Learning Corner: The Hard Conversation with Your Boss

Estimated Time to Complete: 25 minutes

Objective:
To prepare for a difficult conversation with your manager about a concern, a workload issue or a disagreement.

Materials Needed:

• The concern you want to raise

• A notebook

Activity Steps:

1. Get clear on your goal (5 minutes)
Write down what you want to come out of the conversation. A decision? Support? Understanding?

2. Think about their view (5 minutes)
Write what your manager cares about most right now and how your concern connects to it.

3. Plan your opening (8 minutes)
Write two or three sentences that name the issue, why it matters to the work and what you'd like to explore. Bring one possible solution.

4. Ask for the time (7 minutes)
Request a specific time instead of raising it in passing. Practice your opening out loud once before the meeting.

Key Takeaways:

• Tying your concern to your boss's goals makes it easier to hear.

• Bringing a possible solution shows ownership.

• A scheduled conversation gets better attention than a hallway one.

Reflection Prompt:

What is one concern you've been carrying that your manager doesn't know about yet?

Want help bringing this to your team? Book a free 30-minute conversation with Tony.