Tough Conversation Guides

Management

Frameworks for the conversations that define your leadership.

advanced 7 min read 10 min practice

How to Deliver Layoff News: A Framework for the Hardest Conversation in Management

You've rehearsed it six times in the shower. You've tried starting with "Unfortunately.

Practice with Maria Santos Read guide →

intermediate 7 min read 8 min practice

How to Give a Performance Review to Someone Who Thinks They're Doing Great

Jordan walks in grinning. "I feel pretty good about this quarter," he says, settling into the chair like someone expecting applause.

Practice with Jordan Kessler Read guide →

intermediate 7 min read 8 min practice

How to Mediate a Technical Conflict That Has Gotten Personal

Yesterday at 4:47pm, Raj posted in #engineering-architecture: "If anyone actually understood distributed systems here, this wouldn't be a discussion." Priya hasn't responded publicly.

Practice with Raj Patel Read guide →

beginner 6 min read 7 min practice

How to Tell a High Performer They're Not Ready for Promotion Yet

Aisha booked this meeting three days ago. She has bullet points on her phone.

Practice with Aisha Thompson Read guide →

beginner 6 min read 7 min practice

How to Delegate a Career-Defining Project to Someone Who Doesn't Believe They Can Do It

Your biggest client — 20% of annual revenue — needs a complete portal redesign in six weeks. Your senior designer is on parental leave.

Practice with Sam Whitfield Read guide →

advanced 7 min read 10 min practice

How to Break Through When Your Best Employee Insists They're "Fine"

Tyler used to be the first person to crack a joke in standup. Last Tuesday he said "Let's just get through this" and turned his camera off.

Practice with Tyler Chen Read guide →

Healthcare

Communication frameworks for the moments that matter most.

advanced 7 min read 10 min practice

How to Deliver a Difficult Diagnosis: What Patients Need to Hear and When

He walked in smiling. Cracking a joke about beating the lunch rush.

Practice with James Okafor Read guide →

intermediate 7 min read 7 min practice

How to De-escalate an Agitated ER Patient Who Is Shouting at Staff

Four hours. Tony Russo has been sitting in a plastic chair with a hand that looks like a purple baseball glove.

Practice with Tony Russo Read guide →

beginner 6 min read 6 min practice

How to Counsel a Patient Picking Up Their First Antidepressant

She approached the counter like someone returning a stolen item. Eyes down, voice barely above a whisper.

Practice with Priya Sharma Read guide →

intermediate 7 min read 8 min practice

How to Handle a Desperate Family Facing a $47,000 Insurance Denial

Carmen Delgado walks into the billing office carrying a manila folder that's been opened and closed so many times the edges are soft. Inside: the insurance denial letter, three pages of call records with timestamps, the ER admission paperwork, and her husband's discharge summary.

Practice with Carmen Delgado Read guide →

advanced 8 min read 12 min practice

How to Discuss End-of-Life Care When the Family Disagrees

The family conference room has soft lighting, tissue boxes, and chairs arranged in a circle. Angela Washington is sitting with perfect posture, legal pad on her knee, pen uncapped.

Practice with Angela Washington Read guide →

Financial Services

Turning difficult financial conversations into paths forward.

intermediate 7 min read 8 min practice

How to Decline a Mortgage Application: Turning a Denial Into a Path Forward

They're sitting across from you holding hands. Sarah is five months pregnant, nervously smiling.

Practice with Sarah and David Torres Read guide →

intermediate 8 min read 10 min practice

How to Deliver Bad Portfolio News to a Retiree Without Triggering Panic Selling

Robert is already standing when you walk in. He didn't sit when your assistant offered him coffee.

Practice with Robert Callahan Read guide →

advanced 7 min read 8 min practice

How to Explain a Claim Denial to a Furious Long-Term Policyholder

Frank Moretti doesn't have an appointment. He has a letter, a raised voice, and fifteen years of premiums behind him.

Practice with Frank Moretti Read guide →

beginner 6 min read 8 min practice

How to Guide an Elderly Fraud Victim Without Making Them Feel Foolish

Dorothy Palmer is sitting in the lobby with her purse on her lap and a manila folder in both hands. She's been here since the doors opened.

Practice with Dorothy Palmer Read guide →

advanced 8 min read 10 min practice

How to Mediate a $2M Inheritance Dispute Between Grieving Siblings

Katherine arrives first. She sits in her father's usual chair without realizing it.

