Steak, Whiskey, and Cigars — And Why That Sales Culture Is Dead
In one of my earlier interviews for a sales leadership role, the co-founder proudly described their sales team like this:
“We’re red meat-eating, whiskey-drinking, cigar-smoking killers. We’re aggressive as hell. That’s our edge.”
He said it with pride.
I walked away from the opportunity.
Why? Because I’ve seen how that story ends.
Aggression without accountability. Ego over execution.
High churn, inconsistent results, and a reputation no customer—or candidate—wants to touch.
I chose to join DocuSign instead.
What I found there wasn’t soft.
It was the highest-performing sales culture I’ve ever been part of.
But it wasn’t built on bravado.
It was built on something far more durable: trust, collaboration, high standards, and shared purpose.
High Performance ≠ Toxic Culture
Some sales leaders still believe that to drive performance, you need to crank up pressure, turn off empathy, and tolerate “alpha” behavior—as long as it produces results.
Let me be direct:
That’s not high performance.
That’s weak leadership.
The best sales teams I’ve built delivered consistent growth and crushed targets—without making the workplace a mental battlefield.
In fact, our top reps:
Shared deal strategy openly
Supported each other in late-stage cycles
Coached new hires without being asked
Built real friendships that lasted years after they left
And still… they closed eight-figure deals, created new industry verticals, and helped scale the company from $100M to nearly $3B.
So no—collaboration and high performance are not mutually exclusive.
They’re fuel for each other.
How We Built That Culture
Here’s what made the difference:
We hired people with values, not just resumes.
We didn’t chase résumé rockstars who “crushed quota” but left a trail of broken teams.
We hired people who wanted to win with others, not at their expense.Leaders led with consistency, not intimidation.
We coached in the open, shared feedback, and held ourselves to the same standards.
There was no yelling in war rooms. No harassment disguised as “urgency.” No power plays.We celebrated how the win happened—not just the number.
Deal closed? Great. Let’s walk through the playbook. Who helped? What worked? What can we scale?
Sales wasn’t a solo sport, and we didn’t pretend it was.We protected the team from toxicity.
No matter how much revenue a rep brought in—if they violated trust, disrespected colleagues, or spread fear instead of focus, they were gone.
Non-negotiable.We made work meaningful.
We didn’t just chase commissions. We built careers. We helped each other grow.
Some of my closest friendships today were forged in those years. That’s not soft—it’s sticky.
Culture Is a System, Not a Slogan
A great culture doesn’t mean ping pong tables or motivational posters.
It means designing a system where:
Great people want to join
Top performers want to stay
Everyone knows the bar—and wants to rise to it
No one gets a free pass for bad behavior
And leadership doesn’t confuse fear with respect
We hunted as a team, learned as a team, and grew as a team.
And we didn’t need steak, whiskey, or cigars to get it done.
Final Word
If your sales culture depends on fear, bravado, or burnout—it’s not a performance culture.
It’s a liability waiting to happen.
High standards don’t require hostility.
You can demand excellence without sacrificing values.
In fact, that’s the only way to scale it.
If you want a team that delivers consistent growth, attracts top talent, and builds something worth being part of—
ditch the steak-and-whiskey fantasy.
Build something better.