Knowing What’s Actually Going On: 10 Things I Learned About Transparency & Trust

One of the biggest personal values that I’ve carried into business is an appreciation for transparency.

Change is the only constant in life and business. Some days you’re up, some days you’re down. At times you’re crystal clear and charging ahead. At other times, you’re just trying to figure out the next baby step to make progress without effing it all up.

No matter the situation, I want to work for leaders who will tell it to me straight. I want to be on a team where we look at reality together and make informed decisions. The kind of team that can join hands and say, “This might not work!” while taking an educated plunge into the void.

A culture of transparency is really hard to create, and it’s easy to lose. These are some of the practices we came back to again and again at Sercante. We didn’t execute them perfectly, and some worked better at certain stages of the company than others. But when we were at our best, these were usually part of the equation.

1. When in doubt, do it in public

In a physical working environment, you can overhear things, see things, and observe things that are outside your daily scope. This isn’t possible in the same way in a digital, all-remote environment.

To try to replicate that opportunity to “overhear” at the watercooler, the ask I made of the Sercante team was to discuss everything in public Slack channels unless it was really a secret. If it’s sensitive, create a private Slack channel. If it’s truly top secret, okay fine, bust out a DM.

Did people like doing this? No. No, they did not.

It went against most people’s natural inclination to keep circles small and then broadcast when something was “fully baked.” But there’s no better way for someone to learn than by watching the proverbial sausage get made on Slack. And when we added someone new to the team, we didn’t have to start new threads or send them screenshots—they could dive right into the feed and see where we’d been.

The more the team would “build in public,” the more others were inspired to do the same.

2. All questions are welcome (really)

Leaders always SAY that they’re open to questions. But then they show something different.

I’ve seen CEOs flat-out ignore slightly tricky questions in town halls. Or they’ll answer the question, but before they do, they’ll say:

“Who asked this? Why do you want to know?”

Or they’ll receive a question with the subtlest face scrunch that makes it look like they need to poop (sorry for the gross mental visual).

This is extremely counterproductive.

As a leader, you’ve got to recognize that asking a question when you’re not in a position of power takes guts. The act of asking means they’re invested. It means they care (even if they’re mad). And if they’re asking, someone else is thinking it.

Showing that you’re open to questions means:

• Actually taking them—with seriousness and respect
• Doing your best to provide an answer
• Being honest and direct
• At times, answering the question behind the question and sharing broader context
• Thanking the questioner (and meaning it!)

People can feel if you’re faking any of the above.

3. Lay out the fact pattern / show your work

When you’re in the driver’s seat, you’re not OBLIGATED to explain yourself. Sometimes you don’t even want to explain yourself. You just need people to get in line.

But there is tremendous value in explaining how a decision was made and what you considered.

In addition to demonstrating genuine care and thoughtfulness, “showing your work” models how you expect the team to make decisions when they’re at the wheel. Bona fide IRL examples are infinitely more valuable than any corporate training or process manual could provide.

One moment where this was especially poignant in Sercante’s journey was during COVID. We were all scared, and the business was vulnerable — we were 30 people at the time. We didn’t try to hide that. Our ELT hosted a weekly “situation room” with the whole team where we reviewed:

• Financial performance
• Clients that were growing
• Clients and deals that were slowing down
• What we knew about the market outlook and forces impacting our clients — and what we didn’t (mostly the latter)
• Expenses and how we were trying to get ahead of the need to cut costs
• An open mic check-in on how everyone was holding up

COVID ended up turning into a huge boom in business for us, so these huddles didn’t continue forever.

But during the period when emotions were running high, the whole team knew what cards were in play and how we were approaching the game. We came together as humans and treated people like the smart operators they were. And I truly think we came out of the experience stronger for it.

4. Build a rhythm around metrics

I’ll be honest—we went through periods where we were really tight on metrics and reporting, and times when we let it fall by the wayside. But in all the eras when we were crushing it and performing our best, a common denominator was a relentless focus on the numbers.

We followed an EOS-style methodology where we kept a weekly scorecard of the things that mattered most to the business, i.e.:

• Monthly Revenue – Projected
• Monthly EBITDA – Projected
• All Billable Team Utilization Rate – Previous Week
• Utilization by Team
• % Variance from Forecasted Utilization
• MQLs Generated
• SQLs Generated with Stage 2+ Opportunities
• Registration Counts for Active Events
• Bookings MTD
• Sales-Led Bookings
• Delivery-Led Bookings
• Total Pipeline Created
• Total Pipeline Closing in Quarter
• Late-Stage Pipeline (Total Volume)

Each leader was responsible for pulling the numbers for their department (usually from a Salesforce or Looker report) and inputting them into the spreadsheet. We were always on a quest to fully automate this and add a 13-week trailing view for these numbers, but we never quite got there.

When we were aligned around a common set of data, it removed a lot of “weather report” status updates that took up our exec team’s meeting time. It helped us spot what was important, zero in on what needed intervention, and move on.

Where we always fell off the bandwagon was tracking a set of metrics for six months and then saying to ourselves:

“This number isn’t really moving that much week to week, and we keep forgetting to update the spreadsheet. Should we just drop it?”

