Scripts for the Hard Stuff: How an Executive Coach Handles Feedback, Firing and Founder Fights

Host Lenny Rachitsky admits he dreads difficult conversations and rehearses them endlessly, yet they never go as planned. Cohn responds by asking him to say precisely what is hard. His answer is that he does not want to make people sad and worries about the extra drama and work a reaction would create.

Cohn's point is that we are always putting meaning on events, and finding that meaning helps both with motivating yourself and with making the conversation go well. If you never raise the issue, you also never get the chance to help someone improve or to repair the relationship. On the far side of discomfort there can be a revelation, and even "a lot of joy and freedom."

She says the most common hard conversations are a missed promotion, a termination, and performance feedback, which comes in two flavors: you are screwing up, or I would like to see you develop in some way. Before any of them, she says, check your motive. If you are speaking to vent, wait until you can reframe the reason: you are doing it to help the person get better, because they will not be promoted or successful if the behavior continues.

Rachitsky recalls a story Kim Scott told about an employee who was terrible for eight months and then was told so, only to ask why nobody had said anything sooner. Cohn adds a client story: a division head avoided giving a colleague feedback because she would cry. When he finally did, she cried, went home, and returned the next day to thank him, saying she wished someone had told her 15 years earlier.

Cohn offers a model script for an employee named Matilda who misses deadlines without warning her peers. It opens by naming the topic, reports what the manager is hearing, reminds her that "we both know" how she succeeds here, and ends with a stated outcome: leave the meeting knowing how she will keep peers and team in the loop. Rachitsky notes how the framing makes clear it is not just the manager's grudge and gives a concrete action item.

Tone matters as much as words. Cohn wants the delivery matter-of-fact, in the spirit of "it's Tuesday, we have to have this conversation, I'm not mad." It works best when you have also built a relationship by regularly praising what goes well, so people hear you as someone who wants to help. She says you should make scripts your own, but a reliable formula that gets you to act is worth keeping.

When the concern comes from your own perception rather than from other people, such as weak writing, she suggests starting with "what I've observed." You then point to good examples to model, offer extra help, and tie the standard to the person's thinking, since writing quality reflects thinking quality. Rachitsky links this to nonviolent communication, and Cohn agrees that the goal is observable facts and stated expectations, with as little judgment as possible.

Cohn has a script for defensiveness as well. Pause, restate that you are raising this to help the person's career, observe that emotions are running high, and ask whether to continue now or later. The real value, she says, is being prepared so you do not react in kind and start a fight. If "emotional" triggers a bad reaction, use words like "I can see this is really upsetting you" or "the temperature between us has changed."

For a promotion denial, Cohn says to start by recognizing the person's disappointment and thinking through why they expected the role. The script is direct: I know this will be hard to hear, we are going external, here are two reasons, and here is my commitment to your growth, including hiring a strong people leader who will help you build skills. Rachitsky notes that stating the decision up front ends the suspense, and that the reasons help the person understand your thinking.

Cohn stresses that leaders rushing to deliver bad news forget there is a human being who needs hope for the future. She suggests following up the next week and sending a clear "I care about you" message, because people take disappointment home with them. A leader who signals care helps people stay resilient and engaged through setbacks.

If the person disagrees, the typical response is not a rebuttal of your reasons but an argument about tenure or being the only internal candidate. Cohn recommends acknowledging that view, explaining why the company's stage has changed what it needs, and refusing a "yes I do, no you don't" exchange. Rachitsky calls the mirror-back technique powerful because it makes people feel heard, and Cohn adds that you can pause and say you see it differently but the decision has been made.

Cohn says that when you fire someone, it should not be a surprise, and that this holds for the whole company's culture. Before termination comes a "final warning" conversation. Her client check is to ask, "Have you been crystal clear?" and she notes that the hand-wobble answer of "sort of" means no. Her script names the pattern, notes six months of discussions, sets a 30-day deadline, acknowledges what the person brings, and says that otherwise they will have to part ways.

Rachitsky observes that this clarity is more valuable than the firing script because it may fix the problem and avoid a firing. Cohn agrees and says it also makes a later termination easier, since nothing is new. The termination conversation itself is simple: recap the earlier talks, state that the changes were not made, bring in HR for logistics, and state the decision. She repeats that people should consult HR and a lawyer, and says she is not a lawyer.

Cohn prefers to call these "delicate" rather than merely difficult conversations, because many leaders also avoid specific praise. One manager in a training program told her she preferred negative feedback because positive feedback was just "good job" while criticism taught her something. So praise should be as specific as critique: what you saw, what benefits followed, and what to keep doing. That builds a reservoir of goodwill that helps when tougher messages come.

