How do you approach an issue where you're tasked with winning over a team's trust, after they feel like trust has been broken seemingly forever?

That's the invisible constraint that nobody warns you about. 

When you inherit a team as a new leader, you are building it on top of Organizational Scar Tissue. And if you don't understand where the scars are, you'll keep triggering old wounds without knowing why your team is flinching.

Fixing the Organizational Scar Tissue: listen, damn it!

Early in my career as an operator, I remember being part of an org that hired its first senior leader from outside the org. (Cue the "ooooohs" and "ahhhhs" - we felt like a REAL big kid company now!)

I remember being initially skeptical of him - was he going to be the kind of leader we needed, or was he going to be more of the same? (To be clear: "the same" was not working, and we were going to need a huge shift to get anywhere successful.)

I remember being impressed (and I'll admit it, pleasantly surprised) that my initial read on this senior leader was totally wrong. I didn't think he was going to be great. Then, it turned out he was awesome. He was moving in a very different way than the original leaders, something we desperately needed.

I thought he was going to jump in from Day One and shake things up. But what he did instead was a Listening Tour: he went and spoke with a wide range of people in the org to get their perspectives.

In hindsight, this strategy made a lot of sense: he wouldn't be able to fix problems if he couldn't diagnose them first. And he made sure to talk to people outside of leadership, because he knew the boots on the ground were going to give him the perspective he wanted but leadership didn't yet have.

To this day, I think Listening Tours are incredibly effective. They don't have to be forever, but spending 1-2 weeks building rapport and listening is incredibly necessary.

Listening Tours are already common practice in many other industries, and I'm not quite sure why startups don't do them more often. My guess is people get antsy and anxious when it feels like they're not doing anything active. But to me, jumping in without listening is like trying to hike a mountain and not taking a second to figure out which path is the right path to take you to the view you want to see.

Remember the CTO from the beginning? The first thing I told him was to do a full round of 1-1s before changing anything.

Listening Tours are not "get to know you with no agenda" 1-1s where you ask about people's hobbies and favorite snacks.

They are REAL conversations about what's working, what's broken, and what they need from their new leader to do their best work. (Yes, you can and are encouraged to learn about their hobbies and favorite snacks...but maybe another time, you know, when things aren't burning to the ground. 🧑‍🚒)

The CTO came back from those conversations and told me:

"Some people want me to be really hands-on. Others are fiercely autonomous and just want clear goals and room to run. And a few of them are what I'd call Founder Types, engineers who want to think about the product holistically, not just write code."

That last category is interesting, and I'll come back to it. But the big insight from those 1-1s wasn't just about individual preferences. It was a clear signal that there was a HUGE gap between what the team needed, and what the team had been getting.

That gap is your prerogative. Let it inform you on where to start.

You don't need to do a Listening Tour forever. I've seen new leaders spend so long in "Listening Mode" that the team starts to wonder if they're going to lead at all.

Once you've done this for long enough (1-2 weeks max!), you need to start making moves, even small ones. Otherwise the team starts forming a new kind of distrust: "This person doesn't have a plan either. They are all listen, no action."

Roll out structure in layers

Remember how you're inheriting a team? Inherited teams already have a default way of working and existing.

Don't drop a new operating system on people on day one. Roll it out in layers.

This CTO started with the basics:

• He organized the team into small groups, pairing a senior person with a more junior one.

• He introduced weekly sprints, which they hadn't had before.

• He created async channels for each direct report so they could communicate without everything being a meeting.

None of this was revolutionary. And that’s the point! When a team has been operating without structure, even simple systems feel like a massive upgrade.

By starting small, you give people the experience of structure being helpful rather than oppressive. Each layer earns you the credibility to introduce the next one.

Here's the sequence I usually recommend:

Step 1: Establish a regular 1-1 cadence first. 

This is non-negotiable, because it's how you build the individual relationships that everything else depends on. Without regular 1-1s, you're operating in the dark.

Step 2: Introduce a shared planning rhythm. 

This includes sprints, weekly priorities, and whatever fits the team's work. The point is that everyone knows what "this week" means, and can hold themselves accountable to it.

