Does Your Team Know What Winning Looks Like?

Why a hard-working team can still pull in different directions, and three questions to find out where yours stands.

"How do I get everyone pulling in the same direction?"

Managers ask me a version of this all the time.

Everyone is working hard. The calendar is full. Work is getting done. And the team still feels like it's heading five different places at once.

One person pushes hard on a goal you mentioned once in passing. Another is waiting for you to tell her what matters. Someone else is doing great work on something nobody asked for.

Managers tell me, "I don't understand why some people are doing it and some people aren't." Or, "Nobody on my team is reaching out to help those folks." Or the one I hear most: "How do I get people to work with me instead of waiting for instructions?"

It's easy to read that as an effort problem, or a culture problem you inherited along with the team. Usually it's something simpler.

Everyone brought their own scoreboard

The real issue is that your team doesn't share a picture of what winning looks like.

Each person walked in carrying one. Most of the time it's the definition of winning from their last team, their last manager, or their last company. For one person, winning means shipping fast. For another, it means nothing ever breaks. Both are working hard. They're playing different games.

That's how you end up with a golf team. We're on the same team, but you shoot your round, I shoot my round.

That's not a team. That's a collection of individuals with the same manager.

Here's the part managers miss. You probably do have a clear picture of winning. You've talked it through with your boss. It shapes every call you make.

But if the vision only lives in your head, it doesn't exist.

More goals won't fix this. Goals tell people what to hit. A vision tells them how to act when two goals collide and you're not in the room.

What your team needs is a shared understanding of the outcomes you're expected to deliver, and why those outcomes matter to each person on the team. The scoreboard, plus the reason each person cares about it.

What this looked like with a brand-new team

A while back, I flew across the country to lead a workshop in person for a client's customer success team.

The team was brand new. Nobody had been there more than a few months. The newest hire was still in onboarding.

I usually suggest picturing the team three years out. This manager told me they were moving too fast and there was no way his team could picture that far ahead. So we used one year.

The number isn't the point. The point is to get people looking past the normal planning cycle, far enough out that this quarter's fires stop crowding the picture.

I gave everyone a short block of time to write ideas on sticky notes, one idea per note. The prompt was simple: "What will it be like one year from now when everything on this team is going exactly the way we want it to go?"

On average, each person wrote about a dozen.

What stood out more was what came next. When we came back together, every person wanted to walk through every one of their notes. Nobody skimmed. Nobody said the rest were pretty similar. Walking through all of it took a long time, and nobody wanted to rush.

Most of these people had only known each other a few months. They had plenty to say about what great would look like, and it mattered to them that the rest of the team heard it.

The split that keeps this from getting fluffy

The most common objection I hear to a session like this is that it's soft. Or that the team will invent a vision the boss doesn't care about.

That risk is real if you skip a step. So you split the work in two.

1. What's non-negotiable. The outcomes the business needs from your team. You decide those with your boss first, and they aren't up for a vote.

2. What's theirs. How your team wins those outcomes. "Here's what the business needs from us. Now let's decide how our team will deliver these outcomes in our own way."

The first part keeps you honest with the business. The second part is where ownership comes from. People don't take ownership of a plan they had no hand in shaping.

That customer success team built a vision and values document with a simple structure. First, the common challenges their customers face. Then, the solution their team provides. Then, the impact of that work rippling outward to customers, to the customer success function, to the broader sales org, and to the company.

The manager's next step was to cascade the vision into methods and measures, their more tactical OKRs. Vision first. Then goals.

Later, I asked him what value he'd gotten from my program and what he'd tell another manager who was thinking about it. He said the biggest value was building the shared vision of success with his team.

Your move this week

You don't need a workshop to discover where your team stands. You need three questions and your next round of 1:1s.

Ask each person, separately:

1. "What do you think our team is here to deliver for the business?"

2. "Why does that matter to you?" If they give you the company's reason, ask again. You're looking for theirs.

3. "Picture us at our very best, a year from now (or two, or three). What does that look like?"

On the timeframe for that third question, pick a horizon past your team's normal planning cycle that people can still imagine. On a fast-moving team, one year might be the limit. In a more traditional organization, two or three years works. If people can't picture it, you've gone too far out.

Don't correct anyone. Listen and take notes.

Then lay the answers side by side.

1. If the answers to the first question don't match, you have an alignment gap.

2. If people struggle with the second, or answer only in company or metrics terms, you have a gap in meaning or purpose.

3. If their pictures of "our best" barely overlap, you don't have a shared vision yet.

Answers that only talk about metrics aren't wrong. They tell you people know the scoreboard and haven't connected it to anything they personally care about.

Whatever you hear becomes raw material. When you sit down to build the vision together, you'll start from what your team already told you.

The picture of winning in your head is a good start. This week, start getting it into theirs.

Best,

Jeff

P.S. If you've taken over a team that's working hard but pulling in different directions, let's talk. Book a Strategy Session and we'll look at the picture of winning your team is carrying right now, and how to build one they'll own together. You will meet directly with me. Here's a link to my calendar.