Cohn works mostly with founders, whose entry-level job is leader and who often lack management experience. Many absorb the idea that they should be the leader everyone loves, and so they bend over backwards for morale and avoid pushing anyone. She says this leads, ultimately, to the demise of the company because results never come and underperformers never learn there is a problem.

High engagement, in her view, is a product of a winning culture: a clear structure, everyone understands their role and its impact, they hit milestones together and celebrate. Rachitsky summarizes it as working backwards: if we win, people will be happy. Cohn adds that the right people, those who like results, then want to join.

She tells of a leader whose "avocado toast at 10 AM" ritual grew into evening socials and a culture committee while results lagged and expectations stayed vague. A cliquey, gossipy culture formed. The fix was for him to confront his discomfort with sounding like a "corporate drone," codify what culture really meant, such as measuring twice and cutting once, and part ways with one or two toxic people. After that the team gained traction.

Rachitsky recalls Sheryl Sandberg telling an Airbnb audience that constant reorgs and shifting goals are a sign of hypergrowth, and that the opposite is worse. Cohn then describes a visionary founder who failed to see that her company needed structure and accountability, which was her job to provide, perhaps via a COO. Rachitsky adds Joe Gebbia's early aversion to process at Airbnb, and Cohn says founders who try to reinvent leadership should pass through that stage quickly, since the ways to organize people to win are "well trod."

Cohn says she loves the potential of meetings, but too often teams keep meeting without continuity, so they re-meet and re-decide. Her three closing questions are: what did we decide here, who needs to do what by when, and who else needs to know. She says executive teams often make decisions and then fail to tell anyone, and that asking each person what was decided yields different answers.

On operations, Cohn likes making it one person's job, someone who enjoys follow-up, and baking the ritual into the agenda with five or ten minutes reserved at the end. Rachitsky imagines a product manager putting a doc on screen and confirming it with the room. Cohn likes that but warns someone might not speak up, so the culture should invite "No, that's not what I see."

For a six-person team she suggests going around the room, and for larger groups sampling two or three people. She adds that you do not have to be the meeting leader to start this. Rachitsky says this is how people become leaders: by doing the useful thing until everyone notices that meetings go better with you in them.

Rachitsky compares choosing a co-founder to a marriage in a business context. Cohn cites Noam Wasserman for the claim that 65% of startups fail because of conflict with founders or the founding team, and says people enter the relationship with much less care than they should. She has an extensive questionnaire, which she plans to share through a link.

The first topic is values. Cohn suggests picking about 20 from a list, narrowing to 10, then to three to five core values, and revisiting yearly. Co-founders whose values differ, for instance excellence versus work-life balance, should talk about what each means. She describes a founder frustrated that his co-founder ignored weekend messages, a conflict that came from unspoken assumptions about downtime.

Next is the vision: what success looks like when the company reaches its potential. She tells of two co-founders, five or six years in and venture backed, where one wished the company were smaller while the other had very lofty ambitions, a mismatch that was painful because it had never been discussed. Rachitsky adds that people's goals can change over time, so the conversation should be repeated.

The remaining questions cover how each person handles conflict, ideally checked with a spouse or close friend, since you may think you are neutral when you actually seethe. They also cover how you decide when you disagree, for example the person who cares most wins, the one with expertise wins, or you alternate, and what company culture each founder wants. Cohn notes that a family-like culture and a results-focused one can coexist, but pulling in opposite directions makes employees feel as though there are two companies.

In the show's "Fail Corner" segment, Cohn tells of a low point early in her coaching practice, when after a bad conversation she lay on her hardwood floor crying for an hour, afraid of what would become of her. She then took a stress nap and got up and made more calls. Her lesson is to pick yourself up and keep taking action, win or lose.

Her second story is of an early offsite that went badly, when her client suggested ending it. She was humiliated but used it to improve: aligning with clients in advance, choosing activities tied to goals, and learning the rhythm of bringing people together, through training and a mentor. Rachitsky ties both stories to imposter syndrome, noting that things did not crumble and she built from there.

Cohn also distinguishes patience problems from process problems, using a CEO who kept waiting on a stalled launch while an inexperienced product manager hid issues and fought with engineering. Signs of a process problem include having no picture of how the thing will come together, not having talked to people, and an uncomfortable silence. She also recommends a "Personal Operating Manual" covering communication style, work blocks, pet peeves, how to earn a "gold star," and delegation style, so teammates need not guess.