The Hard Conversation Prep Checklist for New Technical Managers

A simple, practical checklist you can use before a difficult conversation - so you're clear on what to say, what to avoid, and what really needs to change.

DOWNLOAD THE CHECKLIST

If you’re postponing a conversation because you’re not sure how it will land, this checklist is for you.

Most new technical managers don’t avoid hard conversations because they don’t care.
They avoid them because they’re trying not to make things worse.

This checklist helps you stop guessing.

What This Checklist Helps You Do

Before a hard conversation, you’ll use this checklist to:

  • Identify the real issue (not just the symptom)

  • Separate facts from assumptions

  • Get clear on the outcome you actually want

  • Choose clarity over comfort

  • Anticipate reactions without overthinking them

  • Decide what happens next

No scripts.
No therapy.
No corporate fluff.

Just a clear way to prepare for conversations that matter.

This checklist is designed for:

  • Newly promoted technical managers

  • First-time people leaders

  • Engineers, developers, and technical professionals now responsible for people

  • Managers who know a conversation needs to happen—but keep putting it off

If you manage people and find yourself replaying conversations in your head before they happen, this will help.

This checklist is not for:

  • People looking for motivational leadership advice

  • Managers who want to avoid difficult conversations altogether

  • Anyone expecting a script that works in every situation

This is a thinking tool—not a shortcut around responsibility.

When you sign up, you'll receive:

 

  • A one-page Hard Conversation Prep Checklist (PDF)

  • A practical tool you can use again and again

  • Something you can apply immediately—before your next 1:1, feedback discussion, or difficult meeting

 
If you’re avoiding a conversation right now, this checklist will help you prepare for it.
GET IT TODAY

Download the Checklist

It’s free. Use it before your next hard conversation.

DOWNLOAD THE CHECKLIST
A QUICK NOTE FROM ME

When I was a new manager at a med-tech startup, I avoided holding hard conversations longer than I should have.  Not because I didn’t care, but because I didn’t know how to handle them without making things worse.

I didn’t have a framework. I didn’t have a checklist. I just hoped issues would resolve themselves.

They didn’t.

This checklist is what I wish I’d had back then, something practical I could use before a conversation, when clarity actually matters.

~ Dr. Janel Anderson

Founder, Leadership 4 Geeks

This checklist is part of a larger framework I teach to technical managers who want to handle difficult conversations clearly—without damaging trust or creating bigger problems later.

If it’s useful, you’ll hear more.
If not, no pressure.