Difficult Conversations

The Situation

Rob is a sales rep who's been at the company for several years. He's 5% below quota. You've had prior conversations with him about performance, but nothing has changed. Now you need to have the conversation that actually lands — one where Rob walks away understanding the gravity of the situation.

The Hard Conversations

• Telling Rob directly that his job is at risk if performance doesn't improve
• Acknowledging your own role: "Maybe I wasn't clear enough in our previous conversations"
• Setting a concrete timeline and measurable expectations
• Navigating Rob's emotional response without retreating into vagueness

Good Practices

• Be direct about where they stand. Don't let ambiguity be mistaken for compassion — it's actually unkind to let someone think things are fine when they're not.
• Take partial ownership: "I may not have been clear enough before, and I want to fix that now."
• Ask yourself: after this conversation, will Rob know exactly where he stands? If the answer is no, you haven't been direct enough.
• Avoid the "sandwich" of burying bad news between compliments — it dilutes the message.
• Tell Rob his job may be at risk. As Kira said in class: ambiguity is the antagonist of joy.

The Situation

Steve Miller (41, highly experienced, long tenure) expected a promotion. Instead, it was given to Sally King (late 20s, 16 months at the company). Jonathan, Steve's boss, must deliver this news. Steve has a prior relationship with Jonathan and is emotionally invested in the outcome. He has a family depending on the raise.

The Hard Conversations

• Telling a loyal, experienced employee that a much younger, newer person got the job
• Managing Steve's emotional shock, hurt, and potential accusations of unfairness
• Avoiding comparisons like "be more like Sally" that feel demeaning
• Addressing the question: "Is there a path for me here, and what does it look like?"
• Handling allegations that the process was unfair or suspicious

Good Practices

• Lead with the decision. Don't bury it in a preamble. State the news, then explain.
• Anticipate emotional response. You're delivering logic to someone feeling emotion — those don't connect. Plan for how the person will feel, not just what they need to hear.
• Don't read through a prepared script robotically. Be present and responsive to the emotion in the room.
• Avoid comparing to the chosen candidate ("be more like Sally") — it's jarring and demeaning.
• Have a concrete plan for their future — don't offer vague platitudes. "The one- to two-year range" with no specifics feels hollow.
• Show you recognize what they bring — tenure, mentorship, relationships — even as you explain the decision.

The Situation

A young GSB graduate (based on a real person named Chase) is sent by Alpine to take over as CEO of a SaaS company in Southern California just weeks after being hired. The existing VP team is older, more experienced, and one VP immediately pushes for a raise, claims the VP of Ops is a "slacker," and questions the new CEO's authority.

The Hard Conversations

• An aggressive VP demanding a raise and pushing to test the new CEO's boundaries
• Being asked to make commitments (raises, personnel judgments) before you have full information
• Handling gossip and characterizations of other team members ("the VP of Ops is shady")
• Establishing authority without alienating a team that was there before you

Good Practices

• Don't make promises you can't keep. "I don't have full details yet" is a perfectly valid answer.
• Don't accept characterizations of other employees at face value — as Irv noted, "if the VP of Ops came to you and said the same things about this person, you wouldn't immediately act on it."
• Acknowledge their contributions and concerns while maintaining your process. You need time to assess the organization on your own terms.
• Be who you are. Don't try to act like a seasoned veteran. The team knows you're new — authenticity builds more trust than pretending.
• Schedule one-on-one meetings across all business units to build your own understanding.

The Situation

Tristan is a top-performing salesperson at Lighthouse who repeatedly pushes or breaks the company's gift and entertainment policies. His supervisor Josie failed to catch it. The issue is material enough to bring to the board. The question: do you fire the star, bend the rules, or find a third path?

The Hard Conversations

• Confronting Tristan about policy violations without losing him as a top performer
• Holding Josie (Tristan's supervisor) accountable — what role did she play in this?
• Informing the board about a material compliance issue
• Deciding whether to fire, warn, or work collaboratively with Tristan
• Communicating a team member's departure to the rest of the organization

Good Practices

• Frame it as "the genius of AND" — how can I have both compliance and this person's productivity? Don't default to either/or.
• Work with the person, not against them. Sit beside them and say: "Here's the issue. Let's find a way forward together."
• Ask yourself: "What role did I (or the supervisor) play in this?" Before blaming Tristan, recognize the oversight.
• Bring problems to your board early. Don't wait until they're crises. The board should hear it from you first.
• If you realize you made the wrong call, reverse it. Admitting mistakes shows judgment, not weakness.
• Great salespeople are the scarcest resource. Invest disproportionately in retaining them (but not at the cost of values).

