How To Have the Conversations You Desperately Want To Avoid (Part 1): 10 Tips for Holding People Accountable

I’ve gotten pretty good at having conversations most people want to avoid. My first “business” was actually The Conversation Coach, which I shut down when I realized that communication skills alone was not the problem I wanted to work on and when I found that all my clients were education startup founders anyway. However, it remains an obsession and the skills are useful for everyone. So, here’s my first installment in the How To Have the Conversations You Desperately Want To Avoid series!

1. Make it clear that your first goal is to understand the other person.

“Just letting you know, my first goal is to understand where you’re coming from.”

2. Make it clear that your second goal is to find a win-win.

“I also know that there is a solution that will meet both of our needs. Are you ready to work with me to figure that out?”

3. Agree on the facts first.

Facts are specific, measurable observations. “I noticed that you’ve been late to our morning stand-up meeting every day this week. Is that what you noticed, too?”

4. Approach the conversation without assumptions.

Ask questions. “Could you help me understand what’s going on?”

5. Speak using “I” language.

“I’m feeling frustrated because I need my team members to be on time to meetings. We have a lot to accomplish and late starts prevent us from being as effective as we could be.”

6. Constantly monitor for safety and backtrack if necessary.

“I notice you’re tearing up right now. Is there something I can do to help get this conversation back to a safe place?”

7. Ask your partner to help make the conversation safe for you as well.

“I want to hear what you’re saying. It would help me a lot if you could start your sentences with ‘I’ instead of ‘you.’ Again, this is so I can better hear you.”

8. Check for understanding to help the other person feel heard.

“What I’m hearing you say is that you’re struggling to get enough sleep because you feel overworked. You’re also extremely frustrated because you think that I haven’t been acknowledging your work at all. Did I hear you right?”

9. Be need specific, solution agnostic.

Every person’s needs deserve to be addressed and honored, even if they are different from your own.

“I thought that our project management system would prevent people from being overloaded, but it sounds like you need something slightly different. Let’s figure out what that is.”

At the same time, be very cognizant of your own needs so that they are met as well. Being empathetic does not mean being a doormat or not holding people accountable. Being empathetic means understanding each other’s needs so that you can come up with a win-win or win-walk away.

10. Problem solve together.

“How about this, let’s first figure out what projects are on your plate and see where you’re spending the most time. Maybe there’s a project that should be deprioritized, or maybe there’s an expectation you’re placing on yourself that’s more stringent than it needs to be. I’ll also make sure to check-in with you twice a week for now. How does that sound?”


For further reading, I recommend Crucial Accountability: Tools for Resolving Violated Expectations, Broken Commitments, and Bad Behavior by Kerry Patterson, Joseph Grenny, Ron McMillan, Al Switzler, David Maxfield