Practice with Katherine Hayes Read guide →

Customer Support

De-escalation and retention frameworks for frontline teams.

intermediate 6 min read 8 min practice

How to Handle an Angry Customer Escalation: When "I'm Sorry" Isn't Enough

His voice is shaking. Not with sadness — with the kind of anger that builds when you've been failed by people who promised to fix it.

Practice with Marcus Reed Read guide →

beginner 6 min read 10 min practice

How to Help a Non-Technical User Through Tech Support: When Patience Is the Product

She's been staring at the same error message for two hours. Linda runs a flower shop — three employees, a Valentine's Day rush in six days, and an inventory system she paid for but can't install.

Practice with Linda Cho Read guide →

advanced 7 min read 10 min practice

How to Save a Cancellation When the Customer Has a Spreadsheet: Retention Beyond the Script

David Okafor isn't angry. He's worse — he's prepared.

Practice with David Okafor Read guide →

intermediate 6 min read 8 min practice

How to Communicate During a Service Outage: When Your Customer Is Losing $15,000 an Hour

Rachel Simmons is not screaming. She's doing something worse — she's taking notes.

Practice with Rachel Simmons Read guide →

advanced 7 min read 10 min practice

How to Resolve a Billing Dispute Before the Chargeback: When Trust Has Already Broken

Priya Nair has a folder on her desktop labeled "billing dispute evidence." Inside: a screenshot of the double charge on her bank statement — $299 twice on January 23rd.

Practice with Priya Nair Read guide →

Sales

Win more deals by mastering the conversations that close them.

beginner 7 min read 5 min practice

How to Cold Call a Busy Executive: Breaking Through in the First 15 Seconds

Your palms are damp. You've dialed 47 numbers today and heard 46 voicemails.

Practice with Rachel Nguyen Read guide →

intermediate 7 min read 8 min practice

How to Handle Price Objections: When the Prospect Loves Your Product but Not Your Price

The demo went perfectly. He nodded at every feature, asked the right follow-up questions, told you he could "see his team using this.

Practice with Marcus Chen Read guide →

intermediate 7 min read 10 min practice

How to Run an Enterprise Discovery Call: Earning a Second Meeting With Fortune 500 Buyers

Diana Whitfield has done this forty times. The vendor call.

Practice with Diana Whitfield Read guide →

beginner 7 min read 7 min practice

How to Upsell an Existing Customer: The Annual Review That Grows Revenue Without Selling

Tom answers the call like he's catching up with a friend. "Hey! Good to hear from you.

Practice with Tom Bradley Read guide →

advanced 7 min read 10 min practice

How to Displace a Competitor: The Long Game That Wins Enterprise Deals 8 Months Early

She told you upfront: "I should be honest — we are not in a buying cycle." Priya Sharma, SVP of Customer Experience at a national insurance company, agreed to this call out of professional curiosity, not purchase intent.

Practice with Priya Sharma Read guide →

advanced 7 min read 10 min practice

How to Close a Stalled Deal: When Your Champion Can't Get It Done Internally

Three weeks ago, Jason Park looked you in the eye and said, "We want to move forward." You updated your CRM.

Practice with Jason Park Read guide →

Human Resources

Navigate the most sensitive workplace conversations with confidence.

beginner 6 min read 10 min practice

How to Interview a Candidate Who Sounds Great But Says Nothing Specific

Marcus Chen shakes your hand, makes perfect eye contact, and settles into the interview chair like he's done this a hundred times. He has.

Practice with Marcus Chen Read guide →

advanced 7 min read 12 min practice

How to Handle a Harassment Complaint When the Accused Is a Senior Leader

Priya is sitting in your office gripping a folder she printed at home last night. Inside are three screenshots, two email timestamps, and a handwritten timeline she reconstructed from memory at 2am.

Practice with Priya Sharma Read guide →

intermediate 7 min read 8 min practice

How to Get the Truth in an Exit Interview When They're Being Polite

Jordan is on his last week. VP of Product at a competitor — a title he asked for here and was told "maybe next cycle.

Practice with Jordan Ellis Read guide →

intermediate 7 min read 8 min practice

How to Respond When a Key Employee Brings a Competing Offer You Can't Match

Derek sent the meeting request at 8:47am with the subject line "Compensation Discussion." No preamble.

Practice with Derek Washington Read guide →

beginner 6 min read 7 min practice

How to Rescue an Onboarding That's Quietly Failing

Aisha's onboarding buddy mentioned it casually: "She eats lunch at her desk every day — I think she's just really focused." That is one interpretation.

