The Three Conversations Every Sales Leader Is Avoiding

July 29, 2026 • 5 min read

Most of us got into sales leadership because we were great at talking to customers. We were really good at selling stuff.

Nobody ever taught us how to talk to our team.

That's not a knock on you. It's just true. You don't know what you don't know, and most of us got promoted because we were the hardest worker in the room. Not because anyone trained us to lead people.

I know that firsthand. I prided myself on outworking everyone. More calls, earlier mornings, later nights. Then I became a leader, and I expected my team to do the exact same thing. When they didn't, my question was always, "What's wrong with them?"

Here's what's crazy, great salespeople know how to ask questions. Thing is, with our own team, we avoid the hard conversations every time. It's a little weird when you think about it isn't it? We will do one but not the other.

There are three conversations that fix this. First, someone has to have this one with you, or you have to have it with yourself. If can't, rather, won't, don't expect them to be on board.

1. The Expectations Conversation

Get clear on the standard. Activity, attitude, communication, results, follow-through. All of it. The clearer, the better.

Stop keeping this between their ears. We think it, we assume our team knows, then we get frustrated when they don't deliver. Is that on you? Or is that on them?

Say it out loud. Lay out what they can expect from you, ask them what you can expect from them. When they say it out loud, they own it.

It's as simple as: "I'd love to get clear on what success looks like to both of us. Here's what you expect from me. Once that is explained. I'd to know what I can expect from you." That's communication. And it's what opens the door to real trust. Now it's a conversation both ways. Not just you to them.

2. The Development Conversation

This is not a performance review. It's a growth conversation. It should happen every week or every other week, not in passing, not "when we get to it." Be a leader.

Ask your people where they want to improve. A good salesperson who wants to become elite knows where they're struggling. The numbers will tell you the rest.

Narrow it down, not everything, one thing. One habit, one skill, one responsibility they can own for a set period of time. Put a date on it. Make it easy

3. The Accountability Conversation

Accountability isn't "I'm telling you to do this because I want you to." It starts with the agreed-upon expectation, not your emotion, not your frustration. Be with them.

Look at the gap between where they are and where they want to be. Ask what's getting in the way. Personal? Professional? What needs to change going forward? Listen.

When you ask instead of tell, they own it. It becomes something they want, not something you want for them. That's the difference between micromanagement and real accountability. They want you to hold them to it.

Why This Works

Expectations create clarity. Your team will do the right thing because they want to, not because you make them.

Development creates growth. Growing your team is why you are the leader. Own it. You're not there to make every call and do every deal. You're there to build the people who do.

Accountability creates consistency. Consistency, not motivation, is what moves a team forward.

Most of us don't need more motivation. We don't need another video. Motivation starts the fire. Consistency is what keeps it burning.

Stop waiting for the "right time" to have these conversations. The right time is the time you make it. Put this into play at your next one-on-one and watch what happens.

Ready to build these conversations into your leadership?

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