Ask any scale-up CEO what keeps them up at night, and you’ll hear the usual suspects: Market shifts, competitive pressure, or hitting that next revenue milestone. But the real challenge, the one you won’t find on any dashboard, is keeping your team connected as the pace of technology accelerates and complexity multiplies.
And yet, building a scale-up shouldn’t just be challenging. It should be energizing. You’ve already done the hard part of getting here. Now it’s about leading with clarity, fostering connections, and creating something meaningful together.
Some of the hardest moments I’ve faced as a leader didn’t fracture my teams; they brought us closer. That’s the power of consistent alignment, mutual trust, and a shared sense of purpose. And it’s up to the CEO to cultivate it.
CULTURE IS BUILT IN THE SMALL MOMENTS
Culture isn’t something you print on posters or reserve only for company-wide events. It’s built and reinforced in the quiet, everyday moments: How leaders show up, how feedback is received, and how people treat one another under pressure.
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At every offsite meeting, I share a slide that reminds the team what we stand for, and frankly, how I expect them to behave and participate: Collaboration, mutual respect, and accountability. Not because we’ve had issues, but because it sets the tone before any problems arise.
Years ago, a mentor told me, “I used to work in an emergency room. That was stressful. This is software.” It’s a reminder that we can navigate complex challenges without panic. If leadership is steady, curious, and composed, that behavior cascades throughout the organization and becomes the company’s ethos.
ALIGNMENT IS A DAILY HABIT
Misalignment doesn’t happen all at once. It builds slowly when there’s a gap in clarity or communication. That’s why rhythm and structure matter. Scheduling regular off-site meetings, holding 1:1s, sending team updates, standups, and pipeline meetings are essential. These aren’t box-checking exercises. They’re vital recalibration points that keep everyone on track.
When alignment is strong, people don’t feel burdened. In fact, it becomes a source of momentum. Problems become shared puzzles to solve, not individual battles to fight. You don’t need to micromanage if everyone knows why they’re doing the work and how it ladders up to the broader mission.
BE VISIBLE. BE CURIOUS.
Leadership doesn’t just live in the boardroom; it shows up wherever trust is built. When I joined Alteryx, I dove into product challenges. I asked people in the company how to solve them. I genuinely wanted to learn.
I’d sit down with engineers and say, “Walk me through this. Help me understand what’s working and what’s not.”
That kind of curiosity speaks for itself. It tells your team through action that you care about what they are building.
Leadership isn’t about having all the answers, it’s about showing you care enough to ask the right questions and truly listen.
GET CLOSE TO FEEDBACK AND OUT OF THE ECHO CHAMBER
As your company scales, it becomes harder to stay close to what’s really happening. Hierarchies form. Reporting structures grow. And before you know it, important insights are filtered, softened, or delayed.
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Don’t wait for formal processes like large-scale surveys or formal meetings. The most valuable feedback often comes from unscripted conversations. I prioritize informal moments, I prioritize informal moments, such as grabbing coffee with team members during office visits or checking in with customers. If you’re only hearing good news, you’re missing the whole picture.
COHESION REQUIRES CLARITY (AND TRUST)
The biggest threat to a team isn’t disagreement, it’s distrust. Suppose a leader brings up concerns regarding a colleague in another department. It might be tempting to commiserate, especially if some of those concerns mirror your frustrations. But the moment you show daylight between yourself and another leader, you weaken the whole system.
The better move is harder. While still acknowledging the concern, it’s important to reinforce your confidence in the team. For example, you could say: “I hear you. We’re working to define a new category, and that comes with some trial and error. They are still finding their footing, but your last meeting with them sounded like a step forward.”
This doesn’t mean brushing aside valid issues. It means addressing them directly, with a plan, not through side conversations.
Yes, this approach takes more intention and energy. But it preserves trust and cohesion. People expect transparency, fairness, and support. And when they feel those things from you, they bring their best in return.
And then, importantly, bring folks together cross-functionally to address the issue raised together, moving the business forward to maintain faith and trust in your leadership team.
KEEP IT HUMAN
The best teams aren’t just productive; they’re connected. That sense of connection takes effort to create. Leaders build it through repeated, intentional acts of trust, engagement, and shared experience. When employees feel heard and customers feel valued, momentum follows.
You can’t be everywhere, but you can be present in the moments that matter. Stay curious. Stay consistent. Reinforce the “why.” Keep your ear to the ground. When people see that from their leaders, even the most challenging work becomes meaningful. If hard things look energizing, not terrifying, people want to be part of that kind of team.
At the scale-up stage, it’s easy to focus on metrics and mechanics. But what truly sets exceptional companies apart are the human intangibles: Trust, culture, and emotional glue that hold everything together. And those start with you.
Andy MacMillan is the CEO of Alteryx.