What if that pit in your stomach before a difficult conversation isn't weakness—it's wisdom? Most founders think nervousness before hard talks signals they're unprepared. The reality? Zero anxiety means you're about to be too harsh or unclear. That discomfort is your nervous system telling you the stakes are real and the relationship matters.
The Seven-Month Problem
According to VitalSmarts' 2021 study of 1,025 managers, leaders delay crucial conversations an average of seven months before addressing them. Seven months of declining performance. Seven months of team frustration. Seven months of a problem metastasizing into something much worse.
Steli Efti, founder of Close CRM, learned this the hard way when delaying a co-founder equity conversation cost him six months of resentment. That avoidance nearly tanked the company before they restructured around honest, uncomfortable dialogue. The conversation he was dreading for half a year took thirty minutes. The damage from delaying it took months to repair.
The Calibration Check
Elite leaders don't eliminate nervousness before difficult conversations. They calibrate it. Too much anxiety and you freeze, letting problems poison your team. Zero anxiety and you come across as robotic or unnecessarily harsh. The sweet spot? Just enough nervousness to stay human and thoughtful.
If you feel nothing before firing someone or delivering hard feedback, delay the conversation. You're too detached. That detachment will come through in your tone, your word choice, your body language. The person across from you will feel it, and the conversation will damage the relationship more than necessary.
Specificity Is Kindness
Leaders think vague feedback softens the blow. "You need to be more professional." "Your communication could improve." "We need to see better results." This feels gentler in the moment. It's actually crueler because the person receiving it can't identify what to fix.
The 3-Example Rule solves this: Never enter a performance conversation without three specific incidents, complete with dates. "On October 3rd in the all-hands meeting, you interrupted Sarah twice. On October 10th, you missed the client deadline without communicating. On October 15th, you made a joke that shut down dialogue."
Concrete examples aren't harsh—they're the only kind thing you can do. They give people exactly what they need to change. Vagueness paralyzes.
The 24-Hour Telegraph
"We need to talk" without context triggers immediate panic and defensiveness. The person spends the next 24 hours imagining worst-case scenarios, which actually works in your favor if you do it right.
The 24-Hour Telegraph: Tell them a day ahead what the topic is. Not "We need to talk." Instead: "I'd like to meet tomorrow to discuss the client communication breakdown last week." Now they can prepare their perspective. They can enter the conversation ready to engage rather than defend.
Research shows this approach doubles receptivity rates. You're not trying to catch people off guard. You're trying to solve problems together. That requires both parties showing up mentally and emotionally ready.
When the Conversation Is a Surprise, You've Already Failed
If someone walks into your office and asks "Am I fired?" you've let the problem go too long. That question means they've been picking up signals you thought you were hiding. They've been anxious for weeks, performing worse because of it.
Difficult conversations should never be surprises. Small course corrections in the moment prevent big, scary conversations later. "Hey, that comment in the meeting landed poorly, here's why" takes thirty seconds. Waiting three months to address it in a formal performance review takes thirty minutes and creates resentment.
Build a rhythm of continuous feedback. Make giving and receiving corrective input normal. When hard conversations become routine, they stop being terrifying.
The Empathy-Objectivity Paradox
You need deep empathy for the person sitting across from you. They have a mortgage, kids in school, an identity tied to this role. You also need complete objectivity about whether this arrangement is working. Those requirements are in direct conflict.
If you're naturally empathetic, objectivity will be hard. You'll delay too long and fail to protect your team from a bad fit. If you're naturally objective, empathy will be hard. You'll damage relationships unnecessarily and lose people who could have been saved.
The skill to develop: Hold both at once. Be deeply empathetic about the impact on this person while skillfully separating the person from the problem. "I care about you and I see this role isn't working" can both be true.
From Avoidance to Action
That conversation you're avoiding is poisoning something right now. Team morale. Customer relationships. Your co-founder dynamic. The longer you wait, the worse it gets.
Nervousness before difficult conversations isn't something to eliminate. It's information. It tells you the stakes are real and the relationship matters. The goal isn't to feel nothing. It's to calibrate: enough anxiety to stay human and thoughtful, not so much you avoid the conversation entirely. Leaders who master this calibration build stronger teams, clearer partnerships, and faster problem resolution.
Have the conversation tomorrow.
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