How To Handle Sales Conversations So You Can’t Lose

Selling expertise should be fun.

A client put it this way (after rethinking an upcoming sales call): “I can’t lose!”

“Jamie” had been feeling stressed about this call. He was already heavily booked (with a goal to create more free time) and in theory, a “no thank you” could have been a viable response.


The lead was a former (good) client in a new role with a marquee organization. And while she dropped some clues that the budget might be small, there were also a few tantalizing signs that it could be game-changing work.

Jamie’s worry? Making sure he didn’t just say yes out of a genuine desire to help—and take on a less than ideal client.

He wanted some guardrails for the meeting to protect from over-committing.

Ironically (?), Jamie’s current client base includes one client who is no longer ideal—the kind who eats up a ton of the wrong kind of time and yet is highly fee-conscious.

Once Jamie realized that swapping out a time consuming, low profit client was on the table, well, let’s just say his stress level dropped.

Instead, we focused on how he could decide—in the sales conversation—if this new client opportunity was an exciting replacement or a non-starter. We narrowed it down to three things to learn from this call:

Does the main client have the right stuff to lead the transformation they want Jamie to help deliver?

Are they ready to embrace Jamie’s worldview which will probably mean taking a few challenging actions that they wouldn’t otherwise?

Will they commit the time and budget needed to achieving the vision with Jamie?

If they can’t or won’t jump all of these hurdles, Jamie walks away.

And if they will, Jamie decides how to integrate this new client into his practice.

“I can’t lose.”


Every sales conversation becomes a winning proposition when we reframe it as deciding if there’s an ideal fit between us.

Nothing more. And nothing less.

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