5 Things Quietly Killing Your Strategy

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Hey Coach Will here…….

Why is it nobody really talks about how their business might be going off track, and why does it often seem no one knows the reason?

It’s like their strategies are wobbling just like a flimsy beach chair, and honestly, about 70% of well-intended strategies end up in the trash!

Not "underperform." Not "need adjustment." Flat-out fail.

Here's the part that'll sting: it's usually not the market that kills your strategy. It's not your competitors.

It's not bad timing or bad luck.

It's what happens—or doesn't happen—after your planning session ends.

Harvard puts the failure rate at 90%. McKinsey says that when transformations crash and burn, it's often due to poor execution, misalignment, and a lack of discipline—not because the ideas themselves were flawed.

Most entrepreneurs spend months building the strategy. Then, maybe only 10% of that time is spent figuring out how to actually do it.

The strategy is presented once, everyone nods, and then it quietly disappears in a Google Drive folder while everyone goes back to firefighting.​

Sound too familiar?

I've watched this pattern kill more good ideas than bad markets ever could. And it's almost always the same five things.

Let me show you what's actually happening.

🧨 Thingy #1: Strategy is Not a Daily Habit

Be honest with yourself for a second.

Pull up your calendar from last month. What percentage of your time was actually spent on your top 3 strategic priorities?​

For most leaders? Under 20%. The rest is meetings about meetings, urgent-but-not-important tasks, and putting out fires that somebody else should be handling.

Research tells us 67% of well-formulated strategies fail because they never get translated into concrete actions.

Leaders acknowledge that 74% feel their strategies aren't effectively broken down into concrete steps, and 79% are concerned about insufficient resource allocation to achieve their goals.​

Translation?

Your beautifully crafted strategy deck won't mean anything if Tuesday at 9:15 a.m. looks the same as it did before the retreat.

The gut check: If your strategy doesn't show up as recurring blocks on your calendar with clear owners and measurable milestones, you don't have a strategy.

You have a hope and a prayer!

🔥 Thingy #2: Shiny Objects are Bleeding You Dry

LinkedIn's CEO said it at Stanford: companies in hypergrowth "draw resources away from the core too quickly in pursuit of the next bright shiny object".

Your competitors attack your core while you're distracted. Then you're forced to pull everything back just to defend what you already had.​

Here's real data: 78% of B2B startups are failing at content marketing.

Why?

Because 60% have zero documented strategy and 90% keep jumping channels—Facebook ads to cold email to short-form video to SEO to AI SEO to LinkedIn.

They never build systems to make any single channel actually work.​

One supplements company making 7+ figures went through this with communication tools: Gmail → Microsoft → Front → abandoned → unruly Slack → Enterprise Slack → still broken.

The tools weren't the problem. They never committed long enough to build proper workflows.​

Every time you jump to the "next thing," you reset to zero. No compounding. No learning. No momentum.

The pattern: You quit after 2 weeks when it doesn't work immediately, then chase the next "perfect" solution instead of figuring out why the first thing didn't work.​

And you wonder why nothing sticks.

💀 Thingy #3: Mistaking "Big Goals" for Actual Strategy

"Hit $10M ARR by next year."
"Be the go-to expert in our niche."
"Dominate this market."

Cool. That's not strategy—that's outcome worship.

The Economist found that 90% of senior executives fail to achieve their strategic goals due to poor implementation.

One big reason? Vague goals that sound impressive in the boardroom but mean nothing on the ground.​​

Here's the truth: Real strategy is about saying no.

• Who are you not serving?

• Which offers are you killing?

• Which channels are you ignoring on purpose?

• What trade-offs are you making?

Research suggests that taking on too many initiatives can quietly drain your energy—trying to handle thirty projects when just three could really get you to your goals.

If everything is a priority, nothing is.​

⚠️ Thingy #4: Your Team Isn't on Your Page…

When your team isn't aligned, everyone works hard but optimizes for different assumptions about what actually drives growth.​

Marketing talks to one type of customer. Product builds for another. Sales pitches to a third: same company, three different movies.

The data is brutal: 67% of strategies fail because you and your team are not on the same page, and execution is broken.

Why?

People often struggle to understand how their daily work relates to strategic priorities.​

And here's the tricky part: most organizations lack systems to track progress or hold people accountable for results.

Without clear KPIs and accountability, you can't execute a strategy—you can only hope.​

🎯 Thingy #5: You Want Simple Answers

Here’s a fact that gets lost in the shuffle—progress stalls after initial goals are reached.

Disciplines fade once transformation ends. Incentives and financial plans are often bound to outdated goals, leaving new ideas and ambitions unsupported.

Most are content with past achievements, neglecting to sow seeds for the future, only to be caught off guard by the unforeseen challenges that lie ahead.

But there's something deeper happening.

You’re trying to simplify complex strategic questions into straightforward formulas because dealing with all the brain-drain nuance can be overwhelming.

"Just post more."
"Just add AI."
"Just raise prices."
"Just niche down."

The word "just" is doing a lot of heavy lifting on situations that are anything but simple.

Markets are messy. Customers are inconsistent.

External forces rewrite the rules overnight.

Every time you reach for a one-sentence solution to a multi-variable problem, you're choosing comfort over truth.

And your strategy dies a little more over time.

🤖 AI Power Prompt: Strategy Check

Use this with ChatGPT, Claude, or your favorite LLM to surface what's actually killing your strategy:

Run this. Then actually do what it tells you.

📣 Call to Action – Your Reality Check

Choose one and do it this week:

The Calendar Test:

Identify and highlight all blocks from last month that directly contributed to your top 3 strategic priorities. What percentage of your total blocks does this represent? If it’s less than 30%, your strategy is likely failing—you're just too busy to realize it.

The Shiny Object Audit:

List every initiative, tool, or channel you started in the past 12 months. How many are still active? How many got abandoned before they could compound?

The Clarity Test:

Without reviewing your plan, can you identify your top 3 priorities and explain how someone in operations would know if they're making the right decisions to support them? If not, you don't have alignment.

Be honest, this is your business.

📊 Quick Poll

🎬 That's a Wrap

I've built companies, led transformations, and watched brilliant strategies die in execution more times than I care to count.

The 70% failure rate isn't about bad ideas. It's about the gap between planning and doing—and the five repeatable mistakes that fill that gap.​

Strategy isn't a document you present once; it's a process you continually refine. It's a discipline. It's what you do every Tuesday morning, not what you said at the retreat.

Kill what's killing your strategy. Stop confusing activity with progress.

The market will take care of the rest.

Thank you for reading, and I wish you success!

—Coach Will, The Strategist

p.s. If you'd like more information, please don't hesitate to drop me a note!

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