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3 Questions the Best Interviewers Always Ask Their Future Boss

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Lionseye insights from AC Lion

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Yesterday, you completed the phone interview with Human Resources. Today, you’ve pretty much aced the onsite interview with the boss. In closing, they ask you the one question you’ve been dreading- 

“Do you have any questions for us?”


Don’t sweat – you’ve prepared for this.  Now, while it’s never a bad idea to take this opportunity to inquire about company culture, or about the new acquisition you read about in the paper, or some other headline-worthy recent happening. These are all tried-and-true questions that help you to understand a bit more about the company and expectations of your prospective job responsibilities.

But why stick to tried-and-true? 

Why not use this as an opportunity to conduct an interview of your own?

It’s rare for job seekers to pay attention to a future boss’s personality and methodology; however, a disparaging or insecure boss can prevent you from getting ahead.  As we see in the digital space, the value of a good manager is on the rise, with more and more processes becoming automated.  Chances are, you’ll be spending a lot of time getting to know (and working with) this person, so making the most of this opportunity is critical.  You might even spend more time with your boss than your S.O.  A pleasant, progressive-thinking manager can help you not only perform your present job well, but assist you in procuring promotions, raises, and better opportunities. That’s the type of boss you can only hope you find yourself sitting across from on interview day.

As digital recruiters who have been around for over 20 years, we’ve compiled a great deal of feedback and intel on our candidate interviews.  And to be frank, most applicants are focused on selling themselves and not vetting their direct reports. It might not be a problem or an epidemic per se, but more of a chance for you to stand out from the pack.

When you do your due diligence, you should try these three questions only the best interviewers use to help them get a solid read on their next employer.

startup11. “How would you describe your work style?”

Does the manager look serious and use hard-driving descriptions? Notice if they communicate decisively while making it difficult for anyone else to talk. Maybe they will be closed to listening to the advice or suggestions of employees, and see duties as a checklist: Just get it done!

Perhaps they admit that they don’t like to micro-manage. He or she gives credit to their employees for being smart and says they’re “hands off” so that they can ferret out their own processes. If you’re the type who would rather take orders and have directions clearly spelled out, maybe this isn’t a fit. But if you are independent and can’t tolerate a boss who hovers over you and double-checks on everything you do, this could turn into a harmonious relationship.

2. “How would you measure my success if you hired me?”

This is a great question to ask as it can give you a broader sense of expectations that are being placed not only on you, but on your peers.  Really honing in on your boss’ response could give you the roadmap to start day 1 on the best foot possible.  Also, you may get the sense that there is additional training you need – better to know now rather than later.  Listen to your boss’ answers very carefully and take his or her response home with you as you consider your options.

Do their ideas about what you should accomplish sound unrealistic or extremely demanding? Do they set goals together with his employee, or prefer to stick to their own compass?

Some managers will emphasize how they value people skills and how that is a big part of the position. In other words, they think that being a team player is paramount and they want their employees to work together for the greater good.  If you’re the competitive type to your core, you may feel you’d be missing out in that instance.  Or if you prefer collaboration, maybe that answer would pique your interest.  These are the sort of things you might not pick up on unless you ask – so ask! 

Predicting the Future with a Crystal Ball3. “Where do you see this company in 5 years?”

As applicants, we are often asked this one ourselves, and it can honestly cause some uneasiness in the gut.  But there really are merits to this line of questioning.  When you get a handle on your boss’ vision for the company, you can get a handle on how it aligns with your personal career goals.  

Furthermore, if they have a solid plan to the point that they’re comfortable talking about it with an outsider considering employment at their company, you know you’ll be working for someone who is proud of what they’ve built.  It’s a sure sign that they’re taking care of their own – prospective and current.

Taking the time to assess your overall compatibility with the person who you will report to every day is well worth the minimal time it takes. While your boss might have an entirely different work style than you, that can also work out well. It all depends on the two individuals in the equation: you + them.  After you leave, determine if you feel comfortable and positive about the interview. Your gut feeling should say, “Yes, I’d be happy at this company and I’d enjoy working for X”. If not, no matter, it’s a wide-open field out there. 

Circle back with a recruiter and keep looking until you find the perfect fit.

If you feel it’s time for a change, follow us on LinkedIn and let us help join you in the hunt!

Or jump straight into our complete listings here.

Alan Cutter

Alan Cutter founded New York City's premier digital recruiting agency, AC Lion International, and continues to lead the growing company as their fearless CEO. For over 20 years, AC Lion has been the trusted provider of revenue generating talent in the digital and technology landscape. Our reach spans from innovative venture-backed startups to enterprise level organizations. AC Lion is a proud member of the Lionseye Group, a collective of brands furthering talent acquisition through Venture Capital, HR Technology and Thought Leadership.