In September 2011, I met Ben Knelman, CEO of Juntos, for our very first coaching session on a sidewalk bench in Palo Alto — he had no full-time team or office space yet. I have coached him ever since. Coaching can be hard to explain, so I invited professional storytellers Miki Johnson and Jackson Solway to the Juntos office in San Carlos to help Ben tell his coaching story.
What initially prompted you to start working with a coach?
Ben: My initial goals were to feel more confident managing the team, and also to have more alignment between work and the things I cared about on a personal level. I wanted to understand myself better: my tendencies, strengths, and weakness.
I have to admit, I had always thought of myself as a fairly self-aware person. I knew there were lots of things I still needed to learn, but I thought it would be like the law of diminishing marginal returns: that as I got older, I’d discover fewer big things about myself. Instead I was blown away by how many epiphany moments there were during my work with Anamaria.
For someone who feels fulfillment from that kind of self discovery, it’s rewarding to see yourself become a stronger person than you were before. Coaching accelerates that process in a way I never would have expected. Being a startup CEO is already one of the environments where you’re most forced to learn about yourself. Yet even that wasn’t unlocking as much as having a coach.
Was there a particular epiphany that you remember from your coaching sessions?
Ben: One thing I realized was, as Anamaria says, how much “heavy lifting” I was doing for others. Most people will hear that and think I was taking on all the work. And in some ways that was true. But in my case it was more about emotional weight. Going into a situation, I would imagine all of these things the other person might feel, and then I would do all of this work to try and make sure they felt this way and not that way. That is incredibly exhausting.
Anamaria helped me realize I was doing that, and I realized it was liberating if I didn’t take that on all the time. In some cases I even learned that all that hard emotional work was counter to my values of honoring and respecting people. You know, you think you’re doing it because you care about a person, but in truth you’re kind of taking away their agency — their emotions are theirs, not yours, right?
What is a typical coaching session like?
Ben: Usually Anamaria will start by asking what I’d like to talk about. Sometimes I want to discuss something specific, but often there will just be something that’s nagging at me. I’ll start talking about it, even though I’m not really sure what the issue is, and Anamaria will ask me more questions.
I think this is what sets Anamaria apart from most coaches, and most friends: She guides the conversation but she’s not usually providing advice. It’s more like, in some invisible way, she orchestrates it so I reach a new understanding — and then I’m able to come up with the solutions. She pulls that out of me. A lot of times that’s by holding up a mirror; like, she’ll say, “So what I’m hearing is this.” Once someone else says it back to you, suddenly you realize, maybe there’s something you’re blinding yourself to.
With Anamaria, it’s not an advisor relationship. We don’t talk about strategic or tactical business decisions. I have lots of advisors and other people who I talk with about that stuff. This is more about leadership and interpersonal, or intrapersonal, dynamics.
How often do you meet? Is it in person or on the phone?
Ben: We meet every other week for an hour and 15 minutes. When we first started we would meet in person, and then we began meeting on the phone. I normally find phone conversations much more difficult than speaking in person because I can’t see how the other person is reacting. But with coaching there’s very little difference. It’s not about what the coach is thinking. Their job is to create this space for you.
Are there people around you who have noticed a shift because of your coaching?
Ben: I think my cofounders and I would both say I’m more comfortable and effective with fundraising today than I was three years ago, when I started working with Anamaria. Part of that, of course, comes from practice doing it. But a huge amount is from Anamaria making me aware of dynamics that were making fundraising difficult for me.
“I’m more comfortable and effective with fundraising today.”
Everyone has their own challenges for fundraising. For me, Anamaria helped me see that, when I’d feel upset in fundraising environments, it was often because I felt like they had all the power and didn’t respect or trust me. For example, if funders asked a lot of questions, or requested more information, that would trigger a wide range of negative emotions. I felt they were doubting what I had said — and I care a lot that people feel I’m an honest person.
Anamaria helped me realize that my initial internal reactions to these moments were often blinding me to a very different reality. Funders are actually in a vulnerable position, too. Their job is to deploy all this money that’s sitting over their head. Their LPs are pressuring them and they’re being asked to take this big risk, but they know relatively little about the company. Even when they invest, they have much less information than I do as the CEO.
So when they’d ask these questions, which I thought was because they didn’t trust me, it was actually because they were interested, excited — or perhaps worried that they wouldn’t make the right decision. That’s why they wanted to know more. That really changed the dynamic with investors, to make it more of a collaborative partnership. By sweeping away that old interpretation, I was able to create tighter bonds with funders. Now we can relate across the table, where both sides are just trying to understand if we’re the right fit for each other.
You’ve been working with Anamaria for over 3 years now. Did you think it would be for so long at the beginning?
Ben: I think coaching is a flexible thing. Some people will have a coach for a while and then they’ll stop and maybe start again later. But for me, it was consistently some of the best money I’ve ever spent. I think about it as an investment in learning, as well as personal and professional development, and it just continued to have such high yield.
That was actually something that surprised me. I thought I would learn some things but, again, it would be diminishing marginal returns. But I continue to be amazed. Even when I go into a session thinking I know what’s going on, by the end of my conversation with Anamaria, I’ll realize something totally different than what I initially thought. Or maybe that situation will illustrate something much bigger about myself and my own tendencies, which I can leverage far beyond that particular instance.
Would you recommend coaching to other people?
Ben: I always recommend coaching to my friends who are entrepreneurs or leaders in entrepreneurial organizations. It usually comes up when someone shares something they’re really struggling with. I’ll talk it through with them, but I’ll also suggest they consider getting a coach. I find that if someone is able to share things they’re struggling with, even if it’s just with a friend, they’ll likely be open to coaching.
“Even when your company is on a successful path, [as a CEO] you have the daily experience of feeling like you’re doing a bad job.”
Most CEOs and startup leaders I talk to have experienced the same things I have: It can be a very hard and lonely job. The thing you realize is, it’s not your job to do it perfectly. All you have to do is do it well enough to get the company what it needs. By the time you’ve learned to do something even decently well, it’s time for someone else to take it over. If you stick around doing the same thing so much that you get really good at it, you’re probably not growing fast enough. As a result, even when your company is on a successful path, you have the daily experience of feeling like you’re doing a bad job. Because you’re always going to be at the frontier of your company’s needs. And that means you’re also always at your own personal frontier.
As a result, one of the main constraints on your company’s growth is how well you can push out your own personal frontier. That’s why it’s so valuable to have someone like a coach to help you. In the case of Anamaria, she has her own experience on an early-stage startup team, and she can also draw on the experience of all her other clients. That helps you see that you’re not alone, and it provides you with a new perspective on how to move forward.
Did you expect being an entrepreneur would be so hard?
Ben: I didn’t expect anything because I wasn’t planning on being an entrepreneur. Before I stumbled into this, if you asked me what the job of a CEO or entrepreneur was like, I would have imagined one of those dramatic moments where you come to the board meeting and you convince everyone to sign onto your idea, a huge triumph! Or everything is falling apart, and you come in and find a way to save the day.
But it’s really the unglamorous — and harder — task of just having the resilience to keep going. To keep moving forward on things that are necessarily going to be ten failures on the path to one success. Again, that’s why it makes sense to invest in coaching. I paid for coaching myself, but it’s one of the best investments in the company I could have made.
The only thing that ever made me resistant to coaching was that it felt kind of indulgent, like something I was just doing for myself. It was helpful for me to see it as something I was doing for the company, not just for me. Because, in truth, the coaching helps me to keep getting up from the mat and putting myself out into the ring again. And that’s ultimately what makes you a more powerful leader and strengthens your business.