Problems with Authority

Hiring your own boss poses a unique set of challenges

Back Article Aug 6, 2014 By Suzanne Lucas

I work at a small, privately owned company of 15 people. I am third in the chain of command. Our CEO/owner is near retirement and at this point in his career is really only acting as a figurehead. My direct boss has just put in his notice, and now I am in the odd position of having to hire myself a new boss, since I, not the CEO, will be the one training this person. The CEO has already made it clear that I am not ready for the promotion. I’m fine with that, but how do I make sure that the boss is the right fit?

This is a complicated scenario, although one that happens quite a bit in small businesses. Why? Because there are often huge gaps in experience between the levels. Like you, many people do great jobs but aren’t ready for the big promotion. So, how to begin?

Make sure the job description is accurate. There may or may not be one on file. If there’s not, you’ll need to start from scratch by listing all the tasks, including the day-to-day boring ones like signing checks, doing performance appraisals and holding team meetings.

Figure out what your (former) boss was terrible at. When you went home at night and complained, what did you complain about? Was he too much of a micro-manager? Too hands off? Demanded too many late nights? What were the problems? This is a critical step because, as long as you’re replacing your own boss, it’s a good idea to find someone who doesn’t bug you. This will, of course, vary from person to person. You may be a checklist kind of a guy, so a boss that gives detailed instructions is awesome. But if you’re a do-it-however kind of person, you’ll want someone who’s more hands-off.

Figure out what your (former) boss was great at. What made your boss awesome? And even if he was truly awful, what did the CEO like about him? Because while you’re doing the hiring and training, the CEO will make the final decision, and you’ll need to find someone that has the proper traits.

Network for candidates, and post the position on niche-specific job boards. Everyone always talks about networking to find a new job, but it’s equally important to network to find good job candidates. Tell people you know about the position and that the new hire will be your boss. Your friends may have the perfect solution.

Check references — and not just the normal ones. Yes, we all call former supervisors to find out about a candidate, but if you’re hiring someone to be your boss, you will want to speak to this person’s former employees. Yep. When you get close to making a decision and you ask for references, ask that they include three of their former direct reports. Ask those people what kind of boss he or she was, what they liked, what they hated and if they would be interested in working for this person again. Listen to what these people say. You don’t want a bad boss.

Don’t be afraid to ask hard questions. You’re likely to be a bit intimidated when you interview people who not only have more experience than you, but who could also become your boss. After all, you’d never ask probing questions to a current boss, but it is critical in this circumstance. For instance, you can present the candidates with a true situation (either something that the company faced in the past or is currently facing) and ask, “What would you do in this situation?” If you choose a past experience, say, “Well, when we faced this, we did X and the result was Y. How do you think your solution would compare?”

Make sure the owner/CEO does his part. Even though he wants to be more hands off, it’s still his business, and he needs to make the final decision. This means he must go through the interview process as well, even if he doesn’t want to. And any great candidate wouldn’t accept a job where the owner didn’t even bother to meet with him.

Don’t be surprised if the candidates ask you probing questions. After all, they want to make sure they will be great fits, and additionally, senior people are used to choosing their direct reports, rather than the other way around. If the candidates have lots of questions for you, that’s a good sign they’re really interested in the job and want to make sure they’ll make a good match. And that’s a good thing; you don’t want a new boss that is miserable in the job.

Tell the truth. This should be obvious, but it’s not always in a job interview. While candidates want to put their best foot forward, companies often want to pretend there are no problems. You should tell the candidates what problems they will face.

Take advantage of this opportunity to find the best new boss for your company. And, for once in your life, you can only blame yourself if your boss drives you nuts.


Sick of missing out? Sign up for our weekly newsletter highlighting our most popular content!

Recommended For You

The Quick Quit

Employee retention hinges on a smooth onboarding process

Have you ever arrived at work and realized you don’t remember driving there? It’s kind of a weird feeling, but your consciousness was somewhere else while your subconscious did all the work of traveling, turning, merging and parking. You can do this because your commute is so ingrained that it doesn’t involve any real decision-making. 

May 1, 2014 Suzanne Lucas