Casey Putschoegl: How to Bring on an Incredible Executive Assistant

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“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

For more, explore the full transcript of this episode. Transcripts for all episodes can be found here.

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. 

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