Table of Contents
Transform your leadership effectiveness with specific scripts for performance feedback, promotion denials, and terminations from a top-50 global executive coach who's worked with Fortune 500 CEOs.
Stop dreading difficult conversations and start using these battle-tested scripts that help employees improve while building stronger relationships and trust.
Key Takeaways
- Difficult conversations become easier when you understand you're helping someone improve rather than hurting their feelings—the alternative is leaving them in the dark about critical career barriers
- Use observable facts and "what I'm hearing from others" language to make feedback feel neutral and less personal than opinion-based criticism
- Start difficult conversations with clear, direct statements rather than burying the lead—people need to know the bad news immediately before processing solutions
- Prepare for defensive reactions with scripts that pause conversations and remind people why you're having the discussion—their career success and your investment in their growth
- The three essential meeting questions are: "What did we decide here?" "Who needs to do what by when?" and "Who else needs to know?" to ensure alignment and follow-through
- Leaders' primary job isn't making employees happy—it's creating winning cultures where results and structure enable team satisfaction through success
- Hope for the future is crucial in difficult conversations—always provide a path forward and demonstrate continued investment in the person's career development
- Founder relationships require "prenups" covering values alignment, company vision, conflict resolution styles, decision-making processes, and desired company culture before starting ventures
- Most startup failures (65%) stem from founder conflict, making upfront alignment conversations more important than product development discussions
Timeline Overview
- 00:00–04:48 — Introduction to Alisa Cohn's background as executive coach for startups and Fortune 500 companies, plus the importance of addressing difficult conversation avoidance
- 04:48–12:48 — Psychology behind difficult conversation avoidance and the transformative power of reframing these as helping conversations rather than hurtful ones
- 12:48–20:20 — Performance feedback scripts using observable facts, peer feedback, and clear behavioral expectations with specific language examples for common scenarios
- 20:20–25:07 — Handling defensive reactions with pause scripts that remind people of your investment in their success while managing emotional responses effectively
- 25:07–31:00 — Promotion denial scripts that deliver bad news upfront, explain reasoning clearly, and provide hope for future advancement through specific development paths
- 31:00–35:44 — Termination conversation preparation including crystal-clear warning conversations and final termination scripts with HR coordination requirements
- 35:44–38:49 — Positive feedback importance and specific scripts for meaningful praise that motivates employees and builds relationship foundation for difficult conversations
- 38:49–44:55 — Leadership mindset shifts from employee happiness focus to results-driven culture creation, with examples of misguided happiness-focused leadership approaches
- 44:55–49:38 — Common leadership blind spots including visionary founders who avoid structure and accountability, plus the necessity of reinventing traditional management approaches
- 49:38–55:57 — Meeting effectiveness through three ending questions that ensure decision clarity, action item ownership, and communication cascade throughout organizations
- 55:57–01:08:24 — Founder prenup questions covering values alignment, company vision, conflict styles, decision-making processes, and culture preferences to prevent startup relationship failures
- 01:08:24–01:13:00 — Failure stories from Alisa's coaching career including business development struggles and offsite facilitation disasters that became learning opportunities
The Psychology of Difficult Conversation Avoidance
Understanding why we resist difficult conversations is essential for overcoming the paralysis that prevents effective leadership. Most avoidance stems from fear of emotional reactions and additional work rather than actual harm to relationships.
- The primary fear involves making people sad or upset, followed by concern about dealing with emotional reactions and potential relationship damage afterward
- Leaders worry about being wrong or lacking complete information, creating hesitation that prevents necessary feedback conversations from happening
- The alternative to difficult conversations is leaving people uninformed about career barriers, potentially damaging their long-term professional development significantly
- Employees often express gratitude for difficult feedback, wishing someone had provided guidance years earlier to change their career trajectory
- Successful difficult conversations can actually strengthen relationships and build trust when handled with clear intention to help rather than hurt
- The "Bob story" illustrates how avoiding feedback conversations for months or years creates worse outcomes than immediate, direct communication
- Reframing difficult conversations as opportunities for growth and revelation helps leaders overcome natural resistance to causing temporary discomfort
When leaders avoid these conversations, they deprive employees of crucial information needed for career advancement while creating organizational problems that compound over time. The temporary discomfort of honest feedback pales in comparison to the long-term damage of silence.
Performance Feedback Scripts: Observable Facts and Peer Input
Effective performance feedback relies on specific language that emphasizes observable behaviors and external validation rather than personal opinions or judgments about character.
Basic Performance Feedback Structure: "Matilda, I want to chat with you about the way you're interacting with your peers. What I'm hearing from them is that you're missing deadlines on a regular basis and not letting them know you're missing the deadlines, and also you're not fully keeping your team up to speed and so they're kind of confused and wondering around. Now we both know that the most important way you can be successful here and also achieve your goals is to make sure that you are working with your peers in a way that's consistent and that they can count on you and you can count on them. So I want to let you know about this, I want to certainly hear what you have to say, but the most important thing is that we leave this discussion knowing how you're going to make sure that you're keeping your peers in the loop and also your team in the loop."
