Coaching, or How to Have (Successful) Difficult Conversations


I just spent the last few weeks talking to many managers about coaching and after dozens of role plays, I identified 5 top tips for successful coaching. (The first one is, by far, the most important one.) Enjoy.

Tip #1: Have the conversation!

The worst possible outcome is that you never broach the topic. Yes, it’s uncomfortable to talk about what’s not going well and no, you cannot know in advance what the outcome will be–but do it.

Tip #2: Prepare

What exactly do you want to change? Is there one particular customer interaction that went badly, or do you see a trend? Line up your examples and what you see is the issue. Keep it simple: if you see multiple issues, concentrate on the most egregious one.

Tip #3: State the issue and listen

Make your case succinctly (a good preparation helps) and stop talking. Do not lecture. You need to get the team member’s perspective.

Tip #4: Make sure the issue is agreed upon before proceeding to the solution

If the team member does not see the problem, it’s useless to try to “resolve” it. They may not think that the problem is a big deal, but they need to acknowledge that it exists. For example, say the team member failed to send any updates to a customer while they were resolving an issue. As long as they assert that the only thing that matters is problem resolution (and not communication), you will not be able to create behavior change.

Tip #5: Get to a joint agreement on the action plan

In our haste to get the conversation over with, we may stay with a vague agreement to “not do it again”. That’s a recipe for a a recurrence. What words, exactly, do you want the team member to do for updates? Is there a standard cadence they can use? What wording can they use when there is no clear timeline for resolution? And how will you evaluate their success?


What are your secrets for successful coaching? Please share in the comments.