And she sends me a morning digest so I get a glimpse of my day, the things that have come in or maybe that I forgot to act on that she is reminding me, giving me those nudges about, and then I get an end of day recap and a glimpse ahead to tomorrow.

Casey Putschoegl (00:41:41):

So that communication cadence has been really helpful and it helps her see, I think, the whole picture in ways that as we were warming up in our relationship, she didn't have as much context and that was on me. So I realized, I give this advice a lot, I need to put it into practice myself.

Daniel Scrivner (00:41:56):

There's so many good things you touched on there. So I want to try to go a little bit deeper on a few of them, but one of them is that I love that the framing and the phrasing, I think you said glows and grows. Can you talk a little bit about that and what each of those stands for?

Casey Putschoegl (00:42:09):

I don't know when we adopted this as an organization, but we love it. We use it for everything that we do, including performance reviews, even just casual feedback conversations. To us, a glow is like strength. What are you showing up in? I actually like it better than strengths because it's calling out what is going well, what am I seeing in you that's just superb, exceptional? And we like to break it down by our core values and the key competencies of the role. So proactivity might be an example. Here are a couple glows that you have in productivity. I saw you do X, Y, and Z and that totally set me up for that meeting in a way that I had not thought I could have been as prepared. So sharing a couple of examples with actual projects they've completed and/or just themes of ways they've supported you is the glow theme, and the grow is really opportunities for improvement. And I prefer grow to weaknesses or even opportunities for improvement. I think it just gives it more of...

Daniel Scrivner (00:43:11):

That's an opportunity. It's not a negative.

Casey Putschoegl (00:43:13):

Yeah. It's not a negative. It's, here's a place where we can grow. So one of our core values as an organization is growth and we believe everybody has opportunities to grow in their skills. We always want to grow in the direction of our strengths, of course, and focus on continuing to enhance those. But with a growth minded culture, we're always asking, what can we do to grow from here? What feedback can we use to continue to grow and continue to level up year after year? And so that question and that word we use specifically is really geared around where are there opportunities for growth? And sometimes it's simple, sometimes they're larger things, but again, we go by competency.

Casey Putschoegl (00:43:48):

So giving an example, a grow in productivity would be, "I noticed that..." and this isn't with my EA, but, "I noticed I had to follow up with you on that. And usually you're all over it. So next time, can you loop back with me on that or put it in your project digest so that I know that it's complete." So there are various things that you can include in that, but it's a good way of calibrating. And we have it on our weekly agenda, actually glows and grows are part of our weekly agenda. Sometimes there aren't any new things to discuss, but I want to show up and also give praise and kudos to her because I'm always looking for opportunities for growth and I don't want to forget that in this important relationship, I want to call out all the great things she's doing and that uplifts, I think, her desire to do well.

Daniel Scrivner (00:44:32):

Yeah, especially on a weekly basis. You touched on that. That was part of your weekly review. What other items are consistent in that? What things do you make sure that you do every single week?

Casey Putschoegl (00:44:43):

During our weekly calls, we have the glows and grows section feedback. And I ask her as well for feedback. The other two key pieces are big rocks. So what are the big rocks coming up? And let's look through the trees to see what we've forgotten, or if there's anything there that we just want to scope out. So she'll always have questions for me, diving deep in there, asking me about my priorities for the week ahead and really diving into discussion on those. And then there is a logistics and update section, if there's anything bigger that we haven't covered in our decision streams, but those are the key areas. And then quarterly, we do have that step back agenda. We have experimented with doing it monthly, but I think quarterly is a good cadence for us where that digs into the start and stop.