Practice with Aisha Robinson Read guide →

Professional Communication

Advanced frameworks for specialized professional conversations.

advanced 7 min read 10 min practice

How to Survive a VC Q&A After Your Series A Pitch: When the Slide Deck Stops Protecting You

The pitch is over. Your 12 slides told a beautiful story — market size, traction, team, vision.

Practice with Rachel Whitfield Read guide →

advanced 7 min read 10 min practice

How to Handle a Crisis Media Interview: When a Journalist Has the Memo You Hoped Would Stay Internal

David Chen's voice is warm and unhurried, which is how you know this is dangerous. He's a senior investigative reporter at The Business Chronicle.

Practice with David Chen Read guide →

intermediate 6 min read 8 min practice

How to Ask a CFO for More Money When Everyone Else Is Cutting: The Art of the Counter-Cyclical Budget Request

Margaret Okafor has been in budget meetings for eight hours straight. Three department heads before you accepted their 10% cuts.

Practice with Margaret Okafor Read guide →

beginner 6 min read 7 min practice

How to Tell Your Biggest Client the Project Is Late: When Honesty Is the Only Retention Strategy

Tom Brennan is your favorite client. Straightforward, reasonable, never yells.

Practice with Tom Brennan Read guide →

intermediate 6 min read 10 min practice

How to Negotiate a 40% Vendor Price Increase Down to Something Reasonable: When Switching Is Painful but Paying Is Worse

James Gallagher's email arrived on a Tuesday: renewal proposal, $252,000. Your current contract is $180,000.

Practice with James Gallagher Read guide →

Negotiation

Structured approaches to high-stakes negotiations.

beginner 7 min read 8 min practice

How to Negotiate a Partnership Without Giving Away Exclusivity You Can't Afford

Elena just said the word you were dreading: exclusive. She said it warmly, almost casually, like it was the natural next step after two months of productive conversations.

Practice with Elena Vasquez Read guide →

intermediate 8 min read 10 min practice

How to Hold the Line on Pricing When Your Best Client Asks for 30% More at the Same Rate

Tom starts every renewal call the same way: "Love working with you guys." Then comes the ask.

Practice with Tom Harrington Read guide →

advanced 9 min read 12 min practice

How to Survive a Due Diligence Interview Without Killing Your Valuation

Katherine Langford is on the other side of the table with a leather portfolio, your last four quarters of financials, and the patience of someone who has killed 12 deals out of the 40 she has evaluated. She does not smile.

Practice with Katherine Langford Read guide →

intermediate 7 min read 8 min practice

How to Ask for a Raise When You Are 25% Below Market and Afraid to Sound Greedy

You have spent three weeks building the spreadsheet. Levels.

Practice with James Park Read guide →

advanced 9 min read 12 min practice

How to Win a Three-Way Partnership Negotiation When Everyone Has a Side Deal

Richard Okonkwo suggested meeting bilaterally before tomorrow's three-way call, and you said yes because refusing would have been suspicious. But now you are staring at the real landscape: Richard has already had a side conversation with TechForge, the third party in this alliance, and TechForge offered him a 45% revenue split to go direct — cutting you out entirely, using their own inferior inventory tool.

Practice with Richard Okonkwo Read guide →

Recruiting

Attract and close top talent with the right conversations.

beginner 6 min read 7 min practice

How to Cold-Call a Passive Candidate Who Gets 10 Recruiter Messages a Week

Kevin Park answers the phone the way someone answers a call from a number they do not recognize — polite, guarded, already planning the exit. "Yeah, this is Kevin.

Practice with Kevin Park Read guide →

advanced 8 min read 12 min practice

How to Close a VP of Engineering Candidate Who Has Offers from Stripe and Datadog

Samira Okafor calls you at 4:37pm on a Thursday. She is measured, professional, and transparent: "I have offers from Stripe and Datadog as well.

Practice with Samira Okafor Read guide →

advanced 8 min read 15 min practice

How to Interview an Overqualified Executive Without Getting Steamrolled

Margaret Sullivan walks into the video call the way someone walks into a room they have owned for 25 years. Shoulders back.

Practice with Margaret Sullivan Read guide →

intermediate 7 min read 10 min practice

How to Handle a Candidate Asking for 30% Above Your Range Without Losing Them or Breaking Your Comp Framework

Jason Reeves opens the call exactly the way you hoped he would not: "I am really excited about the role and the team. I just want to make sure the comp reflects the level.

