“How Do You Evaluate Senior Executives?”

Like most things at a startup, hiring senior execs is really hard. Unlike most things, it creates unique and very powerful leverage. Hiring great talent is arguably the best use of your time as CEO. First, I think the CEO’s job is three things: setting and evangelizing the vision; attracting and retaining talent; and making sure you don’t run out of money. Attracting great executives pays dividends for all of the others in unique and valuable ways. It is one of the things you can do that will compound on itself — in both good and bad ways. Great execs can improve the culture, evangelize the vision in ways that resonate uniquely, and hire terrific talent. Bad execs can be cancerous to the culture, miss targets, and hide mistakes. But in my experience, the worst execs are 7s (i.e. 7s out of 10s). As Sarah Tavel says, “7’s kill companies”. Why? Because they are harder to spot than bad execs, and thus stick around, occupying valuable positions that could be filled by 9s and 10s and encouraging mediocrity from the company. 

So how do you find and cultivate great senior execs? 

Job Description– Setting the hiring process, the candidate, and the organization up for success starts with how you design the role. Spend time on the JD — focus on what you want the person to really do. Start with how/where they will fit in the organization. Don’t worry about 5 years down the road, but you should think through the org structure for the next 12-18 months and hire with that in mind. What do you want them to own in terms of responsibilities? Be clear about that yourself and make sure it shines through in the JD. Some questions to consider as you draft the JD include: 

-What does it mean to be great at this role?

-What would success look like in the first 6 months? In 12-18 months?

-What do we want this role to add to the company that we don’t currently have?

-What impact do we want the role to have and over what time frame? 

Candidate Traits– I tend to subscribe to the Bill Belichick theory of talent: hire for strengths, not the absence of weakness. Look for spikes and focus on those, not for someone who has no flat spots. Consider articulating in writing the strengths you want and won’t compromise on. What questions will test for these traits? Most likely this senior exec will be a manager and not an individual contributor. If that’s the case it places particular importance on their ability to attract and manage a team, to build an effective culture and to scale. Managing a team includes understanding the functional topics, but they may no longer be the best coder in the room. That’s ok provided they can be a really effective VP of Engineering by building a fantastic engineering team. Communication with you and others across the company is also critical. Do they speak clearly and concisely? Are they appropriately responsive? Can they focus on the three issues that matter most at a startup and ignore the 97 fires that aren’t urgent or important? Have they demonstrated an ability to be successful in a startup environment? Do they have an owner’s mentality? Whatever traits you think will be important, articulate them to yourself and the hiring panel upfront.

Outreach– I’ve found that an external professional recruiter is uniquely helpful for senior execs (and counterproductive for most other roles). Pre-Series A, the CEO is probably reaching out on their own, but after that a recruiter is appropriate and effective. Even with a recruiter I’ve found that maintaining a hiring pipeline is necessary for success. Consider companies you admire that have roles like this — either to poach from or to inspire your hiring. Consider building relationships and talking directly with those execs so you can get a sense of what excellence looks like. 

Interview panel– The interview panel should probably include the entire current exec team, any possible team members that would report to this executive, and depending upon the role and its importance, perhaps a board member with relevant interview experience. Consider using Lever (or equivalent) to collect feedback without biasing other interviewees. 

The interviews– The most important thing I’ve found when interviewing hundreds of senior executives is that ensuring alignment on vision and values is absolutely critical. This isn’t apple pie and puppies stuff — I’ve seen first-hand how painful it is when vision or values are misaligned and heard the same from countless CEOs. How does your vision for the company over the next 18 months compare with theirs? Next 5 years? What is your vision for their role and how will the pair of you work together to make critical decisions? What values are important to you and to them? How do each of you live those values in reality? Saying to someone “do you work hard” or “have you demonstrated grit” is insulting and a waste of time. Focus hard on seeing if you can spot examples in their life.

Beyond vision and values, I think it’s important to see how candidates perform in a variety of different scenarios. Group interviews, 1:1s, a walking meeting, a meal, in-depth conversations about life and the role, shorter conversations and ideally a longer working session where you are both rolling up your sleeves on a real-world topic. Consider asking them to do a presentation on a real opportunity/challenge you are facing and give them access to ask questions and collect relevant data. The candidate that says they want to sign up for 5 years at the company but won’t spend 3 hours digging into a key topic is probably not a teammate that will last. If you ask for a 6-month plan and the candidate says that question is too vague, imagine what that person would be like to work with. Do they need a lot of hand-holding or are they comfortable in ambiguous situations without a roadmap? 

Hiring, much like funding these days, seems sexier when it goes super quick. I’m a big believer in inputs leading to better outputs and a super quick process to me feels like gambling. I don’t like to gamble. Yes, you can fire quickly, as all VCs will tell you. What they don’t always appreciate are the 2nd and 3rd order effects of firing a senior exec a month into the job. I’m not talking about the pain of the initial conversation and the sleepless nights (for you and the employee), I’m talking about the fear it creates for others that may now be worried about their own job or the soundness of your judgment; the pain of navigating a new search with that person’s team; the signal it sends to external stakeholders (customers, investors) about an exec that left. So while I think firing quickly is the right answer, it comes with non-trivial pain that a few extra days/weeks in the hiring process can avoid. 

 References– I have rarely found references truly helpful. I know many people disagree. Having said that, I think backdoor references are dramatically better than front door references. Also, consider doing some of them yourself and involving others on your team in the reference process.  Being able to talk out loud about what you and others are learning in the references helps to ensure you’re being intellectually honest with yourself about what you’re hearing.  (But you definitely should be doing most.)

Decision– This isn’t a group decision, and if you make it one, the decision will be worse. I don’t believe that about all important decisions at a startup, but I do when it comes to hiring a senior executive. It’s your job to make the final call.

A great senior team will make the company more valuable and will dramatically improve your quality of life as CEO. Building a machine that can effectively find, evaluate, hire and retain great senior executives will pay dividends throughout the life of the company.