The Goal Setting Meeting I Run Every Quarter (And Why It's Become My Favorite Hour of the Year)

Why I Started Doing This

A few years ago, I noticed something. We were great at setting company goals. OKRs, KPIs, quarterly planning. We had all of it. But we had no real container for the humans doing the work to step back and ask: what do I actually want?

Not what the company wants. Not what their manager wants. What they want.

So I started running a voluntary, quarterly goal-setting session. No agenda tied to work projects. No output that feeds into a spreadsheet somewhere. Just an hour to look back, look inward, and look forward.

The first time I ran it, just a handful of people showed up. On Monday, we had 45 on Teams.

The Structure

The session runs about an hour and follows a simple arc: look back, look inward, dream big, get focused.

Look Back (15 min)

We start by honoring the quarter that just happened before we touch what's next. If we don't take time to celebrate ourselves, who will?

I ask four questions, one at a time. Everyone writes silently for a minute, then we share.

• Celebrate — What's one thing you want to celebrate from this quarter?

• Memory — What's your favorite moment?

• Pride — What was your greatest accomplishment?

• Lessons — What's one lesson you want to carry forward?

The Lessons question is the one I added most recently and it's become my favorite. It's the pivot. It takes everything heavy or hard from the last 90 days and turns it into something useful. People open up in a way they don't in any other meeting.

I also ask: What's one thing that is not serving you? The Ditch question. Subtraction is underrated in goal-setting. Sometimes the most powerful thing you can do is stop doing something.

Dream Big (10 min)

Complete silence. Music on. Everyone writes.

The prompt is simple: across every area of your life — health, relationships, finances, career, spirituality, fun, learning, rest — write down anything you want. No filter. No reality check. Just get it out of your head and onto paper.

This is the most important block of the session. Cameras off, no narration. It signals that this time is serious.

Get Focused (15 min)

From the brain dump, everyone picks their Top 3 — the three goals they'll focus on for the next quarter.

Not five. Not ten. Three.

Then for each goal, they answer three questions I call Why / When / What If:

• Why does this truly matter to you?

• When specifically — what's your milestone?

• What happens if you don't achieve it?

That last one creates constructive urgency. Not anxiety, but motivation. A goal with a strong Why, a deadline, and real stakes is a fundamentally different thing than a vague intention.

Finally, for each of the three goals, they pick one microhabit. Something so small it takes 60 seconds or less. Read one page. Drink one glass of water before coffee. Check your account balance for 60 seconds. The point is: make it so easy you cannot fail. Identity follows behavior.

What I've Learned Running This

Presence is a choice, and it signals something. The fact that this meeting is optional matters. The people who show up want to grow. That self-selection makes the room feel different from the first minute.

Write before you speak. I'm religious about this. Silent individual writing before any group sharing consistently produces more honest, more personal answers. It removes the pressure to perform and gives people permission to be real. Sharing is completely optional.

Celebrate louder than you think you need to. People dramatically undervalue what they've accomplished. When someone shares a win and the room claps, that's not just nice — it's recalibrating. We move so fast that Q1 wins feel like ancient history by March. Slow it down. Make it count.

The Lessons question is the missing piece in most retrospectives. Most retros are either too analytical or too positive. Asking for one lesson someone wants to carry forward is different, it's hopeful. It says: what happened has value, and you get to decide what that is.

Want to Run This Yourself?

The full deck I use — with every slide, every question, facilitator timing, and notes — is something I've built and refined over several quarters. If you want to run this with your own team, steal the whole thing. The questions are the magic. The structure just gives them room to land.

The one thing I'd tell any leader who wants to try this: don't over-engineer it. You don't need a perfect deck. You need a room, an hour, and the willingness to go first.

When you share your own answers, people realize this is real. That's when it becomes something.

My Favorite quotes from this session

• This was my micro habit from 2024 for saving - that I still do to this day ... i set aside $28 every day and every 2 weeks I transfer that over into savings .... this is what helped me reach my goal!  

• I added a 60 second of reading micro habit in January and I'm already 8 books down for the year.

• 4 years after our first goal setting session, I still drink water before coffee because of that.

• Thank you for the reflection time, v appreciated.

• I cut out sugar this in January. I've made it almost 3 months so far. 

I run this every quarter at Bravo Store Systems. It's optional. It's personal. And I look forward to it more than almost any other hour on my calendar.

If you've run something like this with your team, or if you try this and want to share how it went, I'd love to hear from you.