Daniel Scrivner (00:45:27):

And I want to also talk about that for a second because, well, one, in the interview so far, reflection has come up time and time and time again. With everyone that I've spoken to, obviously, step back's just another phrase for that. I really like it. It sounds like you have a quarterly step back you do with your assistant. My understanding is maybe you have some other personal step backs that you do. Can you talk a little bit about your perspective on why that's so important and why that time is so valuable and how often you try to do that, at all the different levels. Because I know, obviously, for someone like you, I'm sure you want to make time for personal reflection, you want to make time for reflection with your EA, I'm sure also at the company level, with your leadership team. Can you share a little bit around that.

Casey Putschoegl (00:46:07):

Absolutely. I believe reflection is so important and especially for leaders who are leveling up, scaling businesses, becoming busier than ever. Reflection is a great process. And I like to call them step backs because it really does feel like an accurate visual, you're stepping back from being in it to work on it and work on yourself as a leader as well. And I do step backs... I've filtered recently, but weekly on Thursdays. And it's a time for me to... my team knows I will be offline. I will not be on Slack. I will not be responding to email. My EA is really protective of my time on Thursdays, which I love. And I'll sit down with a series of questions. A lot of times it's the same questions that I'll review week after week. And sometimes I'll have something on my mind that I'll want to dig into or analyze or brainstorm on.

Casey Putschoegl (00:46:57):

So I do weekly step backs, professionally, and monthly step backs from a leadership level. So personal leadership reflection step backs. And I look back to all the goals that I set for the month. How did I do on those? Where did I show up in alignment with my core values and where did I not? And what can I do differently this coming month? What can I keep doing this coming month in order to contribute at my highest level? And oftentimes it is involving my executive assistant in ways that she can continue to support me. So I love doing that, having a day to myself with a hot cup of coffee, sometimes sitting out on my deck, just reflecting with a notebook, no tech, and kind of breathing in, drinking in, what I need to do or what I want to do next.

Casey Putschoegl (00:47:40):

And that helps me. I find I come refreshed back into my conversations with our leadership team. It encourages them to do the same practice. And so our leaders have been taking step backs personally to reflect, and as they manage others, think about, "How can I help cultivate a culture where this is part of us, this is part of how we operate?"

Casey Putschoegl (00:48:02):

And the other thing I would say, on our team, what we do is we do leadership team step backs on a monthly basis. And then we also do one-to-ones. So for anyone on our leadership team, that we have a quarterly step back where I'm... I like to think of them also as impact meetings, where can we continue to move the dial? And some, I think open ended questions just to unlock discussion and say... trying to give some examples. This recent month, we went through the five levels of leadership and talked about what do these mean to us, and where do you fall on these levels of leadership? And I think it's a great practice. What I want our company to be is a company that cultivates leaders at any level of the organization, and so reflecting on leadership and reflecting on personal impact and personal values. You said earlier, your unique zone of genius, everybody has one and I'll be bringing out the best in everyone. And so using that reflection time has helped us excel as an organization and has given me a lot of personal ahas as well.

Daniel Scrivner (00:48:58):

Yeah, that makes a lot of sense. And that's clearly a very well thought out strategy. I love that. I wanted to talk a little bit about just your experience. So you've built an incredible business and you have an incredible team around you, but clearly you're the CEO of the company, you're leading that team. What has that process been like for you over the last seven years? What were some really difficult moments? What was it like? Because I can certainly relate. I think part of the experience of being a leader in a fast growing company is always just very clear the things that you need to work on, the areas that you need to continue to develop, and that can be painful. That can also be really exciting. But what has that process been like for you of growing alongside the company, growing to be the leader that you want to become, to create the company that you want to create?

Casey Putschoegl (00:49:43):

It has been a journey, quite honestly. I'll be very frank that I never set out to be a CEO. I always wanted to run my own business, but never quite put my finger on what it would mean to be a CEO, to lead a growing team, and I think the unique challenges that come along with that. I'm a people person. I want to develop our people and uplift our people. And I think one of the golden nuggets of all of it is watching our team develop. So our COO started out as an EA with 33Vincent, immediately saw her, saw much promise and ability in her and worked with her over years to continue to elevate her through the organization and look at new challenges along the way. And being able to, I think through my role, see, support, and craft that uplifting of leaders has been far and away the biggest asset and biggest win.