Practice with Jason Reeves Read guide →

Customer Success

Retain, grow, and champion your most valuable accounts.

beginner 6 min read 10 min practice

How to Run an Enterprise Onboarding Kickoff When the Client Already Oversold the Timeline

Derek signed the contract two weeks ago. $180K.

Practice with Derek Holloway Read guide →

advanced 7 min read 12 min practice

How to Save a $240K Account When Your Champion Left and Usage Collapsed

Kevin was your champion. For 14 months, he drove adoption across three departments, answered your emails within the hour, and showed up to every QBR with a slide about how much the platform saved his team.

Practice with Vanessa Okafor Read guide →

intermediate 6 min read 10 min practice

How to Pitch Cross-Department Expansion to a Budget Gatekeeper Who Thinks in Spreadsheets

Sarah from marketing has been your biggest fan for ten months. 92% weekly active users.

Practice with Nina Castellano Read guide →

intermediate 7 min read 12 min practice

How to Run an Executive Business Review When the VP Thinks You're a Line Item to Cut

Robert Tanaka has been your client's VP of Revenue for three years. He signed off on the $200K purchase thirteen months ago because his Director Jordan said it would move the needle.

Practice with Robert Tanaka Read guide →

advanced 7 min read 12 min practice

How to Handle a Product Gap When Your Best Client Just Saw the Competitor's Demo

Claudia Reinhardt staked her reputation on your platform two years ago. She led the competitive evaluation herself, presented to the C-suite, and told her peers it was the right choice.

Practice with Claudia Reinhardt Read guide →

Leadership

Communication frameworks for leaders at every level.

intermediate 7 min read 10 min practice

How to Tell a Top Performer She Was Passed Over for the Promotion — and Keep Her

Patricia cleared her afternoon for this. She already knows something is coming — the restructuring rumors have been circulating for weeks, and she has been telling friends she is "cautiously optimistic.

Practice with Patricia Langford Read guide →

advanced 8 min read 12 min practice

How to Defend Your Strategy to a Board Member Who Voted Against It — After Missing the Quarter

The board meeting ended twenty minutes ago. The slides showed $18.

Practice with Richard Hargrove Read guide →

advanced 7 min read 10 min practice

How to Lead at 11 PM When Your Platform Is Down, Your VP Is Spiraling, and 2,200 Clients Are Waiting

It is 11 PM on a Tuesday. Your phone has not stopped vibrating for six hours.

Practice with Kenji Nakamura Read guide →

intermediate 7 min read 10 min practice

How to Get Your CRO to Stop Sabotaging the Strategy She Was Hired to Execute

Vanessa Drake was the best CRO hire you could have made eighteen months ago. She brought a sales machine from her last company, rebuilt the outbound engine, and closed $8.

Practice with Vanessa Drake Read guide →

beginner 7 min read 8 min practice

How to Face 255 Employees the Day After You Let 45 of Their Colleagues Go

It is 10 AM. You are looking at a grid of 255 faces on a video call.

Practice with Samara Osei Read guide →

Hospitality

Handle high-stakes service situations with professionalism and grace.

intermediate 7 min read 8 min practice

How to Handle a Hotel Overbooking with a VIP Guest: Turning Betrayal into Loyalty

It is 8pm on a Friday. Richard Hargrove is standing at your front desk with his wife on his arm.

Practice with Richard Hargrove Read guide →

intermediate 7 min read 7 min practice

How to Handle a Food Safety Complaint in Your Restaurant Without Losing Control of the Room

Sandra Kim is holding up a plate with a piece of plastic wrap sitting on top of her pasta. She is not being quiet about it.

Practice with Sandra Kim Read guide →

advanced 8 min read 10 min practice

How to Confront an Employee About Theft: Holding the Line Without Destroying the Person

DeShawn Mitchell trained three of the people on your floor. He stayed late during the holiday rush without being asked.

Practice with DeShawn Mitchell Read guide →

beginner 6 min read 6 min practice

How to Cut Off an Intoxicated Regular Without Losing a Loyal Customer

Mike Brannigan is your Thursday guy. Tips 30%.

Practice with Mike Brannigan Read guide →

advanced 7 min read 8 min practice

How to Handle a High-Value Luxury Client Return Without Breaking Policy or Losing the Relationship

Victoria Lane does not raise her voice. She does not need to.

