Direct answer: I don't trust reps who've never struggled because they haven't built the resilience that separates good from great. If you've never watched a sure-thing slip or fought through a slump, you haven't developed the judgment that pressure demands.
I once ran a deal that had everything: a mutual action plan, a coaching champion, C-level visibility, a signature date on the calendar. Then a first-time procurement lead showed up late, refused coaching, and the deal stalled out like a plane losing lift. Leadership pushed. I pushed back harder than I should have, and I fractured relationships I'd spent months building. We eventually closed it, but we lost revenue and trust along the way.
Even a Perfect Process Can Still Lose
Looking back, the signals were there. We assumed procurement was a formality. We never built a fallback communication plan. We didn't confirm who actually owned the budget path, and I let urgency override empathy. Deals aren't decided by your methodology. They're won or lost in how you adapt when pressure hits.
Struggle Builds the Reps Naturals Never Become
We love celebrating the naturals, the reps who hit quota without prep and make it look easy. They get promoted fast. But the moment market conditions shift, cycles stretch, and urgency disappears, those naturals often get exposed. They've never had to fix a broken deal, fight through a slump, or ask for help. Struggle builds humility. Humility leads to preparation. Preparation leads to consistency.
Pressure Is the Environment, Not a Moment
Your champion will leave. Procurement will delay. Legal will blow up your timeline. You can't prevent this, only prepare for it. The best reps build a plan for what happens when things go off script: what's the next move if someone goes quiet, who else can help internally, what if the budget changes, what does success look like now.
How I Hire and Coach for It
When I interview reps, I ask one question early: tell me about a deal that slipped out of a quarter. A soft answer, or one that blames the buyer or the pricing, tells me they're not ready. A rep who pauses, reflects, and walks me through what they learned earns my attention, because that kind of learning is earned, not taught.
On my teams, we train before the breakdown. I call it the vision of good: practicing what great looks like in real scenarios, not theory. How to write a recovery email when a buyer ghosts. How to slow down a deal that's getting rushed. What to say when the champion doesn't have access to power.
Want your team trained for the pressure moments, not just the easy ones?
See Sales LeadershipFrequently Asked Questions
Why does struggle matter for sales reps?
Struggle builds humility, humility leads to preparation, and preparation leads to consistency. Reps who've never lost a deal haven't been forced to build a plan for what happens when things go off script, which is most of enterprise sales.
What question reveals whether a rep has really struggled?
Ask a candidate to describe a deal that slipped out of a quarter. A soft answer, or one that blames the buyer or pricing, is a red flag. A candidate who pauses, reflects, and walks through what they learned is worth a closer look.
Is it bad to be a naturally talented seller?
No, but naturals who've never had to fix a broken deal or fight through a slump often get exposed the moment market conditions shift, cycles stretch, or urgency disappears. Talent without struggle is untested.
Why is asking for help a strength, not a weakness?
Nobody closes a seven-figure deal alone. Reps who pull in support from pre-sales, legal, execs, and peers make fewer assumptions and close more predictably than reps who try to carry the deal by themselves.