Ten questions to help you and your employees get better results together

How are you as a leader supposed to help your employees improve when most discussions are a variation of the polite-but-ineffective interchange of “How are you doing?” “Oh, I’m fine, and thanks for asking” even when that may be pretty far from the truth?


Here is a short list of questions that can help you get past the typical blockages to communication. These work well because they were created with the following assumptions and understanding in mind:

  • We probably don’t know the fully extent of the other person’s abilities, and it’s likely the environment we’re creating is somehow getting in the way of those abilities being fully expressed.
  • Most people are uncomfortable speaking truthfully to others, especially at work, because vulnerability and trust is underdeveloped in most relationships.
  • When given permission and an approach which feels mutual in intent, most people will welcome the opportunity to influence their situation and improve results for themselves and others.
  • Questions that have a single yes/no answer, or start with “Why” are very challenging to answer. Similarly, questions asking for “the MOST important” or “single reason” are much harder to get right than “some of the most important” or “a reason” kinds of questions.

With these concepts in mind, feel free to use questions from the list below – or develop your own!

  1. What kinds of things would make a significant difference around here if we started doing them?
  2. What kinds of things are we tolerating now, yet could cause significant problems in the future if they are not addressed?
  3. Where do you see are the overlaps and gaps between your work role and mine?
  4. If we continued to do things just as we are doing them, at the end of the year what would we be regret not having done?
  5. What does coming here add to what you could do all by yourself? What does coming here take away…?
  6. What do you see as the more valuable parts of what you do here?
  7. What do you see as the least appreciated parts of what you do here?
  8. How much has working here helped you grow as a person?
  9. How would you say I am personally – for better or worse – impacting your work?

Note: the most commonly asked question “How are you doing?” is very challenging for people to answer, because you are asking them to diagnose their own challenges and disclose potential weaknesses. Leaders frequently add insult to injury by following that question with “So how can I help you?” which puts a further burden on the other person to prescribe their own treatment. Much better to ask them questions about the work environment, the situational challenges, and others – and then ask yourself how you can show up differently as a leader to make a positive difference.

What other questions have you found to be successful in helping understand where you can help others? (Note: not a rhetorical question - this is the reader-involvement part of the blog ;o)

Chris Hutchinson, CEO

Chris Hutchinson, CEO


Chris Hutchinson

As CEO of Trebuchet Group, Chris Hutchinson thrives working with clients and his team to improve organizational clarity, teamwork, and leadership impact.

After years of building Legos® and tree houses around the world, Chris earned his Mechanical Engineering degree and followed that with an MBA. His experiences in the military and the business world taught him great leadership can be learned, and everyone is in some way a leader.

Clients and peers describe him as an inspirational catalyst for positive change. He is the author of Ripple - A Field Manual for Leadership That Works.

Chris and his wife live, garden, and bike in Fort Collins, Colorado, and have four children. He has an unrequited love affair with brownies.