More startups die from suicide than homicide…
We work with a great number of venture capital firms. Successful investors bring a mix of science and art, rigor and intuition. They rely on both quantitative and qualitative patterns to identify the next great company. They know what metrics to scrutinize, from product usage to evolving market dynamics.
Most investors are far more comfortable evaluating the potential of a business than the coachability of the person running it. It’s not for lack of interest. Founder dysfunction is one of the top causes of death for a young startup.
The CEO who believes themselves all-powerful, all-knowing, and above criticism or advice rarely comes out on top. But interviewing is a famously flawed process, and most people — and most investors — are bad at it.
They might spot the soft spots in a financial plan, the weaknesses in a product road map, or the faulty thinking in a GTM motion instantly, but determining whether a founder will listen to their board, heed advice from others, or be sufficiently self-reflective to improve in the job? That’s much harder.
From Visionary to Learner
Make no mistake, a founder must evolve. Successful startups require more than a decade of devotion to reach an exit. And the job for that founder changes radically over that journey, from inventor to builder to scaler, until, if the founder is skilled and lucky, they find themselves overseeing thousands of employees across the world.
No one has all the answers all the time. But those who approach the journey with an open mind, a sense of their own fallibility, and a growth mindset have the best chance to see their company all the way through. I’ve written before about what happens to those who don’t.
Inside the Interview
So if you’re an interviewer, how do you break through the facade? How do you see past the airbrushed artificiality of the interview setting to reveal whether the person in front of you is truly curious and accountable … as opposed to simply performing?
At Enjoy The Work, we pride ourselves on getting in the trenches with our founders. In fact, our promise to our founders is that no matter what they ask of us, short of doing their jobs for them – our answer will be yes. My partners and I have led leadership off-sites, reviewed board materials, revised financial models, prepped for M&A negotiations, scrutinized product demos, led positioning exercises, edited investor materials, and role-played performance reviews.
We’ve also done a lot of interviews. Many, many interviews.
There is no senior role one of our startups could hire for where one of my partners has not held the role or hired for it many times over. But that’s not the only reason our founders ask us to step in as interviewers. It’s because we are experts at uncovering coachability.
Testing for Coachability
With that in mind, I want to share some of the questions we use. The uncoachable employee, no matter how skilled or competent, tends to be a toxic drain on those around them. And while I trust founders to eventually make the hard call and remove these cultural parasites from their teams, wouldn’t it be nice if they never joined in the first place?
So with that as a backdrop, let me introduce you to the seven questions my partners and I use when we evaluate a founder for coachability. You can see how they might be modified to address many different types of positions. Use them in good health.
The Seven Questions We Ask Founders
- Let’s imagine it’s 12 months from now, and your company completely failed to reach its milestones. What are the most likely reasons, and what mistakes must you have made along the way? (Looking for recognition of their own fallibility.)
- How do you make really hard decisions today? (Looking for evidence of nuanced thinking versus black-and-white thinking.)
- Who do you go to for advice? What’s a recent specific example? (Just looking to see if they trust anyone.)
- What’s the most recent thing you changed your mind about because someone else convinced you? What led to that shift? (Looking for willingness to admit being wrong.)
- All of our founders have some magic — they’re an amazing salesperson, or can write incredible code, or design products, etc. What’s your superpower at work? (Softball question to open the door for the next question.)
- What is your kryptonite? What is the part of the CEO job where you know you still struggle and have a lot to learn? This is not about what your company has to improve (e.g., find PMF) but more specifically, what you need to improve as a CEO (e.g., maybe you don’t know how to build a financial model, or what good hiring looks like, or how to give feedback or how to run a great meeting). (Looking for self-reflectiveness.)
- Tell me about a mistake you’ve made recently. How did you uncover it, and what did you learn? (Looking for accountability and absence of blame-shifting.)
Want to Hire Better?
I recognize that many of you may be curious how these questions might be folded into your hiring practice. If you’re a startup founder who wants to get better at hiring, two offers for you. First, download our Enjoy The Work Hiring Playbook. Second, if you have a particularly complex talent situation, we are happy to talk through it with you directly. Just send us a note here to set up time with us.