Casey Putschoegl (00:50:36):

There have been challenges too. And admittedly, this season that we're all in with COVID-19 has been one of the biggest challenges for us as an organization, for me as a leader to think about how do I show up and what can I bring to the team and to the table that helps our leaders continue to contribute at the highest level, even if they now have children schooling at home or maybe their spouse or their partner has been heavily impacted from COVID. And so being able to show up, I would say it's almost a challenge to be both authentic and also steadfast in a sense, and know that I want to make the right decisions for our team, I want to make the right decisions and support that resilience as we all navigate changing circumstances. And we've had a lot of clients need changing circumstances as well.

Casey Putschoegl (00:51:28):

So how do we remain agile and continue to level up and show up even when it's hard sometimes, even when we feel like the world is collapsing around us, but we want to be strong. We want to show up for our clients. And so I think that uniting mission helps. But yeah, each year in my leadership, I find that the playing field gets bigger and I'm invited to step onto that playing field. And I do see it as an invitation. It requires new skills for me, it requires that I'm continuing to level up as well. And I love my coach. I have a leadership coach who I adore and she's been instrumental in that process.

Daniel Scrivner (00:52:05):

That's incredible. How did you find that coach? And can you talk a little bit about what that relationship has been like and why you felt like you needed that? Why that was so important?

Casey Putschoegl (00:52:14):

It felt like a non negotiable for me, especially once I'd had that first session, because I think similar to what you were sharing about your perspective on engaging an assistant and coming into that space, I had a similar mindset of, "Do I need a coach? I love to coach others. Why would I need my own coach?" And I do find that in my position, I don't have someone I can go to.

Casey Putschoegl (00:52:38):

I of course have my co-founders and go to them regularly with thoughts and requests for feedback, but not someone I can speak to directly around, "Here's what I want to work on. And here's where I'm struggling in. And I have this vision for my company. How do I get from here to there?" And helping to, I think, dissect some of that, having that resource, it feeds me so that I can feed others with the same spirit and come to... it's a cliche, I would say, but I want to have a full bucket. Because if I don't have a full bucket, I can't fill others' buckets. And for me, that coach fills my bucket. She helps me reflect in the moment, she asks me questions that I might not have asked myself, and she calls me out. She knows me well enough to say, "Hmm, you just told me this. But what I'm hearing in your voice is actually something totally different." And she'll help call that out. So I have found her involvement to be one thing I would never trade. I'll put it that way.

Daniel Scrivner (00:53:35):

Reading in between the lines a little bit, one thing I would guess is that it seems like you have a very integrated approach of... clearly, you have a lot of responsibilities. You're a mom with three children, you're married, you have, I'm sure, a lot of responsibilities at home, I know you also care a lot about just health and wellness, and then you have this growing business. What's your thought process on how to approach that? Is there even a separation between work and the rest of the areas of your life? Any thoughts on the philosophy and just approach there?

Casey Putschoegl (00:54:05):

It's all one and the same. I see it as part of one big whole. And I always think of others and look to others as a whole person. So there's the professional you, there's the personal you. To me, those aren't compartmentalized. Yes, we may try to compartmentalize them in our day to day lives, but for me, I look at our clients, at our team, and I try to see as much of the whole person as I can. And for me, I have to give myself that grace as well and see, I am the sum of all of these parts. I'm not just a mom, I'm not just a CEO or a business owner, I'm not just a spouse. And all of these come together and make me who I am. They, one working well in contact with one another, help me show up in every area better than I would if one thing was out of whack.

