Every management book, every “how to run better meetings” post, every leadership-tips list tells you: start your staff meeting by asking each person for a win. I do it. I’ve done it for years. But I noticed that the write-ups usually stop at the prompt. And, while important, I think the prompt is the least interesting part.
Asking for a win takes ten seconds. The value is in the context you add on top of it.
The Prompt
When someone shares a win, you need to respond to it. Not just “great, thanks, next.” Connect it to the right things. Where does this fit into the strategy? How does this help the business? What does this do that people may not have realized? Here are 2 examples:
- “In case everyone didn’t realize, this used to take the onboarding team 2 weeks and now it’s a single workflow that takes 10 minutes. This enables them to do more creative problem solving and less rote manual work, creating a better experience for new customers.”
- “All the work being done by teams X and Y are gated until this service is live and it just went live. Now we can do the full end-to-end tests and teams X and Y aren’t building against mock responses, they can use the live service with real data.”
Think of it like enriching an event in a distributed system. The work itself is the event. Your job is to enrich it with the missing context that explains why everyone else should care.
Whatever the specific link is, say it out loud in front of everyone else in the room. The person sharing the win naturally explains what they built or finished. As the leader, you’re in the best position to bring that context into the conversation. You’re one of the few people who can see how that piece of work connects to the roadmap, other teams, customer outcomes, or company priorities. One of the highest-leverage things you can do as a leader is take that context that’s trapped in your head and distribute it to everyone else. Don’t assume everyone else sees what you see. Once you make that knowledge explicit, it stops being your understanding and starts becoming the team’s.
And yes, sometimes the context will be obvious or already known by some of the people in the room. Say it anyway. There’s a difference between everyone knowing something and everyone hearing it said in the same room — reinforcement is part of the job.
Leaders aren’t just responsible for recognizing good work. They’re responsible for explaining why that work mattered.
Executing this moment well works because of who’s in the room. It reinforces a context-not-control style of leadership. The person who just spoke gets a chance to be proud of what their team accomplished and to have that accomplishment recognized by their peers. Your response makes sure that recognition reaches the people who would never claim it for themselves. Everyone else is already paying attention because there’s a spotlight on one person. If you skip the connection and move on, then you’ve asked for a ritual and thrown away most of the value. Skip it and the ritual is just morale theatre. Make the connection, and everyone in the room walks out knowing a little more about how the whole thing fits together.
That’s enough. If all you ever do is ask for a win and consistently add the missing context, you’ll get most of the value this ritual has to offer.
Once that becomes natural, then it’s worth evolving the prompt.
The Progression
Even now, this is still the version I use most of the time. Once in a while, we add a little flair to keep things fresh. It always starts with “one win.” My 2 favorite flair options are:
- Add one thing you’re excited about.
- Add one thing that you’ve learned this week.
I think of these prompts as sharing progressively richer context with the rest of the room. “Share a win” tells everyone what happened. “What are you excited about?” tells everyone where you or your team see opportunity. “What did you learn?” tells everyone how your understanding changed, whether that learning came directly from you or from your team.
Notice that each step asks a little more of the person sharing it. A win is safe — you did something and it worked. Excitement admits what you care about. Learning admits what you didn’t know.
“One thing you learned” is the hardest, because saying you learned something means being vulnerable. It also means that you’re saying there was something you didn’t know in front of your boss and peers. That prompt needs a room where people trust each other enough to say, “I got this wrong” or, “I finally understood how X works” without paying for it later. Every time someone says, “I learned something,” and nothing bad happens, everyone sees that it’s safe to do the same.
Each version tells you something different as a leader. When someone shares what they’re excited about, you get a read on what’s going on in their head. Usually this isn’t what’s on the agenda, which is exactly why it’s worth hearing. It’s also totally fine if the answer is something outside of work.
Work is often a grind, and a minute of someone else’s real enthusiasm can be contagious and carry into the rest of the day. Excitement is hard to fake. You can hear when someone really means it. And when they’re really into it, they might even try to keep going past their “allotted moment”. You may have to pull them back so the rest of the room gets their time. Don’t discourage that enthusiasm. Their energy is exactly what was asked for, and the room already caught it.
The learning prompt surfaces things that would otherwise stay in someone’s head or wait until a retro. When someone shares what they learned, hopefully other people in the room nod. Sometimes because they were about to hit the same wall, sometimes because they had the same insight recently and forgot it was worth sharing. The lesson might be technical. It might be about a team, the market, or the organization. It doesn’t really matter. The value is that the lesson stopped being one person’s learning.
Which prompt you can comfortably use is a read on where the team is. If you go for the “one thing you’ve learned” in a group that isn’t ready for it, you’ll get shallow answers or long pauses. You’ll also likely have burned the ritual for quite some time afterwards. So watch which prompt fits, and only escalate when there’s enough trust to hold space for the harder ones. You also have to hold the line in case there are any “bad reactions” (like laughing or “how could you not already know that?”). The defense is the same move as the rest of this: respond. If the first thing the room hears after “I got this wrong” is you treating it as useful, the snark never gets a foothold. And if someone does take a shot anyway, deal with it right there — a quick “that’s exactly what this is for” costs five seconds and reminds everyone what the norms are.
Protect the Ritual
Do this kind of thing long enough and there will come the inevitable, “I don’t have a win this week.” You might even have the urge to do this yourself during a hard week. Don’t let that stand for you or your team. Shrink the definition until something qualifies: something shipped, something that didn’t break, a conversation that went better than expected. The point is rarely the size of the win. It’s the act of stopping to find one and connecting it to the bigger picture. And if the same person can’t find one week after week, that’s information too. They may be underwater, or they may not be seeing the value of their own work. Either way, that’s a 1:1 conversation, not a staff meeting moment.
Picture the two versions of the same meeting. In one, everyone rattles off a win, the leader nods, and the room moves on to the blocker list. Box checked, nothing changed. In the other, someone mentions a migration that finally finished, the leader tells the room that three teams just got unblocked by it, and everyone in the room understands a little more about how the organization is achieving its goals.
The prompt isn’t the ritual.
The ritual isn’t just asking for the win. The ritual is taking context that’s scattered around the room and making it common knowledge.
“Share a win” just happens to be one of the easiest ways to do it.
