Strategic Interview Questions to Ask Candidates

5 Strategic Interview Questions to Ask Candidates

This article about strategic interview questions to ask candidates is part of a series intended to help new business founders. Check the others here.

One of the greatest pieces of professional advice I ever heard — from my father and also from the interviews of the billionaire Jack Ma — is to not have an enterprise as your first job.

Meaning: be an employee before becoming an employer. To have a boss and receive a salary may sound dreadful for some, but it has its benefits. Benefits that contribute to entrepreneurial formation.

One of these benefits from working for others is to take part in job interviews as a candidate, not as the interviewer.

Before starting my first business, I worked for 5 different companies, and at each of them, I attended one or multiple interviews.

Some questions and activities were brilliant. Even if I never got the job, I would leave it with a great impression of their hiring processes. Others, not so much.

When I became an entrepreneur, during the first year of my business, I needed to hire twelve people for the initial team. That meant close to forty interviews. From my previous experiences as an employee and candidate, I knew the basics of interviewing, but I lacked the deep insight into what mattered.

That, in part, caused an unsatisfactory staff turnover.

Fast-forward to 2020 and I put my hands in a book written by Scott Belsky called The Messy Middle. Scott is the Chief Product Officer from Adobe, the gigantic software developer from San Jose, California. More than a manual about how to start a business or impress new investors, Scott wrote an easy regarding the often ignored obstacles that appear in the middle, when a company is already flying, but struggling to take altitude.

When turning the pages written by Belsky, I recalled my own experiences as a candidate and realized that the best interviewers I faced followed the same axioms he mentioned.

I joined the dots, and realized 5 — or 3, depending on how you define them — crucial points that often recruiters ignore.

Problem Solving – The Chief Among Strategic Interview Questions to Ask Candidates

Let me be more aggressive: we are largely better at doing than we are at thinking, thanks to antifragility. I’d rather be dumb and antifragile than extremely smart and fragile, any time.
Nassim Nicholas TalebAntifragile: Things That Gain From Disorder

Problem-solving is one of these abilities that nobody knows if it is a soft or a hard skill — or both.

It would be foolish to expect that a candidate for a junior position solves a problem of proprietary systems out of blue — training exists for this reason. But problem-solving skills go beyond that.

Way beyond that.

Here I give the example from my final interview when applying for a job as a revenue analyst for a global airline. My previous experiences were as a stockbroker and a financial analyst. I had little idea how airlines worked, and that is why I was applying for a trainee position.

The final interviewer was the area director. The boss of the boss of my boss.

Few questions about my college degree and previous experiences, and he gave me a case to solve. A case about airline pricing and demand management.

Blimey, I will never get this job.

Knowing that my chances were negligible, at least I tried to ask a few questions about things out of my understanding.

Is this plane single-cabin, or does it has multiple classes like Economy, Business, and First-Class? What ancillary services can we sell to increase the revenue? Etc.

The interview took longer than I expected. The solution I gave, in my understanding, was at best laughable.

I will not get the job anyway, but at least they served me a good coffee.

Back home, two weeks later, I received a call. Although I applied for a trainee job, they offered me a position as a senior analyst.


Weeks later, I started my new job, never asking why they offered me a position above my expectations. If they made a mistake, sorry, but it will not be up to me to remind them.

A certain day, at the company cafeteria, I met the director with one of his managers, and they greeted me. When I presented myself, the manager commented:

Oh, you are the one that realized it was missing a lot of information in that case study!

Me? All that I did was ask questions and try to solve the case without shaming myself!

Years later, reading Scott Belsky, I realized that identifying incomplete information is one of the greatest demonstrations of problem-solving skills (and a technique mastered by great negotiators too). Oh, now I see why they chose me.

Picture to illustrate 5 Strategic Interview Questions to Ask Candidates
5 Strategic Interview Questions to Ask Candidates

Listening Skills and Self-Consciousness

Paragraphs before I wrote about how non-sense is focusing on questions about specific systems that can be easily learned on the job. Instead, we should focus on strategic interview questions to ask candidates.

But there is a problem with learning on site.

We are living in an era where human attention span decreased to levels smaller than that of a Goldfish.

The widespread attention deficit often hinders the learning curve. Even worse: it makes people bad listeners, turning them into individuals attempting to solve questions they didn’t listen to.

In customer-facing positions, this is a recipe for disaster. But even for the back-office guy whose most interactions are with the secretary, it still doesn’t help. Nobody likes to get interrupted or to repeat the same sentence five times

Besides hampering problem-solving and social interactions, bad listening abilities walk hand in hand with a lack of self-consciousness. That means a bad understanding of one’s own acts and consequences. For smaller businesses, this can be tragic. Scott Belsky explains why:

In small companies and for freelancers, the tendency is to blame clients or circumstances. So much energy goes into directing blame and expressing disappointment rather than just taking initiative to tackle what you’re criticizing.

A bad listener with a lack of self-consciousness will often blame you or the customer. Most customers don’t like to get the blame for others’ mistakes.

Adverse Situations in Life and Past Initiative

As you build your team, seek people who have endured adversity. Ask prospective team members about their most defining challenges. Life matures you a lot faster than time, and a lot of life can happen in a very short amount of time. Scott Belsky, The Messy Middle

There is a question that was almost omnipresent during the best interviews I had.

What has been the most challenging circumstance you faced?


Tell me about a difficult situation you experienced.

We grow during tough times — as long as we survive them with no serious sequels, of course. They test our limits and stretched our capabilities. They make us more robust, resilient, sometimes even antifragile. Still, no one wants to struggle, preferring an Instagram life, and often, that is what candidates present during interviews.

Big mistake, because life does not work this way. Interviews that focus on immaculate grades and seamless careers, not approaching obstacles, are a waste of time for both candidate and executive.

Hard times providing important lessons is one of the few things we can rely on. Even better when these troubles excite human initiative.

The past initiatives are the best indicator of future initiatives. As Belsky said, look beyond the formal résumé and ask candidates about their interests and what they have done to pursue them.

To assess them, after the previously suggested question (What has been the most challenging circumstance you faced?), it is enough to ask:

How did you react to it?


Did you solve it? How?

Using this set of questions, in a matter of minutes, you will analyze 2 critical points.

  • Problem-solving skills: You will listen to the candidate’s trial story, and also know how he approached the challenge, and the skills used.
  • Behaviour in stressful situations: You will grab insights from the candidate in his conduct under stress and, from that, examine different situations at work.

Conclusion about Strategic Interview Questions to Ask Candidates

I consider final interviews focused on technicalities a waste of time — time that is expensive since busy executives often are responsible for it.

The technical knowledge of a candidate should be vetted before the final interview because these flaws often can be solved by training. What training does not solve — at least not that easily — is what we should assess before hiring. Abilities like:

  • Problem-Solving Skills
  • Self-Consciousness and Attentive Listening
  • Past Initiatives
  • Reaction under Adverse Situations

During final interviews that often take less than half an hour, time is better used asking about these instead of GPA scores.

All the Hows of a First-Time Business Owner: There is a thin line between bankruptcy and the freedom to be an entrepreneur: An idea for a present for yourself (or to any entrepreneur).
An idea of a present for yourself (or to any entrepreneur).

If you liked this article about strategic interview questions to ask candidates, check also:

The 5 Imperatives of All Business Survival Strategies

Employer Attractiveness: Turn Your Small Business into a Talent Magnet

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Levi Borba is the founder of, creator of the channel Small Business Hacks and the same website for Small Business Owners, and best-selling author. Subscribe to my articles (for free) and receive (also for free) the ebook “The Blueprint for First-Time Business Owners”.

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