Excerpted from chapter 11 with the permission of the author & publisher of Work Happy – What Great Bosses Know by Jill Geisler

Jill Geisler’s Top Ten Coaching Questions:

  1.  How can I help you?  It’s a friendly opening line- with a purpose.  It’s designed to get people to state their goal at the very start of the conversation.  Too often, people say, “Can I run something past you?” and launch a long story while you figure out where all this is going.  “How can I help you?” leads them to give you a headline in advance.  It can expedite the process.
  2. What’s the worst that could happen?  The question works when you are coaching people who lack self-confidence or are sensitive about risks.  Getting them to state their worst fears enables you to follow up with questions about how realistic their fears may be- like this:  “You said you’re worried that Sam might quit if you give him these new responsibilities but no raise.  What are you basing that on?  How bad would it be if it really happened?  What alternatives do you have?”  The “worst case” question can actually free people to talk about what they thought was unspeakable.
  3. Can you tell me more about how you know this?  I use this one when people seem convinced there’s only one reason something is the way it is.  It’s a great way to find out whether they are operating on faulty facts (rumors, assumptions, old information) or have put blinders on and aren’t looking for other possibilities.  It inevitably opens the door for more questions- and insights.
  4. What does this person do well?  This is a question I’ve learned to ask when bosses are describing a problematic employee.  After I’ve heard a litany of all the person’s weaknesses, I ask, “What does this person do well?”  It’s often an amazing game-changer, especially when the manager has avoided a difficult conversation for a long time, while collecting a list of grievances.  Asking this question helps me determine whether the boss (rightly or wrongly) has written off the employee as irredeemable- or wants to salvage the situation.
  5. Knowing what you know now, would you hire this person today?  This is definitely a close-ended question- designed to elicit a yes or no answer.  I ask it when managers are struggling with decisions about employees who are mediocre or have a jumble of strengths and weaknesses- but don’t approve, despite the boss’s best efforts.  The question, “Knowing what you know now, would you hire this person?” can lead to less emotional and more rational decision making.
  6. Who else has a stake in this?  Asking this question is a nonjudgmental way of reminding people that it’s not all about them.  It prods them to look in all directions around an issue to see how it affects others.  Identifying other stakeholders is one of the most important things a coach can do.  It can also lead to the next valuable question:
  7. Who could be your allies in this?  I’m a big believer in encouraging people not to go it alone.  Asking them to enlist allies challenges them to collaborate with others- who can both help them meet their goals and also hold them accountable.
  8. What happens if you do nothing?  This question can serve as a call to action- or inaction.  Their answer may describe how difficult things will be if they fail to act, and push them to finally do what they’ve been avoiding.  On the other hand, if they have overstated a problem or are worrying needlessly, their answer can lead them to recognize that the status quo may be just fine.
  9. So, what’s success going to look like?  Think back to our friend Jim in my coaching conversation.  This is a question I would ask him as we wrap up.  It’s an upbeat question, which sets a positive tone.  It’s also my last chance to hear him spell out his goal- which might have shifted a bit during the coaching, as is often the case.  We agree on what he plans to accomplish and how he will measure whether he’s achieved it.  It’s a push for specificity.
  10. What are your next steps?  This is a good closer.  It can turn goals into plans and plans into action.  It’s a check to see if the person I’m coaching is going to follow through.  If a solution is somewhat challenging or complex, it chunks it down into a series of smaller, defined actions.  It gives me one last opportunity to make sure the person I’ve coached is better off than when our conversation began!

Jill Geisler holds the Bill Plante Chair in Leadership and Media Integrity at Loyola University Chicago. She teaches and coaches leaders worldwide and serves as an ethics professor at Loyola. She is the author of the book “Work Happy: What Great Bosses Know” and produces a podcast for aspiring leaders on iTunes U: “Q&A: Leadership and Integrity in the Digital Age.” Each episode tackles a specific management question.  Click “HERE” for Jill’s podcast.



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