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Why Salespeople Fail (And What To Do About It)

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Why Salespeople Fail (And What To Do About It)

I know — it sounds a little harsh.

But it’s true. Many of us, salespeople, fail… and fail a lot. This is not criticism; I am here to offer my two cents if you allow me.

Now, before you start thinking this is going to be one of those “motivational tough love” speeches — don’t worry. This isn’t about beating ourselves up. It’s about being honest.

Because the truth is, failure isn’t the issue. The issue is what we do about it.

Some people sit in it. Others sprint away from it. Few actually stop long enough to ask, “What just happened, and what can I learn from it?”

I’ve been in sales long enough to know that the only way to fail less is to fail better. And that requires one thing: reflection.

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Failure Isn’t a Sales Problem — It’s a Human One

Failure is universal. It doesn’t care about your title, territory, or quarterly target. Everyone fails — teachers, athletes, parents, even the “top 1% club” on LinkedIn.

But sales make it personal. When a deal falls through, we don’t just lose business — we often lose a little confidence, too. And that’s when the mental chatter begins:

“Maybe I’m not cut out for this.”

“They just didn’t get it.”

“Next quarter will be better.”

Sound familiar?

Here’s what I’ve learned: failure always brings data. Every “no,” every ghosted email, every conversation that didn’t convert is information — and when we use it right, it becomes growth fuel.

The trick is having a process to translate that pain into progress.

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Why I Have a Process

Years ago, I realized I was letting sales define my emotional weather. A good day meant sunshine and confidence; a bad day meant clouds and self-doubt. I needed a way to stabilize — to stay grounded, whether I closed a deal or lost one.

Especially because emotions do not serve us in any way if we don’t understand what triggers them.

What I mean is that beating yourself up when you fail and not looking back at what causes it is definitely not a way to get better. Also, celebrating that great win and not checking what you did to get there doesn’t serve you any better as well.

Can I give you an example?

Back when I was selling IT, I closed a deal that represented my whole year's quota. I was thrilled; everyone was celebrating me. Then, the month ended, and the next month started. I wasn’t able to close a big deal during the new month; actually I didn’t close anything, for that matter. I was too concentrated on that one deal that I completely neglected the rest of my pipeline.

What happened? Everyone expected that I would continue to close big deals (me too), but the truth was that I didn’t know how I got that one in the first place.

That’s how my reflection process was born. It’s what keeps me centered when things go wrong and curious when they go right (so I can repeat it).

I promised my two cents, right? Over the next three weeks, I’ll walk you through it:

  • Next week: How your attitude shapes your performance (and your paycheck).
  • Week 3: Why technique matters more than talent.
  • Week 4: How behavior — those daily actions — makes all the difference.

These are the same principles I use myself and with my clients — practical, not theoretical.

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Two Things to Try This Week

  1. Normalize failure. Write down one deal that didn’t go as planned and identify three neutral reasons why. Avoid judgmental words like “bad” or “lazy.” Just capture the facts.
  2. Celebrate micro-wins. Every good call, every scheduled follow-up, every “let’s talk next quarter” is progress. Stack those small wins, and watch your confidence rebuild itself.

Failure doesn’t make you a bad salesperson — it makes you a learning one.

And that’s exactly where growth begins. If that makes sense to you, schedule a discovery call and let’s have a chat.

Talk soon, Tati