Key Script Elements:
- Start with direct topic introduction: "I want to chat with you about..."
- Use external validation: "What I'm hearing from them is..." rather than personal opinion
- Include specific observable behaviors: missed deadlines, lack of communication, team confusion
- Create shared understanding: "We both know that..." to avoid feeling attacked
- End with clear expectations for resolution and next steps
Individual Observation Feedback: "Matilda, part of your job is to be able to create these documents and I appreciate that you do them on time. What I've observed is that they can often be not as structured as I'd like them to be and they also lack a conclusion. So what I'd love you to do is look at these three or four examples of some folks who are doing them really well and see if you can model your writing on theirs. If you need to take additional classes or if you need help in any way let me know, but ultimately I want to get your writing to the level where everybody is appreciating what you bring to the table because the level of your writing really reflects the level of your thinking."
This approach emphasizes "what I've observed" rather than character judgments, provides specific examples of desired outcomes, and offers concrete support for improvement while connecting the skill to broader career success.
Managing Defensive Reactions
Defensive reactions are predictable responses to difficult feedback. Having prepared scripts prevents leaders from becoming defensive themselves and enables productive conversation continuation.
Defensive Reaction Management Script: "Let's pause for a second. First of all, I want you to know that I'm telling you this actually just to make you better because I know how important your career is to you. I know how important success is to you and it's important to me too as your leader. The second thing is my observation is that you're getting a little bit emotional. I want to know if we can continue having this conversation now or we need to kind of pause it. At the end of the day we really have to have this conversation and I really want to see you make changes, but I understand you might need a few moments to digest it."
Core Components:
- Immediate acknowledgment of changed energy or defensive response
- Reminder of positive intention and investment in their career success
- Option to continue or pause based on their emotional readiness
- Clear statement that the conversation must happen eventually
- Recognition that processing time may be necessary for productive dialogue
The preparation aspect is crucial—knowing you have these tools prevents reactive responses that escalate conflict rather than resolving the underlying performance issues.
Direct Delivery with Future Hope
Promotion conversations require immediate clarity about decisions followed by comprehensive reasoning and future pathway development to maintain employee engagement and motivation.
Promotion Denial Script: "Matilda, I know this is going to be challenging for you to hear. I know you were hoping to get that promotion, but I want to let you know that we are going to actually be looking for an external candidate. I want to give you a few thoughts about why. First of all, in discussing this with my peers, I'm realizing that we need someone who has done this role multiple times in the past and has that experience. Number two, I think it's really important that they have expertise in a specific realm that we've identified is really important. So for those reasons we're going to bring someone in from the outside, not going to promote you. But I want you to know this: number one, it's really important to me that you're able to succeed in your career here, and so I want to continue to help you find opportunities to build your skills and to advance. And then number two, when we bring this person in, I'm committed to finding someone who's a great people leader who is going to help you build those skills."
Script Structure Analysis:
- Immediate bad news delivery: "I know this is going to be challenging for you to hear"
- Clear decision statement: "we are going to actually be looking for an external candidate"
- Specific reasoning with concrete requirements: experience level and specialized expertise
- Future hope and investment: continued career development and learning opportunities
- Commitment to supportive leadership when new person arrives
Handling Disagreement or Alternative Arguments: When employees respond with unrelated points (tenure, being only internal candidate, peer comparisons), acknowledge their perspective while redirecting to your decision criteria: "Yeah listen Matilda, I really understand that you were thinking that after a year you'd get promoted around here... That's not the place we're at right now as we scale, we really need to think about not just what we need for today and tomorrow but for the future, and that's why I want these specialized skills in here."
Essential Quotes: The Leadership Mindset Transformation
The most powerful insights from Alisa Cohn's approach reveal fundamental shifts in how effective leaders think about their role, responsibility, and impact on team performance.
On the True Purpose of Difficult Conversations: "The reason that you're giving someone this so-called constructive feedback is because you're helping them get better. You need them to change the behavior. They'll never get promoted if they keep doing that. They'll never be successful if they keep doing that. And so it's your job as a leader and as a manager to help them out of that problem and help them do something different."
This reframes difficult conversations from potential harm to necessary help. Leaders often avoid feedback to prevent discomfort, but this perspective reveals that avoiding conversations actually harms employees by leaving them unaware of career barriers. The shift from "I might hurt them" to "I'm helping them succeed" transforms the emotional weight of these interactions.
On Employee Reactions and Long-term Impact: "She cried, of course she did... The next day she came in and she said 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 different career."
This story illustrates the disconnect between immediate emotional reactions and long-term value. Leaders fear tears and upset feelings, but employees often recognize the gift of honest feedback even when initially painful. The 15-year perspective shows how withholding feedback can damage entire career trajectories, making temporary discomfort a small price for long-term success.
On Leadership Purpose and Employee Happiness: "Their job is not to make employees happy... What really needs to happen very often is we need to drive towards results... ultimately that leads to the demise of your company... you're dancing around hoping and praying they're going to get there and they don't really know there's a problem."
This challenges the common misconception that good leadership means avoiding conflict and maintaining constant employee satisfaction. Happiness focused leadership often enables poor performance by avoiding necessary corrections. True leadership creates winning cultures where employees find satisfaction through achievement and clear expectations rather than artificial harmony.
