How to Pick the “Right” Boss

I have lifted the following words from a recent Harvard Business Review article. It scratched an itch for me, given the long string of great bosses I had in my business career. A long string that was marred by one terrible boss.  There is therefore no question in my mind that one of the greatest predictors of happiness at work is one’s relationship with “the boss.”  I have lived that statement.

Students coming out of our MBA Program at UW have, by and large, never had a boss. They go from their undergraduate degree straight into the MBA program.  They tend to look upon rigorous graduate classes as a proxy for a tough boss. Not so.

It can be hard to assess whether you and your prospective boss are the right fit. Especially since in an interview you’re working hard to demonstrate why she should hire you. But it’s important to evaluate her as well!  What sorts of questions should you ask to understand her management style?  Should you try to talk with other people she manages? Are there red flags you should watch out for?

What the Experts Say

“The primary reason people leave a job is because of either a mismatch in culture or a boss who drives them up the wall,” says John Lees, author of How To Get a Job You Love.  My one experience with a terrible boss proved the rule: I left Microsoft shortly after my one and only run-in with “Michael” and decided after 25 years, I didn’t need to put up with such crap.

Of course, you’ll never know exactly what it will be like to work for your potential boss until you have the job — and in some cases you might not even meet your manager until your first day — but you should gather as much information as possible in advance. And it’s not just negative impressions or red flags you should be on the lookout for.  “You must understand the person as she is,” says Claudio Fernández-Aráoz, a senior adviser at global executive search firm Egon Zehnder and author of It’s Not the How or the What but the Who.  “Failing to realize someone is a terrific boss is a very costly mistake, perhaps even more costly than failing to realize someone is a bad boss,” he says.  Terrific jobs — and managers — are hard to find.  Read on for tips on how to discern between the good managers and the bad.

Know what you’re looking for

The first step is to do some thinking about what you want and don’t want in a boss.  According to Fernández-Aráoz, there are three minimal conditions that must be met.  Is this an honest person, offering you a sustainable job for which you have something unique to contribute?  You might also spend some time visualizing the kind of relationship you want.  Are you looking for someone who will stand back and let you run with your work?  Or are you hoping for someone who can be an involved mentor?  This will give you some criteria against which to evaluate your potential manager when you’re in the interview.

Trust your instincts

It’s also important to check in with yourself throughout the process.  Being laser-focused on getting the job can sometimes cloud your judgment.  After each step, ask yourself whether this is the job you want and the manager you want to work for.  Did you get a good feeling from the person?  Is she someone you can imagine going to with problems?  Or someone you could have a difficult conversation with?  When the stakes are high, it’s best to trust yourself.  “Usually people say something like, ‘I should have known,’ because there are those small things that lead to a gut feeling we often ignore,” says Lees.

Be on the lookout for clues in the way you’re treated by your potential manager.  Of course, he doesn’t have total control over the process (likely HR runs it), but observe how you’re handled as a candidate, from the quality of the information the manager gives you to the way he looks after you when you arrive for the interview.

Ask questions, but tread lightly

You can often get a sense of your potential manager by asking probing questions, but be careful how you phrase them.  “People say an interview is a two-way process,” Lees says.  “In practice, that doesn’t work very well.”  The interviewer might misinterpret multiple questions about his management approach as disinterest in the job.  Fernández-Aráoz agrees: “What you should not do is ask direct questions, like ‘Tell me about your leadership style,’” he says.  Not only could this signal hesitancy on your part, but it’s unlikely to get you an honest answer, because your interviewer is in selling mode.  Instead, ask questions that will help your potential manager visualize you actually doing the job.  “What will I do on a day-to-day basis?”  “How will I learn?”  Phrasing your questions as if you already have the job will help the hiring manager create a mental picture of you in the role.

At the same time, you can watch how she responds.  “Look for her willingness to engage in dialogue, rather than asking you pre-established questions,” says Fernández-Aráoz.  “Think of it like rehearsing a collaborative working session with your future boss. ” If she’s willing to engage with you during the interview, she’ll likely engage with you in a working relationship.  After (and only after) you’ve built rapport, ask questions that will elicit her expectations for the person filling the position, and any potential downsides of the job.

