When Strategy Becomes Personal

 You can tell when it shifts.

At first, strategy is something leaders talk about like it’s external. A plan someone else made. A target someone else set. A deck they were asked to present.

But if they lead long enough and care deeply enough, it changes.
It becomes something they own.
Something they shape.
Something that starts to sound more like them.

That’s what came through in our conversation with Chris Strammiello on Episode 25 of Some Goodness.

It wasn’t just strategy.
It was strategy with fingerprints.

From Execution to Creation

Most sales leaders earn their place by being exceptional executors.
They follow the plan. Deliver results. Run the playbook with discipline.

But Chris drew the line clearly: there’s a moment when following the plan isn’t enough. At the top, you're no longer judged by how well you execute someone else's strategy.

You're measured by how well you build your own.

And that kind of leadership doesn’t reward precision.
It rewards perspective.

You’re not just driving outcomes anymore. You’re shaping direction.

What You Don’t Like Might Be What You Need

There was a line in the conversation that stuck with me.

Chris said: “Sometimes the body part you like to train least is the one you really need to train most.”

He was talking about marketing events, not his favorite, but it applies to just about everything.

The parts of leadership we tend to avoid?
They're often the ones growth will eventually demand.

You don’t get to skip what makes you uncomfortable.
You have to grow through it.

Not because you love it.
But because the business needs it.

Seeing Beyond the Center

Chris pointed out something that’s easy to miss. A lot of sales leaders know their customers. They know their space. They’ve built playbooks that work.

But what they often lack is the ability to discern what is happening outside of that center.

They don’t see what’s next.

Growth isn’t just about going deeper into what you’re good at.
It’s also about looking sideways, at adjacent opportunities, neighboring needs, emerging gaps.

That’s where leadership starts to move from tactical to strategic.
And from narrow wins to new markets.

If You Want Support, Bring the Proof

When it comes to board conversations, Chris doesn’t sugarcoat it.

“It’s all about the numbers,” he says. Strategy without proof is just an idea.

If you want momentum behind your growth plan, show why it works:

• Back it up with numbers.

• Show it’s repeatable and scalable.

• Lay out the upside and the risk.

• Demonstrate that your peers support it, too.

You’re not just trying to be persuasive.
You’re trying to be credible.

And credibility is the bridge between your vision and their approval.

Alignment Comes from Ownership, Not Agreement

One of my favorite parts of the conversation was this:
If you want your team to align, involve them.

Let them help shape the last 10 percent.
Ask the questions you’re actually willing to act on.
Don’t surprise them with a plan, help them see their fingerprints on it.

Because when people help build something, they’re far more likely to carry it.

Chris said it simply: “It’s not your pitch, it’s our pitch.”
That’s true inside the company, not just in front of the board.

Leading When the Strategy Isn’t Yours

Of course, not every leader gets to build the plan.
Sometimes, you’re handed one.

Chris’s advice? Ask the questions anyway.
Don’t fake alignment. Get to the truth of it.

Then once you’re clear, own it.

Because your team will take their cue from you.
If you hesitate, they’ll hold back. If you second-guess, they’ll stall.

Leadership doesn’t require agreement.
It requires conviction.

Even when you didn’t write the strategy, you're now its advocate.
And that means clarity has to start with you.

Own the Morning

At the very end of our conversation, Chris shared something quiet. Something real.

He gets up early. Not because he’s a morning person. But because that’s when the day still feels like his.

He reads. He walks. He puts his feet in the sand. Watches the sunrise over the water.

“It’s hard to have a bad day after that,” he said.

It reminded me: we don’t just lead teams or shape strategy or drive outcomes.
We carry weight. A lot of it.

And we need spaces to reset.
To breathe.
To remember who we are before the meetings start.

Because that’s where clarity begins.
And clarity is what others are following.

🎧 Listen to the full conversation with Chris Strammiello on Some Goodness