The Traits Investors Use to Evaluate the Coachability of Entrepreneurs

There’s no comment that will end the evaluation of an early stage founding team more swiftly than someone on the investment committee saying “They just don’t seem coachable.”

While I’m just as guilty as anyone of making this statement, I’d never seen a good explanation of what this really means. And when an entrepreneur asked me directly, my response was trash.

“It’s a feeling.”

“You know it when you see it.”

“It’s all in how you respond.”

I was embarrassed. And I understood their frustration. When everyone nods their heads in agreement at this unquantifiable metric, what does it really mean to be coachable?

Coachability isn’t a skill set, it’s an attitude, a mindset. When it comes to entrepreneurs it’s an approach to the way you think about your business and is defined by three personality traits — humility, openness, and vulnerability. Here’s some insight into how investors evaluate each one.

Humility: Your Response to Tough Questions

When VCs ask you a tough question about your plan or about why you made a certain decision, they’re not trying to trip you up, they’re trying to understand how you think, how self-aware you are, and how open you are to sharing your thought process.

Questions investors ask to evaluate the trait of humility include:

• Have you thought about doing it this way?
• Why are you doing it that way?
• What factors led you to making this decision?
• What’s stopping someone else from doing what you’re doing?

They’re not looking for a specific response to these questions, they’re evaluating the way in which you respond to being questioned. They are evaluating how you react and how willing you are to have a conversation, talk things through, and accept feedback from other points of view.

You may think that acknowledging there are other options may make investors question your leadership. But confidence and the demonstration that you know you aren’t the end-all expert on everything will make people trust your judgement more. Don’t be afraid to engage in this dialogue and turn these kinds of questions into conversations. It will only make you more investable.

Openness: Your Willingness to Learn

This isn’t the first time you’ve heard this but it’s true — great entrepreneurs and great leaders surround themselves with people who are smarter than them. The VC to founder relationship is no exception. A great entrepreneur demonstrates a drive to take guidance and feedback into consideration from those that have walked the path before them. It doesn’t mean that they take every suggestion made, but it means that they are actively listening and learning from the advice and mistakes of others.

Things that investors use to evaluate the trait of openness include:

• What’s the tone when the entrepreneur asks questions?
• How does the entrepreneur ask for and respond to feedback?
• How does the entrepreneur respond to new and different ideas?
• Does the entrepreneur respond negatively, defensively, or passive aggressively?

The caveat to this adage is that it’s easy to be open to feedback when all the feedback around you is positive. You have to be open not just to feedback but challenging feedback. An uncoachable person surrounds themselves with people that make them feel comfortable, people who believe they are always right, people that believe they are the smartest person in the room. They build themselves an echo chamber. This may hide itself in being surrounded by a “great team” of friends they’ve known for years, or a “great business model” that to the entrepreneur is “undeniably proven.”

If you don’t want advice or input from others, particularly your investors, don’t fake it. It will only lead to heartache in the end and if everyone is doing their jobs it will get sussed out. And if it doesn’t before the check is written, it will lead to significant conflict in the future.

Vulnerability: Your Ability to Reflect

No matter where you are in your career when you decide to start a company, there is a reason, there’s a story, and there’s an honest truth about how you got there. It’s easy to talk about the great things, the successes, the big wins. It’s much harder to reflect on the challenges you’ve faced. But it’s in the stories of those challenges that the core DNA of an individual is exposed.

Questions investors ask to evaluate the trait of vulnerability include:

• What’s the hardest thing you ever had to go through in your career?
• When have you failed?
• How did your failure affect you?
• What is something that you will always do differently in the future?

You can’t win all the time. But you have to win more often than you fail. Being a person that is willing to riff with honesty, and not tell only the shiny, sanitized version of their path, is the one that will change their ratio of successes to failure over time.

For Next Time

What I should have said to that entrepreneur was “Coachability is a choice.” In the same way that I believe that people can choose to have a growth mindset, entrepreneurs can choose to have a coachability mindset. It’s up to them to make the shift and do the learning.

With COVID, it’s become even harder to evaluate and demonstrate coachability. The body language, the tone in the voice, a smile, the delayed connection and missed remark that leads to a personal anecdote, many of the cues we rely on as people building new relationships are being reconfigured through this distortion by the blue screen. I hope when we get to the other side, what we’ve learned makes us all more humble, open, and vulnerable.

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Welcome to the Squadra Blog. Each week we’ll be sharing advice, stories, and how we make hard decisions as we work with our portfolio companies to build extraordinary teams and companies.

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