Do your homework

One of the greatest mistakes you can make is failing to do your due diligence.  Don’t go into a job with your eyes closed.  “It can be a shock to people. They find out the culture is too formal, or pressurized, or there’s too much solitude for their taste,” Lees explains.  “You should know that before committing.”  Prepare for the interview by gathering as much intel as you can.  “You might find information that raises red flags, or information about the interviewer’s interests, which will allow you connect with the other person,” says Fernández-Aráoz.

Do a Google search on your potential manager.  Check out his online profiles, as well as those of people who used to work for him.  “LinkedIn profiles can tell you a lot about a person’s interests and relationships,” says Fernández-Aráoz.  Do people under him tend to leave the organization quickly or stay a long time?  “Low retention and high turnover rates are a clear indicator of problems,” says Lees.  If you find people who have left, try reaching out to them and ask what it was like to work for that manager.  You’d be surprised how many people are willing to respond to inquiries and share their experiences working for a manager, particularly if they had an especially positive — or negative — experience.

Meet the colleagues

“Perhaps the best approach is to ask to get to know a few of your future colleagues,” says Fernández-Aráoz.  Talk with people who would share the same boss and ask what it’s like to work for her — both what they enjoy and what they find challenging.  Don’t insist beyond what is appropriate, however.  There may be reasons, like confidentiality, that prevent such conversations.

After you’re offered a position, ask to spend a half-day with the company and your future team.  “Chatting about what work is like brings about huge amounts of incidental information,” says Lees.  The hiring manager is likely to see it as a sign of commitment and motivation, and you’ll get the chance to interact with your colleagues and get a feel for the day-to-day environment and how your potential boss influences it.

Principles to Remember

Do:

• Pay attention to how the manager treats you throughout the interview process
• Research the manager, and if possible find former employees to ask for their perspective
• Request to spend a half-day at the organization so you can interact with your potential colleagues and boss

Don’t:

• Ignore your gut instincts about the manager as you go through the interview process
• Ask direct questions about leadership style — you’re unlikely to get an honest answer, and they might signal that you don’t want the job
• Neglect to look up your potential boss’s social media profiles

Case Study #1: Don’t ignore the red flags

In 2010, Joe Franzen was searching for a position as a software developer. He went through several interviews for two different positions with a large health care company.  During a one-on-one interview, he noticed his potential manager read from a list of prewritten questions.  “Software development is anything but standard. When your potential manager reads from a list of standardized questions, it sends a signal the work will be treated the same way,” Joe said.  Later on in the interview process, Joe also noticed the manager and other panel members, including several other people higher in the chain of command, tried to assert dominance over him throughout the interview.  The panel members asked questions that began with “When you’re told” or “When your manager tells you,” which gave Joe the impression he would be an expendable resource at best.  “It’s a creative role; there’s a need for structure, but you don’t want to be looked down upon,” he said.

• Joe took the position when it was offered and soon discovered that he should’ve paid more attention to those red flags. It turned out to be one of the most mundane positions he ever held. “It was cubicle work, I wasn’t challenged, and I wasn’t happy,” he said.
• The experience led him to quit and create his own company. Now on the other side of the fence, he creates a relaxed, conversational atmosphere and engages in a two-way dialogue to make sure candidates know exactly what kind of manager he’ll be.

Case Study #2: Do your homework

Stephanie Jones (not her real name) was looking for a new job after spending two years out of the workforce to be with her newborn.  She wanted to work in an entirely new field for her: social media.  She hadn’t been searching for very long when she found the perfect opportunity with a national marketing company.

• At the end of her first interview, she felt uneasy. Although she had performed well, her potential boss hadn’t answered an important question.  “When I asked him about the previous person in the position, he glossed over his response,” says Stephanie.  “I brushed it off because the next day I was offered a second interview.”
• The second interview went off without any red flags, but afterward Stephanie decided to do some research. She searched for employees of the company using LinkedIn.  After a little digging, she noticed a couple of former employees had short tenures in the same department she was hoping to work in.  Stephanie sent messages to all three, and one of them responded.  “It turns out this manager was a nightmare to work for,” she says.  “Although he was hard on everyone in general, he had a tendency to be harder on women than men.”

When a company representative called to offer her the job a week later, she had to decline. Although it was a hard decision, it paid off. “I now do contract work for the same company. I’ve been working with the company for about three years now, and in that time, the position I initially applied for has been vacated and filled at least once a year,” she says.