Illustration by Ryan Garcia


How to Have Tough Conversations

Conflict won't solve itself. But a good talk can clear the air - and the misunderstandings

By Karen Sherlock

December 10, 2018 •

You know those difficult conversations you avoid? Whether it's a problem with your co-worker, kid or boss, you would rather sidestep it or hope it resolves itself. (Which, let's admit, rarely works.)

Well, Kristen Cumming, '09 BA, has tools you can use to tackle those tough conversations head-on. The business consultant and founder of Cantos Performance Management teaches the techniques at conferences and to organizations of all types and sizes.

"Conflict doesn't have to be bad. Our ability to manage it well is one of the keys to unlocking really remarkable possibilities," says Cumming. In fact, it's often high-performance environments that are prone to conflict, she says. Why? "Because people really care, and if people care, the potential for conflict rises."

She offers tips to get the most out of these tricky conversations.

Have a conversation with yourself first
  • Confront your assumptions and dig down to observable facts. "You've been late five times in the last two weeks" rather than "You don't care about your work."

  • Assess your motives. As parenting author Barbara Coloroso would ask, says Cumming, are you trying to get someone into - or out of - trouble?

  • Take nothing personally. "People assume that impact is equal to intention," says Cumming. Don't jump to the conclusion that a person is trying to set you back or bother you through his or her actions.

  • Be prepared to go the distance. Go in ready to spend whatever time it takes and to dig into possible underlying topics. "That changes the whole tone of the conversation and will change the outcome."

During the conversation
  • Agree on what you're talking about. This helps create a common starting point.

  • State the objective. "I'd like to figure out a solution to you coming in late." Try not to put the other person in the wrong.

  • Brainstorm multiple solutions and actions. Listen first and contribute second on this step. "So often we go in with predetermined answers," says Cumming. The goal is to find a solution that works for both of you.

  • Agree on which action to take first. Make sure it's practical, tangible and doable. Perhaps it's as simple as starting and ending the workday later.

After the conversation
  • Track what happens and always follow up to make sure the plan is working and to plan further steps. "Change in this kind of situation is never one and done," Cumming says.

  • Check in with the other person. How's it going for each of you? "That builds trust, which then reduces conflict."

Bonus tip

"Blame has not solved a problem yet," says Cumming. Focus on finding a solution and moving forward.


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