Tom Truly is project manager on a project that has recently missed a deadline and lost a key customer.

Sarah, the project sponsor, has called a meeting to discuss progress. Sarah has been under pressure from senior management to “fix” the high-visibility project. She is angry that Tom didn’t inform her in advance about the project issues. Every time she asked Tom how things were going, he answered: “Tip top!”

Let’s see how the meeting between Sarah and Tom goes:

Tom, I heard at the last steering committee meeting that the project has some major problems. Last time I asked, you said everything was fine. Are you going to tell me what’s going on?
Yeah, I guess we did miss a deadline.
Not only did you miss a deadline, you also lost a key customer! Why didn’t you tell me?
Well, it wasn’t because of the delays. The customer thought the investment was too high.
Look, I don’t care why the customer left! Fact is: your performance is not acceptable! I expect you to get the project back on track—soon! From now on, I want a detailed status report on my desk by 12 noon every Friday.


Clearly, this meeting was not productive. Sarah gained no insights about why the project is troubled and Tom leaves feeling demotivated. What could Sarah and Tom have done differently? I’ll come back to their conversation with some suggestions for improvement at the end of this article.

We all face conversations at work that we dread—giving someone negative feedback, saying “no” to a colleague, asking our boss for extra time off. Every interaction can also be a “learning conversation” according to the authors of Difficult Conversations: How to Discuss what Matters Most. What can we do to turn a difficult conversation into a learning conversation?

Be aware of the three levels of conversation

Difficult conversations often have three levels. First, there is the what happened level which is mostly about facts (e.g. the project missed the deadline). Second, there is the feelings level which often remains unspoken (Sarah felt angry about not being informed). Third, there is the identity level, which revolves around issues of self-esteem, self-image and worthiness (Sarah is concerned about looking unprofessional in front of her peers).

Explore both points of view

A difficult conversation is best approached from the perspective of the third storyneither what I think happened nor what you think happened, but rather the differences between our views about what happened. Include both points of view in the discussion and ask for the other person’s help in sorting out the situation.

Look for how each person contributed to the situation

Usually, each person has contributed to the problem in some way. A learning conversation occurs when both people are able to acknowledge their contribution to the problem. This is far easier for most of us than accepting blame!

Engage the other person in problem solving

Look for solutions that will satisfy each person’s needs, encourage communication and support a continued relationship. Let’s revisit Sarah and Tom and see how they could have turned their meeting into a learning conversation:

Sarah:Tom, I wasn’t aware that we were going to miss that deadline. The steering committee also gave me a lot of grief for losing the customer. How do you feel about that? I want to hear your perspective on the project and discuss what we can do to get things back on track.
Tom:We do have some issues, but I didn’t want to burden you with problems. The team has been working around the clock, but we just can’t keep up with the changing customer requirements.
Sarah:Oh, I didn’t know that the requirements had changed. I thought we had frozen the specifications at the last design meeting.
Tom:True, but the customer continued to ask for changes. They used their connections to push the changes through. I was told by a senior manager to “just make it work.”
Sarah:Hmm, I’m surprised you didn’t come to me with that. Can you tell me more about the changes?
Tom:I know it was a mistake not to inform you. The changes were small enough that I thought we could just implement them and make the customer happy. But the customer kept asking for more and it was hard to say no.
Sarah:Tom, I’m glad that you shared this with me. Do I understand you correctly that customer change requests are causing most of the delay? What can we do to ensure the problems won’t continue?
Tom:Well, I guess it would be helpful to know when I should accept a change request and when I can safely reject it.
Sarah:I agree. I should have supported you on this from the beginning. Let’s schedule a meeting with the team and stakeholders to agree on a change request process. Once we have that in place, I will inform the project customers.


And with that, the meeting ends. Sarah has gained important information and Tom is motivated to continue leading the project.

Summing it all up

  • Be aware of facts, feelings and identity issues (three levels of conversation)
  • Include both points of view and ask for the other person’s help (I want to hear your perspective on the project and discuss what we can do to get things back on track.)
  • Don’t make statements disguised as questions (Are you going to tell me what’s going on?)
  • Don’t use questions to cross-examine (Why didn’t you tell me that?)
  • Ask open ended questions (How do you feel about that?)
  • Ask for more concrete information (Can you tell me more about the changes?)
  • Paraphrase for clarity (Do I understand you correctly that customer change requests are causing most of the delay?)
  • Engage in mutual problem solving (What can we do to ensure the problems don’t continue?)

Further reading

Stone, Douglas, Bruce Patton and Sheila Heen. Difficult Conversations: How to Discuss what Matters Most, Penguin, 2000.

Image: Conversation by Sharon Mollerus licensed under CC BY 2.0