I still remember the day I met Sam, a former Navy SEAL who had pivoted into the corporate world after his military service.
I was in my previous digital marketing role, and the company had just brought him on board as a consultant for leadership and hiring strategies.
The plan was that he’d help us weed out the “talkers” from the “doers” — the folks who make big claims yet never follow through.
Sam was no cliché action hero. He wasn’t the loud, overly assertive type. He spoke in calm, measured phrases that hinted at an underlying steeliness.
There was a weight to his words; he had a knack for cutting through fluff with a single sentence.
Over our first cup of coffee together, I asked him how his background as a SEAL influenced the way he judged candidates.
He told me about an interview question he’d been using for years — one that, in his experience, pretty much always predicted whether a person would be successful. I was intrigued.
After all, having spent over a decade in digital marketing myself, I’d seen plenty of interview “scripts” that tried to evaluate culture fit, grit, and ambition.
But Sam claimed his approach was simpler, more direct, and nearly foolproof.
The story behind the question
The moment that changed everything for Sam, he explained, occurred during “Hell Week” in SEAL training.
Sleep-deprived, physically exhausted, and mentally drained, Sam reached a point where he was sure he had nothing left.
He planned to ring the bell — the sign of quitting — because he felt his body was literally about to break. But then he looked around and noticed a few of his teammates were in far worse shape, still pushing on despite injuries and tears.
One of them even cracked a joke about how “this was the easy part.”
Sam didn’t quit.
Instead, he tapped into a reserve of resilience he never knew existed.
That’s when he realized something: success often has little to do with your initial strengths or talents. It’s about how you respond once you’re stretched beyond what you thought were your limits.
As Tim Ferriss says, “Conditions are never perfect. ‘Someday’ is a disease that will take your dreams to the grave with you.”
That quote echoed in my mind as Sam shared more about his pivotal Hell Week moment.
When he started working in leadership roles outside the Navy, Sam wanted to pinpoint how that same spirit — of pushing through discomfort — manifested in the corporate or startup world.
The result?
One single question he asks in nearly every job interview:
“Tell me about the toughest problem you’ve faced in the last year — and walk me through how you handled it, step by step.”
Why this question matters
On the surface, it’s not the flashiest or most original question.
You won’t see it in a trendy HR manual with 50 cute or quirky questions to “break the ice.”
But Sam believes it zeroes in on what truly matters: how someone reacts when they’re up against a wall, and whether they own their response or deflect blame onto others.
What sets his question apart is the step-by-step part.
He’s not satisfied with broad statements like “I persevered” or “I stayed positive.”
He wants details.
How did you define the problem? How did you identify potential solutions? Did you rely on data, gut instinct, collaboration? Why did you choose one path over another? And crucially, what was the outcome?
By forcing candidates to break down a real-life scenario—preferably one that they’re not 100% proud of—Sam can see if they:
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Take responsibility for setbacks, rather than pointing fingers.
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Reflect on their own process, acknowledging mistakes or blind spots.
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Adapt in the face of uncertainty and keep moving forward regardless.
It’s a bit like a pop quiz on self-awareness.
Sam says he can usually tell if someone is exaggerating or stumbling through a made-up story, because the details won’t align.
They might skip steps or give short, clichéd answers. People who have actually lived through tough situations, however, tend to remember them vividly—sometimes with a mix of frustration and humor.
The hidden benefits
Sam’s question doesn’t just reveal whether a candidate has the perseverance to handle pressure. It also sheds light on communication skills.
If you can’t articulate how you overcame a major hurdle, you might struggle to clarify goals or expectations on a daily basis.
Similarly, he looks for signs of humility — did this person credit other team members for helping them, or do they hog all the glory? Do they describe learning something valuable from the challenge, or do they frame it as an unfair situation they were forced to endure?
From my perspective, having worked with new hires who eventually flamed out, I can attest that blame culture and lack of self-awareness are some of the biggest red flags.
It’s easy to look good in a polished résumé.
It’s even easier to recite the “greatest weakness that’s actually a strength” line. But it’s far harder to fake an authentic story about a genuine challenge — especially if you have to break down each move you made along the way.
Putting it into practice
While shadowing Sam during a few candidate interviews for a marketing role, I saw the magic unfold.
One candidate, a guy named Jeremy, boasted about doubling online sales at his last job.
Sam listened politely, then hit him with the tough-problem question. Jeremy said something generic about “not hitting quarterly targets,” but he talked in circles for the next few minutes.
He eventually pinned the blame on his old boss for having “unrealistic goals” and never once admitted what he could have done differently.
After Jeremy left, Sam didn’t even glance at me. He just murmured, “Not the right fit.” That was that.
Two interviews later, we met a woman named Clara who started off pretty calm, almost reserved. When Sam asked his go-to question, Clara’s posture shifted.
She leaned forward, took a breath, and shared how she discovered a major flaw in her startup’s product design two weeks before launch.
She had to break the bad news to her CEO — who was notorious for hating last-minute changes — and then rally her small team to fix the bug.
Clara confessed that in the scramble, she lost her temper once, but she quickly apologized, offered to work through the weekend, and managed to push out a patch the following Monday.
Sam’s face lit up a bit.
He probed deeper: “How’d you approach the initial conversation with your CEO, especially knowing his temperament?”
Clara outlined a thoughtful communication plan that started with solid data, eased in with a potential fix, then ended with a request for more time.
She owned her mistakes and highlighted what she’d do differently next time to avoid such a crunch. Sam didn’t break his gaze once; he was locked in.
By the end, it was clear Clara had the grit, self-awareness, and resourcefulness we needed.
The bigger lesson
After we wrapped up the interviews that day, Sam explained why that question works just as effectively in the corporate world as it did in the SEALs.
“We can teach skills,” he told me, “but we can’t teach character.”
Skills are what you learn through training, repetition, mentorship. But character — the willingness to adapt, own mistakes, and keep going when it’s not comfortable — that’s formed over time, through failure, reflection, and a healthy respect for growth.
He used a phrase I’ll never forget: “You learn more from your worst days than you do from your best.” It reminded me of a principle Seth Godin often talks about—how real growth happens at the edges of your comfort zone.
Sam’s question is basically a flashlight shining right into that edge:
Where did things get uncomfortable? Did you step up, or did you shrink back?