Casey Putschoegl (00:54:50):

And so I look to... in my best moments, look to ways that I can set my priorities around those different areas, knowing something's got to give. I've learned one thing that I think was a myth I always thought was true, which is that I can have it all. I can do all of it. And I have found along the way that it's not true. You can have the best of what you set as your priorities. And if you don't prioritize though, you're going to have like 20% of everything. And so I found really quickly that for me, it is, and having a family has been that filter to say what are my top priorities. It shines a spotlight pretty quickly on what I definitely want to do and what I want to say no to, because I know that everything comes with the trade off, I know that my family is my number one, but also I love to work, I love to contribute, and those can coexist in a way that I didn't want to think was possible.

Casey Putschoegl (00:55:45):

So for me, it has been a journey of letting go of a lot of guilt and also finding those non-negotiables. I'm really grateful to be where I am and to have the setup that I have, because it allows me the flexibility to drop my kids at school, it allows me the flexibility to shut down at the end of the day, walk 20 feet and there they are, but it also comes with challenges in that same vein. And it has been years of continuing to improve and refine my approach.

Daniel Scrivner (00:56:11):

I'm sure that's going to be a never ending process because anyone with kids knows too that every month can be different, every year certainly is different, they're changing people all the time. There's a lot in flux. So I want to start getting into a few of the closing questions and I'm going to change them slightly. One thing you've touched on a couple of books and principles that I'm guessing maybe you discovered in books. It seems to me that you're clearly an avid reader, and then knowing that you've had this massive growth curve, both professionally and personally over the last seven years. So typically I'll ask someone for just one book recommendation, but I'm curious for someone listening to this that is just inspired by your own journey and knows that they want to embark on that for themselves, are there a couple of books that have been really helpful for you? And they can be books, they can be courses, they can be people, but are there a couple of things that have been really impactful for you that you would pass on and recommend to somebody else?

Casey Putschoegl (00:57:04):

One of the books I recently read which really lends itself to the conversation we've been having is Essentialism by David McKeown. And I think I have almost every other page in that book flagged down with notes in the margins because it speaks to the heart of why I'm in business. Also what drives me, which is less but better. And I love the framework. He has an illustration in the book where there's a circle and an arrow pointing up in one direction, and then there's a simultaneous circle next to it of the non-essentialist. So the first circle is the essentialist, the second circle is the non-essentialist. And there are arrows shooting in every direction, but only for an inch in each direction.

Casey Putschoegl (00:57:45):

So do you go an inch in each direction in 20 different directions, or do go 20 inches in one direction? And how does that impact how you show up? And it speaks to me because I, number one, when I work with clients and talk to clients, it's really about how can you do less, but do the things that you do best even better. And if we can show up and think about like addition by subtraction and really inviting in an executive assistant to help with that process, then that's really what we're here for. So that book really resonated with me personally and professionally. And it helped me to realize some areas where I was being a non-essentialist, and to carve out opportunities to straighten my arrow in a sense.

Casey Putschoegl (00:58:26):

And the other one that I love it's in a similar vein, a popular one is The ONE Thing and love the methodology around The ONE Thing, especially when it comes to setting priorities and goals and having a relationship with your goals. So that one stands out far and away, and we've worked with Jay Papasan and Geoff Woods directly. So love them and love the work that they're doing. So that's another one.

Casey Putschoegl (00:58:49):

And then the third is sort of an offshoot. It is by Gay Hendricks. And it's a book called The Big Leap, talking a lot about how we set these sort of ceilings for ourselves around what we think we can accomplish or a barometer for our success and where we set those kind of indicates where we're going to wind up. So if you have a barometer that you set low for yourself, "I don't deserve more than this much success," well, if you bump up against that barrier, you're going to find ways to bring yourself back down. So it talks a lot about self limiting beliefs, the stories that you tell yourself, and how to kind of identify and break through those in order to take a big leap towards success. And so I've found that's really helpful. I think for most founders, you have those voices in your head that tell you, "You can't do that." And so being able to address those and I think change the narrative internally is important.

