Mentoring when you see thinking gaps

You know those situations where you ask an executive to present their best ideas and their analysis misses some critical context.  How do you get them to see their thinking gaps without sparking a stress response?

One option is to deliberately and intentionally wear a “contrarian hat.”  When done supportively this technique introduces productive skepticism and alternative viewpoints to strengthen the mentee’s original idea.  It shifts the discussion from a validation exercise to a stress-test of ideas, ultimately leading to a more robust approach and more critically-minded mentee.

But, how it is done is important if you want to elevate the team and create psychological safety.  Here are three tips.

Announce A “Hat Change.” 

When in a mentorship session explicitly state your intent to be contrarian, but frame it as a “hat change.”  Explicitly state that your shifting into the contrarian role as a mentorship technique.  You are wearing the “contrarian hat.”

Example, “You have demonstrated good ideas here.  For the next ten minutes I am going to be a contrarian and focus on the weak spots before the market or our clients do.  This is a way to elevate your ideas, not judge what you have done.”

Highlight the Benefit of Elevating Ideas

Remind the mentee that by challenging their ideas in your mentorship sessions, you are equipping them to better defend their ideas to stakeholders, leadership, and customers. The rigor you require is easier than the skepticism that clients or market analysts will offer.  By linking your approach to success, it sets a tone of support.  The most thoroughly vetted ideas move forward.

Example: "Let’s think about what you have presented from different lenses so we can think through the various counter-arguments our stakeholders might have.

Ask, Don’t Lecture

Don't just lecture or offer alternative solutions immediately. Let the mentee respond to the contrarian challenge and see if they have a solid counter-argument.  If they do, validate it and move on.

Example: “Your data on the customer is solid. Okay, let's pivot to make this stronger. What's the biggest threat you haven't solved for yet?"

The goal is not for the mentor to be right, but for the mentee to think more deeply. Keep the focus on enabling their discovery, not just handing them a solution.

Of course, time is a factor in all of this.  It’s always better to give yourself years, not months, to mentor someone.