Practice with Victoria Lane Read guide →

Education

Navigate the conversations that shape students' futures.

intermediate 7 min read 8 min practice

How to Handle a Combative Parent-Teacher Conference About a Failing Student

Karen Whitfield walks in ten minutes late, still in her blazer from a showing, phone in one hand, purse slung over her shoulder like she is between appointments -- because she is. She sits down and fires before you can finish your greeting: "Before we start, I want to know what you are doing to help my son, because clearly something is not working.

Practice with Karen Whitfield Read guide →

intermediate 7 min read 8 min practice

How to Confront a Student About Plagiarism Without Losing the Teaching Moment

Ethan Brooks writes solid B papers. You have read four of them.

Practice with Ethan Brooks Read guide →

advanced 8 min read 10 min practice

How to Respond When a Student Reveals a Mental Health Crisis: The Most Important Conversation of Your Career

The bell rang three minutes ago. Your room is empty except for Mia Chen, who is standing near your desk pretending to organize her backpack.

Practice with Mia Chen Read guide →

beginner 6 min read 7 min practice

How to Handle a Disruptive Participant in Corporate Training Without Losing the Room

You are thirty minutes into a half-day leadership communication workshop. Fourteen senior managers are watching.

Practice with Greg Patterson Read guide →

beginner 6 min read 8 min practice

How to Advise a Student Switching Majors When Their Parents Are Threatening to Cut Funding

Jordan Reeves sits down across from you and says the sentence they have been rehearsing in their car for twenty minutes: "I am thinking about switching my major. From pre-med to art history.

Practice with Jordan Reeves Read guide →

Real Estate

Master the negotiations and conversations that close deals.

intermediate 7 min read 8 min practice

How to Present a Lowball Offer to a Seller Who Raised a Family in That House

Eleanor Webb answers her own door. She's wearing a cardigan and reading glasses pushed up on her head, and she welcomes you into a kitchen that smells like coffee she made twenty minutes ago because she remembered you were coming.

Practice with Eleanor Webb Read guide →

beginner 6 min read 7 min practice

How to Mediate a Noise Complaint Without Losing Either Tenant

Lisa Owens has a spreadsheet. She opens it on her laptop before she even sits down — three months of timestamps, durations, and descriptions.

Practice with Lisa Owens Read guide →

advanced 8 min read 10 min practice

How to Negotiate a Rent Reduction With a Commercial Tenant Without Setting a Precedent

Marco Benedetti hasn't taken a paycheck in two months. He doesn't tell you that immediately — he tells you his revenue is down 35%.

Practice with Marco Benedetti Read guide →

beginner 6 min read 8 min practice

How to Talk a Panicking First-Time Buyer Off the Ledge Before Closing

Your phone buzzes at 9:07pm on a Tuesday. Aisha Patel is calling, and she's not the calm, analytical software engineer who spent six weeks methodically evaluating condos and running her own spreadsheet models on price-to-rent ratios.

Practice with Aisha Patel Read guide →

intermediate 7 min read 8 min practice

How to Explain a Doubled Renovation Cost to a Homeowner Who's Been Burned Before

Janet Morrison got your text at 7:14am: "We need to talk about the kitchen. Found some things when we opened the walls.

Practice with Janet Morrison Read guide →

Startup

Communication frameworks for founders building something from nothing.

intermediate 8 min read 10 min practice

How to Close Your First Enterprise Deal as a Founder: Turning Vendor Risk into Startup Advantage

Derek is on your side. He just can't tell you that yet.

Practice with Derek Ramos Read guide →

beginner 6 min read 5 min practice

How to Cold Call as a Startup Founder: Earning 30 Seconds From Someone Who Gets 10 Pitches a Week

Priya has five minutes before her next meeting. She picked up a number she didn't recognize because her warehouse manager has been calling from a new line.

Practice with Priya Menon Read guide →

advanced 8 min read 10 min practice

How to Survive Demo Day Q&A: Handling the Investor Who Stress-Tests You in Front of 50 People

Fifty people are watching. You just finished your five-minute pitch.

Practice with Victor Aldridge Read guide →

intermediate 7 min read 10 min practice

How to Talk to Your First Employee About Declining Performance Without Losing Them

Casey was there before there was a company. Before the LLC paperwork.

