How to Run an End of Quarter Planning Workshop
End of quarter’s coming.
I hear this in Ned Stark’s voice. But it’s better this way than:
That’s right. It’s that time of the quarter where you look at your teammates and think “we’re supposed to know what we’re doing next quarter, right?”. This post is for anyone with a team, and who needs to get aligned fast—without forcing it or making people feel like they’re in group therapy.
Whether you’ve got innovation in your job title or you’re just trying to steer the ship while it’s still being built, this is the playbook I used this week for the coming quarter.
So here’s a lightweight but powerful workshop format I used this quarter. Total time investment: ~3 hours. Outputs: shared understanding, basic trust, and a quarterly plan.
TL;DR
Don’t let the end of quarter sneak up without taking a beat. New team or not, you need space to reflect, align, and make the next 90 days count.
Here’s your sequence:
Set the tone
Build connection
Reflect honestly
Choose what you’ll actually do
Write it down and move
If you're managing innovation, change, or just trying to herd the cats more intentionally, this format gives you a way in.
Let’s break it down.
The 5-Step Planning Workshop
1. Welcome + Purpose Setting
Quick and human. “We’re here to reflect, align, and figure out what matters most next quarter.” That’s it.
Pro tip: People engage way more when they know why you’re asking them to show up fully.
2. Feelings Circle with Picture Prompts
Sounds soft. Works hard. Lay out cards with images—landscapes, abstract art, random objects. To make this, get an AI or search terms from a Feels Wheel to give you ideas for topics, and pull out free stock photos from platforms like Pixabay. Tell the team to:
“Pick one that represents how you feel about your role or the team right now.”
Ask them to share why they picked it. This isn’t a confession booth—just a vibe check that builds empathy. Thank everyone for each individual share.
Why it works: workplaces build up emotions - this helps clear the air to focus on logic.
Pro tip: Open Spotify or YouTube and play some melodic or relaxing music in the background. The atmosphere it creates helps the team lean-in.
3. Reflection: Rose, Thorn, Bud
The classic.
Rose = something that went well
Thorn = something tough or frustrating
Bud = a possibility, idea, or opportunity
Give people 5–10 minutes to jot their own notes down. You can use sticky notes or place three boxes on an A4 page as a worksheet. Then share in pairs, followed by whole-group highlights.
Why it works: It lowers the temperature, validates lived experience, and surfaces insights fast.
4. Quarter Planning: Must–Should–Could Map
Classic Eisenhower-style triage, but for projects.
Have the team propose tasks, themes, or projects. Then collaboratively sort them into:
Must: Critical for KPIs or known commitments
Should: Valuable but not urgent
Could: Nice-to-haves, stretch goals, or experiments
It creates a reality check and a sandbox.
5. Bring it Home: Document and Follow Up
You don’t need a Notion wiki the size of “War and Peace,” but do capture:
Triage criteria
Must/Should/Could map
Any clear next steps or owners
Even just a follow-up email saying “Here’s what we came up with and what’s next” gives the session legs.
Then maybe, just maybe, you might be like this guy:
