One of the things that’s true about our line of work is that we have a lot of stakeholders. As a result, we have a lot of hard conversations. That’s because stakeholders are people and people, as Brent likes to say (and we’ve all adopted the saying), are messy. 

It’s for that reason that the piece of content on our website that I refer back to the most is our Tactical Guide to Tough Conversations. And I refer back to it before each time I think I am going to have a hard conversation (there is, by the way, no difference between a tough or hard conversation, but the person who titled that piece liked alliteration and went against my recommendation to call it The Hitchhiker's Guide to Hard Conversations) because hard conversations are by definition hard and you’re probably only going to get one shot at having one and having it go right, so you need to make sure you’ve thought it all the way through and are prepared for whatever direction it might go. In other words, read The Guide.

Further, another thing that’s true about hard conversations is that if you’re the one initiating one, the person you’re having it with may not have known ahead of time that a hard conversation was on the horizon and therefore may not be at all prepared for it. This is important to recognize because if it’s true, that person is likely to react emotionally, which puts the onus doubly back on you as the initiator to make sure that the conversation is trafficking in facts in pursuit of an achievable and desirable outcome. 

How can you do that? Here’s what our Guide says:

1. Know why you’re having the conversation and what the achievable and desired outcome is.

2. Recognize going in that one conversation won’t solve everything, so appreciate that this conversation is likely the beginning (and not the end) of a larger conversation.

3. Prepare and practice for the conversation out loud. 

4. Be specific and direct with examples.

5. If the conversation is escalating or getting emotional, bring it back to its purpose and achievable and desired outcome. 

The reason these principles work is that they solve for the developments that tend to make hard conversations go off the rails. Namely:

1. Asking for something that’s not achievable.

2. Expecting resolution and becoming frustrated when it can’t be reached.

3. Saying something off the cuff that’s stupid.

4. Not being able to support a point of view with evidence.

5. Open-endedness; when one thing becomes about everything.

The other key to a hard conversation is ending it, and the best way to do that is by identifying an agreed upon next step. After all, the only way forward is progress, so be satisfied if, after what’s probably been an emotionally draining experience for both parties, you’re able to agree that you’ve made it.

-Tim

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