Practice with Casey Morales Read guide →

beginner 7 min read 10 min practice

How to Close Your First Engineering Hire When You Can't Compete on Salary

Noah can do the math. He earns $195K base with a $60K RSU vest.

Practice with Noah Beckett Read guide →

beginner 6 min read 6 min practice

How to Handle a Data Loss Bug When You're the Founder and the Support Team

Devon imported three weeks of client data last night. This morning, it's gone.

Practice with Devon Castillo Read guide →

intermediate 7 min read 8 min practice

How to Recover When Your First Support Hire Drops the Ball on Your Best Customer

Rachel used to hear back from you within an hour. She'd message about a bug at 9pm and by 10pm you'd reply with a fix or an honest "I'll look at it first thing tomorrow.

Practice with Rachel Liang Read guide →

advanced 9 min read 12 min practice

How to Push Back on an Aggressive Term Sheet With 4 Months of Runway

The term sheet arrived yesterday. $4 million.

Practice with Richard Calloway Read guide →

intermediate 7 min read 8 min practice

How to Negotiate SaaS Vendor Pricing When You Have Zero Leverage

You've been on DataForge's free tier for eight months. The product is woven into every layer of your stack — data pipelines, analytics, customer dashboards.

Practice with Natasha Kim Read guide →

advanced 8 min read 10 min practice

How to Negotiate a Co-Founder Equity Split Without Destroying the Founding Team

Elliot wrote 30,000 lines of code. Nights and weekends for six months, while keeping his day job at Google, while telling his partner it was going to be worth it.

Practice with Elliot Park Read guide →

intermediate 7 min read 10 min practice

How to Keep Your Biggest Customer When They're Evaluating Your Competitor

Megan scheduled this call — not you. That detail matters.

Practice with Megan Torrance Read guide →

beginner 6 min read 7 min practice

How to Ask for Your First Case Study Without Making It Feel Like Homework

James just said the words you've been waiting to hear: "My team loves the product. Someone literally said it was the best tool we've added this year.

Practice with James Okafor Read guide →

intermediate 7 min read 8 min practice

How to Rally Your Team After a Product Launch That Bombed

Twelve signups. Three of them were test accounts.

Practice with Damon Reyes Read guide →

intermediate 8 min read 12 min practice

How to Recruit a Senior Leader Away From FAANG When You Can't Match the Comp

Martin is 38. He has two kids — ages 4 and 7 — a mortgage, $3,400 a month in daycare, and a FAANG offer for $580K in total comp with liquid RSUs that vest predictably every quarter.

Practice with Martin Aldric Read guide →

advanced 8 min read 10 min practice

How to Tell Your Team You Have 5 Months of Runway Without Causing Panic

Sam already knows. They saw the payroll — you haven't taken salary in two months.

Practice with Sam Chen Read guide →

Job Interview

Preparation frameworks for high-stakes interviews across every role.

beginner 7 min read 15 min practice

How to Ace a Behavioral Interview: The STAR Method Done Right (Not the Way You Think)

You have practiced your STAR stories in the mirror. Situation, Task, Action, Result — you can recite them in your sleep.

Practice with Sarah Kim Read guide →

advanced 8 min read 20 min practice

How to Crack the Case Interview: The Framework Behind the Framework

The partner across the table just said: "A consumer goods company's profits dropped 15%. Revenue is flat.

Practice with Michael Torres Read guide →

advanced 8 min read 20 min practice

How to Pass the System Design Interview: Architecture Is a Conversation, Not a Diagram

"Design a notification system for 500 million users." Your hand is already reaching for the whiteboard.

Practice with Priya Patel Read guide →

intermediate 7 min read 15 min practice

How to Pass the Leadership Competency Interview: What CHROs Actually Score

You have led teams of 30. You have delivered projects worth millions.

Practice with David Nakamura Read guide →

advanced 7 min read 10 min practice

How to Survive a Stress Interview: Composure Is a Skill, Not a Personality Trait

"Sit down. You have exactly thirty seconds — tell me why I should keep talking to you instead of the next candidate waiting outside.

Practice with Victoria Cross Read guide →

beginner 7 min read 12 min practice

How to Ace the Startup Culture Fit Interview Without Sounding Rehearsed

Alex Rivera is wearing a faded climate tech t-shirt and Birkenstocks. They built this company from a dorm room and still push code on weekends.

Practice with Alex Rivera Read guide →

intermediate 8 min read 15 min practice

How to Crush the Product Sense Interview by Starting with the User, Not the Feature

"How would you improve Instagram for creators?" Jennifer Okafor leans back. Her pen is down.

