The Difficult Employee Conversation

Writing reviews for your team and want them honest AND motivating? Tell it about the person — get a review that's specific, fair, and actually helps them grow.

Hiring someone and want the offer to land well? Give it the details — get a warm, clear offer letter that makes them excited to say yes. Have HR/legal review the formal terms.

Need a clear policy people actually understand — remote work, PTO, conduct? Describe it — get a plain, fair draft. Have HR/legal check compliance for your region.

Having to let someone go is one of the hardest parts of managing. Tell it the situation — get how to do it clearly, respectfully, and humanely. Confirm the legal steps with HR.

Hiring on gut feel leads to bad hires and bias. Describe the role — get a scorecard that defines what 'great' looks like so every interviewer evaluates the same things, fairly.

Bad delegation = doing it twice. Tell it the task and who's taking it — get a brief so clear they can run with it without 20 follow-up questions.

Rejection emails are most candidates' last impression of you. Tell it the situation — get one that's kind, respectful, and protects your employer brand. Most companies botch this.

Someone needs to hear something tough and you're dreading it. Tell it the situation — get how to say it so it lands as helpful, not an attack, and they actually change.

A new hire's first weeks decide if they thrive or quietly check out. Tell it the role — get a structured onboarding plan that gets them productive and feeling welcome.

New to managing, or want to be better at it? Tell it the situation — get practical help with 1:1s, feedback, delegation, and the people stuff nobody trained you for.

Before you build it, let it poke holes. Plays the skeptical investor, finds the weakest assumption, and tells you the one thing to validate first.

Running a meeting, class, or party and need to warm people up? Tell it the group — get icebreakers people actually enjoy, not 'two truths and a lie' again.

Paste your numbers. Get the one chart that tells the story — and the headline a busy boss will actually remember.

Pitching a collab or partnership? Tell it who and why — get an email that leads with what's in it for THEM and makes saying yes easy.

Dump your to-do list. It cuts the busywork, picks the 3 things that actually move the needle, and time-blocks the day around them.

Don't wing the money conversation. This roleplays the negotiation, plays the tough recruiter, and tells you exactly where you left cash on the table.

Get the process out of your head so someone else can do it. Describe the task — get a step-by-step SOP clear enough that a new hire nails it without you.

You're bleeding money on stuff you forgot you pay for. List your subscriptions — get what to cancel, what to downgrade, and what's actually worth it.

Launching something and don't want it to land with a thud? Tell it what and when — get a week-by-week plan: pre-buzz, launch day, and the follow-through.

Debt across a few places and no plan? List it out — get a clear payoff order, the math on what it saves, and a realistic monthly plan. Not financial advice, just clarity.

Returns policy that protects you without scaring buyers off. Describe your product — get clear, fair terms in plain language, not legal scare-text.

About to drop real money and not sure? Tell it the purchase and your situation — get an honest gut-check on whether it's worth it, not just permission.

If people don't get why you in 5 seconds, you lose them. Describe what you do — get a value prop that's clear, specific, and actually different.

Want extra income but most 'side hustle' lists are junk? Tell it your skills and time — get realistic ideas that fit you, with how to actually start.