The ultimate 4-step system for GREAT 1-on-1s

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So I got tagged at least 10 times in the video of Brian Chesky (AirBnB CEO) famously saying last year that he doesn’t run 1on1s… And I just had to laugh.

Because yes, he’s the CEO of Airbnb. He of course knows his stuff.

But he’s also running a global company with layers of leadership between him and most employees.

He’s not in the weeds anymore.

But for us mere mortals, newer managers, team leads, even senior heads of department - 1on1s are the work.

They’re where respect is built, where our people feel seen, supported, and stretched.

So unless you’ve got 500 direct reports and a Chief of Staff handling your calendar...
Block the time. Run the 1on1s.

Done right, they can literally stop a team member from quitting, unlock innovation, and fix performance issues before they blow up into deep drama.

And you need a system to do that.

Luckily for you, I have spent years testing and refining this system, testing the questions, the frequencies and more, so it’s now literally plug and play ready for you to start using.

Today I’m laying out my Ultimate 4 step 1-on-1 system.

We’ve got it in:

1. Blog format (here)

2. A YouTube video

3. And even an agenda download for you to use

But first, it’s important we talk about…

The 3 big mistakes

These 3 mistakes quietly erode trust, motivation, and performance. Even in otherwise great teams. Let’s break each one down:

1. Assuming our team's priorities are the same as our own 
   You might want promotions & pay rises, they may prioritise creativity or rest

2. Only doing ‘appraisals’ annually
   Bottling up feedback, praise and general performance improvement work until it’s all way too late

3. Just saying ‘my door is always open’
   This isn’t enough, our team naturally don’t want to ‘bother’ us

The Ultimate 4-Step System for Great 1-on-1s

Let’s go

Step 1 💬 Every Day – Praise & Difficult Conversations

• Why it matters:
  Small things build culture. Daily micro-moments of praise create motivation and belonging. And tackling issues in the moment (instead of hoarding them for reviews) prevents drama, resentment, and performance dips.

  What to do:

  • When someone does something great, say it. Be specific. “Great job on X” is 10x better than a vague “well done.”

  • When something’s off, don’t let it slide. Use language like:
    “Can I offer you a quick bit of feedback on that?”
    “I noticed something just now, can we talk about it?”

  • Stay kind but clear.

🔁 Every 2 Weeks – 30-Minute Catch-Up

• Why it matters:
  Consistency builds psychological safety. These are a soft space for connection, concerns, and coaching. The absence of these can make team members feel ignored or hesitant to raise issues.

  What to do:

  • Add a 30-minute, recurring calendar invite.

  • Never cancel it. Ever. Your reliability here is what builds trust.

  • No agenda needed. Just open with: “What’s on your mind?” or “Anything you want to talk through today?”

  • Let them lead. Listen more than you talk. Guide where needed.

  Step 3🗓️ Every 90 Days – In-depth 1:1

  Why it matters:
  This is your quarterly "zoom out." Unlike regular check-ins, these are a chance to review big-picture performance, role satisfaction, future growth, and team dynamics.

  What to do:

  • Book at least 90 minutes, uninterrupted.

  • Bring structured questions: What’s working? What’s not? Where do you want to grow? (agenda below)

  • Ask for feedback on your leadership, the team, and systems.

  • Document key takeaways and actions for accountability.

  Step 4 🗓️ Every Year - Salary Review

  Why it matters:
  People want to feel fairly paid, but even more than that, they want transparency.

  If you skip structured salary reviews, people will assume they’re being undervalued or overlooked, leading to resentment or them job hunting silently

  What to do:

  • Have a formal sit-down where you discuss compensation, wins, and how their contribution is being recognised.

  • Come prepared with data: performance and your rationale.

  • Give space for them to make their case, this should feel like a two-way conversation, not just a verdict.

  • Even if there’s no increase this time, clarity goes a long way.

Why you still need 1-on-1s (even if Brian Chesky doesn’t)

Airbnb’s CEO might not run 1-on-1s anymore, but for the rest of us managing real teams, they’re non-negotiable.

When done right, they build trust, prevent drama, and stop great people from quitting.

Excited for you to get started

Peace,

H

P.S. We’re only running these free 45 min online workshops for another few weeks, make sure you grab your spot