3 Questions You Need to Ask at Your Next Meeting

3 Questions You Need to Ask at Your Next Meeting

How often do you meet with your direct reports? If you don’t have any, how often do you meet with your boss? What is the nature of these conversations? Are they rambling and unstructured or is there a set agenda? Who does most of the talking? What is the objective of these meetings? Are they effective? Why or why not?

One-on-one meetings between the boss and employees are an important venue to discuss progress and development, but in my experience, they can easily go off-track without intention and structure.

How’s It Going?

For instance, my boss always started with, “So, how’s everything going?” I would launch into progress on various projects, team dynamics, upcoming vacation, and any concerns I may have. From there, the boss would give direction on what I should do – collaborate with this person or department, delegate something else, get on this committee, etc. Often the meeting ended with the question, “Do you need any help from me?” Invariably, my answer to this question was no. I can handle it.

What’s wrong with this approach? Maybe nothing. Except that you may be leaving with different perceptions of reality. At the same time, by giving direction, you’ve lost a coaching/development opportunity.

When you ask, “how’s everything going,” the answer can be highly variable depending on the employee. An over-achiever who holds himself to a high standard may say that things are not going well at all and that he is frustrated by a lack of progress. In contrast, a low-performer who is overly and unduly confident may respond that everything is going well, meanwhile leaving out key details.

Three Questions

Enter the 5 Coaching Kata questions. Even the first three questions can re-frame the conversation and level the playing field – so you are all speaking the same language.

  1. What is your target condition– one month from now? This could be in relation to any number of issues, a big project, an employee issue, a conflict the person is having with another team member. What is the destination you are striving for?
  2. What is your actual condition? In other words, where are you now – in relation to that target?
  3. Finally, what are the obstacles keeping you from achieving that target?

And if you have time, what is your next step? What do you expect to happen as result of taking that step?

Asking these questions reveals so much more about what your employees are thinking and whether you are on the same page. You might find that their idea of a target and yours are completely different. As well, their perception of obstacles might give you much different information.


Setting clear structure for the conversation eliminates confusion and creates clarity about the topic at hand. The obstacles in particular are great ways to understand the most important issues. By saying these out loud, assumptions can be questioned and a true understanding of what is keeping you/your direct reports from making progress can be had.

These three questions cut through the “everything is fine” niceties and create clarity and focus for the conversation.

Give it a try at your next meeting and let me know what you learn!



  • Lisa Schanhals
    November 15, 2018 at 6:27 pm

    My discussions with students sometimes aren’t productive. They sound like you describe above – just a recap of the steps they’ve done so far – and not really accurate. I’m really looking forward to asking these questions when I sit down with my students to ask about the progress of their independent research projects. I’ll let you know how it goes.

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