Tough Interview Questions: What Is The Most Difficult Decision You’ve Had to Make?

By Jeff Altman, The Big Game Hunter

This interview question can be asked of people at any level but will usually be directed at a manager level and above. There is a typical answer and I add a twist to it.

My Manager/Boss Found Out I’m Looking!

What is the most difficult decision you’ve had to make? This is a great question for senior leadership in an organization. But it really could be asked at almost any level. And I want to address this in the typical way, but then give you an enhancement.

The typical way is to try and connect the dots to talk about a situation that you might face in this role and something similar that highlights a strength related to this role that would help you excel. That’s a softball kind of answer. And I think most people will go with that. But I think there’s a way of enhancing it with aRecruiter slight twist.

The twist I’m talking about, ‘I stepped into a situation where I had incomplete information, and I had to make decisions.’ Notice, I’m setting a context for the role by saying I stepped into a situation where I had incomplete information, and I had to make decisions. And then from there, what you’re trying to do is talk about how you got that information, how you made quick choices, how you brought certain strengths to bear, notice, we’re tying it back to the typical answer at that point.

You’re tying it, you brought certain strengths to bear that would be relevant for this role, enrolled other people in providing you with information, tested your hypotheses, and then, from there, was able to deliver a successful project, successful outcome, deliver improvements of X or Y percentage, you get the idea. 

Think of a STAR story. You stepped into a situation where (fill in the blank). I was a new manager stepping into a role where I had to, I had incomplete information to work with. So what I did was and that becomes the action that you took. And thus, you’re tying in the emotional components, the things related to this job that would be an asset in the role that would help you be successful. And then from there, you delivered a great result.

Hope you found this helpful, especially with a twist to it. I’m Jeff Altman. Visit my website, Go to the blog; go exploring. There’s just 1000s of posts that will help you with interviews, and with Job Search, in general, with hiring more effectively, management, leadership, resolving workplace issues, how to write a great resume, negotiate salary– again, a lot of great information to help you.

While you’re there, you can find that about my courses, books, and guides. You can schedule time for a free discovery call or schedule time for coaching. I’d love to help you. Lastly, connect with me on LinkedIn at Have a terrific day and be great!

I Keep Sending Out Resumes, Following Up and Getting No Results


Jeff Altman, The Big Game Hunter
Jeff Altman, The Big Game Hunter

Jeff Altman, The Big Game Hunter is a coach who worked as a recruiter for what seems like one hundred years. His work involves career coaching, as well as executive job search coaching, job coaching, and interview coaching. He is the host of “No BS Job Search Advice Radio,” the #1 podcast in iTunes for job search with over 2400 episodes.

Are you interested in 1:1 coaching, interview coaching, advice about networking more effectively, how to negotiate your offer or leadership coaching? People hire me to provide No BS career advice whether that is about a job search, hiring better, leadership, management or support with a workplace issue. Schedule a discovery call at my website, 

My courses are available on my The courses include ones about Informational InterviewsInterviewing, final interview preparation, salary negotiation mistakes to avoidthe top 10 questions to prepare for on any job interview, and starting a new job.

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