Daniel Scrivner (00:59:41):

Yeah. And I think that principle's expressed so many different ways of like the five people you spend the most time with is the person you're going to become. I've heard that same idea stated different ways, but I love that and I've not heard of that book. So I'm excited to read that. So something else that I'm curious is, for someone else that's listening to this, that's inspired by your story... and one reason I wanted to have you on the show is, I want to highlight more women that have built incredible businesses. And you've clearly done that. Now just in seven years, scaling to have a team of 65, I think is an amazing feat. So for someone listening that wants to kind of follow in the same direction, do you have any words of wisdom, any advice, even just like a pep talk that you would give that person so that they can be willing to take that first step forward?

Casey Putschoegl (01:00:23):

My advice would be that the first step is the hardest, and if you have something you're working toward, an idea, a concept, a passion that you think you could turn into a tangible business, the risk is worth the reward. And of course, when I talk to friends, they say, "How do I leave my corporate job and do something am not passionate about, do something that gets me excited and makes want to show up every day?" My answer is, "Well, what are you passionate about? What gets you excited?"

Casey Putschoegl (01:00:52):

And I think our guts tell us a lot that we ignore. Following those areas, carving out maybe an opportunity to trial an idea, trial a service, trial a product, and see what kind of demand you get for that, if you sense, "I'm onto something," the risk is worth the reward. I had a really hard time leaving my corporate job, my cushy job as I called it, my company car. It was really hard for me, and friends always said, "You have the golden handcuffs, you have the golden handcuffs." And I felt very privileged to be in the place that I was deciding to make that leap.

Casey Putschoegl (01:01:22):

And at first it wasn't easy. There were trials and tribulations. I was always looking at cashflow and financials and all of those things, but I knew that we were onto something. And I knew that if I led with my values, if I led with my passion and kept showing up, it would turn into good results. And inevitably it did. Along the way, I think part of my leadership journey, and I would challenge anyone who's growing a company to say, trust others to help lead, find a way to set up the right people in the room and then step out of the way as much as you can, because that has been the key to our success as we've scaled is finding the right people, putting the right resources in the right places, and stepping back to let them contribute.

Daniel Scrivner (01:02:08):

So I want to talk a little bit just personally, one of the questions that we ask every guest is the things that they do every day. And you shared a little bit of this, just your principle about doing step backs, taking that time to reflect, but I'm sure there are other things that you do every day, and these could be practices, routines, tools that you use that help you show up as your best self. Can you share some of those with us?

Casey Putschoegl (01:02:31):

One thing that I do every day, try to do religiously every day, is my shutdown ritual at work. So I'll touch on professional and personal as well. I think the theme of rituals in general is a big one for me this year. How do I, especially in times when the circumstances around us have been changing, my kids were home for six months, schooling from our basement, how do I create replicable rituals that help me feel grounded and centered, that help me show up better to work, better at home, and create a little bit of a boundary between the two. And so that includes my morning ritual, getting up early and having a little time before the kids wake up, having a workday startup ritual, I won't get into all of these, but a workday shutdown ritual, and then a nighttime ritual and making sure I get the rest I need to show up again tomorrow.

Casey Putschoegl (01:03:22):

So the one that I'm focusing on the most is the workday shutdown ritual, lately. And for me, that is a process, and I learned it from Michael Hyatt & Company, that is the process of, for me, having a 30 minutes, sometimes 20 or 15, depending on how busy the day was, but a little period of time at the end of the day where I take that breath in a sense and look back at the day, capture anything that's still bouncing around in my mind and get it down, get it out of my head, and into my to do list or into my project tracker with my EA and make sure I get those notes captured, because if I try to remember them tomorrow, they're not going to be as clear.