Practice with Jennifer Okafor Read guide →

intermediate 8 min read 15 min practice

How to Ace the Coding Interview by Thinking Out Loud

Ravi Krishnan doesn't use whiteboards. He doesn't time you with a stopwatch.

Practice with Ravi Krishnan Read guide →

intermediate 8 min read 15 min practice

How to Solve the Analytics Case Interview by Asking "So What?" at Every Step

"Our premium subscription conversion rate dropped from 12% to 8% last quarter. Where would you start?" Dr.

Practice with Dr. Elena Vasquez Read guide →

intermediate 7 min read 12 min practice

How to Win the Sales Roleplay Interview by Discovering Before You Pitch

Brandon Mitchell has hired 200+ sales reps. He designed this roleplay to simulate the hardest 15 minutes of a real sales cycle.

Practice with Brandon Mitchell Read guide →

intermediate 7 min read 15 min practice

How to Present a GTM Strategy in a Marketing Interview That Actually Impresses

"We're launching a premium skincare line for Gen Z. Walk me through how you'd bring this to market.

Practice with Lauren Zhang Read guide →

advanced 8 min read 15 min practice

How to Walk Through a DCF in a Finance Interview Without Guessing at Assumptions

"Let's say we're looking at acquiring a SaaS company. Walk me through how you'd value it.

Practice with Robert Kwon Read guide →

advanced 8 min read 18 min practice

How to Navigate a Panel Interview Where Three Executives Want Different Things

Three chairs. Three agendas.

Practice with Margaret Sinclair (CEO), James Wu (CTO), Diane Foster (CFO) Read guide →

intermediate 7 min read 15 min practice

How to Handle the "What Would You Do If..." Interview Without Guessing

"It's Friday at 5pm." Caroline Webb's voice is calm, steady, almost gentle.

Practice with Caroline Webb Read guide →

advanced 8 min read 18 min practice

How to Walk Through a Deal Using MEDDPIC Without Just Reciting the Acronym

"Tell me about the most complex deal you've closed. Walk me through it using MEDDPIC.

Practice with Thomas Brennan Read guide →

Consulting

Build trust, deliver truth, and earn lasting client partnerships.

beginner 7 min read 8 min practice

How to Run a Discovery Call When the Client Already Hates Consultants

Richard made the introduction three weeks ago. Laura agreed to 30 minutes — "and not a minute more.

Practice with Laura Meier Read guide →

advanced 8 min read 12 min practice

How to Tell a CEO Their Signature Initiative Should Be Shut Down

Twelve million dollars. Eighteen months.

Practice with Robert Townsend Read guide →

intermediate 7 min read 10 min practice

How to Push Back on Scope Creep Without Losing the Client

You're six weeks into a 16-week EHR integration project. Your team of four is running at 95% utilization.

Practice with Vanessa Okafor Read guide →

advanced 8 min read 12 min practice

How to Align Two Executives Who Fundamentally Disagree

David Kern arrived early. That's your first signal.

Practice with David Kern Read guide →

The Tough ConversationsLibrary

Management

How to Deliver Layoff News: A Framework for the Hardest Conversation in Management

How to Give a Performance Review to Someone Who Thinks They're Doing Great

How to Mediate a Technical Conflict That Has Gotten Personal

How to Tell a High Performer They're Not Ready for Promotion Yet

How to Delegate a Career-Defining Project to Someone Who Doesn't Believe They Can Do It

How to Break Through When Your Best Employee Insists They're "Fine"

Healthcare

How to Deliver a Difficult Diagnosis: What Patients Need to Hear and When

How to De-escalate an Agitated ER Patient Who Is Shouting at Staff

How to Counsel a Patient Picking Up Their First Antidepressant

How to Handle a Desperate Family Facing a $47,000 Insurance Denial

How to Discuss End-of-Life Care When the Family Disagrees

Financial Services

How to Decline a Mortgage Application: Turning a Denial Into a Path Forward

How to Deliver Bad Portfolio News to a Retiree Without Triggering Panic Selling

How to Explain a Claim Denial to a Furious Long-Term Policyholder

How to Guide an Elderly Fraud Victim Without Making Them Feel Foolish

How to Mediate a $2M Inheritance Dispute Between Grieving Siblings

Customer Support

How to Handle an Angry Customer Escalation: When "I'm Sorry" Isn't Enough

How to Help a Non-Technical User Through Tech Support: When Patience Is the Product

