Matt and his mentor, Anne Marie, have been meeting regularly for nearly four months. With each meeting, Matt feels more confident and grounded. He thinks he has made significant progress and that relationship is on track (but he isn’t 100% sure). He assumes that Anne Marie is good with it as well. But is she? Is Matt’s assumption correct?

Matt won’t know until he checks out his assumptions with Anne Marie, but he worries that he might appear insecure or needy to a top-level executive. His biggest fear is that revealing any hint of uncertainty might suggest that he lacks confidence, which could influence his advancement and promotability.

Why is it so important to check out assumptions?

Assumptions determine how and what we perceive. They guide our actions and tend to be self-reinforcing. If mentoring partners don’t check their assumptions out to see if they are valid, they can find themselves moving forward on false assumptions that can easily erode trust in the relationship and ultimately upend it.

If you find yourself in a mentoring relationship where you haven’t checked out your assumptions, you’ve probably got some work to do. Checking out assumptions requires dedicating time to honest and open conversation about how things are really going.

So, how do I approach my senior level mentor without appearing needy?

Set the stage by talking about why you want to check things out. For example, Matt might approach Anne Marie this way:

It’s been four months since we got started and I’ve been thinking that it would be important to make sure that we both agree that we are are on the path to achieving our goals and making good use of our time. I know that having you has a mentor has made a significant difference to me and I want to make sure that I am getting the most out of our mentoring relationship. If that makes sense to you, maybe we could set aside some time at our next meeting to review my progress and assess how our relationship is going, and see if we need to make any changes in our timeline or goals.

What kinds of questions should I be asking?

Here are some questions to guide your conversation when you want to find out if you are on track and the relationship is mutually beneficial. However, before you engage in this conversation, you will want to be prepared. First, honestly assess the relationship for yourself.

  • How do you think we are doing?
  • What indications do we have that we have made progress?
  • Are we on the right path?
  • Are we satisfied with our results? What could we be doing more of? Less of?
  • What can we do differently to improve this relationship?
  • What value has this relationship provided for you so far?


Make sure you are on the right path. Check out your assumptions about your progress and your relationship regularly.