So we would drop it.

And guess what number would slip next?

5. Aggressively retro

One of the most formative books I read when starting Sercante was Extreme Ownership by Jocko Willink. In the book, Willink talks about the “after-action reviews” his SEAL team did together to evaluate a completed project, event, or incident by comparing expected outcomes with actual results.

The idea is simple: review what happened, what went well, and what could have gone better. Discuss the facts of what happened and their implications without blame or judgment. Then use all of that to do better next time.

We had a process for retroing all client projects and many internal initiatives. There is an art to this, and it absolutely needs care and reinforcement (similar to item #1 on this list).

Left to their own devices, many people will NOT share anything negative in a retro.

“The project is over. We can move on. No need to dwell on the negative,” they might reason.

While well-intentioned, this restraint is really unproductive. Encouraging a blame-free environment where you can give constructive feedback on live examples is critical.

6. “Thanks for the feedback”

There is an insane body of work on how to GIVE feedback. There’s very little guidance on how to RECEIVE feedback.

I have a favorite book on this one too—Thanks for the Feedback: The Science and Art of Receiving Feedback Well is the #1 resource if you want to do a deeper dive on this topic.

To sum up the book in one sentence: the only “right” response to feedback — whether good, bad, ugly, well/poorly intentioned, well/poorly delivered — is THANK YOU.

Feedback gives you a new data point. Without the giver being willing to make themselves uncomfortable and say something hard, you wouldn’t have that data point. Be grateful for it.

What you decide to do with that data point, of course, is entirely up to you. But now you have a new asset to deploy and consider.

7. Pulse check surveys

Starting in mid-2018, we did a monthly survey with standard questions about personal job satisfaction and satisfaction with how the team was working together. We wanted the questions to stay largely the same so we could measure longitudinal changes over time. Example questions:

• I know what I’m supposed to do every day.
• I enjoy what I’m working on.
• I have what I need to complete my work.
• I am happy with my workload.
• I feel comfortable sharing my thoughts, ideas, and differences in opinion.
• I feel like my voice is heard and respected.
• I understand Sercante’s goals and how I contribute to them.
• My pod/team is effective at sharing responsibilities for tasks.

We included comment boxes throughout so folks could provide more context on their answers if they wanted to.

All questions were rated on a five-point scale, and the expectation was that if someone answered with a 3 or lower, their manager would review it. Sometimes it pointed to a known issue they were already working to solve. Sometimes it was surprising and warranted a conversation to learn more.

We did it monthly because if someone was upset about something, we didn’t want to let too much time pass before they were heard. Weekly seemed crazy. Quarterly wasn’t enough. Recruiters are relentless, and it just takes one call on a bad day to put good people at risk!

8. No anonymous feedback

This was controversial, but it’s a hill I would die on.

I don’t believe in anonymous feedback. Pretty much ever, in any context. I believe if you have something worth saying, you should say it. You should also take the time to wordsmith it, consider your audience, and consider who your comments impact.

If you’re in an environment where honest, well-intentioned feedback is punished… well, I hope you can leave. If you’re in a better environment than that, then it’s an invitation to be brave and speak your truth.

(PS — I know a lot of very smart people disagree with me on this subject! And if you do, I would love to hear your thoughts.)

9. Mea culpa

When you fuck up — and you’re going to — just say that. There is nothing more refreshing than leaders owning their shit.

Our best leaders were quick to say:

“I did X, and expected Y. That didn’t happen. So now we’re going to try Z.”

In most cases, the team responded with grace and patience. It’s really healthy and refreshing to be part of a culture where people can own their mistakes.

10. As a leader, you own the plot

One of the biggest values leaders can provide their teams is helping everyone see the forest through the trees. That means sharing the context of where you’ve been, where you are now, and where you’re going.

We did monthly All Hands business updates at Sercante, and I always found it helpful to center myself on the last few updates we had provided the team. Nothing should feel “sudden” or “surprising” if you’re regularly communicating the health of the business.

I am often guilty of feeling super intense urgency around the ONE THING that has my attention in the moment—and intentional resetting in the context of the broader picture helped me put new asks or new headlines in perspective.

Avoiding the potholes

I know there will be Sercante alumni who read this and think:

“We could have been better at XYZ,” or, “Yeah, but we definitely didn’t do that perfectly every time.”

They’re right.

We drifted. We had periods where too much happened in DMs. We took our eye off of metrics we really should have kept tracking. We avoided hard conversations. We had to reset on these things over and over again.

That might actually be the biggest thing I learned about transparency. It isn’t a culture you create once. The natural pull is almost always toward what’s more comfortable: smaller circles, polished answers, sidebars, waiting until you have the whole story before you share any of it.

So you keep pulling the other way.

You reinforce it with new hires. You redirect when things start moving behind closed doors. You celebrate people who ask the uncomfortable question, own the mistake, or put the messy work out there for everyone to see.

We never did any of this flawlessly. But the periods when we got closest were some of the best periods we had as a team.

Turns out, transparency and everyone knowing what’s actually going on is a pretty great way to work.