How to Save a Cancellation When the Customer Has a Spreadsheet: Retention Beyond the Script

How to Communicate During a Service Outage: When Your Customer Is Losing $15,000 an Hour

How to Resolve a Billing Dispute Before the Chargeback: When Trust Has Already Broken

Sales

How to Cold Call a Busy Executive: Breaking Through in the First 15 Seconds

How to Handle Price Objections: When the Prospect Loves Your Product but Not Your Price

How to Run an Enterprise Discovery Call: Earning a Second Meeting With Fortune 500 Buyers

How to Upsell an Existing Customer: The Annual Review That Grows Revenue Without Selling

How to Displace a Competitor: The Long Game That Wins Enterprise Deals 8 Months Early

How to Close a Stalled Deal: When Your Champion Can't Get It Done Internally

Human Resources

How to Interview a Candidate Who Sounds Great But Says Nothing Specific

How to Handle a Harassment Complaint When the Accused Is a Senior Leader

How to Get the Truth in an Exit Interview When They're Being Polite

How to Respond When a Key Employee Brings a Competing Offer You Can't Match

How to Rescue an Onboarding That's Quietly Failing

Professional Communication

How to Survive a VC Q&A After Your Series A Pitch: When the Slide Deck Stops Protecting You

How to Handle a Crisis Media Interview: When a Journalist Has the Memo You Hoped Would Stay Internal

How to Ask a CFO for More Money When Everyone Else Is Cutting: The Art of the Counter-Cyclical Budget Request

How to Tell Your Biggest Client the Project Is Late: When Honesty Is the Only Retention Strategy

How to Negotiate a 40% Vendor Price Increase Down to Something Reasonable: When Switching Is Painful but Paying Is Worse

Negotiation

How to Negotiate a Partnership Without Giving Away Exclusivity You Can't Afford

How to Hold the Line on Pricing When Your Best Client Asks for 30% More at the Same Rate

How to Survive a Due Diligence Interview Without Killing Your Valuation

How to Ask for a Raise When You Are 25% Below Market and Afraid to Sound Greedy

How to Win a Three-Way Partnership Negotiation When Everyone Has a Side Deal

Recruiting

How to Cold-Call a Passive Candidate Who Gets 10 Recruiter Messages a Week

How to Close a VP of Engineering Candidate Who Has Offers from Stripe and Datadog

How to Interview an Overqualified Executive Without Getting Steamrolled

How to Handle a Candidate Asking for 30% Above Your Range Without Losing Them or Breaking Your Comp Framework

Customer Success

How to Run an Enterprise Onboarding Kickoff When the Client Already Oversold the Timeline

How to Save a $240K Account When Your Champion Left and Usage Collapsed

How to Pitch Cross-Department Expansion to a Budget Gatekeeper Who Thinks in Spreadsheets

How to Run an Executive Business Review When the VP Thinks You're a Line Item to Cut

How to Handle a Product Gap When Your Best Client Just Saw the Competitor's Demo

Leadership

How to Tell a Top Performer She Was Passed Over for the Promotion — and Keep Her

How to Defend Your Strategy to a Board Member Who Voted Against It — After Missing the Quarter

How to Lead at 11 PM When Your Platform Is Down, Your VP Is Spiraling, and 2,200 Clients Are Waiting

How to Get Your CRO to Stop Sabotaging the Strategy She Was Hired to Execute

How to Face 255 Employees the Day After You Let 45 of Their Colleagues Go

Hospitality

How to Handle a Hotel Overbooking with a VIP Guest: Turning Betrayal into Loyalty

How to Handle a Food Safety Complaint in Your Restaurant Without Losing Control of the Room

How to Confront an Employee About Theft: Holding the Line Without Destroying the Person

How to Cut Off an Intoxicated Regular Without Losing a Loyal Customer

How to Handle a High-Value Luxury Client Return Without Breaking Policy or Losing the Relationship

Education

How to Handle a Combative Parent-Teacher Conference About a Failing Student

How to Confront a Student About Plagiarism Without Losing the Teaching Moment

How to Respond When a Student Reveals a Mental Health Crisis: The Most Important Conversation of Your Career

How to Handle a Disruptive Participant in Corporate Training Without Losing the Room

How to Advise a Student Switching Majors When Their Parents Are Threatening to Cut Funding

The Tough Conversations
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