Casey Putschoegl (01:03:58):

So I'll get them out today and then I focus on closing out. So what do I need to address before I wrap up? What's coming up for tomorrow? One practice I love, which is so simple, is closing out all the tabs I have open. Right now, I look at my screen, I've got probably 10, 15 tabs open. I don't need all of these. So let's do honestly like a refresh and shut down what I don't need, open up the agendas I need for tomorrow, and have my computer teed up, then literally put my computer to sleep, turn off my office lights, close the doors. For me, it sounds so simple, but it is the process, and I don't have a commute.

Casey Putschoegl (01:04:31):

So it is my process of leaving work. And it helps me leave work at work, even though it's 20 feet from my living room. And it helps me show up with my children and be more present, it helps me sleep better at night. And so I found that that ritual for so long, I'm like, "Okay, workday shutdown ritual." I've heard about that before. Actually putting it into practice has been game changing for me. So that's one I do every day.

Casey Putschoegl (01:04:53):

The other thing for me, I'm big into health and wellness, and I believe that what I put in my body and what I output helps me stay mentally sharp, it helps me show up and have energy. And so without getting into too much detail, my husband and I have been plant-based for about six years. And for me, it's a morning smoothie, fruit, spinach, kind of just a veggie fruit smoothie that helps me kind of jumpstart for the day and gives me the energy alongside the coffee. I still do drink coffee. I haven't been able to knock that habit, but... I've tried mushroom coffee and I'm like, "I like it. It's just not the same." But having that combination in the morning is really helpful. And then working out.

Casey Putschoegl (01:05:36):

One of the blessings of the pandemic is that I decided early on, I'm going to come out of the pandemic better than I went in. I'm going to be a healthier, more refined version of myself. And part of that process has been working out every day. I used to work out a few times a week and do more of a hour, hour and a half workout, and I said, "I'm going to commit to doing a little bit every day, even if it's 20, 30 minutes of strength or cardio, I'm going to do it every day." And tried a bunch of different apps. I've settled on the popular Peloton. I don't have any other equipment. I'm hoping someday to invest in a bike or a treadmill, but having the app and just the ownership over, or I guess the ease of the ability to show up for 30 minutes any day, that has been a game changer for me.

Daniel Scrivner (01:06:23):

Peloton's, I'm curious to see how it stacks up against I know Apple's just releasing their new kind of fitness videos, but yeah, it's wonderful that we have those now because especially obviously with COVID, you need to work out from home. And I think so much of it is like, you actually don't need that much equipment, but it certainly helps and lowers the barrier to doing it if you've got somebody that will show you how to get great workout at home.

Casey Putschoegl (01:06:44):

Well, you don't need that much time either. I think you just need to have a trigger and a ritual to do it.

Daniel Scrivner (01:06:49):

And that's something that we've explored a little bit in previous episodes as well too, is just debunking that myth that you need "the 60 to 90 minutes". And no, if you actually just chunk it down, you can do much less. Just if you can do it consistently, it can be just as effective. And that whole concept, which I love is, yeah, underneath that umbrella of kind of minimum viable. So there's minimum viable workouts, minimal effective workouts, but she's super interesting. So the last question we always ask every guest is for a person or experience that you are eternally grateful for, and if you can share that story with us.

Casey Putschoegl (01:07:21):

For me, one of the experiences that I've had that has been the most impactful and that I'm eternally grateful for is the journey of becoming a mother. And I always had my career aspirations that high and always knew that I wanted to also be a mother, never knew how those two would work well in tandem. And what... I think the cliche thing is like I found my purpose. And in a sense, yes, I did. I think for me though, it has been the practice of cultivating patience and perspective through the process of having children, I have three boys and their whirling dervishes, but cultivating those skills has gone through all facets of my life. So the patience that I have at work, the perspective that I have now that I have kids has shifted tremendously.

Casey Putschoegl (01:08:09):

And then in terms of priorities, like I said earlier, I see it almost like through a spotlight effect. What is most important? What is vital and essential? And time is moving fast. So for me, I need to be clear on what's most important. I'm not willing to, and I firmly believe that you can be as successful in business as you want, and your family can fall apart at the same time. And so for me, success is that well-rounded view of nothing has to be perfect by any means, but I want to be investing in the right areas, in alignment with what I believe. And so, yeah, it's just a stronger filter for me. It's been a really great reminder of what's most important.

