One of the advantages of being an experienced inside sales leader is that you’ve probably heard just about every sales problem imaginable.
You’ve coached salespeople through stalled opportunities, difficult customers, missed prospecting commitments, disappointing results, and the occasional situation that makes you wonder what on earth someone was thinking.
Over time, you begin recognizing patterns. A salesperson starts describing a situation, and something sounds familiar. You’ve heard this before. You remember what worked last time, and you’re already thinking about what advice to give.
Sometimes you’re absolutely right.
But I wonder how often we get so caught up in recognizing a familiar problem that we stop paying attention to what’s different about the situation in front of us.
Your Experience Can Create Expectations
Imagine a salesperson comes to you frustrated because they’re having trouble getting prospects to agree to appointments.
You’ve coached this issue before. You know the salesperson’s opening statement could use some work, and you’ve been meaning to spend more time practicing it with them.
So when they tell you they’re struggling, you immediately start thinking about how to improve their opening.
Except you haven’t asked enough questions to know whether that’s what’s happening.
Perhaps they’re reaching the wrong people. Maybe their conversations are going well, but they’re uncomfortable asking for the appointment. They could even be doing everything you’ve coached them to do, but they’re measuring their progress against expectations that aren’t realistic for the market they’re calling into.
Each situation requires a different coaching conversation.
And your experience, valuable as it is, may have led you toward a solution before you understood the problem.
What Happens When You Think You Already Know?
I think one of the more difficult leadership habits to recognize is how quickly our own thinking can take over a conversation.
We’re listening to our salesperson, but we’re also comparing what they’re saying to what we’ve experienced before. We’re deciding what the problem probably is, thinking about what they should do differently, and figuring out how to explain it.
Meanwhile, the salesperson is still trying to tell us what’s happening.
It’s particularly easy to do when you’re busy, when you’ve had the same conversation several times, or when you’re frustrated because the salesperson isn’t making the progress you expected.
And sometimes we’re so certain we understand the situation that we don’t recognize how much of the explanation we’ve supplied ourselves.
Diagnose Before You React
One of the leadership principles I keep coming back to is Diagnose Before You React.
Before deciding how to help a salesperson, you need to understand what’s preventing them from being successful. Are they unable to do what’s expected? Are they choosing not to do it? Or do they genuinely not know how?
Those are very different situations, and they require different leadership responses.
The challenge is that you can’t diagnose effectively when you’ve already decided what you’re going to hear.
That means being willing to ask another question, consider an explanation you weren’t expecting, and occasionally discover that your original assumption was wrong.
Your experience should help you recognize what might be happening. It shouldn’t prevent you from discovering what actually is happening.
Pay Attention to Your Own Expectations
Think about the next coaching conversation on your calendar.
Before you walk into it, consider what you already believe about the salesperson and the situation you’re planning to discuss.
What do you expect them to say? What explanation are you anticipating? Have you already decided what needs to change?
Those expectations may turn out to be correct, but they’re worth recognizing before the conversation begins.
Because once you’re aware of what you expect to hear, you have a better chance of noticing when your salesperson tells you something different.
Your leadership challenge this week: Before your next coaching conversation, identify one assumption you’re bringing into it. Then make sure you give your salesperson enough room to challenge that assumption.
You may find yourself having a very different conversation than the one you planned.

