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6 Mistakes to Avoid when Hiring an Executive

April 11, 2024
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I have succeeded and failed as an executive at a startup. I have seen other executives succeed and fail at different startups. Here are the things I would avoid when hiring a C-Level executive into your team. You could succeed despite doing these things and you could fail despite avoiding them. Nonetheless, avoiding these things will dramatically increase your odds of success.

  1. Thinking you need a generic “rockstar” - Executives tend to shine in some scenarios and not others. A CMO might do great under a war-time CEO but fare poorly under a peace-time CEO (see The Hard Things About Hard Things). A CFO might be great at leading a large multi-disciplinary team but be too far removed from the day to day nuances to build a department from scratch. A CRO might be great at bringing in large deals while building a sales team but have no patience to build data-driven processes that scales. How big of a team do you need the person to build/manage? What technical expertise do you need? How much time will the person spend executing vs coaching? How fast do you need the person to move and how much room will you give her to fail? How much are you willing to invest in and wait for this person? How will you measure her success? Answering these questions will help you avoid hiring the right person for the wrong company.
  2. Ignoring culture, values and work styles - Hiring an executive is like getting a heart transplant. You can get the heart of a 20-year-old olympian but if your blood types are not compatible, you are setting yourself up for failure. Have honest conversations about your values, management style, what it is like to work with you under pressure. Share the good, bad and ugly of your company. Encourage the executive to talk to a few people in the company who can speak candidly about what it is like to work there. Even better, see if you can work on a short (paid) project with her to see what it is like for the two of you to work together. This will minimize the risk of incompatibility.
  3. Skipping the onboarding process - Your new executive is very expensive. You are in a time crunch and need to show results to your investors quickly. It is tempting to throw them into the deep end to see how they fare. They might do well but if they never have time to understand how your company works, they will likely break lots of things and build things that duplicate or contradict existing workflows. The bigger the organization, the more time the executive will need to understand how people think and behave in the company. Having the executive spend a few hours each day shadowing people in the company (including yourself) is an effective way for the person to get a strong grasp of the company and its culture. The person can contribute to the team and have goals during their first quarter in the company. Nonetheless, make sure they spend at least a quarter understanding the company before making any major changes like firing people or changing the structure of the team.
  4. Not defining the decision-making process - You were probably doing the executive’s job before you hired her. She will definitely do things differently and you will feel the urge to step in and take over. You should have a clear decision-making process to avoid disempowering your executive by stepping in or ruining the company by letting her make mistakes you already made. A simple way of doing this is defining what decisions you need to approve, who should she consult with for different decisions and what decisions are outside of her domain. Defining this clearly (preferably in writing) will enable her to make decisions quickly without breaking (too many) things.
  5. Increase ambiguity, pressure or fear - Phrases like “everybody’s head is in the chopping block at all times” increase fear and will make your executive more likely to look for a reason to leave. “No feedback is good feedback” will leave your executive uncertain of whether she is meeting, not meeting or exceeding your expectations. “If I stop giving you negative feedback we already started looking for your replacement” will ensure your executive will panic if you ever get too busy to give her feedback. Working at a startup is ambiguous and risky enough. Do not make it harder for your executive to do her job.
  6. Give them the title on day 1 - Bringing in a Chief _______ creates a world of expectations from your board, your team and the executive herself. Bring in your executive under a different title and give her 3-6 months to reach certain milestones before being promoted to a C-Level role. Doing this is tricky as you will need to do a very good job defining the milestones (they will need to be relevant, realistic and measurable) and you will likely pay her significantly more than other employees in non-executive positions (ie. this is not an excuse to pay her a lower salary for a few months). Nonetheless, by having her come in at a non-executive role, you give her some time to understand how your company works and earn the trust of the team before you delegate a large department to her.

Bringing in an executive is one of the most impactful things you will do at your startup. Not taking the time to avoid these mistakes is like getting an organ transplant without checking to see if your donor has a compatible blood type.