Casey Putschoegl (01:08:46):

And then one experience that also speaks to me is around a trip that my husband and I took three years ago now. He got a medical grant to work in Austria and we took our three kids overseas and they were, oh gosh, five, three and six months old at the time. Oh, three months old, excuse me. So we had a little baby traveling overseas and we went to live in Austria for a month. And through that experience, living there and working there and exploring a different culture with the family really inspired us to create a life that gave us flexibility, that gave us flexibility to go overseas and to travel the world.

Casey Putschoegl (01:09:28):

Our goal right now is to do a worldwide classroom and with our kids for one year. My husband needs to get a little more flexibility in his medical career, but we want to unlock and be able to take a year off and go travel with the kids. And I want to have the business functioning in a place where my team is and they are super strong and able to handle business while I'm gone. And the ability to then go and explore with my family while my kids are still small. So that experience unlocked for me, I think, vision around what I want and what I'm doing all of this for. It helped unlock the why behind every day.

Daniel Scrivner (01:10:02):

One last question that I have to ask is any advice for other moms, other dads, trying to survive life with three boys, I guess? I know that's a lot.

Casey Putschoegl (01:10:12):

Oh, it is a lot. It is a lot. I think I heard Will Ferrell say in an interview like he just wants to shoot a fire hose at his kids all the time because he has three boys. For me, I think the biggest advice I would have for moms is not to underestimate your role as the woman in the boys' lives. And I think that there's such tremendous impact that a mother can make on a son. So yes, it's a lot of work upfront. And I think that work pays off, especially for me setting systems and structures. Hey, I run an EA company, so no surprise. But setting systems and structures that give them accountability and autonomy, that has gone so far for our family, and I hope sets them up with skills that will help them succeed in life.

Daniel Scrivner (01:10:55):

That's great advice. Thank you so much. It's been incredible. You have a really crisp way of thinking about everything that you're doing. You have an incredible track record. You've built an incredible business. So thank you so much for your time and for coming on and for sharing some of that. I really appreciate it.

Casey Putschoegl (01:11:08):

This has been great. Thank you so much.

‍

‍

On Outliers, Daniel Scrivner explores the tactics, routines, and habits of world-class performers working at the edge — in business, investing, science, and so much more. In each episode, he decodes what they've mastered and what they've learned along the way. Start learning from the world’s best today. Listen to past episodes for free, be the first to hear about new episodes, and subscribe to Outliers on your favorite podcast platform.

Daniel Scrivner and Mighty Publishing LLC own the copyright in and to all content in and transcripts of the Outliers with Daniel Scrivner podcast, with all rights reserved, including Daniel’s right of publicity.

What’s allowed: You’re welcome to share the following transcript (up to 500 words, but not more) in media articles (e.g. The New York Times, Forbes, etc), on your personal website, in non-commercial articles or blog posts (e.g. Medium), and/or on a personal social media account for non-commercial purposes provided that you include attribution to “Outliers with Daniel Scrivner” and link to the episode’s URL on DanielScrivner.com. For the sake of clarity, media outlets with advertising models are permitted to use excerpts from the transcript per the above.

What’s not allowed: No one is authorized to copy any portion of the podcast’s content or use Daniel Scrivner’s name, image, or likeness for any commercial purpose. Similarly, no commercial use is authorized, including without limitation, inclusion in any books, e-books, book summaries, or synopses. Use on a commercial website or social media site (e.g. Facebook, Twitter, Instagram, etc) that offers or promotes your or another’s products or services. For the sake of clarity, media outlets are permitted to use photos of Daniel Scrivner from the media page on DanielScrivner.com.

‍