LLenny's Podcast
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Alisa Cohn (executive coach)05 January 2025

Scripts for difficult conversations: Giving hard feedback, navigating defensiveness, the three questions you should end every meeting with, more

7Frameworks
14Insights

Frameworks in this episode

Leadership4 steps

Patience vs Process Diagnostic

When something's stalling, know whether it needs more patience or a process intervention

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Communication6 steps

The Constructive Feedback Script

Deliver hard feedback with observable facts, shared-knowledge framing, and one clear leave-with action

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Entrepreneurship5 steps

The Founder Prenup

Talk through values, vision, conflict, decisions, and culture before you co-found

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Communication5 steps

The Personal Operating Manual

A working-style 'read me' so teammates know how to work with you before friction starts

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Leadership5 steps

The Pre-Firing 'Crystal Clear' Conversation

Before you fire anyone, have the deal-breaker conversation that makes firing never a surprise

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Leadership5 steps

The Promotion-Denial Conversation

Deliver the no upfront, give the reasons, then paint hope for the future

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Productivity4 steps

The Three Questions to End Every Meeting

Close every meeting with: what did we decide, who does what by when, and who else needs to know

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Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Hot Take· 3

Hot Take38:30

Your Job as a Leader Isn't to Make People Happy

Alisa pushes back on the instinct, common among first-time founder-leaders, to be the leader everyone loves. Bending over backwards to keep morale up while avoiding hard feedback lets subpar performance fester and can ultimately kill the company. The real job is to drive toward results and build a winning culture, even when that means ruffling feathers.

  • New founders default to being the leader everyone loves
  • Avoiding hard feedback to keep people happy lets poor performance fester
  • Happiness is a byproduct of winning, not the goal itself
  • A winning culture requires redirecting people and sometimes ruffling feathers

“so you're just going to keep hoping it works out ultimately that leads to the demise of your company”

Alisa Cohn · 40:00

“sometimes in doing that you have to redirect people and ruffle their feathers essentially”

Alisa Cohn · 41:00
#leadership#founders#culture#management
Hot Take48:00

Founders Try to Reinvent Leadership, Then Reinvent Process Anyway

Many founders are mavericks who want to run a company with no process, no hierarchy, and pure autonomy. Alisa blesses the experiment but notes they almost always end up reinventing the same process, roles, goals, and OKRs for themselves. The ways to organize people to win are well-trodden, so she advises getting through the reinvention phase quickly.

  • Founders often want no process, no hierarchy, and total autonomy
  • They usually end up reinventing process, roles, and goals anyway
  • The mechanics of organizing people to win are well-established
  • Move through the experimentation phase fast rather than reinventing the wheel

“so many of the founders I've worked with want to reinvent leadership right they want to have it with no process they want to have…”

Alisa Cohn · 48:00

“the ways to like structure a group of people and get them organized so they can win are kind of like well trod”

Alisa Cohn · 49:00
#founders#leadership#process#scaling
Hot Take1:19:30

The Joseph Campbell Line That Animates Her Life

Alisa shares the Joseph Campbell quote she lives by: if you can see your whole path to the end, you're following someone else's; your own path only becomes clear step by step. She finds it empowering because not knowing where it all leads is normal and even a good sign.

  • Seeing your entire path means you're on someone else's path
  • Your own path clarifies moment by moment, as each foot hits the ground
  • Not knowing the full route is normal and even a positive sign

“if you can see your path all the way through to the end you are following someone else's path your path only becomes clear Moment…”

Alisa Cohn · 1:19:30
#philosophy#motto#career#mindset

Explainer· 2

Explainer05:30

Why Difficult Conversations Feel Hard (And What You're Adding On Top)

Alisa coaches Lenny through why difficult conversations feel so daunting: the discomfort comes less from the facts and more from the meaning we layer on top of them, like fear of the extra work or the other person's reaction. She reframes the upset as the doorway to a new possibility rather than something to avoid, arguing that avoiding the conversation robs the other person of the chance to improve.

