Ryan Caldbeck's site

As a CEO, you learn a lot about yourself — both in terms of skills and deficits. Here are some of the things I have learned: some are things I already did and will continue to do, and some are things that I would do differently. You will see these are not Mutually Exclusive Collectively Exhaustive and I will add further insights over time. Nevertheless:

–I will define upfront what I look for in teammates and create a process to help institutionalize that throughout hiring. I don’t like dealing with people who are low in integrity, intelligence, or don’t work hard. I struggle to be an effective teammate to someone that demonstrates any of those qualities. Low integrity looks like whispering, people talking behind others’ backs, not being direct and transparent with thoughts or feelings and advocating for things/resources that are good for the individual but not the company. A person with low integrity makes decisions based on how it will make them look rather than how it will benefit others. People with low integrity pass on blame. Teamwork and professional pride are the characteristics I really value, respect and require of others.

–I will actively recruit teammates that have a growth mindset. I love working with people who have a growth mindset. I feel empowered. I feel challenged in constructive ways. I can feel growth in myself and the organization when the people around me have a growth mindset: they prepare for the interview, demonstrate problem-solving skills, highlight commitment to continuous learning and admit their failures.

–I will push to create a culture that is intellectually honest. I like working with teammates who are intellectually honest. I trust them more. I feel more confident in our alignment of interests. I feel more confident in letting them run with projects and managing themselves. I want to empower teammates that are intellectually honest. For me, intellectual honesty means personal beliefs or incentives do not interfere with the pursuit of truth. It’s when being excited to just find the truth outweighs winning the argument. Intellectual honesty is holding your beliefs loosely and being open to change when presented with better data or logic: it is the relentless pursuit of the truth.

–I will value startup experience over big company experience. I like working with teammates who have startup experience and understand the ups and downs. I feel more alone when I’m the only one with a startup background. I feel lonely when I have to remind the executive team that all startups, even the best, can feel like dumpster fires internally. I like people who are resourceful and think it’s fun to be scrappy, not those who roll their eyes. 

–I will lean into professional development. I love to see others develop. I feel impactful and worthwhile when I help teammates develop. I feel satisfied and happy when I can hand things off to others so they can own projects and grow/step up while that’s happening. At CircleUp we paid for an education stipend and management coaches for effectively all our managers. We had regular 1:1s, conducted 360 feedback for managers and encouraged that it be direct and open. I learned that I really enjoy being a part of the development of others and want to create more space for that going forward. 

–I will build a culture that encourages data-driven decision-making. I like being in an environment where people are hungry to make data-driven decisions. I feel more trusting of others when they recognize the value of reliable data and will harness its power to inform their decisions. 

–I will recruit executive teammates that have tremendous interpersonal energy. I feel exhausted having to motivate others that don’t want to be motivated. Whether I’m good at it is a different question. I just don’t want to be alone in an ability to motivate and inspire others. 

–I will openly use the trust equation as a framework. The topic of trust comes up often when building something that has the potential to be huge. Roles change, priorities change, things go really well, things don’t go so well. Throughout it all, trust is needed to build a solid foundation. Trust is not binary (yes or no) and trust is not universal (I could trust you to run a spreadsheet but not to perform open heart surgery on my daughter). The most helpful framework I’ve seen is the Trust Equation. I feel more calm and understood when we can talk about that openly. Trust = [Reliability x Credibility x Intimacy]/(Self-interest).

–I will lean into key hires. I think I’m good at recruiting — I don’t always enjoy doing it, but I think it’s an asset. I feel valuable when I can land a great recruit. The recruiting style I feel most comfortable with is the anti-sell, where I talk about all the reasons someone shouldn’t join. If I only relay the positive stuff I sometimes feel like a fraud because I know the company, *every* company, has 100 fires to put out. So the anti-sell works for me. I like providing my 360 to key potential hires as well as internal pulse surveys. I find that when someone joins the company knowing all the major warts, they are much more likely to be long-term teammates. 

–When I think about letting someone go, I will just do it. We fired people for sure. I did it personally and other leaders did it. But frankly I wish I had done it more quickly and I wish I had created a culture that facilitated those decisions being swift. In several instances, especially early on in our journey, we debated those decisions for months. I’m ashamed of that because I think it hurt both the company and the individual (it doesn’t help someone to keep them in a job they are failing at). I realized that when I’m thinking about firing someone it is 100% the right thing to do. I love the quote that “7s kill companies” from this interview with [[Sarah Tavel]] https://www.youtube.com/watch?v=FpvTlHaKrJ0 

–I will have a #2 that I really trust. I trust Rory with my life. On at least two occasions I believe he literally saved my life. Throughout the building of CircleUp we often disagreed but I never questioned his intentions. I really like having someone who can and will step in for me in a lot of situations. Whether it’s the COO or an experienced Chief of Staff, it has to be someone with shared values but also complimentary skills and experiences—for example, a #2 that can help lead interpersonal conflict resolution. 

–We will have an executive team that is world class. Here the quote “7s kill companies” comes up for me again. I like having a strong executive team that I can trust, not only in terms of competency but also in terms of intention. I want an exec team that is better than I am in all of their functional areas. As CEO during a difficult time with an exiting board member, I was reminded of something I learned about myself when I played basketball: I’m at my best — most confident, most clear minded — when my teammates believe in me or when my enemies don’t.

–I will travel less. I don’t like to travel. CircleUp was a B2B2C business that had both enterprise (selling to companies and institutional investors) and consumer (selling to individual investors in our first 6 yrs) components. Enterprise sometimes requires travel, it’s just a necessity, but while I think I perform well in sales meetings, I don’t enjoy traveling and being away from my family. 

–I will lean into product. I leaned in at CircleUp and I will do it again. I will also recruit a head of product and put myself out of a job, but I still want to stay involved. I love working on product. 

–I will regularly talk to the company about vision. I really like helping to lead the development of a vision. I tend to think vision isn’t done by committee and I think it’s the CEO’s job, so I’m glad I like it. I also like developing and reinforcing the values and the mission. I feel consistent, clear minded, and empowered when I’m doing this. I like communicating mission, vision and values to the company on a regular basis and incorporating those frameworks and words into our culture, be it through performance reviews, 1:1s, marketing, recruiting or any other avenue. 

–I will write publicly. I don’t know in which form, but I like getting my voice out into the world.

–I will be a vulnerable and transparent leader. I enjoy being vulnerable as a leader. I feel more seen, more confident and more honest when I’m truly being myself. 

–I will create infrastructure to support myself as CEO. I realize I need a lot of support to be a healthy and effective CEO. I need a management coach, a CEO group that’s willing to be vulnerable, a therapist, and a strong executive team (no 7s!). I would also like an independent board member that I trust. To be clear, I had much of that infrastructure by the time I left CircleUp, but I think it took me far too long to build that support system.