Do You Have Answers to the Really Tough Questions?
Curt Skene’s In2Win! Career Coaching Supplement.
You likely know (or should know) which tough questions will be coming your way so prepare great responses to them now. Depending on your situation these may be questions that explore a perceived lack of experience (especially if making a career shift), questionable work history, length of time in transition or concerns about being overqualified. When responding, acknowledge their question, state you have thought about these same issues and provide your great response.
Just know that an experienced interviewer has already heard all of the best canned responses and read all of the interview books so if you feed them a line they will read right through you. Always take the high road, be sincere, soulful and reflective with your answers. Give enough detail to answer the question but never give too much to bore them.
Most companies will respect the discretion you show so be very wary of when and where you use names and dollars. Never ever put any of this in writing. When answering tough questions, self-awareness is an important skill to possess so demonstrate your mastery of it.
Employers may forgive mistakes but only when you have created a desire for them to do so. Demonstrate remorse and show how you have learned from your experience(s).
Honest acknowledgment of a weakness makes your strengths and the rest of your story more believable.
Why I Wrote This Page
Because a completely spotless narrative is subconsciously read as incomplete or curated. No one’s record is actually perfect, so a suspiciously perfect one quietly raises doubt rather than removing it.
Strategic vulnerability, a real, well-handled admission, builds more trust than flawlessness, because it’s what makes the rest of your story credible by association. If you can be honest about the one thing that didn’t go well, the listener starts believing the things that did. Hide the weak spot, and even your genuine wins start to feel like they might be spin.
This only works with real discretion. The goal isn’t oversharing, it’s choosing the one honest admission that builds trust without undermining the case you’re making.
Action Steps
- Prepare one honest, well-framed answer for your most likely tough question, gap, termination, overqualification, before you’re asked it live.
- Practice acknowledging the question directly in the first sentence, rather than deflecting or over-explaining before you get to the answer.
- Show what you learned or changed as a result, not just what happened. The lesson is what makes the admission work in your favor.
In2Win! Afterthought
Curt’s current observations and updated guidance will be added here.
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