Abigail has been a mentee of mine for almost twenty years. The most gratifying thing about our relationship is this: After we talk over a challenge she’s facing, brainstorm ideas, analyze approaches, and then develop solutions or options, she takes action. In fact, I don’t recall a single time in almost two decades that we’ve rehashed a past discussion.

But all conversations—whether in a mentor relationship, a supervisory performance review, or a colleague chat—don’t pan out so well. Instead, with some people you have far too many reruns.

That is, some coworkers have been initiating the same conversations for months—or even years. They complain about their job. They give you a weekly run-down on their love affair that’s in jeopardy. They ask for, but never take, advice on the new business venture they’re considering.

Ways to End Circular Conversations

Are You Helping or Hindering?

Consider whether you’re really helping the other person by following them along as they go in circles. Have you become the de facto therapist to a coworker or friend whose problems are bigger than you feel qualified to handle? Have you felt depressed or drained after conversations with coworkers who seem stuck in a quagmire?

I tend to agree with Mark Twain’s observation: “Few sinners have been saved after the first twenty minutes of a sermon.” Maybe you’re simply delaying the coworkers getting to the real source and resolution for their issue or situation.

Of course I’m not suggesting that you turn a cold shoulder to someone who needs your help—even if that help involves simply listening and empathizing.

But after you’ve listened and listened and listened even longer, you may discover that your listening not only fails to improve the situation; it has instead become a substitute for action. In other words, do you sense the speaker has become stuck in place much like that little spinning wheel that hangs up and prevents you from accessing a website?

Questions to Lead Coworkers to Action

Participating in such circular, repetitive conversations devours valuable time and saps your emotional energy. Instead of listless listening, focus these coworkers or friends by tossing back questions like these:

• “So what do you think your next step should be?”
• “So what specifically do you want me to do at this point?”
• “So what do you plan to do now with this new information he/she gave you?”
• “So how have things (or your plans or the relationship) changed since the last time we talked? “
• Is this something different from what we’ve discussed before?”

If such questions don’t help them focus and come to resolution, you may need to be even more direct:

• “Gee, I’d really like to be able to offer some help, but I’ve exhausted all my ideas on the issue.”
• “I really empathize with your situation. And I wish I could say something to help. But I have nothing more to offer you.”
• “I’m becoming as emotionally involved and upset about the situation as you are. Do you mind if we change the subject?”

Insist on Accountability

If the conversation is one in which someone repeatedly asks your advice but disregards it, try these questions that aim to hold them accountable for inaction:

• “What did you decide to do about the last bit of advice I passed along?”
• “What were you able to do with the information I passed along last month?”
• “I’m afraid you won’t find my current advice any more usable than what I offered last time we talked. By the way, what happened when you tried what I suggested earlier?”
• “Gosh, I really fresh out of new ideas about the situation. How about you? What ideas have come up with it? How did they work out for you?”

If necessary, say it again or ask it again. And again. Without your willingness to continue to follow the other person around and around the circular conversation, the laps will eventually come to an end.

Learn more ways to move conversation forward with Communicate Like a Leader: Connecting Strategically to Coach, Inspire, and Get Things Done

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