What Your Team Really Thinks About Your Strategy

Two Rooms

Picture the room. The strategy presentation is finished. The final slide: Questions?

Nobody raises a hand. The meeting ends. People move to the hallway — and somewhere in that chatter is the most valuable input you’ll never hear.

Now picture a different room. Same presentation. Same slide. But someone raises a hand and wonders aloud if the priorities are in the right order. Someone else isn’t convinced the sales targets are achievable. A third person expresses their concern about whether the support team can handle a significant volume increase without diminishing customer satisfaction.

That’s the meeting every leader should want. The healthy one.

And the strategy that comes out of it is more likely to work — because the people responsible for executing it already helped shape it.

Build It With Them

The most important question any leader can ask before presenting a strategy: have the people in this room been part of building it?

Not executing it. Building it.

Strategy built without the people who have to execute it will be interpreted individually. They’ll fill in the gaps. Make their own calls. Prioritize what they know and quietly sidestep what they don’t. When something goes wrong — and something always goes wrong — they’ll wait to be told what to do next. Because the strategy was never really theirs. There’s no buy-in.

For challenger brands especially, this isn’t a luxury concern. You’re competing with a shorter runway, fewer resources, and less margin for error than the established players. A team executing your strategy rather than the strategy isn’t just a cultural problem. It’s a competitive liability.

Set the Bar at the Right Height

Achievability is where strategy gets real.

An honest gap assessment isn’t a sign of weakness. It’s a prerequisite. Most strategies look right on paper — in the leader’s mind, on the spreadsheet, in the presentation deck. What often goes unexamined is the harder question: can this specific team, with these specific resources, actually get there?

I’m not talking about lowering the bar. I’m talking about setting it at the right height.

There’s a version of stretch that energizes people — a goal that feels challenging but possible, and feels extraordinary when it’s reached. And there’s a version that quietly breaks teams: targets nobody believed were achievable, and nobody said so, because the culture didn’t make it safe to say so.

Part of setting the right bar is also deciding what’s not on the table — at least for now. Focus is a deliberate choice, and in our industry it’s often where challenger brands lose the thread. Good product. Real opportunity. And then too many fronts opened at once.

The Part Nobody Plans For

Even when you get the strategy right, there’s still a way to lose the win.

Here’s something I’ve seen more than once: a brand breaks through. Real growth. The kind of numbers that make investors and board members happy and competitors nervous.

And then the wheels come off.

Not because the product failed. Because the support infrastructure — the team handling orders, the service techs fielding customer calls, the people managing operations and logistics — wasn’t ready. Newly won customers can’t get speedy resolution and take to social media. Channel partners get frustrated and revert to trusted and reliable suppliers. Hard-earned momentum reverses itself and ground gained in the market is lost.

Here’s the thing: someone on that team knew this would happen. Your support manager probably had a quiet concern about service turnaround time. Your ops lead likely had a throughput calculation that didn’t add up. They just weren’t in the room when the growth targets were set.

The buy-in conversation isn’t only for sales and marketing. It belongs to everyone who has a role in executing — and protecting — the win.

When the Team Wins, the Company Goes Faster

Achievable goals do something beyond the quarterly number: they give people the experience of winning.

And winning compounds.

A team that hits a hard goal believes the next one is possible. They stay bought in. They engage. They bring solutions instead of problems. They take risks — because they’ve seen what happens when well-considered bets pay off. They might even push your organization to move even faster than you planned. And they’ll own the work when they do.

The opposite is equally true. A team that keeps falling short of goals they never believed in doesn’t just miss the number. They disengage. Quietly. Professionally. The best ones leave. The rest stay and wait for instructions.

The Culture That Makes It Work

None of this happens without a specific kind of room.

A room where someone can raise their hand — not to undermine the leader, but because they were invited to. Because they understand they have an obligation to dissent. Because speaking up is how strategy gets stronger, not how careers get ended.

What your team really thinks about your strategy is either being said in that room — or in the hallway after.

You decide which one.