Should You Hire Your Own Boss and Other Mistakes

Steve Jobs and John Sculley

Steve Jobs and John Sculley

Like dipping into the summer water of Northern California (Wow! Pretty cold!) if you’re teaching someone to swim in the San Francisco Bay, I spend time for the executive and career coaching part of my work with recruiters, executive search consultants, and sometimes applying for jobs.

How else to know how the job market works if you don’t experience it first hand?

And while occasionally I come across a role that I find personally interesting (something at Yelp as well as a role at an earlier stage startup both come to mind) that could take me away from my consulting practice, most of the time it’s field research simply to see what the job market is like and how candidates get assessed and treated.

So I chuckled the other day when I got a no-thank-you note from Visa for a role that I applied to online. A role, by the way, that I had been offered at Visa a few years ago.

Thank you for your application to the position of Head of Global Talent Acquisition,” it read. “While your skills and background are impressive, we have identified other candidates that more closely match the position requirements.

Most likely the knock-him-out screen was by somebody at Visa (the wonders of “who has viewed your profile” on LinkedIn), who happens to be one of the would-be direct reports of this role; a former Russell Reynolds associate who now heads up executive recruiting at the firm.

And that begs the question; should you hire your own boss? And should you even be screening your potential boss in our out of the process?

The short answer is “no.”

Here’s the long answer.

Similar to guidelines regarding physicians treating themselves or family members, hiring somebody ( or even screening out candidates as in this case) who is going to be your boss is fraught with peril primarily because it undoubtably becomes highly subjective.

Success in a role is not only how well someone manages you as their boss, but how well someone will manage laterally (peers), their boss (CEOs or boards of directors), and any externals such as clients or vendors.

And as a subordinate, you’re most likely to get locked on one area; what does it mean for me?  You will likely under want someone who punches below their weight (easy or known boss) compared with someone who punches at or above weight (tougher or someone you don’t know).

In doctor’s family’s the standing joke is that anything short of a massive hemorrhage is met with the phrase “take two aspirin, check it out in the morning.” Doctors are notorious for missing significant things about family members because they’re too close to the situation; they’re too subjective. (And in our family’s case, my Harvard educated physician spouse has missed my herniated disc, our son’s case of the kroop as an infant, and my hip that needed to be swapped out; “the pain will go away”  was the hip diagnosis.)

While I’ve had the opportunity to interview a number of potential bosses, I’ve never been the primary gatekeeper or screener. And for better or worse, I can’t think of a single would-be boss that I interviewed who turned out mostly like I thought they would. Most of the ones I liked a lot didn’t get hired, and frankly some of the ones that did get hired turned out to be great bosses.

As an aside, Apple co-founder Steve Jobs got to pick his boss in the mid 90’s, and hired John Sculley as the new CEO. We all know how that turned out. What happened? “I hired the wrong guy,” said Jobs.

So when you have an opportunity to hire  candidates who might be your boss, take a pass; find someone who is more objective to do the initial screening out part. It’s a hard thing to do, and many folks don’t do it so well.

Take part if you’re asked to interview. But just remember that you’re likely not the best person to make a great decision.


Life Back West is an occasional set of writings focused on ways people, teams and organizations can be both more effective (doing the right thing) and more efficient (doing the right thing well). More about executive, career and team / leadership coaching services can be found at the “About J. Mike Smith and Back West, Inc.” sidebar or the “Hire Me” tab above. You can also read an online interview with me at WhoHub, as well as participate in my learning community courtesy of KnowledgeCrush.


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