What Most Teams Get Wrong About New Year Planning

Why New Year planning so often lock teams into last year’s patterns

January is when most leaders run the same play.

They look back at what didn’t quite work last year.
They look ahead at what has to be different this year.
And they respond the only way that feels responsible:

They set new annual goals.
New priorities.
New initiatives.
New commitments layered on top of the old ones.

On the surface, this looks like leadership. It feels disciplined. Intentional. Forward-looking.

But here’s what shows up year after year:

Annual goals rarely fail because the goals are wrong.
They fail because nothing beneath the goals has actually changed.

The same assumptions are still in place.
The same dependencies are unresolved.
The same decision bottlenecks remain.
The same teams are expected to execute a plan they didn’t help shape.

So the goals don’t collapse all at once. They erode.

They get deprioritized.
They get reinterpreted.
They get pushed to “next quarter.”

And by the end of the year, the gap between what you hoped would happen and what actually happened feels familiar in the worst way.

Not because you didn’t care.
Not because your team wasn’t capable.
But because the conditions required for success were never built.

1. The goal isn’t a shared vision of success

Most annual goals are written as outcomes. Numbers. Milestones. Deliverables.

But outcomes don’t move people. A shared vision does.

A real vision answers the questions your team actually cares about:

What does winning look like?
What will be different about how we operate?
Why does this matter enough to push through the hard parts?

And just as important: do the people doing the work feel like they helped shape that vision, or does it feel handed down?

When a vision lacks meaning and authorship, people comply. They don’t commit.

If this sounds familiar and you want help pressure-testing your team’s goals before the year gets away from you, you can book a complimentary consultation with me today.

2. The plan is too complex to execute

This one is straightforward.

If every person on the team can’t explain the plan in plain language, you don’t have a plan. You have a document.

Complex plans create a predictable outcome: people nod in meetings, then improvise in real life.

The goal isn’t to oversimplify reality. It’s to create enough clarity that people know what matters most, how their work connects, and where to focus without constant translation.

When plans are too complex, alignment exists on paper, not in practice.

3. Stakeholders and dependencies aren’t truly aligned

This is where many solid goals start to unravel.

A priority can be critical for your team and functionally optional for someone else.

When a goal depends on another group that doesn’t treat it as a priority, progress slows in ways that feel confusing and unfair to the people doing the work.

Deadlines slip.
Hand-offs stall.
Escalations increase.
And your team starts to internalize failure that isn’t actually theirs.

This isn’t an execution problem. It’s an alignment problem.

If a goal has real dependencies, alignment has to be built deliberately—and revisited as conditions change.

4. The team didn’t help build the plan they’re expected to execute

Many leaders feel pressure to show up with a fully formed plan.

So they do the planning in a small group, then roll it out as direction.

When reality doesn’t match the plan, the response depends on who authored it.

If the plan was handed down, it’s easy for the team to think, “This was never going to work. Leadership should have asked us.”

But when the team helped build the plan, something changes.

Now the plan feels worth saving.
Now people adapt instead of disengaging.
Now effort increases instead of blame.

Teams don’t need to vote on strategy. But they do need authorship in the path.

5. The team isn’t empowered to decide, or doesn’t feel safe doing so

Even motivated, aligned teams will stall if decisions are centralized.

If everything has to flow upward, work queues. Risk gets avoided. Momentum slows.

But authority alone isn’t enough.

If people believe they could be punished, shamed, or sidelined for making the “wrong” call, they won’t commit. They’ll gather more data. Seek more consensus. Delay action.

Decision-making requires both authority and safety.

People need clarity on what they own, how much risk is acceptable, and what support looks like when outcomes aren’t perfect.

Without that, empowerment stays theoretical.

The point

If you’re setting annual goals right now, here’s the question worth sitting with:

Are you changing the goals, or are you changing the conditions required for those goals to succeed?

When the vision isn’t shared, people execute tasks instead of pursuing outcomes.
When plans are too complex, alignment breaks under pressure.
When dependencies aren’t aligned, progress becomes negotiation.
When teams don’t help build the plan, commitment fades when reality shifts.
When decision-making isn’t safe, momentum slows to a crawl.

Before adding another goal to the year, ask a different question:

What has to be true for this goal to actually happen?

Not in theory.
In practice.
With real people.
Inside your actual organization.

Because the most expensive kind of planning isn’t ambitious planning.

It’s planning that changes the goals while leaving everything else exactly the same.

P.S.
Most leaders don’t need better goals. They need a clearer picture of what’s preventing the goals they already have from becoming real. If this letter hit close to home, that’s usually a sign worth paying attention to. Let’s talk about it.