On the Power of Hope in Difficult Conversations: "Hope for the future is so important... hopefully if they're a good employee hopefully they have hope for the future... when you as a leader signal I care about you I care about your feelings I care about your career you are always going to be able to help people stay resilient in the face of setbacks."
This reveals why promotion denial and performance feedback conversations must include future pathways. Without hope, employees disengage or leave. With clear development paths and continued investment, temporary setbacks become growth opportunities. The care demonstration builds loyalty that survives disappointments.
On Meeting Effectiveness and Decision Alignment: "If you really go around the room at the end of a meeting of six people and you say to everybody what did we decide here and they all write it down, you will get six different answers even though we're in the same meeting."
This exposes a fundamental problem in organizational communication. People attend the same meeting but leave with different understandings of decisions and next steps. The three-question framework prevents this misalignment by forcing explicit clarity about outcomes, responsibilities, and communication needs.
On Founder Relationship Importance: "65% of startups fail because of conflict with founders or the founding team... you're stepping into this relationship with a lot less care than you should... it's essentially marrying someone in a business context and you're stuck with this person for a long time."
This statistic reveals that founder alignment is more critical than product-market fit for startup success. Most founders focus extensively on product development while spending minimal time on relationship development. The marriage analogy emphasizes the long-term commitment and intimacy required for successful business partnerships.
Practical Implications: Building Leadership Communication Systems
Alisa Cohn's frameworks translate into specific organizational practices and personal leadership behaviors that create cultures of clarity, accountability, and continuous improvement.
Conversation Preparation and Mindset Management: Develop systematic approaches to difficult conversations by first examining your own resistance and motivations. Practice distinguishing between helping someone improve and venting frustrations. Create pre-conversation rituals that center you on positive intent and specific observable evidence. Build relationship foundations through regular positive feedback so difficult conversations occur within context of care and investment rather than criticism.
Script Customization and Practice: Adapt provided scripts to your communication style while maintaining core elements of direct delivery, observable facts, and future hope. Practice these conversations with trusted colleagues or mentors before high-stakes situations. Develop comfort with pausing defensive reactions through role-playing exercises. Create personalized versions that feel authentic while preserving the structural elements that make conversations effective.
Meeting Culture and Follow-through Systems: Implement the three-question framework at meeting ends to ensure decision clarity and action accountability. Assign specific roles for capturing and distributing meeting outcomes. Build organizational habits around decision documentation and progress tracking. Train teams to expect and contribute to clear closure processes that prevent repeated discussions of the same topics.
Performance Management Integration: Integrate difficult conversation skills into regular performance review cycles rather than saving feedback for formal periods. Create monthly check-in processes that normalize corrective feedback as part of ongoing development. Establish clear performance expectations that make difficult conversations about gaps rather than surprises. Build manager training programs that emphasize these communication skills as core leadership competencies.
Founder and Leadership Team Alignment: Implement founder prenup processes for new leadership teams and business partnerships. Schedule annual values and vision alignment discussions for existing teams to address changes and conflicts early. Create conflict resolution protocols that teams agree to follow before disputes arise. Establish regular communication style discussions that help team members work more effectively together.
Organizational Culture Development: Shift from happiness-focused to results-focused culture development while maintaining employee care and support. Create clear connections between individual performance and team success to motivate improvement conversations. Establish celebration rituals around achievements and problem-solving rather than conflict avoidance. Build feedback cultures where difficult conversations are expected and appreciated rather than avoided and feared.
Personal Leadership Growth: Develop self-awareness about your conflict avoidance patterns and triggers. Practice giving specific positive feedback to build comfort with direct communication. Seek feedback about your own communication effectiveness from direct reports and peers. Create personal development plans that address leadership blind spots revealed through 360-degree feedback processes.
The ultimate goal involves transforming leadership from conflict avoidance to conflict competence. Leaders who master these communication skills create high-performing teams that address problems quickly, develop people effectively, and achieve results through clarity rather than hoping and praying that issues resolve themselves.
Common Questions
Q: How do I start a difficult performance conversation without making it feel like a big deal?
A: Use casual language like "I want to have a conversation with you about..." and maintain an even, matter-of-fact tone rather than dramatic buildup.
Q: What if the employee disagrees with my feedback or gets defensive?
A: Pause the conversation with scripts like "Let's pause for a second" and remind them of your positive intent and investment in their career success.
Q: Should I save difficult feedback for formal performance reviews?
A: No, integrate these conversations into regular management practices so people aren't surprised by formal review feedback.
Q: How do I deliver bad news about promotions while keeping the person motivated?
A: Deliver the news directly, explain your reasoning clearly, and provide specific hope for future advancement through skill development.
Q: What's the most important thing to remember when having difficult conversations?
A: Your job is to help them improve and succeed, not to make them happy in the moment—frame conversations around their long-term career benefit.
Mastering difficult conversations transforms leadership effectiveness by enabling clear communication, faster problem resolution, and stronger team relationships built on trust and mutual investment in success.
