Why Transparency Never Gets Easier (And That's Actually Good)
The compound effect of choosing courage over comfort
I need to tell you something that might surprise you.
After 20+ years of leadership, hundreds of difficult conversations, and countless moments of radical transparency—I still get scared every single time.
That knot in your stomach before you have to tell your team the funding didn't come through? Still there. The mental rehearsal before explaining to your boss why the roadmap is in jeopardy? Still happens. The stories you tell yourself about how everything will fall apart if you're completely honest? They never fully go away.
And here's the thing: that's exactly as it should be.
The Transparency Myth We Need to Bust
Somewhere along the way, leadership advice started treating transparency like a light switch. "Just be transparent," they say. "Just tell the truth." As if courage is something you flip on once and never have to think about again.
That's complete nonsense.
Transparency isn't a destination you arrive at—it's a tax you pay every single time you choose to lead with integrity instead of taking the easy way out.
Why Your Fear Makes Perfect Sense
Let's be honest about what transparency actually costs:
When you explain your decision-making logic to your team, you're opening yourself up to challenge. Someone might disagree. Someone might see a flaw in your reasoning. Someone might have a better idea that makes you look foolish for not thinking of it first.
When you share the real financial situation with your organization, you're risking panic, résumé updates, and that awkward conversation with your top performer who suddenly wants to "explore other opportunities."
When you admit to your leadership team that you don't actually know the answer, you're betting your credibility on the chance that honesty will build more trust than fake confidence.
These fears aren't irrational. They're completely logical responses to real risks.
The Stories We Tell Ourselves
Your brain is an expert at catastrophic storytelling. Before every transparent conversation, it helpfully provides a full disaster movie:
"If I tell them we might have layoffs, half the team will quit immediately."
"If I admit I made the wrong hire, they'll question every decision I make."
"If I show uncertainty about our strategy, they'll lose confidence in my leadership."
"If I'm honest about our competitive position, it'll demoralize everyone."
Here's what I've learned after countless scary conversations: your brain is usually wrong about the ending.
What Actually Happens
Yes, transparency is uncomfortable. Yes, it opens you up to challenge and debate. Yes, sometimes people don't like what they hear.
But here's what your fear-brain doesn't tell you:
People can handle way more truth than you think they can. In fact, they're probably already sensing most of what you're afraid to say. Your transparency doesn't create the problem—it creates the opportunity to solve it together.
When you explain your logic, smart people don't attack you for having gaps. They help you fill them. When you share difficult realities, committed people don't run away. They lean in to help figure it out.
And when you admit you don't know something? That's when real collaboration begins.
The Courage Compound Effect
Here's the secret about transparency courage: it doesn't get easier, but you get stronger.
Each time you choose the hard conversation over the comfortable silence, you're building what I call "transparency muscle." Not because the fear goes away, but because you get better at acting despite the fear.
You start to recognize the stories your brain tells you. You develop better instincts about timing and approach. You learn to trust that your team can handle the truth, even when it's difficult.
Most importantly, you start to see the compound returns: teams that trust your honesty, decisions that get better because they're made with full information, and organizations that solve problems instead of hiding from them.
Your Transparency Toolkit
Before your next scary-but-necessary conversation, try this framework:
Ask yourself: If I don't share this information and someone finds out later that I had it, how would they feel? How would I feel in their position?
Remember: You're not sharing information to make people feel good. You're sharing it so they can make informed decisions about their work and their lives.
Get practical: You don't need the same conversation with everyone. Tailor your message to each audience, but don't use that as an excuse to avoid the conversation entirely.
Check your logic: Are you explaining your reasoning clearly? Smart people can disagree with your conclusion while respecting your process.
Own the outcome: If people are surprised by something you should have communicated earlier, don't blame them for not listening. Ask yourself how you could have communicated more effectively.
The Leadership Differentiator
I've come to believe that transparency is one of the clearest dividing lines between managers and leaders.
Managers filter information to avoid discomfort. Leaders share information to enable better decisions.
Managers tell people what they think they want to hear. Leaders tell people what they need to know.
Managers avoid difficult conversations until they become crises. Leaders have difficult conversations to prevent crises.
Your Courage Permission Slip
If you're reading this and thinking about a conversation you've been avoiding, consider this your permission slip to be scared and do it anyway.
That fear you're feeling? It means you care about the outcome. It means you understand the stakes. It means you're taking your responsibility to your team seriously.
The story your brain is telling you about how everything will fall apart? That's just your brain trying to keep you safe in the short term, even if it hurts you in the long term.
You don't need to wait until you feel brave. You just need to act while you're scared.
The Truth About Truth-Telling
Leading with transparency isn't about being fearless. It's about being afraid and choosing courage anyway.
It's about valuing your team's right to make informed decisions more than your own comfort.
It's about building the kind of organization where problems get solved instead of hidden, where people can plan their lives around honest information, and where trust gets built through consistent truth-telling rather than comfortable lies.
The fear never fully goes away. But neither does the impact of leaders who choose transparency despite that fear.
Your team is counting on you to be brave enough to tell them the truth. Even when—especially when—it's scary.
Josh Anderson
Editor-In-Chief
The Leadership Lighthouse
From the Studio
This newsletter came from a heated conversation Bob Galen and I had about transparency in leadership—specifically, why so many people treat it like it should be easy when it's actually one of the hardest parts of leading well.
We dove deep into the real challenges: how to share context without overwhelming people, when to explain your logic versus when to just ask for trust, and why the scariest conversations are often the ones your team needs most. Bob and I also explored the subtle art of being transparent in all directions—not just with your team, but with peers and leadership too.
If you want to hear us work through the messy reality of truth-telling as a leader, including some specific scenarios that might sound familiar to your own leadership challenges, check out our latest episode.
Listen wherever you get your podcasts or watch on YouTube.