I once worked with a founder whose company was at an inflection point.

Alex was crushing it as a bootstrapped company. He had millions in revenue with insane profit margins, the kind of metrics that would make the greatest of VCs salivate, and did it all with a lean, five person team.

But Alex’s company operated in a regulated industry.

And one day, there was an overnight change in the regulatory landscape that made him freak out.

Alex started losing sleep.

First, he was worried about whether they could continue growing revenue. Even worse - he was worried about whether they could continue sustaining what they'd already built.

He feared a significant drop in revenue. He feared layoffs. He feared the company dying.

Alex made an emergency call and we met in my office. He laid out all of this to me, and though he tried to maintain his composure, I could see how shaken he was internally.

After listening, I asked him: "How transparent have you been with your team?"

He truthfully admitted that he'd hidden most of those fears. “I don’t want them being afraid, Regina. If I told them, I’d scare them and they might leave.”

Then, I gave him “that look.” If you know, you know. It’s the “you-know-this-isn’t-true-and-you’re-lying-to-yourself” look.

Alex knew the opposite was happening.

The Ostrich Head-in-the-Sand Problem

A lot of leaders think that by hiding things, they keep their team in the dark. That their team won't feel fear if they don't know what's happening.

But most people are smart enough to understand when things change, especially when it impacts their livelihoods and jobs.

I asked him: "Do you think your team is smart?"

"Without a doubt," he said. "Of course they're smart."

"If your team is smart, then they already know these changes are going to significantly impact the business. What do you think is happening when you don't talk to them about it and instead you do ostrich head-in-the-sand?"

"…oh, shit."

The following day, he called a meeting.

Based on our coaching together, here's what Alex said:

"Here's the landscape.

Here's how it impacts our business.

Here are the very real questions we're wrestling with as a company.

I want to be completely honest and transparent with you on the situation."

He paused.

"I do believe we have a way out of this." (He added some hope, some charisma, a silver lining.) "But I want to brainstorm with all of you. You're the people I hired to own your specific roles. I believe you'll have great ideas."

Then, he waited. The silence felt deafening, and he started to think he made the wrong choice. Did he scare them away?

Then, Claire, one of his best employees, raised her hand. She said: "Thank God you said something. We thought you didn't know. We thought you were completely unaware."

Turns out, the team had already been talking about the regulatory change in closed Slack channels and private DMs. They were concerned that Alex didn't realize the impact the regulatory changes would have on the business, or - worse - that he just didn’t care and was oblivious.

In that moment, when Alex was vulnerable with his team, shared what he knew and what he didn't know, and led with hope that they'd figure it out together - his team started trusting him even more.

If he had faked composure, he would have invalidated their feelings, and his own. If he didn’t bring it up, he would be seen as ignorant.

His team would have trusted him less.

They would have said: "I don't believe this is the right person to lead our company."

They probably would have started looking for new jobs, believing the company would be dead in a couple of years.

But because Alex didn't do that, he was able to source really great ideas. The team was relatively small, so it made for a great brainstorming environment.

A year later, they not only survived the regulatory changes; they had their best year ever. They 2x'd revenue on top of where they already were at their peak. The team responded with even more trust in the CEO because he'd been so upfront with them.

The Line Between Vulnerability and Oversharing

There’s an invisible line between vulnerability and oversharing.

There's a concept I call Appropriate Trust - the level of trust that aligns with your leadership goals, team dynamics, and the long-term relationships you want to cultivate. This is one of the key pillars in leading with integrity: you're honest with yourself about what you can actually give and what kind of relationship you actually want with your team.

Ask yourself:

1. What do I want my team to say about me as a leader?

2. Realistically, what kind of relationship can I maintain given my bandwidth and skills?

3. How do I want these relationships to evolve in the future?

Answering these questions gives you clarity on the rapport you want to establish. From there, you can take actions aligned with your goals.

No matter what, the most common places where you should be investing time in building trust are:

• Communicating key information effectively and quickly

• Providing tight, constructive feedback on projects

• Being a reliable expert and clear communicator in your domain

(You can read more about Appropriate Trust here.)

Process Your Emotions Before You Share Them

It's very important for a CEO to process their emotions first before going to the rest of the team.

That usually requires talking to someone you really trust and can be completely open and honest with. That's why it's important to hire a coach.

You can't be fully honest with your co-founders, advisors, or team members:

• Advisors have different incentives in guiding you and your company

• Investors - you can't be honest with them because you worry about whether they'll participate in your next round or lose conviction

• Co-founders are already juggling a lot. Especially in the CEO position, your co-founders look to you for guidance and reassurance. Most co-founders are dealing with their own insecurities. It's not good to turn to each other for the really heavy emotional lifting.

• Your team - it's not their burden to bear your unprocessed fears

Coaches provide a great outlet for airing any feelings you have in a totally confidential, judgment-free, psychologically safe space. It helps you shift out of anger, fear, and judgment and into curiosity and creativity - both of which you need for problem-solving and doing hard things.

(You can read more about why to hire a coach here.)

The Playbook: How to Lead With Vulnerability (Without Undermining Confidence)

When I coach a leader who's about to have one of these vulnerable moments with their team, here's the preparation process.

Faking composure when your team already knows something is wrong isn’t the bravery you think it is. Brené Brown says you can’t have courage without vulnerability. Be courageous, by sharing an appropriate narrative about the truth.

The best leaders no longer pretend they have all the answers. They're honest about what they know, what they don't know, and what they believe is possible.

So my question for you is this: will you choose to be a great leader? Where will you be honest with your team?

Until next time,

📌 Resources mentioned:

• You don’t have to be best friends with your team | Coaching Founder

• The Case for a Coach | Coaching Founder

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