Step 3: Layer in accountability mechanisms. 

This includes demos, check-ins, milestone reviews.

But here's the critical part: if you skip straight to accountability without earning the relationship first, you'll get Compliance instead of Buy-In.

Compliance looks like people nodding (and spacing out) in meetings, and then doing whatever they were going to do anyway. Buy-In looks like people fighting for the plan because they helped build it.

Feedback: Ask for it

Here's something I see new leaders get wrong constantly: they focus entirely on giving feedback, and completely forget to ask for it.

I coached this CTO to build a feedback loop into his 1-1s using a framework I use with almost all of my clients: Start, Stop, Continue. "What should I start doing? What should I stop doing? What should I keep doing?"

Simple, right? But the key, and this is the part most people miss, is how you respond to what they tell you.

When someone gives you feedback, especially early in your tenure, your job is to make them feel heard. Summarize what they said back to them. Thank them for it, and be a little over-the-top about your gratitude.

I know that sounds strange, but think about it: people are taking a real risk giving their new boss feedback. They need to see that it's safe and that their courage is rewarded.

Then, if you can act on even one piece of their feedback quickly, do it. That single action builds more trust than a month of speeches about "open communication."

The second part of the feedback conversation is about their experience: "On a scale of 1 to 5, how satisfied are you in your role right now?"

And finally (and most importantly), ask them: "What would make it a 5?"

Don't solve it for them. Let them sit with it, and DO NOT allow them to say, "I can't think of anything right now."

Most people, when given the space, will identify their own solutions. Your job is to remove the obstacles they identify, not to prescribe the answer. People who feel like they're shaping their own experience will fight for the team in a way that people who are being "managed at" never will.

I learned this from one of the best Chief of Staff operators I've ever worked with: the best leaders don't hand people answers. They give people ownership and autonomy.

Handling the timeline pressure

Most new leaders walk in with some kind of hard deadline. For this CTO, it was a product launch date roughly a quarter and a half out. The team knew about it, but they hadn't been working toward it with any shared sense of urgency or accountability.

The temptation for him was to come in hot and start assigning work. He resisted that.

Instead, he shared the constraints transparently. He said out loud:

"Here's the date. Here's what needs to be true by that date. Here's what I think the timeline looks like." Then, he invited the team to push back: "Tell me where I'm wrong."

Giving people the chance to challenge your assumptions does two things: first, it surfaces real risks you might have missed. Then, it gives the team ownership over the plan. Both of those are worth more than any Gantt chart.

Here's where most new leaders make a critical mistake: they treat everyone the same.

For people who are on track and working independently (High Performers), your job is to define the minimum checkpoint.

• High Performers rarely need daily standups, detailed status reports, or any other form of micromanaging.

• With High Performers, you need just enough visibility that you know things are moving and they know you trust them.

• For these types of workers, demos are usually enough. Over-managing these people is how you will lose them.

For people who are struggling, your job is to close the gap between where they are and where they need to be.

• You can sit with them more frequently.

• With average workers, be explicit about what "done" looks like.

• Make it clear you're there to help, not to hover.

Remember: there's a huge difference between "I'm checking on you because I don't trust you" and "I'm checking on you because I want to make sure you have what you need to succeed."

One-size-fits-all management is the fastest way to lose the trust of a team that already has reason to be skeptical of new leadership.

The Mirror

What's the one structural change your team needs most right now, and what trust do you need to build before you can introduce it?

If you know the change but haven't built the trust yet, that's your roadmap.

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About Regina Gerbeaux

Shortly after her role as Chief of Staff, then COO, she opened her own coaching practice, Coaching Founder, and has worked with outrageously talented operators on teams like Delphi AI, dYdX, Astronomer, Fanatics Live, and many more companies backed by funds like Sequoia and Andreessen Horowitz.

Her open-sourced write-ups on Operational Excellence and how to run a scaling company can be found here and her templates can be found here.

She lives in the Pacific Northwest with her partner, daughter, and dog, and can be found frequenting 6:00AM Orangetheory classes or hiking trails nearby.