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  • Joshua Wilson

Three useful tips for having hard conversations

Almost all organizational work boils down to talking at some point—somebody needs to say something to someone else for anything to get done. Most of the time these conversations aren’t too difficult: they follow norms: meetings, reports, sharing plans, asking for input, etc.

But when the work at hand involves change, then the conversations often can get—and need to get—more real. Things are at stake; people are anxious; there’s difficult feedback to give or hear; we might be asked to do things we’re not excited about, etc. It’s useful to develop some comfort—yourself as a leader, and in your teams—with having conversations that seem hard. So here are a few ideas about how to get better at this important skill!

  1. To reduce some of the tension out of the gate, pick a time when nothing particularly troublesome is on the team's radar—maybe a period after you just landed a big project or deliverable.

  2. Start by telling everyone you want to have a different sort of conversation—one in which you can all say what’s on your mind more than you normally do at work. If they need a justification, refer to the paragraph above.

  3. Invite the team to tell you what sort of ground rules they might wish to have to make it feel safe to say what they really thing. Make a list of those rules and see if the team will agree to them. You’ll likely hit upon a few core ideas:

    1. that what is said won’t be used against people (we call this the “Las Vegas” rule)

    2. that people only have to share what they choose it (we call this the “Vampire” rule)

    3. that we’ll respect each other and not frame problems as personal attacks

    4. that we’ll take turns and make sure everyone gets a chance to talk

Give these tips a try! We'll publish more in the coming weeks!


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