3Qs to Ignite Your Mentoring Relationships

Let’s start by blowing up crazy thinking that keeps lots of people from pouring their lives into others. The truth: you don’t have to be brilliant to be a good mentor.

  • You don’t have to know all the right things to ask.

  • You don’t have to know all the right things to say.

  • You don’t need to have been in the same shoes as your “mentoree.”

  • You don’t have to know Jedi mind tricks as your secret weapon for anticipating exactly what someone needs from you.

The secret to being a life-giving mentor may be as simple as knowing a few good questions.

Photo by Jon Tyson on Unsplash

I don’t know how many times I have been with people who think that being a good mentor means, you use mental super powers to divine what someone needs and then without them knowing it, you help them make breakthrough discovery they never saw coming.

Mentoring—aka, being available and pouring your life into someone—is not rocket science. More than anything else it means showing up and then when you are there, listening.

Here are three deceptively simple questions you can use in almost every mentoring, discipling, or even employee management relationships. I find that these questions and their corollaries open the door to the areas of life where powerful mentoring becomes natural.


Q #1 :: Where are you making Progress these days?

WHY this question? Because people need to celebrate their progress!

Whether tackling a major project or working on your own personal development, it is frighteningly easy to keep you head down, plowing forward, and fail to notice genuine progress. However, the sheer recognition that you are making progress releases new energy for demanding work, for ongoing study, or for the heavy lifting of leadership.

As a mentor, you have the chance to help people pause and take a good look at progress they have made. Your voice of encouragement speaks volumes about the value of what they have achieved. Even baby steps are huge leaps of courage to be celebrated.

Other ways to ask the same question:

  • Where are you seeing success?

  • What kind of positive feedback are you getting from those who know you?

  • Over the past _____ (Month, week, quarter, year, etc) what progress encourages you?

Q #2 :: What Plans or Priorities are you working on?

WHY this question? Because people need help looking ahead.


In the trenches of daily life, people put their heads down and lose sight of the forest amongst the trees. A mentor has the chance to put a gentle hand under their chin and lift their head to look further down the road. Past progress will give perspective on future assignments, but a mentor who asks this questions gets to speak into and clear the pathway ahead.

By asking this question, you will discover where your mentoree is clear and where they are confused. You will have the chance to address that confusion or even the re-direct plans for the future. Without asking this questions, all you have to go on are assumptions. You know where that will get you.

Other ways to ask this same question:

  • What do you hope to get done on this during the next month?

  • If you could make progress the way you hoped, what would your next steps be?

  • What are your best ideas for the next two steps you should take?

Q #3 :: What Puzzles need to be solved in order to move forward?

WHY this question? Because life throws curve balls all the time.


Puzzles are those complex issues where there is no immediate or simplistic way forward. You can ask someone about problems they are facing, but “problems” feels negative. Puzzles call for creativity. Puzzles carry the promise that a real solution exists. Problems imply that solutions might be elusive. Or, worse, the concept of problems can convey a victim mentality. Puzzles are fun


Leadership should be an adventurous series of continual puzzles. If there were no puzzles to solve, anyone could do your job.

Other ways to ask this same question:

  • What is eating your lunch these days?

  • Where are you running into problems?

  • Where are you getting stuck?



I get it. These questions sound so stinking simple. But, let me just say, they open up conversations to layers of nuance and significance that will cause others to mistake you for someone brilliant. Try them and you'll find the person you are meeting with will be opening about the stuff that really matters and soliciting your insight in ways you never imagined.

In the workplace… Use these questions in your supervision relationships and they will transform a shallow reporting conversation into a deeply developmental one. And, who doesn’t want to develop stronger more capable employees?


One unspoken discipline that makes this work. Learn to follow up your questions with listening, not advice-giving! For more, take a look at my post on, “Dialogs of the Deaf.”

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© 2020 by Gary Mayes