The Situation

Lisa Yao is an investor who discovers that Matt Larkin, the entrepreneur she backed, falsified parts of his resume. She now must decide what to do: confront Matt, inform her co-investors, and navigate the tension between transparency and protecting an individual. Trust has been broken at a foundational level.

The Hard Conversations

• Confronting Matt directly about the falsification — without destroying him as a person
• Communicating to co-investors what happened, while being fair to Matt
• Deciding whether to remove Matt or give him a chance to explain
• Managing your own emotional response (betrayal, anger) to stay factual

Good Practices

• Share facts, not judgments. Say "we discovered discrepancies in his resume" not "he's a liar."
• Apply the "overhearing test": if Matt were sitting in the room listening to what you tell co-investors, would you be comfortable with your words?
• Don't throw people under the bus. There's no need to trash someone to communicate a problem.
• Be transparent with co-investors — they need to know — but be proportional and factual in how you share it.
• Trust, once broken by falsification, is extremely hard to rebuild. Acknowledge this reality rather than glossing over it.

The Situation

Seth Hedgefield is a CEO with misconduct allegations. Darren Lowe, a co-director, has some information but not the full picture. There's asymmetric information between board members. The root cause traces back to a hiring process that skipped best practices — no proper reference checks, no structured process.

The Hard Conversations

• Approaching a co-director when you each hold different pieces of the puzzle
• Deciding whether to confront the CEO or build alignment with the board first
• Communicating misconduct allegations with care and precision
• Addressing the systemic failure — the hiring process was broken

Good Practices

• Share what you know first. Leading with openness invites reciprocity. If you come in like a detective, they'll clam up.
• Don't try to catch people in lies — that's adversarial, and it won't serve the outcome you need.
• Prioritize the most acute crisis. Multiple problems may exist; deal with the fire first.
• Always run a proper hiring process. Reference checks, structured interviews, background verification. Skipping them creates downstream disasters that are 10x harder to fix.

The Situation

Bernard Wisley (athletic director) is considering firing Sarah Cohen, a well-liked coach. The information he has suggests she's underperforming, but he hasn't verified through all channels. During the conversation, new information emerges that Sarah may have actually addressed the problem. Now Bernard faces the dilemma: fire her as planned, or absorb the new information mid-conversation?

The Hard Conversations

• Walking into a firing conversation that may be premature
• Deciding in real-time whether to proceed or pause when new facts emerge
• Balancing the desire to look decisive with the need to make the right call
• Potentially reversing course mid-conversation without losing credibility

Good Practices

• Never make personnel decisions with incomplete information. Verify through all channels before you walk into that room.
• Preparation means checking every angle — not just the ones that confirm your initial hypothesis. Watch for confirmation bias.
• Stay open to new information, even mid-conversation. The best decision is always more important than looking decisive.
• Once you say "you're fired," walking it back is nearly impossible. Don't say it until you're certain.
• If you realize mid-conversation that you're wrong, pause: "I'm learning some things here that I want to think about. Can we continue this tomorrow?"

The Situation

Tom Steele is a senior leader within the athletic department who has been bad-mouthing Bernard Wisley (the athletic director) behind his back. Tom was a losing candidate for Bernard's job, so it's tempting to assume the motivation — but as Irv teaches, we cannot see intent, only behavior. The behavior is undermining the organization's culture and must be addressed.

The Hard Conversations

• Confronting someone about gossip and back-channel negativity
• Addressing behavior without assuming motivation ("you're bitter you didn't get the job")
• Making it clear this behavior won't be tolerated while preserving the working relationship

Good Practices

• Address culture punctures immediately. The moment you tolerate bad behavior, you've set a new standard for the entire organization.
• Focus on behavior, not assumed intent. Don't say "I know you're upset because you didn't get the job." Say: "I've heard that you've been saying X about me. That behavior is standing in the way of where you want to go."
• Remove impunity. If talking badly about leadership is tolerated, it metastasizes.
• Use Irv's phrase: "Your behavior is standing in the way of getting where you want to go." It puts responsibility where it belongs without being judgmental.

The Situation

George Vincent is a hospital administrator who is furious about Convenient MD, an urgent care startup, opening locations near his hospital. He comes into the meeting hot — aggressive, accusatory, and adversarial. The Convenient MD team needs to de-escalate, find common ground, and potentially turn an adversary into a partner.

