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1st Team | Casey Rosengren of No Small Plans
Casey Rosengren of No Small Plans on coaching tech executives, evidence-based practices, how one can find and pick the right coach, and more.
We’re excited to share a new 1st Team with Casey Rosengren: founder and executive coach. Casey is currently coaching through No Small Plans, an evidence-based coaching practice for founders & leaders in tech.
Our 1st Team series highlights expert teams that help startups & their execs level up. To be featured here, a provider must be recommended by multiple founders or investors that have worked with them. To learn more or to nominate someone, you can reach us at firstname.lastname@example.org.
Can you tell us a bit more about No Small Plans and what makes your practice unique?
No Small Plans is a coaching practice that uses evidence-based practices to help founders & execs manage their own psychology and become more effective in their work.
Our approach is based on Acceptance and Commitment Therapy (ACT) — a modern framework that is backed by hundreds of randomly controlled trials. At a high-level, ACT helps people stay focused on their goals and connected to meaning, even when challenges arise.
More concretely, when we undertake work that is important to us, we are likely to run into situations that bring up difficult thoughts and feelings. Over time, our work and lives can become more about avoiding pain & discomfort than about moving toward our values and our goals.
Our coaching work is about helping leaders to stay aligned with what’s most important–even in stressful or challenging circumstances.
For more about ACT and how we work, you can check out these pieces we wrote for Every:
At what point does it generally make sense for a founder, executive, or individual to find a coach?
I’ve been skeptical about coaching since my time as a founder. That said, I think there are a few times when it clearly makes sense:
When there is a specific skill you want to learn, it can make sense to hire an expert in that field to help get you up to speed (sales, growth, etc.)
When you’ve got a lot on your plate, and could benefit from talking it through more frequently or more openly than you can with your friends / mentors
When you’re falling into patterns that are below the level of performance you know you’re capable of – when you feel like you’re becoming the bottleneck in your business
There are many different types of coaches, and the value people derive from coaching ranges from accountability to working through emotional blockages to reconnecting with meaning after burnout.
In general, I think folks become more effective with more support in their work and life. That said, it can be hard to find good support.
Do you have any recommendations on how one can go about finding a coach or framework that works best for them?
The first thing to get clear on is what you really want from coaching: if coaching were to succeed, what would be different in your life?
Once you’re clear on that, there are three things I’d think about when meeting potential coaches:
Does this person speak my language?
Does this person know what they’re doing?
Do I enjoy talking to this person, and can I see us forming a meaningful helping relationship?
One of the big differences between coaching and therapy is that coaches come from industry. This shared context means that a lot can be left unsaid in-session.
For example, as someone who has been in startups for over a decade, I tend to connect well with founders and VCs as clients. On the flipside, if someone comes to me looking for help in a more corporate environment, I’ll refer them to someone else. You want to find a coach who has walked a path similar to yours, or is at least familiar with the territory.
There also isn’t any real credentialing process for coaching, and many of the training programs out there for coaches are not that great. As a result, coaches vary widely in quality, and many work on intuition, with no real theoretical orientation to ground their work.
This isn’t necessarily a deal-breaker – there are some good intuitive coaches out there who are helpful, even if they can’t explain how or why. That said, I’d look for folks who have a deeper theoretical basis to their work and who are on top of the modern psychology and performance literature.
A coach can be effective without these mental models, but in my experience, the best ones have both good intuition and a solid grasp of the research.
Finally, one of the biggest correlates of success in coaching is the quality of the relationship between client and coach. Thus, it’s important to find someone you trust and who you feel good about sharing vulnerably with on a regular basis.
What led you to start No Small Plans?
After college, I bootstrapped a company to an exit. While we had a good outcome, I was stressed out and unhappy a lot of the time while running the company. I couldn't see myself doing anything other than entrepreneurship with my life, and yet I didn’t know how I could be happy starting another company.
So, I spent a lot of time digging through psychology research to try and understand my experience and figure out how to be an entrepreneur and also feel like I’m living damn well. When I found something that worked for me (ACT), I realized it could also help a lot of other people, so I began training with several psychologists in how to adapt this particular framework to startup life.
What sort of clients do you work with at No Small Plans?
I typically work with founders and executives of Seed and Series A companies who are looking to manage stress, improve their decision-making, and find more meaning in their work. I also coach a few VCs and university professors.
In particular, I like to work with folks who are exploring what it means to live well while running a company – or as one of my clients put it, “I want work to be a significant part of my life, but I also want LIFE to be a significant part of my life.”
What is the best way to inquire about working together?