Ask Deal Breaking Questions Early

Paul Berggren
3 min readJan 21, 2021
Photo by Brett Jordan on Unsplash

Depending on where you live, how you were raised, or what kind of work you do asking important questions too soon can seem uncomfortable or rude. Waiting too long can make things truly awkward to bring up. How do you strike the balance between being clear and up front and not making the person feel like you are wasting their time?

If you are applying for a job with the American Cancer Society, you will get a question on the application asking if you smoke or use nicotine in some way. Is that rude? No. The job is with the ACS that is committed to ending cancer. Smoking is counter to their mission. It’s what they do.

This applies to other areas of life and every day we have a chance to find that perfect time to ask potentially tough questions that will propel the conversation forward or bring it to a quick end. I see it at work most often in the hiring arena and heard a clear example today.

A client had requested several online talent screening questionnaires for a couple of their leadership roles. While talking through the response graphs, we noticed a few key qualities in the candidates that stood out as strengths. These strengths surfaced in the interviews they had already gone through.

Without this talent screening step, these gaps may have been overshadowed by an upbeat attitude.

There were also several gaps in the candidate responses that were also reflected in the interviews already completed, but in more subtle ways. Looking at the person’s responses gave clues where our client should dig a little deeper for concrete examples to help them decide which finalist to hire. Without this talent screening step, these gaps may have been overshadowed by an upbeat attitude.

As we talked, it became apparent that having a better awareness of a candidate’s clear strengths and gaps earlier in the process would have been immensely helpful. Up to this point the focus had been on knowledge, skills, and impression on who they are as a leader.

What was it like to experience their leadership as a peer, an employee, or those they serve? What about the leadership talent that would make or break their team’s success? Each person had all come so far on resumes and impressions of interview teams without directly comparing them to the qualities like one of their best.

These were all wonderful people at this stage, and yet some were clearly stronger than others in overall leadership talent. Was this the best use of their time and of the interview committee’s time?

In the end, we helped our client recognize the strengths of each person as well as key areas to shine a light that could be deal breakers. Better to ask now and not hire them than discover a red flag 3 months into the job. As we closed the call, our client suggested that after these postings were filled, they would consider moving the talent screening up earlier in the process and add the critical leadership questions that sort top performers before they invest the time with hiring committees.

It comes back to the question of when to ask deal breaking questions. What I hear and see over and over again is do it as early as possible in a kind way. It’s one way to show respect to others and builds trust by describing your expectations in living out your mission.

It’s who you are, it’s what you do.

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Paul Berggren

I help people listen and learn from each other. As President of Crown Global HR, I bring clarity to growing and hiring people.