🗣️ Lead with Radical Clarity
Transparency is a practice at Charlie. Every month, the team shares:
- Cash in the bank
- EBITDA and adjusted EBITDA, with clear definitions
- Gross profit, OpEx, and free cash flow
- A traffic-light company health rating (Red, Amber, Green)
“There were times where we were in red mode… no salary raises, no promotions, no extras. And when we moved to amber, we reintroduced those things. We were very specific about what numbers we needed to see before that happened.”
Even during difficult months, they do not hide performance. This consistency reduces anxiety and builds trust that leadership will not keep the team in the dark.
💡 What you could try…
- Start a simple monthly “state of the business” meeting with just three slides: revenue, costs, and health status.
- Be upfront about what the numbers mean for things people care about like hiring, raises, or budgets.
- Keep the format the same every month so the team builds familiarity and confidence over time.
- You might also like Safely Increasing Transparency on Business Finances (public example)
📚 Teach the Business
Charlie treats financial literacy as a skill-building exercise for everyone. Their monthly 20-minute all-hands follows the same format so the team builds fluency:
- Revenue: total revenue, revenue mix, churn
- OpEx: one cost area spotlighted each month (for example software spend or salaries)
- EBITDA: shared as both monthly and trailing 12-month trends
- Definitions: every metric is defined every single time
“We do this until it grumbles into people’s heads.”
This approach has turned team members into better operators.
One example Ben shared: after a round of promotions and salary bumps, a team member flagged that EBITDA would take a hit and connected that to why a price change was needed.
“That’s the dream- when someone understands how the engine works.”
💡 What you could try…
- Pick one business metric to teach your team this month.
- Explain what it means, why it matters, and how their work affects it.
- Repeat that explanation regularly until it becomes second nature for everyone.
🏗️ Make Transparency Commercial, Not Just Cultural
Ben says most founders will tune out if you pitch transparency as a soft, feel-good idea. Instead, frame it as:
- Building a more commercial and outcomes-focused organization
- Laying the groundwork for fast and decisive action when tough calls are needed
- Creating alignment so the whole company can move in the same direction
“Being transparent isn’t about being nice. It’s about being able to make tough decisions quickly because everyone already understands the why.”
For hesitant CEOs, he suggests finding allies such as other leaders, board members, or advisors to make it a joint effort rather than a solo crusade.
💡 What you could try…
- When asking for more openness, connect it to business outcomes like speed, alignment, and decision-making.
- Start small by sharing context on one upcoming decision and asking for feedback.
- Look for allies who can back you up so you are not carrying the case for transparency alone.
👥 Hire for Coachability and Awareness
When hiring leaders, Ben looks for two things:
- Self-awareness: do they know their own gaps and triggers
- Coachability: are they willing to change their mind when presented with new data
“Strong opinions, loosely held- that’s the magic mix. Strong opinions, strongly held is no use for anyone.”
He recommends six-month probation periods for leadership roles rather than the usual three months because it takes time to truly see if someone is aligned with a culture of openness.
💡 What you could try…
- Add questions in interviews to test for self-awareness and openness to feedback.
- Build in a longer probation period for leadership hires so you can see how they work in real conditions.
- Watch how they respond to coaching or challenges in their first months.
🔧 Normalize Mistakes and Course-Correct Fast
Ben does not pretend to be perfect and does not want his team to expect it.
Earlier this year, he realized he had allowed the company to get distracted and lose focus. Instead of glossing over it, he opened an all-hands by saying:
“Truthfully, this is on me, and I’m sorry.”
He then laid out the refined strategy, the decisions they were pushing down, and how he was personally working on improving strategic focus.
“I can’t promise I won’t make mistakes again, but I can promise that when I do, we’ll be honest about them and fix them fast.”
This approach models humility and makes it safer for the whole company to own and learn from missteps.
💡 What you could try…
- Tell your team about a recent decision you would handle differently if you had the chance.
- Share what you learned and what you will change going forward.
- Encourage your team to do the same in retros and 1:1s.
🪵 Stay Grounded
Even while building a three-year plan, Ben keeps himself focused with the mantra:
“Chop wood, carry water.”
It is a reminder to stay present, do the basics well, and avoid being swept away by big visionary thinking. This keeps the business steady and the team focused.
💡 What you could try…
- Review your own to-do list and cut one thing that is adding noise instead of impact.
- Focus on doing the basics well this week and celebrate that progress with your team.
- Remind everyone that consistency beats heroics over the long term.
🎯 Build with Focus and Intentionality
Charlie deliberately serves micro and small businesses, typically under 100 employees, even though moving upmarket could be more lucrative.
“If we wanted to make more money, we probably could have gone further up market… but we haven’t, because I’m very passionate about what it means to start a company.”
Their product is designed to be quick to adopt, something a founder can set up in about five or six minutes. At that stage, leaders are just trying to survive and do not have time for complexity.
💡 What you could try…
- Get clear on the type of customer you most love to serve.
- Write down why you serve them and what makes that choice meaningful for your team.
- Share that story in a team meeting so everyone understands who you are here to help.