Hey everyone,

Most of the mistakes I see companies make when they're stuck — like, really stuck — start with the wrong diagnosis.

The instinct is to look at strategy: Go-to-market isn't landing. Product roadmap is behind. Pipeline is thin.

So you pull levers on those things. New messaging. New hires. New process. And sometimes it helps. But sometimes the growth doesn't come, the energy stays flat, and you can't figure out why.

In my experience, that's usually a culture problem wearing a strategy costume.

I know "culture" sounds like the kind of thing that belongs in an HR offsite, not a business turnaround. But I've come to believe it's actually one of the most underrated operational levers a leader has, and one of the hardest to fix once it goes wrong.

When I joined Black Duck Software, we had something most startups would kill for: a strong brand, the number one position in our category, and real customer adoption. What we didn't have was energy. The business felt stuck in a way that was hard to name at first.

It took me a while to figure out what I was looking at. I eventually started calling it a culture of optics. You might recognize it: Making your results sound better than they are, Teams optimize for looking good instead of getting better. Honest feedback becomes risky. Problems linger because naming them creates friction.

General Ulysses Grant, of all people, had a useful framework for what we needed instead. During the Civil War, he built what he called a "thinking machine" inside his army — a culture based on trust, where local commanders could take real risks without fear of retribution if they failed. The opposite of a culture of optics. Grant understood that if people are managing their exposure rather than solving problems, you've already lost.

The hard truth is simple: you can't improve what you won’t admit is broken.

Rebuilding Black Duck’s Culture: From Lifestyle Business to High-Growth Startup

When I arrived at Black Duck, the company had what I called ‘a lifestyle business on a peacetime footing’. It lacked urgency and will to win. That had to change.

Luckily, the board and the company responded. We got deliberate about rebuilding culture as a leadership discipline, not an HR initiative.

I want to be careful with that distinction. We had strong HR at Black Duck, the best I ever worked with. But culture and HR are different things. HR keeps a company healthy. Culture determines whether it wins.

One of the most important moves we made was treating culture the way we treated sales. We added it as a standing question in weekly leadership meetings — not a vague vibe check, but a real business conversation. How did it feel to walk into the office this week? Were we recruiting well? Were we retaining top performers? Were we building trust across offices in San Jose, London, and Tokyo? And we actually measured it: employee NPS, regrettable attrition, referral rates.

We put a senior leader, Tim Kenney, in charge of culture, not because HR couldn't do it, but because we wanted it owned the way a number gets owned.

Culture is the only competitive moat remaining

Mark Fusco, the former CEO of Aspen Technology — and one of the leaders I most respect — has a line I think about a lot:

“Don't pay employees to work hard. Pay them to win.”

There's a real difference. Hard work is an input. Winning is an orientation. And if your team isn't organized around a shared goal, Mark says, you'll "Lack alignment and purpose and end up overinvesting in some areas and underinvesting in others." That's exactly what a culture of optics produces.

At Black Duck, we worked to create shared moments that reinforced the winning orientation. After a strong quarter, someone asked, “Can we do a Monty Python and the Holy Grail day?” So we did. Our VP of Culture, Tim Kenney, brought in a REAL trebuchet. There were Knights Who Say "Ni" roaming the halls. It sounds silly, and it was. But it was a signal. This is a place that wins. This is a place that notices. This is a place where effort matters.

One time we even held an Irish wake when we finally retired a piece of software everyone had been quietly cursing for years. That kind of ritual creates what I'd call shared cognition — a common understanding, built over time, of what good looks like, what great looks like, and what the team simply doesn't accept anymore.

Can you put a price on Culture? Yes.

When Synopsys acquired Black Duck, they told us directly that they wanted three things we had:

  • The products and IP.

  • The sales model.

  • And the culture.

Synopsys had grown through acquisitions and hadn't built a cohesive culture across those entities. They believed what we'd built at Black Duck could help reinvigorate the broader organization.

We sold at roughly 9x revenue. Culture doesn't show up on a balance sheet, but it showed up in that outcome.

How to build a winning culture: 3 things to add this quarter

Whether you lead a sales team or run the whole company, here's a simple test: when something goes wrong — a deal slips, a launch misses, a hire doesn't work out — what happens next? Do you get curiosity, honesty, and a real conversation about what to do differently? Or do you get blame, spin, and silence?

That answer tells you everything about the culture you've actually built, not the one on your values slide.

Three things worth doing this quarter:

  1. Put "How's culture?" on the agenda — every week. Not as a vibe check. As a real business conversation with real accountability.

  2. Pick one signal and start measuring it. Employee NPS, regrettable attrition, referral hiring rate — pick one and track it consistently. What gets measured gets managed.

  3. Create one shared ritual that reinforces winning. Not performative. Not expensive. Just real.

The goal isn't to feel good. It's to build the one thing your competitor can't steal.

Next Steps

Culture is the hardest thing to build and the hardest thing to copy. That's exactly what makes it worth obsessing over.

If this resonated, I wrote a lot more about what it actually takes to build and lead a high-performing company in Unlikely Entrepreneurs — including the moments I got it wrong. It's still in the top 10 on Amazon, and I'd love for you to read it: grab a copy here.

And if your organization wants to go deeper on building a winning culture this year, I'm meeting with select teams for speaking and advising engagements. Send me a message on LinkedIn — I'd be glad to talk.

All the best,

Lou

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