  • The difficulty is often the meaning you attach to the conversation, not the conversation itself
  • Naming exactly what feels hard (extra work, their reaction) makes it easier to move through
  • Avoiding the conversation denies the other person the chance to change or improve
  • On the other side of the upset there is often revelation, joy, and a stronger relationship

“no one wants to make anybody upset but through that upset on the other side of that can often be a whole new possibility”

Alisa Cohn · 07:30
#difficult-conversations#leadership#mindset#feedback
Explainer1:13:00

Patience vs Process: Knowing Which One a Problem Needs

Alisa recounts a CEO who kept counseling patience on a stalled launch when the real issue was a broken process he wasn't investigating. Her point: leaders need the wisdom to tell whether a situation calls for patience or for digging into the process. The tell is whether you actually have a plan in your mind for how it comes together, or just hope.

  • A CEO preached patience while an inexperienced PM was hiding a process problem
  • Leaders must distinguish a patience problem from a process problem
  • Warning sign: you have no plan in your mind for how it comes together
  • Hoping it works out (vs seeing a path) usually signals a real problem

“sometimes you need to have patience and sometimes you need to look at the process and I think you as the leader need to have…”

Alisa Cohn · 1:14:00

“you don't really know how this thing is going to come together there's no like plan in your mind”

Alisa Cohn · 1:14:30
#leadership#process#decision-making#management

Story· 3

Story11:00

The Employee Who Cried, Then Thanked Her Boss for the Hard Feedback

One of Alisa's clients dreaded giving a struggling employee tough feedback, certain she would cry. She did cry and went home early. But the next day she came back and thanked him, saying she wished someone had told her 15 years earlier. Alisa uses the story to show that feedback withheld out of kindness is actually a disservice.

  • The client avoided the conversation because he was sure the employee would cry
  • She did cry and left early, then returned grateful the next day
  • The employee felt she could have had a different career had someone told her sooner
  • Leaning into tough conversations is how you actually help someone grow

“thank you so much for telling me that I wish someone had told me that 15 years ago I think I could have had a…”

Alisa Cohn · 11:30
#feedback#leadership#management#empathy
Story41:30

"It All Started With the Avocado Toast": When Culture Substitutes for Results

Alisa tells the story of a sincere founder whose perks (10am avocado toast, socials) turned into a clicky, gossipy culture that displaced real work and results. He'd never codified culture or set clear expectations, so a culture committee just added more layers. The fix required confronting his own discomfort with expectations and parting ways with a couple of toxic people.

  • Perks and socials drifted into a gossipy, clique-driven culture with no results
  • Culture is how work gets done, not avocado toast and hangouts
  • The founder had never codified culture or set clear expectations
  • Turning it around meant setting expectations and removing toxic people

“if I'm writing a book the book would start with it all started with the avocado toast”

Alisa Cohn · 42:00

“culture is not just avocado toast and working together and having socials culture is you know things like we go the extra mile”

Alisa Cohn · 43:30
#culture#founders#leadership#expectations
Story1:09:00

Fail Corner: Crying on the Floor, and Turning Failure Into Fuel

In the podcast's "Fail Corner," Alisa shares two low points from early in her coaching career: balling in the fetal position on her Brookline hardwood floor for an hour after a bad conversation, and having a client end an offsite early because it wasn't working. Both times she picked herself up and turned the experience into skill-building, becoming great at offsites afterward.

  • Early in her practice she cried on the floor for an hour, terrified it wouldn't work out
  • A client once shut down her offsite mid-session because it wasn't working
  • She responded by taking action and training up her skills
  • Anything you learn from a low point can be turned into fuel to get great

“I got onto the floor my hardwood floors in my Brookline condo and I just balled in the fetal position”

Alisa Cohn · 1:09:30

“anything that you're learning from that can then be turned into fuel to build your skills”

Alisa Cohn · 1:12:00
#failure#resilience#career#coaching

Tool· 3

Tool1:15:00

The Personal Operating Manual (and the "Gold Star" Question)

Beyond the co-founder prenup, Alisa recommends a "personal operating manual" any team can use to surface working styles. It prompts questions like preferred communication style, how you like to be reached for something urgent, your pet peeves, and how someone can "get a gold star" with you. Because nobody knows your operating style until you tell them, sharing it prevents needless conflict.

