Why “doing fine” might be the greatest threat to your sales team.
by Brian Sullivan
There’s a slow, quiet way sales teams die.
Not from layoffs. Not from economic collapse.
Not from tariffs.
But from good years.
A string of good-enough quarters. A few reliable accounts. Comfortable margins. A sales team that’s “earned the right” to coast.
Until one day, someone looks around and realizes: We’re no longer growing. We’re just… existing. This week, I met that team.
When no one is challenged
Just a few days ago, I was on a discovery call with a sales leader. He was smart, likable, experienced – and completely aware of his team’s reality.
He told me – without flinching – that their veteran reps don’t prospect anymore.
They don’t go deeper with existing customers.
They don’t use LinkedIn.
And their idea of training? Talking strategy.
When I pulled up several of their LinkedIn profiles, most were blank. I mentioned it.
His response?
“Oh yeah, we don’t use LinkedIn. That’s more for people looking for jobs.”
I just sat there.
Here was a multi-million-dollar company, with a full sales team … proudly choosing irrelevance.
They’ve had a lot of good years. But you could feel it – deep down, this guy knew the good years had made them soft.
He wasn’t defensive. He was resigned.
So, I figured, why not just say what I was thinking?
“Are you telling me that you and your team have decided to stop improving?”
That hit him.
“No, no, no – we want to get better,” he stammered.
So, I pushed.
“You told me your reps don’t prospect,” I said. “They don’t ask deeper questions. They don’t even use the most powerful tool in modern B2B selling. You had a chance to give them two hours of focused skill development at your national meeting – and they voted it down. Why?”
His answer?
“They said there are better things we could do with that time.”
I asked, “Like what?”
He said, “We’ll talk strategy.”
“OK … strategy about what? Because if your team isn’t improving their ability to open new doors or go deeper with clients, what exactly are you strategizing?”
Silence.
And then the truth:
He didn’t want to challenge them.
Didn’t want to make waves.
Didn’t want to be the leader who “pushed too hard” after all these good years.
It hit me right there: This is what death by a thousand good days looks like.
Nobody gets fired. Nobody panics.
They just quietly accept that “good enough” is good enough.
The hidden threat of “fine”
We’re not talking about burned-out teams or failing businesses.
We’re talking about the comfortable ones. The coasting ones.
The ones that show up to meetings, know the product, hit quota – and haven’t changed in a decade.
That’s the danger.
Not the bottom 10%.
The middle 70%.
The reps who are doing “fine.”
But let’s be clear:
- Fine doesn’t disrupt markets.
- Fine doesn’t win competitive bids.
- Fine doesn’t future-proof your business. And fine is always the step before forgotten.
Want to break the cycle? Start here.
Here are 5 ways to wake up a team drifting toward average – without blowing up your culture:
1. Create a “friction ritual”
Ask your team: What did you do this week that made you sweat?
If there’s no friction, there’s no growth. Engineer discomfort. Public call sessions. Shadowing top reps. New pitch rewrites. Track the tension.
2. Audit “improvement avoidance”
What’s something they’ve been avoiding learning? LinkedIn? AI? Asking financial questions? Have everyone write down one skill they’ve avoided – and one step they’ll take to tackle it this week.
3. Replace “strategy talk” with roleplay
Every team says they “talk strategy.” Great. But if they can’t execute it live in front of peers, it’s just talk. Swap 30 minutes of strategy for 30 minutes of application. Watch what happens.
4. Measure curiosity, not just closes
Ask reps to bring one new question each week that uncovered a hidden need, a referral, or a roadblock. Reward learning behavior – not just outcomes.
5. Lead with the mirror, not the megaphone
Leaders: before you demand growth from your team, look at your own habits. Are you getting better? Are you pushing, investing, experimenting – or are you comfortable, too?
The choice to grow
On that call, I told that sales leader something I’ll tell you, too:
“Getting better isn’t for everyone. But I’ve never met someone who said ‘I regret leveling up.’”
If you’re reading this, maybe it’s time to ask the question:
Have we been slowly dying from too many good days?
And if the answer is yes, what are you going to do today to make tomorrow just a little more uncomfortable?
Because comfort won’t kill you today.
It’ll kill you eventually.
Quietly.
Predictably.
And without a fight – unless you choose to bring one.
Brian Sullivan, CSP, is the Founder of PRECISE Selling and a leading voice in B2B sales strategy. He helps companies master the art of prospecting, presenting, and negotiating – while also building elite outsourced sales teams through his PRECISE Performers division. A nationally recognized speaker and author of 20 Days to the Top, Brian’s mission is simple: turn salespeople into champions. Learn more at www.preciseselling.com.