Leadership

September 16, 2025

5 min read

Where Most Plans Fail

Where Most Plans Fail—And How to Finally Get Strategy Right

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It’s a strange thing to watch a plan fall apart.

Not because people didn’t try.

Not because they didn’t care.

But because something got lost between the kickoff and the doing.

I’ve seen it happen in fast-paced startups, in big corporations with full strategy decks, and in scrappy teams trying to make something out of nothing.

It always looks a little different on the surface—missed deadlines, shifting priorities, surprise frustrations—but underneath, it’s usually the same issue:

The team couldn’t see the whole picture.

Maybe the vision was exciting.

Maybe the goals were even measurable.

But without a clear, shared map of how to move forward—week by week, team by team—people defaulted to guessing.

And the thing about guesswork is, it multiplies.

One person guesses here. Another adjusts there.

Before long, everyone’s moving, but no one’s moving together.

If you’ve ever led a project, launched a new initiative, or tried to turn a great idea into a real result, you know what I’m talking about.

This article is about how to fix that.

Because strategy isn’t about sounding smart or setting impossible goals.

It’s about giving your team a simple, repeatable system to move forward, together.

Let’s get into it.

The Silent Breakdown Most Teams Never See

One of the most common frustrations I hear from leaders is this:

"We all agreed on the goal—so why does everything still feel chaotic?"

The answer, more often than not, is that the agreement wasn’t as aligned as they thought.

Everyone liked the same words in the meeting.

But everyone walked away with slightly different assumptions about what to do next.

One person thought: "We’re going to prioritize customer growth."

Another thought: "We need to shore up retention."

A third thought: "Now’s the time to rework the onboarding process."

All good intentions. All rooted in logic.

But headed in different directions.

And the worst part is: no one realizes the plan is unraveling until it’s already happened.

Projects start to overlap.

Timelines get missed.

Teams point fingers—not maliciously, but because confusion builds tension.

When this happens, the usual fix is to call a meeting.

Then another.

Maybe draft a new slide deck. Maybe assign more KPIs.

But none of that solves the real issue: the strategy wasn’t built to be used.

It was built to be presented.

If you want something your team can use, you have to build it differently.

That’s where the Strategic Planning Blueprint comes in.

Strategy That Moves: The Blueprint That Changes Everything

A great strategy isn’t something that only works in a quarterly review.

It should be something your team can live inside of.

It should help people know what to do when they open their laptops on Monday morning.

It should reduce hesitation and decision fatigue.

It should keep people rowing in the same direction even when the waves hit.

The Strategic Planning Blueprint helps make that happen.

It breaks down your entire approach into four core components:

Assess the Present
Set Clear Goals
Develop a Winning Plan
Track Progress and Adapt

Each part serves a different purpose, but together, they keep teams aligned, grounded, and moving forward.

Let’s go deeper into each step—and talk about what happens when you actually use them.

1. Assess the Present

Most teams are so eager to plan that they rush right past where they are.

They want to talk about where they’re going, what success looks like, what the future holds.

That excitement is important.

But if you don’t pause to see your real starting point, your plan will be full of blind spots.

I’ve watched teams set major revenue goals without realizing their churn rate has quietly spiked 20%.

I’ve seen marketing departments invest in awareness campaigns without checking whether the product is ready for that kind of traffic.

When you skip the honest check-in, you’re building your plan on top of assumptions.

And assumptions break under pressure.

Instead, gather your team and ask hard questions:

Why do we exist—today, not last year?
Where are we competing that actually matters?
What’s truly helping us—and what’s quietly hurting us?

This part is messy. That’s okay.

Strategy isn’t clean at the start. It’s honest.

And when you give people the space to be real about what’s working and what’s not, you’ll uncover insights that make every step that follows stronger.

2. Set Clear Goals

Once you understand where you are, you can talk about where you’re going.

But this is another place where teams get stuck.

They set goals that are technically measurable, but not actually useful.

They say things like:

“Grow the business by 20%.”
“Improve retention.”
“Increase engagement.”

Those are fine as metrics, but they don’t guide action.

They don’t help people prioritize.

They don’t help anyone answer, “Should we work on X or Y this week?”

Real goals do that.

Clear goals:

Align with the reality you’ve already assessed
Are broken into both outcomes and behaviors
Guide daily decisions

Want to know if your goals are clear enough?

Ask someone on a different team how your goal changes their work this week.

If they can’t answer quickly, your goals need work.

3. Develop a Winning Plan

Now it’s time to turn your goals into a real plan.

This is where most plans quietly fail.

Teams often stop at the destination without mapping the journey.

Everyone knows what success looks like, but no one knows how to get there.

That’s when people start making their own guesses.

They prioritize based on what they think matters.

They move forward in parallel, but not in sync.

To fix this, you need a plan that breaks things down:

What specific actions get us closer?
What’s the timeline for those actions?
Who owns each piece?

It sounds simple, but most teams skip this part or keep it too vague.

Here’s the truth: If you can’t point to a single document that shows these three things, your plan isn’t done yet.

Make it visual. Make it shared.

Make it something you look at every week.

That’s how you move from idea to actual progress.

Real Workplace Example: What Happens When the Picture Isn’t Clear

A few years ago, I worked with a software company that had just raised a major round.

They were excited to grow, build fast, and take market share.

But internally? It was chaos.

Marketing was launching campaigns for features that weren’t ready.

Product was juggling priorities without clarity on what mattered most.

Sales kept promising things that didn’t exist yet.

Customer support had no idea what was coming next.

Each team thought they were doing the right thing.

But their "right thing" didn’t match up.

I walked in and found no clear shared roadmap.

Just a lot of disconnected planning.

So we started fresh.

We assessed the present, set three clear goals, built a one-page plan with ownership lines, and created a weekly rhythm to revisit it.

Within one quarter, things turned.

They shipped a major feature on time.

They reduced cross-team tension.

And their CEO told me, "This is the first time it feels like we're moving together."

It wasn’t magic. It was shared clarity.

4. Track Progress and Adapt

The last piece is where good plans stay good.

Because even the clearest plan will need adjustment.

Markets shift. People leave. Priorities evolve.

The question isn’t "Did we get it right the first time?"

It’s "Do we have a way to adjust without losing momentum?"

The answer is a simple tracking rhythm.

Weekly, ask:

What actually moved forward?
What didn’t? Why?
What are we changing next week?

Don’t overthink this.

Make it simple. Make it visible. Make it honest.

When your team knows they can adjust without blame, you create a culture of momentum.

The Best Tools, Talks, and Shows to Help You Build Strategy That Actually Works

If you want to get even better at this, learn from the people and resources that have shaped the world’s best strategic minds.

Book: Good Strategy, Bad Strategy by Richard Rumelt

This book changed how I help teams think. It explains why most strategy fails: because people confuse goals with plans. Rumelt shows you how to focus, cut through noise, and build systems that actually work.

Podcast: The Knowledge Project with Shane Parrish

This is for thinkers. For doers. For people who want to slow down and think better. Shane interviews people at the top of their game, and the takeaways apply directly to strategic leadership.

TED Talk: Your Strategy Needs a Strategy by Martin Reeves

If your strategy worked last year but doesn’t now, this talk explains why. Reeves breaks down how different types of challenges require different strategic approaches. Watch it with your team.

Docuseries: Inside Bill’s Brain: Decoding Bill Gates (Netflix)

This one isn’t just about Gates. It’s about solving complex problems with structured thinking, clear delegation, and unwavering focus. There’s so much in here about how to lead with clarity in chaos.