Turn Difficult Questions Into Opportunities

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It’s clear that most interviewers suck at interviewing—and if I’m honest, most candidates do too. Deep down, you know it’s true.

But before you tell me to screw off, I mean no personal offense. 

Instead, I suspect that most people focus on mastering other functions of their role before honing their interview skills. Or, put more plainly, you’re most focused on doing your job than supporting a transition. 

Interviewing and communication inadequacy is an equal opportunity offender that applies to candidates and hiring managers. A shared identity, if you will.  

Let’s help each other out.

Since you can never predict who you will face on the other side of the table, it’s ultimately up to you to improve your preparation and hone the skills required to lessen the adverse side effects if you interview with a dud. 

You might be thinking, “Jacob, if I’m interviewing with a dud, shouldn’t that be a clear sign that I should walk away?” 

And you would be right. Probably. 

In a market that has shifted from candidate-driven to employer-driven—where banks are collapsing, we’re living through a changing world order, and we’re pretending that our money means something—beggars can’t always be choosers. Hell, the beggar’s mindset may apply to undesirable companies as well. 

Sometimes we need to will a job into existence to pay the bills. Unfortunately, that will mean dealing with stupid questions.

I will argue that if you find yourself in these situations frequently, you’re screwing up somewhere else in your career, and there are underlying factors that you need to remedy—but alas—you’re here now, and we need to take action. So let the barrage of dumb questions begin!

What Is A Stupid Interview Question?

During Tuesday’s group career coaching session on interview strategy, we poked fun at dealing with stupid questions. As I polled the audience, the number of “How would you deal with answering STUPID QUESTION X?” became ubiquitous as we went around the room. 

It got me thinking. 

What is the typical makeup of a stupid question? 

I’ve come to a simple definition. 

A stupid question is anything where you fight the urge to answer: IT DEPENDS.

Stupid questions are often asked in a generic checklist-type fashion, devoid of contextual or situational awareness. Or the questions are asked at an inappropriate time, typically too soon.

For example, 

“Excellent to meet you. You have a great background. Much excitement. Much experience. A true leader. This opportunity is huge. I’m looking forward to our conversation. So tell me. You have me so curious.” 

“What’s your go-to-market strategy?” 

(We’ve been unable to understand how to get product-market fit for the last five years, burned through 3 C-suite leaders, and enjoyed favorable market conditions. Oh, we’ve also thrown 50 million dollars of someone else’s money at it. But it would be best to have the correct strategic answer on the spot, friend. Hop hop.)


Enter the heart palpitations, the “are you shitting me?” echo chamber in your noggin, and your fight or flight response to start nervously laughing. 

“Well, it depends.”

You know you need to appear confident and poised—but your interviewer is basically making fart jokes and silly faces like a clown. So how can anyone answer such a vague but elaborate question correctly? 

You may also be thinking:

  • Am I in the right interview?
  • Do they know who they’re talking to? 
  • Does this company want me as an executive or a grunt? 
  • Am I sitting at the kids’ table while the adults gallivant elsewhere?
  • Why do I keep taking interviews from Indeed?
  • Am I a masochist for repeatedly interviewing with startups?
  • I have children older than this CEO. Who the hell put them in charge of all this money? The world really isn’t fair.

Other examples of questions that warrant a similar response could be:

  • What’s your leadership style?
  • What strategy (generally speaking) is best?
  • Can you do this junior-level tactical assignment for us to evaluate?
  • What are your salary expectations?
  • Describe to me a time when…

Rather than pulling your hair out or heading over to the anti-work subreddit to bitch about capitalism, let’s experiment with listening to understand these questions deeper. 

Playing victim will only get you so far—so far as being stuck under someone else’s boot. Plus, the boot owner probably found a way to monetize your plight while stepping on your spine. But I digress.

What’s Really Going On Here?

Although I’m full of bitter piss and poke fun at these scenarios facetiously, you seriously cannot take any of these questions personally. 

You may often find yourself in scenarios where the right answer is impossible to ascertain—or highly subjective. That’s okay. 

Stupid questions don’t need to be answered at face value. But it would help if you treated the interviewer with respect, understanding, and empathy, regardless.

Instead, recognize that interviewers ask stupid questions while often masking their underlying motivations. It’s usually not malignant or duplicitous; it’s simply that if they could communicate their problems perfectly, they probably wouldn’t need to hire you in the first place. 

Nevertheless, the interviewer is doing their best to point the conversation in a direction to get help. Sometimes that means the occasional stupid question or request for a time-wasting assignment. 

Stupid questions represent an opportunity to create alignment and showcase your experience.

You must read between the lines of each question to understand how to respond correctly. If you’re a real executive leader, it will come naturally. 

For example, 

  • What’s your strategy? Becomes, “Help me understand how to collaborate with you to implement the best strategy to meet our business needs. Can I trust you to do this?”
  • What’s your leadership style? Becomes, “I need to ensure I’m not hiring an asshole. This team is important to me, and my ass is on the line if I hire a prick. Can I trust you to care for our people and make smart decisions about their well-being?”
  • Do this tactical assignment for me. Becomes, “I don’t know who I’m looking for, but I’ll know it when I see it.” And if junior assignments happen in an executive interview, add: “I also don’t know how to title this position correctly. Can you help me, please?”
  • What are your salary expectations? Becomes, “I’m worried that you may make more money than I can afford. If we go through this process for eight weeks and fall in love with you but can’t pay you, I will look like an asshat. How can I feel more confident moving you forward?” 

Taking a moment to pause and answer with empathetic patience will significantly elevate your communication game. 


Uplevel A More Meaningful Conversation  

Recognizing that interviewing is essentially a sales process can help executive candidates bring the right mindset. As a result, both parties discover challenges and communicate needs and solutions to the best of their ability. 

Given that you, an executive with integrity, would never sell somebody something they don’t need, pushing back to inquire deeper when you hear stupid questions shouldn’t be a problem. 

Let’s return to the “What’s your strategy” question. 

The following leads will help you move the conversation forward more meaningfully. 

  • “I’m sure you have an excellent reason for bringing up your strategy so early. Can I start by unpacking the question…”
  • “Wow! We’re hopping right into it. I know you recognize the complexity of that question. I have a high-level approach I can share now, but I’ll need to develop more understanding to answer more confidently.”
  • “Great question. I’m sure I’d have the job on the spot if I had the perfect answer. Jests aside, let’s see what’s worked for you in the past, what hasn’t, and why. I’ll go first…” 
  • “Glad you asked. I’ve already started noodling on a few options; however, I’ll need help filling in the gaps. Are you ready to treat today like a working session—or do you have more questions prepared that I can jot down as an agenda? Or we can circle back later.”

This list could expand into 101 more examples, but you get the idea.

Next time you experience the stupid question brigade—get ready to smash the situation with a velvet hammer. Take a moment to read between the lines of what’s really necessary to unpack in the conversation and help guide the conversation to friendly waters.

Be hard on the problem and soft on the people. 

You’ll position yourself as a more authoritative, respected, and trustworthy leader. Plus, your career will thank you for it. 

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