When a leader dreads a conversation, they usually spend their energy on how to say it. The tone, the opening line, how the other person will react. That's the second problem. The first problem is that they're often preparing for the wrong conversation.
The situation isn't the conversation
Take a sales leader who missed the number for the second quarter in a row. The obvious conversation is about the miss. But underneath, there might be a very different one:
- "I'm not sure you're the right person for where the company is going now."
- "You agree in meetings and then don't do what we agreed."
- "I've been tolerating this too long, and that's partly on me."
- "I changed priorities on you three times this quarter."
Each of those is a different conversation, with a different goal and a different outcome. If you have the surface conversation when the real one is underneath, you'll get a polite meeting and nothing will change.
Name what you're afraid might be true
The fastest way to find the real conversation is to write down the situation without cleaning it up. Include the history, the politics, and especially the part you're worried about. "I think he may be dishonest about pipeline." "I think she's outgrown the role, or the role has outgrown her." "I think I handled this badly last time."
That last sentence is usually where the real conversation lives. Leaders avoid it because saying it out loud makes it real. But the other person often already senses it, and a conversation that skirts it feels evasive to them.
Sharpen it before you schedule it
Before you book the meeting, answer three questions:
- What do I need to be true when we walk out? A decision, a commitment, or just shared understanding?
- What's my part in this? If you contributed, say so early. It changes the tone of the whole conversation.
- What happens if nothing changes? If you can't say it, the other person won't feel the weight of it.
Then write the first two sentences you'll say. Not the whole script, just the opening. Most hard conversations are decided in the first minute.
What to do this week
- Pick the conversation you've been putting off longest.
- Write the messy version, including what you're afraid might be true.
- Name the real conversation in one sentence.
- Answer the three questions and write your first two sentences.
- Schedule it within five working days.
Straight Talk
Straight Talk lets you describe the messy situation in your own words, or start from a library of the conversations that come up most in growing companies, asks only the questions that sharpen it, and then builds language you can actually use in the room.
Bring the situation. Leave with the conversation.
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Danny Feldman is a 3× founder and the advisor behind Feldman Advisory. He founded and scaled Stellar to $100M in annual revenue across 15 states, raised $55M+ as a founder, and used AI to double revenue before exiting to private equity. Earlier, he recruited and trained 55,000+ sales reps at Cutco and grew a division from 1 to 58 locations. Operator to operator, he now helps founders of $1M–$20M companies get out of the middle of the business, build the leadership team, and raise capital. Book a 30-minute call →