139: How to Have Difficult Conversations at Work

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Let’s talk about how you can have difficult work conversations in a way that doesn’t leave one or both parties feeling like you’ve been run over and left for road kill.

The purpose of this exercise is to move the relationship forward, not to convince the other person that you’re right and they are wrong. There is no upside to having a winner and a loser.

Be willing to be wrong…or at least not right.

Step One – Really Listen

The first part of this process is to allow the other person to tell you why they believe they are right. Your job in this phase is to listen intently without interrupting.


Your temptation will be to defend your position, to argue, or to display body language that clearly expresses your frustration or disbelief.

It will take practice for you to just listen, so the other person feels completely heard. Put yourself in their shoes – what are they thinking and feeling?

Step Two – Your One Sentence

You now get one sentence, and only one sentence, to state your position on the matter.

Your temptation will be to vent, but there’s no upside to that. Be succinct.

Step Three – State the Points of Agreement

After the other person has had their say, you want to state the areas in which you agree.

You’re moving towards the solution phase of this conversation, so even if your points of agreement are few and far between, state them.

Step Four – Brainstorm Solutions

What’s most important here is that you don’t dwell on the problem or points of disagreement, but rather move quickly to possible solutions. You’re not allowed to go back to talking about the problem at this point.

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