Winning in business means choosing battles wisely, saving energy for decisions that truly matter most.
How smart leaders choose when to push back
I used to think good leaders won arguments. Early in my career, I treated every disagreement like a scorecard. If I had the data, the logic, or the seniority, I felt compelled to press until the other side folded.
It took years—and more than a few scars—to realize how wrong that was.
In business, winning every argument is easy. Winning the right ones is hard. And the difference matters more than most people admit.
The Hidden Cost of Being “Right”
Every argument has a cost. Time. Focus. Political capital. Trust.
Most P&Ls don’t show this, but the cost is real. I’ve seen leadership teams burn hours debating issues that moved nothing meaningful. I’ve watched strong operators disengage because every conversation felt like a courtroom.
Being right feels good in the moment. It rarely compounds.
As a CFO and COO, I’ve learned that the best leaders aren’t the loudest voices in the room. They’re the ones who know when to stay quiet.
Arguments Drain More Than Energy
Arguments slow teams down. They create winners and losers, even when everyone is supposed to be aligned.
Once people feel they’re being “beaten,” they stop contributing fully. They comply, but they don’t commit. That’s a silent tax on execution.
And execution is where companies live or die.
Most Fights Aren’t About the Business
Here’s an uncomfortable truth: many business arguments aren’t really about the issue on the table.
They’re about ego. Control. Fear of being sidelined. Old baggage from past decisions.
I’ve sat in meetings where we argued about a $50K expense while ignoring a $5M strategic mistake. Why? Because the smaller fight felt safer. It didn’t threaten anyone’s identity.
Learning to spot this dynamic is a career skill. Once you see it, you can’t unsee it.
Ask One Question Before You Engage
Before stepping into an argument, I ask myself one question:
Does this change the outcome?
If the answer is no, I let it go.
That doesn’t mean I agree. It means I’m choosing my energy. Silence isn’t weakness. It’s discipline.
Save Your Credibility for the Big Moments
Credibility works like a bank account.
Every time you push hard, you make a withdrawal. Every time you listen, support others, or let a small issue pass, you make a deposit.
When the real fight comes—the one that could sink the company—you’ll need that balance.
I’ve seen leaders who argued constantly get ignored when it truly mattered. The room had tuned them out.
On the flip side, I’ve watched quiet executives change the direction of a company with one sentence. Their words carried weight because they used them sparingly.
What the “Best Fight” Usually Looks Like
Your best fight in business is rarely loud.
It’s often uncomfortable. Sometimes lonely.
It might be pushing back on a growth plan that looks good on slides but breaks cash flow in six months. Or calling out a cultural issue everyone feels but no one wants to name.
These moments don’t come often. When they do, you need clarity and courage.
Three Fights Worth Having
- Cash and survival. If liquidity is at risk, nothing else matters.
- Values and culture. Bad behavior scales faster than good strategy.
- Long-term direction. Short-term wins that damage the core are expensive.
Everything else is usually noise.
Letting Go Without Giving Up
There’s a difference between letting something go and giving up.
Letting go is strategic. Giving up is passive.
You can disagree, document your view, and still support the final decision. That’s professionalism.
Some of my best calls were the ones I lost—then watched play out. When they worked, great. When they didn’t, the lesson was obvious without me saying a word.
That’s how trust builds over time.
The Long Game of Leadership
Leadership isn’t a debate club. It’s a long game.
People remember how you made them feel long after they forget who “won” a meeting.
The leaders I respect most aren’t obsessed with being right. They’re obsessed with building teams that think clearly under pressure.
That means knowing when to push. And when to step back.
Pick your fights. Be ready for the ones that matter. Let the rest pass without drama.
Your future self—and your team—will thank you.
Book Recommendation
“The Hard Thing About Hard Things” by Ben Horowitz is often quoted, but the real value is in its quiet moments about judgment, restraint, and timing. Worth a reread.
Your Turn
What’s a fight you wish you’d skipped—or one you’re glad you didn’t?
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