The Scripts That Make
Difficult Conversations Easier

Alisa Cohn

Executive Coach · Top 50 Coach, Thinkers50
#1 Startup Coach, Global Gurus (4 yrs running)

EXECUTIVE COACHING

Core Framework

Why Difficult Conversations Feel Impossible

"You're uncomfortable when they start crying. But honestly, the only way you're going to help someone grow is by leaning into these tough conversations."

Identify what you're really dreading, the reaction, the drama, looking wrong?
The meaning you put on top of a conversation shapes whether you have it
The other side of upset: new possibility, revelation, even joy and freedom
Not giving feedback is a choice, it has consequences too

The Scripts

Exact Language for Performance Feedback, Promotions & More

Script: Peer Feedback Issue

"Matilda, I wanted to chat with you about what I'm hearing from your peers about the way you're all interacting. They're flagging missed deadlines and your team not being in the loop. We both know the most important thing for your success here is that people can count on you, so I want us to leave this conversation knowing how you'll fix that."

Script: No Promotion This Cycle

"I know this is going to be challenging to hear, I'm not going to promote you right now. But I want you to know it's really important to me that you succeed in your career here. I want to help you find opportunities to build your skills and advance."

"What I'm hearing from your peers…", diffuses it from a personal attack to multi-source signal
"We both know…", positions you as an ally, not an adversary; credits their intelligence
"I want us to leave this conversation knowing…", ends with a clear action item, not an open wound
"Hope for the future", even the hardest message needs a path forward attached to it
Even keeled, matter-of-fact tone signals: "This is fixable. I'm not angry."

The relationship reservoir Give specific positive feedback before the hard conversation, so they hear criticism through the lens of "she tells me when things are working too," not "she hates me."

Leadership Trap

Your Job Is Not to Make People Happy, It's to Help Them Win

"They're trying to be the leader who everyone loves. But you don't want to push them because you don't want to upset them, and ultimately, that leads to the demise of your company."

The avocado-toast trap: perks and socials become a substitute for clear expectations and results
High engagement comes from winning, structured goals, clear roles, celebrated milestones, not from making everyone comfortable
Culture = how we get work done, not what snacks we have. "We measure twice and cut once" is culture.
The right people want to join a team that wins, not a team that avoids hard conversations

The reframe Making people happy = not having hard conversations.
Making people actually happy = building a team that wins, then celebrating wins together.

Playbook

How to Build the Difficult-Conversation Muscle

Step 1, Mindset check: Ask yourself, "Am I doing this to vent or to help?" Only proceed when the answer is to help
Step 2, Practice aloud: Literally wrap your mouth around the words before the meeting, not just in your head
Step 3, Open neutrally: "I wanted to chat about something I've been hearing…", matter-of-fact, not a verdict
Step 4, End with action: "I want us to leave this conversation knowing X", closes the loop, creates ownership
Step 5, Build the reservoir: Give specific positive feedback regularly so hard feedback lands in trust, not fear

The "Thank you" data point After a painful feedback conversation: "I wish someone had told me this 15 years ago. I could have had a different career.", Real report to Alisa, the day after she cried and went home early.

Contrarian

Alisa Cohn's Counterintuitive Takes on Leadership

✗ If someone cries, the conversation went badly INSTEAD → ✓ Tears are not failure. The day after crying, Alisa's client said "Thank you, I wish someone told me this 15 years ago." Emotional reaction ≠ bad outcome.

✗ A great culture means a happy, low-conflict team INSTEAD → ✓ Culture is "we measure twice and cut once", the norms around how work gets done. Avocado toast and socials are not culture. Unclear expectations destroy culture faster than conflict ever will.

✗ Visionary founders just need a great vision to lead well INSTEAD → ✓ Vision without structure = wheel-spinning. A founder who inspires but never sets goals or holds people accountable will frustrate and lose the people she inspires. Either build the structure yourself, or hire someone who will.

✗ Scripts make feedback feel robotic and inauthentic INSTEAD → ✓ Scripts are a starting point, not a cage. A formula that motivates you to actually have the conversation beats a perfect improvisation you never give. Make it your own, just start from somewhere real.