How to Keep a Conversation on Track

When you are coaching one-on-one, facilitating a team meeting, or trying to hear out an upset friend, one of the most difficult things to do is to keep the conversation on track to a fulfilling resolution, or at least forward movement. It’s not that the topic changes, it’s that the destination wasn’t made clear. When it is not clear what people want from a conversation, it can feel as if you are chasing them in circles. You often end up where you started.


To keep a conversation on track to achieving something, the first thing you must do is figure out what the person really wants. For example, some people will come to the conversation with a goal to make a decision, but the real problem is they have made a decision they are afraid to implement. This often happens when someone wants to leave a job or partnership. The outcome the person wants is not to make a decision but to muster the courage and/or define the risk parameters for the leap they already decided to take.

Another example is when a person says her goal is to stop feeling overwhelmed when she is actually upset with the direction of her career. If you accept the initial goal as the outcome—stop feeling overwhelmed—you will focus on time management. Instead, she may need your help visioning her future.

In teams, some people continually bring up outside issues that need to be addressed, saying “but” to every idea offered when they really want the team to consider their related project or idea. They might be afraid to say they want to do something entirely different from the current focus. The focus may need to shift but you are still putting the conversation on track to move forward with the conflict on the table instead of impeding the flow.

Dig beyond the presenting topic

People are often unsure about what they really want or they are afraid to speak it out loud. Instead of trying to help them solve the issue that is being debated, help them discover, clarify, and declare what they really want to resolve or have as an end result. Once their real desires are articulated, the actions they will take are easier to define and commit to.

When the conversation feels it isn’t going anywhere, dig deeper by discovering what they are afraid might happen if they make certain choices or what they are not getting in the current conversation that is triggering their negative emotions. Not only will the flow of the conversations be more meaningful but the next steps might become crystal clear without much exploration.

It’s possible the person does not have a particular outcome in mind when you begin the conversation. There may be a topic to discuss, such as what to do at business meetings or how to build relationships with peers. You may still need to prod the person for at least a preliminary outcome of the conversation, asking questions such as “What will you find easier to do once we explore this topic?” or I would be happy to explore this topic with you – what made you bring it up with me right now?”


When starting a recent coaching conversation, the person said her goal was to work with two of the leaders on her project team to create a solid action plan everyone would agree to. She sorted through possible plans. I said, “You seem to have solid options to present to the two leaders. What is the real difficulty you need to resolve to get the result you want?”

She hesitated before she said, “I just want them to get their act together and agree to something. Those two guys are on opposite ends of the spectrum on what we need to do, but neither of them is budging. Time is running out. Jobs are on the line. How do I make them see that?”

Her agitation was palpable. I asked, “How responsible are you for the outcome of the project?”

“My job could be on the line, too, but they don’t report to me so I can’t make them do anything. I’m not sure they will listen to me.”

“It sounds like you don’t need to present them with plans, but to figure out how to get them to listen to you and understand the imminent consequences if they don’t agree to a plan. Right?”

“Actually, I think I know what I want to say. I just need to say it.” The conversation moved into looking at her fear of confronting their conflict. Then she practiced confidently presenting her observations and the urgency for finding a compromise.

Getting a conversation back on track

Even when you think the person has found what they really want as a desired result, the conversation can veer off track. When you feel a conversation has stagnated and is no longer on track:

  1. Listen for emotional trigger points such as words or ideas that spark anger, excuses, or blame.
  2. Share the shifts in emotion and topics you noticed.
  3. Ask if they still want to work on the stated outcome, or if there something else that needs to be resolved first.

Find what people really want from a conversation in order to help them move forward.


1 Excerpt from The Discomfort Zone: How Leaders Turn Difficult Conversations Into Breakthroughs



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