  • A personal operating manual surfaces each person's working style on a team
  • Prompts cover communication preferences, urgency, pet peeves, and delegation
  • The "how can I get a gold star with you" question tells people how to succeed with you
  • Nobody knows your operating style until you make it explicit

“what is one of your pet peeves or some of your pet peeves how can I get a gold star with you”

Alisa Cohn · 1:15:30

“nobody nobody knows what's your what's your operating style until you tell them”

Alisa Cohn · 1:16:30
#teams#communication#management#working-style
Tool1:17:00

Alisa Cohn's Book Recommendations

In the lightning round Alisa names the three books she recommends most: Radical Candor by Kim Scott on giving feedback, Working Backwards by Colin Bryar and Bill Carr on the Amazon management method, and Walt Disney by Neal Gabler for its portrait of how Disney evolved as an entrepreneur. She calls Working Backwards geeky and tactical, devouring it "like Harry Potter."

  • Radical Candor by Kim Scott, on giving feedback
  • Working Backwards by Colin Bryar and Bill Carr, on Amazon's way of working
  • Walt Disney by Neal Gabler, on Disney's evolution as an entrepreneur
  • She found Working Backwards geeky, tactical, and addictively readable

“I slurp it up like Harry Potter it's so good”

Alisa Cohn · 1:17:30
#books#recommendations#management#leadership
Tool1:19:00

Favorite Product: The Ninja Creami

Asked for a product she recently loves, Alisa names the Ninja Creami, which turns anything into ice cream. She converts her mediocre protein shake into ice cream in about 10 minutes with little prep, and praises that it works exactly as expected, unlike so many products.

  • The Ninja Creami turns almost anything into ice cream
  • She turns her protein shake into ice cream in roughly 10 minutes
  • Little prep, simple to use, and it works as expected

“the ninja creamy turns anything into ice cream so you can actually make ice cream”

Alisa Cohn · 1:19:00
#product-recommendation#lightning-round#food

Takeaway· 3

Takeaway17:30

Give Feedback on Observable Facts, Not Judgment

Alisa argues the easiest feedback to give and to hear is framed around observable facts rather than judgments. Starting with "what I've observed" keeps it neutral and grounded in evidence tied to expectations. She routinely asks clients "what's my evidence that this is happening?" before a conversation, since doing that thinking makes the feedback land better.

  • Open with "what I've observed" to keep feedback neutral and non-judgmental
  • Anchor feedback to evidence and to a clear expected standard
  • Ask yourself "what's my evidence?" before the conversation
  • Doing the prep work makes feedback easier to give and easier to hear

“the level of your writing really reflects the level of your thinking”

Alisa Cohn · 18:00

“I always ask my clients what's my evidence that this is happening and you have to spend some time thinking about it”

Alisa Cohn · 20:00
#feedback#communication#management#coaching
Takeaway35:00

Praise Deserves the Same Standard as Criticism

Alisa reframes tough talks as "delicate conversations" and points out that people shy away from specific praise just as much as from criticism. Vague "good job" praise teaches nothing, so positive feedback should be as specific and well-prepared as negative. Consistent, detailed praise builds a reservoir of goodwill that makes the hard conversations land better later.

  • Reframe the whole category as "delicate conversations," not just difficult ones
  • People avoid specific praise as much as they avoid criticism
  • Vague praise like "good job" carries no learning; be specific about what worked
  • Regular specific praise builds trust and a reservoir of goodwill for hard talks

“what I call them is sort of delicate conversations because what I think people also shy away from is just simple praise specific praise”

Alisa Cohn · 35:00

“so the positive feedback should have the same standard”

Alisa Cohn · 36:00
#feedback#praise#management#motivation
Takeaway56:00

65% of Startups Fail Because of Founder Conflict

Choosing a co-founder is like marrying someone in a business context, yet people enter it with far less care than they should. Alisa cites Noam Wasserman's finding that 65% of startups fail because of conflict within the founding team. The takeaway: do the work of getting to know each other before you co-found.

  • Picking a co-founder is akin to a marriage you're stuck in for a long time
  • Noam Wasserman: 65% of startups fail from founder or founding-team conflict
  • People commit with far less care than the decision warrants
  • Get to know each other deliberately before deciding to co-found

“you're marrying someone in a business context and you're stuck with this person for a long time”

Lenny · 56:00

“according to noan noan werstein 65% of startups fail because of conflict with Founders or the founding team”

Alisa Cohn · 56:30
#founders#co-founders#startups#conflict