How to Choose a New Boss

Smiling older man with short gray hair, wearing a teal blazer and a white shirt with a subtle pattern, posing in front of a plain, light gray background.

Richard (Dick) Finnegan is CEO of C-Suite Analytics and the originator of Stay Interviews. A top global voice on employee retention, his strategies have helped organizations reduce turnover by up to 58% and save millions of dollars across six continents. He is a frequent speaker at executive and C-suite leadership conferences, workforce development conferences, industry associations’ annual meetings, and national SHRM conferences. Targeting Turnover is his sixth book and his most direct call to action for frontline accountability.

Most job-seekers approach job interviews with the singular goal of winning the offer, peeking into the mirror one last time to make certain every hair is in place. And this is doubly true if that job-seeker has no current job and therefore no current income.

But is any job better than no job at all? Consider this…

A third of our lives are spent at work, so it’s hardly surprising that it can be a source of stress. However, 60% of employees say their job is the biggest factor influencing their mental health. And specifically, managers are having just as much impact on people’s mental health as their spouse.

Yikes. Let’s rethink how job seekers should approach that all-important potential-boss interview.

First, let’s scrap the idea that we must have a few good questions to ask at the end. We’ve all been taught to have two neutral, non-assuming questions in our pockets, so we look smart, with questions about company culture or benefits or whatever. Let’s develop real ones instead.

And those real questions should be about that manager’s actual leadership style…and we’ll begin by turning this topic upside down. The #1 reason employees stay or leave jobs, or for that matter engage or disengage, is how much they trust their manager. Scores of academically-judged studies tell us this, yet companies continue to think retention and engagement are about pay, or benefits, or pet insurance, or whatever. And many employees think that’s true, too, until they find themselves complaining about their boss over dinner every night. 

A woman stands by a whiteboard giving a presentation on public sector strategies to five seated colleagues in a modern office with large windows and industrial-style decor.
A woman in an orange blouse stands by a whiteboard covered with colorful notes and diagrams, smiling and presenting insights to two colleagues in a modern public sector office setting.

A third of our lives are spent at work, so it’s hardly surprising that it can be a source of stress.

Richard Finnegan

So, let’s rethink which questions we should ask during our part of the interview with our potential manager. I would start with complimenting the interview so far by saying something like this:

“You’ve asked some really good questions, and I’ve enjoyed our conversation.”

Then give a short intro to why you are about to ask your manager-related questions:

“I’ve learned throughout my career that the most important part of any job is how well I can connect with my boss, that this is more important than pay, benefits, or anything else.”

Next, begin with a soft question about that manager’s leadership style such as this:

“So how would you identify your own leadership style?” 

Then after nodding affirmatively, try going a little deeper:

“Do you think that’s always been your style, or have you changed or evolved over the years to where you manage people differently than in the past?”

And then close with a question about others’ perceptions like this one:

“So how do you think your team here would describe your style? What do you anticipate would be the compliments or changes that anyone would suggest? 

The most important answers will be beyond the manager’s words. Look for cues regarding how comfortable the manager is talking about herself, whether she openly describes her strengths and her flaws, and whether she is genuinely open to your inquiries.

Then finish this section of the interview by thanking the manager for her openness, regardless of just how reflective and how open she has chosen to be. That way she will think that she won the interview, too, just in case you decide to accept the job.

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