The Hard Conversations

• Sitting across from someone who is visibly angry and potentially threatening
• Resisting the urge to defend yourself or match their energy
• Finding a way to redirect the conversation from adversarial to collaborative
• Knowing when to speak and when to stay silent

Good Practices

• Don't meet fire with fire. Meet them where they are with genuine curiosity: "I can see this is really frustrating. Help me understand your concerns."
• Silence conveys confidence. You don't have to fill every pause. Let the angry person exhaust their energy.
• Acknowledge what's valid. There's almost always something legitimate in their concern — find it and name it.
• Save your best arguments for when they can rationally hear them. Talking logic to pure emotion is useless.
• Think of negotiations as a dance, not a tug of war. Get on the same side of the table — literally or figuratively.
• Tony's mantra: "I can be as curious as you are angry — until you come down."

The Situation

Peter Thorburn is evaluating a real estate deal involving Phyllis Rosier. There are indications of possible kickbacks or unethical practices, but nothing is confirmed. The deal itself is attractive. Peter must navigate the ambiguity: pursue the deal aggressively while gathering information, without asking the one question that kills the deal prematurely.

The Hard Conversations

• Exploring potential ethical issues without making accusations
• Gathering information through indirect questions and references
• Deciding at what point the ethical risk outweighs the business opportunity
• Walking away from a good deal because the ethics don't check out

Good Practices

• Want the asset until you don't. Pursue it fully — don't talk yourself out of it prematurely. Let facts, not assumptions, guide your decision.
• Ask questions that yield information without painting yourself into a corner. If you ask "are there kickbacks?" the deal dies whether or not there are any.
• Never ask a question you don't already have a good sense of the answer to. Use references, factual questions, and indirect assessment first.
• Know your ethical lines. Ambiguity + poor ethics = a marsh you don't want to walk in. When the information tells you to stop, stop.

The Situation

David Jacobs is the board chair of RCAA who is deeply engaged and enthusiastic — too enthusiastic. He shows up, gives assignments directly to staff (who treat them as top priority since he's the chairman), and walks into the CEO's office unannounced. His heart is in the right place, but his behavior is disrupting operations. The issues aren't catastrophic, but they need to be addressed.

The Hard Conversations

• Telling a well-meaning, powerful person that they're overstepping
• Redirecting energy without killing engagement
• Establishing an open-door policy that still has boundaries
• Doing all of this without creating a turf war

Good Practices

• Start with "what does good look like?" — David walks away feeling valued and engaged, AND you have better coordination. Both things.
• Keep the conversation proportional. The issues are important but not catastrophic. Don't set up a formal meeting that raises the stakes.
• Tony's suggested approach: "David, I love how engaged you are. But when you give assignments directly to the team, they drop everything because you're the chairman. How about we coordinate so nothing falls through the cracks?"
• On the open-door policy: "My door is always open. When it's closed, it means I'm dealing with something private — check with my assistant."
• An alternative approach: don't talk to David at all. Just tell your team: "If David gives you an assignment, accept it, then come tell me, and we'll prioritize together."
• Preserving the relationship matters more than changing the behavior. He's clearly very valuable.

The Situation

Judith Fenton is a top customer service producer whose sales have dropped dramatically. Jack Swain (CEO) discovers she's about to quit — she's polishing her resume and heading for the door. Her team of five (worth ~$15M in revenue, potentially $200M in enterprise value) will likely follow her. Felisha, her manager, hasn't noticed or acted. The video role play shows Felisha and Jack having a pleasant, deferential conversation that does nothing — it's a trap. This is a crisis that requires immediate, decisive leadership.

The Hard Conversations

• Telling Felisha directly: "We have a crisis. Judith is about to leave. We need to act today."
• Working with Felisha on a specific plan for what to say to Judith, then following up
• Speaking with Judith yourself — as CEO, because the stakes warrant it
• Coaching Felisha on what she didn't see, without destroying her confidence
• Contacting departed employees — they may return once the problem is addressed

Good Practices

• In crisis, ACT. This is the warehouse-on-fire analogy: you don't check the org chart. You grab a hose.
• Empowerment without accountability is useless. "I trust you to handle it" is not leadership when the building is burning. Set expectations AND inspect that they're being met.
• Be a coach and teacher, not just a delegator. Help Felisha figure out what to say. Work alongside her.
• Strive for full potential — the genius of AND. You want cost-cutting from Felisha AND the revenue Judith brings. Don't choose 80% of one and 30% of the other.
• Make smart exceptions for A-players. Giving Judith an assistant isn't favoritism — it's recognizing that different producers need different support.
• Your reaction in crisis defines who you are as a leader. People will take notice — and want to work for someone who acts.