There’s a moment before almost every stretch when your brain starts negotiating with you. You know the moment. You’ve done enough preparation. You know what you need to do. You’re sitting there looking at the next call, the next conversation, the next opportunity—and suddenly there are several other things that seem incredibly important.
Maybe you should:
- do a little more research.
- reorganize your notes.
- check that customer’s website one more time.
- get another cup of coffee.
It all feels productive. Except you aren’t actually moving.
Preparation matters in sales. A lot. Walking into a conversation cold, with no idea what is happening in the customer’s world, isn’t brave. It’s unprepared.
Think about an athlete getting ready to run. They stretch. They loosen up. They make sure their body is ready to do what they’re about to ask of it.
Eventually, they run.
That’s where things get interesting for us in sales, because there’s another kind of stretching that happens after we start moving. It’s the stretch that comes when you decide not to do things exactly the way you’ve always done them.
You ask the question you normally avoid because you’re not quite sure where the answer will take you. You call the person who intimidates you a little. You stop relying on the comfortable opening you’ve used for years and try something that might create a better conversation.
Maybe you ask for feedback on something you know you need to improve. Or volunteer for an opportunity that makes you think, “I’m not sure I’m ready for that.”
That stretch feels completely different from preparation. It feels awkward, and sometimes it feels like you’re getting worse instead of better. That’s one of the frustrating things about developing a new skill: the old way feels smooth because you’ve done it hundreds, or thousands, of times. The new way can feel clunky simply because it’s new.
Which makes it tempting to snap right back to comfortable. Don’t.
Give yourself enough preparation to move with confidence.
Then allow yourself to be uncomfortable enough to grow. There’s a difference between being reckless and stretching. There’s also a difference between being prepared and hiding in preparation.
Your job is to figure out which one you’re doing.
So here’s my challenge for you this week. Pick one thing in your sales role where you’ve become comfortable. One.
Maybe it’s prospecting. Maybe it’s asking better questions. Maybe it’s talking about money, reaching higher in an organization, asking for the business, or learning a skill you’ve quietly avoided because you know you won’t be good at it immediately.
Prepare for it. Then do it.
And when it feels uncomfortable, resist the temptation to snap back to what you’ve always done. Stay in the stretch just a little longer. You can prepare forever and never move an inch, and you can keep doing what you already know how to do and become incredibly efficient at staying exactly where you are.
Neither one will show you what you’re capable of next.
What are you going to stretch on this week?

