How the Top 1% of CEOs Handle Tough Conversations
The conversations that shape our companies' futures are often the ones we most fear having.
I learned this lesson the hard way during my second company's growth from $10M to $50M.
My head of growth - someone I admired - was struggling to scale. For three months, I watched problems multiply while I searched for the "right time" to have the conversation.
There never is a right time. But there is always a cost to waiting.
In the end, our growth engine stalled. We lost close to $10M in revenue.
All because one conversation felt too hard to have. Oof.
After building seven businesses, I've learned something counterintuitive about tough conversations: delaying tough talks always costs more than confronting them.
How the Top 1% of Leaders Handle Tough Conversations
After working with hundreds of CEOs, here's what I've noticed about how the best handle these moments:
They Trust Their Gut
When they get that first intuition that something needs addressing, they act. The gap between noticing and action spans days, not weeks.They Build Partnership
Instead of: "Your team's missing deadlines." They say: "I've noticed we're falling behind schedule. How can we solve this together?"They Eliminate Surprises
"Let's meet tomorrow to discuss the Q3 metrics. Bring the latest data so we can problem-solve together."They Accept Emotion
"I know this is hard to hear. Can we pause and acknowledge this is hard for both of us?"
Let's dive into how you can put these ideas into practice, starting with the first skill that makes everything else possible.
Trust Your Gut
The best CEOs narrow the window between spotting an issue and addressing it.
Instead of questioning their instinct or finding excuses, they take decisive action.
They know avoiding hard conversations magnifies risk and drains focus. And waiting doesn’t just impact your business; it steals your mental bandwidth.
I'm sure you've felt it:
The constant monitoring of the situation. The mental rehearsals of the conversation. The energy spent hoping things will magically improve.
This mental burden weighs on every decision you make as a leader.
Take 24 - 48 hours to frame it well. Then, schedule the call.
Build Partnership: Us vs The Problem
Frame the conversation as partners tackling a shared challenge, not opponents in conflict.
Positioning talks as "Me vs You" triggers defensiveness. This not only derails the current conversation but teaches your team to hide future problems.
The best tough conversations unite two people solving a problem together.
The simplest way to make this shift is by replacing "you" with "us."
You can build partnership by using these four tactics:
Start with shared reality: "I've noticed our release velocity has dropped 40% this quarter. Have you seen the same?"
Show commitment: "This matters because I want us to succeed. How can we solve this together?"
Define next steps: "Let’s meet weekly for the next month to track progress and clear obstacles.”
Set explicit timelines: "Let's evaluate in 30 days. What does success look like then?"
Now you have a game plan with strengthened trust. This is winning.
Remove Surprises
I've seen too many CEOs lead these conversations with secrecy and fear.
They withhold context until the very last minute, leaving others in the dark. This completely undermines the partnership.
To solve problems together, build trust through transparency. Start meetings with full context, not secrecy.
“I want to discuss our conversion rates. Please bring last quarter’s data. Add anything else you think would be helpful for our conversation.”
Your team deserves preparation, not ambush.
Accept Emotion
Even with perfect planning, expect emotions to surface. We’re all human.
When defenses rise, acknowledge feelings to find a path forward.
“I know this is a hard conversation. Let’s figure this out together.”
While this requires skill, it starts with shifting your mindset. Your avoidance has nothing to do with the outcome, it's an emotional reaction to having the conversation.
Ask yourself:
What’s the worst outcome of talking now?
What’s the worst outcome if I wait 6 weeks? How does it hurt the business?
What’s the best outcome of acting now?
What’s the most realistic outcome here?
For high-stakes, or when letting go of key people, ask: How long can the business sustain without addressing this?
Ignoring emotions - yours or theirs - always backfires.
Putting It All Together
Tough conversations shape companies more than any strategy or plan. When handled well, they transform relationships, accelerate growth, and build lasting trust.
The hardest part isn't knowing what to say - it's finding the courage to start. But once you master these skills, you'll wonder why you ever waited.
Your ability to initiate difficult conversations early will define your success as a leader. Start small. Choose one conversation you've been avoiding this week. Notice what changes when you lean into discomfort instead of away from it.
Remember:
Trust your gut - when something feels off, it usually is
Make it collaborative - frame every conversation as "us solving this together"
Lead with transparency - no one performs well when ambushed
Honor emotion - humans run your business, not robots
This shift won't just transform your company - it will transform how you lead.
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