Career Tips

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Tell me about a time you’ve had to persuade someone to do something

The Real Question: People are tricky creatures. Do you know how to handle them?

Top-line Tactic: Focus on how you persuaded people, not just that you managed to convince them.

We’ve been through several of these competency-based Tell me about a time you . . . type questions already, so you might ask what’s different about this one? It’s a good point—the basic mechanics of the STAR method remain the same for all of these, so what’s left to consider after you have that mastered?

The next level of analysis is simply to consider the competencies behind the question. What quality or skills is the interviewer hoping to see you demonstrate in your answer? Here, for instance, this question about persuasion is a classic attempt to gauge people skills. The interviewer is probably looking for competencies like:

  • empathy
  • charm or rapport building
  • confidence and possibly assertiveness
  • flexibility
  • ability to handle conflict/difficult conversations
  • ability to put your ego aside, humility
  • ability to understand and motivate others

Of course, the exact skills required vary depending on the role and company culture, so take a moment before answering to think about what abilities the interviewer wants to see. Then use STAR to weave an answer that demonstrates them, for example:

When I was at ABC I was managing a group of six designers. Several of them came to me asking for more flexibility in their schedule and whether they could work from home occasionally. I’d done some research into productivity and I knew that creative people often benefit from this sort of freedom, but that management is often reluctant to give it them. In order to persuade my director, I put together a small presentation from the management literature that included several studies on the effectiveness of flexible work programs, their positive impact on hiring and retention, and best practices for running them.

I knew my boss would be worrying about productivity, so I came up with some key indicators we could track to hopefully counter that concern. I arranged a meeting with the director and also roped in HR, because they would need to approve the policy change. My boss wasn’t wild about the plan, but I stuck to my guns and ran through all the facts, countering each of his objections. He said he was impressed with my preparation and would think about it. After a week, I got the go-ahead to implement the change. My team was over the moon, and not only did productivity rise 20 percent, but soon after that I was able to hire a truly stellar designer, who said one of the main draws of the job was the flexible schedule. Notice that this answer doesn’t simply check the “ability to persuade” box but delves deeper into how the candidate went about persuading others, highlighting key constituent skills like empathy (foreseeing the director’s objections), consultation (roping in HR and listening to the designers) and tenacity (sticking with the debate despite objections).

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What has been the biggest setback in your career?

The Real Question: Are you resilient? Are you honest?

Top-line Tactic: Be frank about your failure but positive about what you learned.

Your first reaction to this question is probably an inward groan. Of course no one likes to dwell on his or her failures, but try not to be too down on questions like this. It’s best to view the interviewer’s attempts to probe your setbacks not as sadism or an attempt to trip you up, but rather as a chance to demonstrate two extremely valuable characteristics—frankness and resilience.

The secret to acing this sort of tricky question is to strike a balance between light and dark. Don’t say you’ve never had one. Instead, speak honestly about a real setback, but also accentuate the positive aspects of the experience—how resilient you were in the face of failure and what you learned from the experience, even if it’s simply that you won’t be making the same mistake again.

The interviewer cares far more about how you responded to adversity than the particular circumstance you faced. Ultimately, you want to present the setback as evidence of both your humility and a lesson learned on someone else’s watch that has made you stronger. For this reason, it’s not necessary to bore your questioner with the particulars of your failure. Just give an overview, such as:

At my last job, I was asked to manage a large project. We worked with consultants to create a project plan and estimate costs, but when we presented our plan to the CEO, he wanted a major change. I could see what he wanted would never work, but I was too scared to speak up in that meeting and say so.

So we tried to accommodate the CEO’s request and it was a disaster. However, being on that project taught me two valuable lessons: first, speak up when you think something is wrong—at least it shows you’re paying attention and it could avoid a potentially serious problem. Second, I now know how to avoid the sunk-cost fallacy, where good money is thrown at a problem in the false hope that it will somehow rectify an inherent flaw.

Younger job seekers or recent graduates may not yet have experienced a significant career setback. Be honest about this with your interviewer but try to offer an example from your education or work experience that conveys the same message of perseverance and your ability to snatch something positive from a negative situation.

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