The Lost Art of Setting Expectations

We offered a better product and cheaper pricing, and I still lost the deal.

The real gut punch?

The client admitted they wanted to choose us.

But I failed at something critical that no one talks about: setting expectations.

Losing deals rarely comes down to the product or price.

It’s almost always about one thing that’s been slipping through the cracks in today’s “value-added” sales playbooks—the art of guiding expectations from the first conversation.

Most clients have no idea what they want, and they certainly don’t know what they’ll get until someone spells it out for them.

And most sales reps don’t know how to do it...

Here’s what we did wrong and what salespeople everywhere are getting wrong every day:

1) We Assumed the Client Knew What They Wanted

Clients are wandering around with 75% of the picture in their heads, max.

They might know they need “better results” or “cheaper alternatives,” but beyond that, they’re clueless about the nuances.

Sure, they’ve read some articles or watched a couple of videos, but a client’s understanding of your product or service will often be shallow at best.

Assume they’ll naturally see the light at your own peril.

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2) We Oversold Features They Weren’t Ready to Value

If you think, “They need this feature, they just don’t realize it yet,” you’re about to miss the sale.

The fact is, clients don’t care about “features” unless you show them how those features translate into specific benefits for their unique situation.

If you throw features at them too early, you’ll overwhelm or worse—bore them.

3) We Never Addressed Trade-Offs

Limitations are gold in building trust.

Clients know every deal has a catch, a compromise, or a hidden cost somewhere.

If you’re not upfront about these trade-offs, they’ll suspect you’re hiding something, or worse, they’ll find it out later and feel burned.

4) We Didn’t Discuss What Success Actually Looks Like

If a client can’t describe exactly what success looks like, they’ll never be happy—even if you deliver twice what they asked for.

We’re talking about measurable outcomes, timeframes, and clear metrics.

When you fail to define these, the client’s “expectations” will morph over time, often outpacing reality and eventually leading to disappointment.

5) We Skipped the Hard Questions

Are you scared to ask the client why they’ve hesitated to move forward?

It’s shocking how many salespeople avoid this, treating objections like a live grenade.

But the reality is, if you’re not surfacing those concerns in early conversations, they’re building silently until they sabotage the deal.

The Rub

Did I lose that deal because our product was worse? No.

I lost because I was too focused on the product to pay attention to the one thing that makes all the difference: managing the client’s expectations.

I went in with assumptions instead of a roadmap, and I paid the price.

Setting expectations isn’t just a nice-to-have—it’s the foundation for every closed deal.

Clients don’t know how to build a successful engagement on their own; that’s our job.

This is the way.

Hanley

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