Previously I talked about hiring employees and gave an overview of a process that I’ve used to good effect in the past.  The perspective there was straightforward: you’re a supervisor or a hiring supervisor and you’re bringing on someone to be a direct report, either for yourself or someone else.

Hiring bosses involves two perspectives, and depending on which best describes your situation you’ll look at it differently.

When you’re choosing who to work for

I think this must be rather frequently overlooked, especially by inexperienced employees.  Having a job offer with compensation and responsibilities that match your goals doesn’t mean you should rush to take the job.  Your relationship with your boss is going to be critical, and you want to know a little bit about him or her before you sign on.  Even if you have to take the job, you should prepare yourself for what’s coming.

There are three things I’d suggest you think about:

1. A lot of bosses got to be supervisors and managers by doing good work as individual contributors (sales, engineering, operations, etc.).  This leaves them woefully unprepared to manage people.  I think Warren Buffet said it, but I can’t find the  source just now: it’s as if the final career step for an award-winning cellist was to become the business manager for Carnegie Hall.  If your boss-to-be has never been coached, you’ll have to suck it up for a while even if you have the conversational grace to coach them yourself.
2. Noam Wasserman wrote in “The Founder’s Dilemmas” that some people (he was writing specifically about entrepreneurs) go into business for wealth, but others go into it for control.  It’s important to get a sense for what your boss is after.  Behaviors in different situations can vary dramatically.  I’ve seen middle-ranking managers make money-losing decisions because it expanded their influence within the organization.  And I’ve seen others forego promotions in order to keep doing what’s best for the company.   It’s usually easier to work in groups where one or fewer are motivated primarily by control.
3. You’re going to spend a lot of your time doing what your boss says.  I’m going to quote Buffett again here, because he’s right on:  “I learned to go into business only with people whom I like, trust, and admire.”  (“Warren Buffett on Business,” edited by Richard Connors, Wiley, 2010, p. 144). This is important in business partners, and if you can find it in a boss, you’ll learn a lot and enjoy the process.

In all these, try to talk to coworkers and the boss to determine their work  history and how things have been going.

When you’re choosing a leader for your organization

The above considerations still apply, but you can be a bit more prescriptive when you’re in control of the hiring process.  I like Jack Welch’s “Four E’s and a P” approach (Jack Welch, “Winning”):

1. high personal Energy
2. the ability to Energize others
3. having Edge (making decisions quickly)
4. Executing (getting results)
5. Passion

When they’re in charge of that group or company you’re hiring for, they’re going to be almost overwhelmed by demands on their time.  Many of these will be important and urgent, and they need to be able to go, go, go.  In their attitude, they have to be like FDR, chin up and positive, in order to inspire other people that the obstacles they all see can be overcome.  And they can’t waste the organization’s time by sitting on decisions that need to be made.

Welch found that some managers that had these things still didn’t get good results.  Maybe that’s because they work on the wrong stuff, or because they’re perpetual optimists, or because they’re very quickly making all the wrong calls.  So he bundled up all that into the fourth “E,” execution, and looked at candidates’ track records.

“Passion” means they’re personally motivated to take your business and do something more with it than you asked or had imagined.  This last is critical, especially for startups, turn-around situations, or other times of crisis.

If you can find all this in a would-be boss, you’re doing good for yourself and for your organization.