The 5-How Test: Why Most Strategies Die at the First Question

The gap between strategy and results is almost always a "how" problem.

I've sat through hundreds of strategy meetings. In the Air Force, at PwC, at Nike, with clients. And I've noticed something: the moment someone says "we need to be more strategic," you're about 15 minutes from a very expensive waste of time.

Here's why.

The Strategy Ladder Most People Fall Off

Every real strategy has five levels. Most people stop at level two.

Level 1: What (What are you trying to accomplish?) Everyone has this. "We're going to grow revenue 30%." "We're going to transform our operations with AI." "I'm going to build a business."

Level 2: Why (Why does this matter?) Most people can get here too. "Because our market is shifting." "Because we're leaving money on the table." "Because I want freedom."

Level 3: Who (Who needs to be involved, convinced, or served?) This is where it gets thin. "Uh, the team? Leadership? Customers, I guess?"

Level 4: When (What's the timeline, and what triggers action?) Now, we're in trouble. "Q3? When we have bandwidth? Soon?"

Level 5: How (What specific actions create the result?) And here's where most "strategies" quietly die.

Not because people don't ask "how." They do. Once. "We'll hire a consultant." "We'll use AI." "We'll figure it out as we go."

Real strategy survives the next "how." And the one after that. And the one after that.

The 5-How Drill

The best operators I've worked with do this instinctively. They don't accept a plan until they can answer "how" at least five levels deep.

Here's what that looks like in practice:

Goal: Use AI to improve customer service efficiency.

• How #1: We'll implement an AI assistant that handles common questions.
• How #2: We'll use an LLM with our knowledge base as context.
• How #3: We'll build that knowledge base by capturing every real customer interaction for 60 days, tagging which responses got high satisfaction scores and which didn't.
• How #4: We'll analyze what the high-rated responses have in common. Tone? Speed? Specificity? We'll extract those patterns into prompts the AI can follow.
• How #5: We'll deploy to 10% of incoming tickets for 30 days, measure resolution rate against human baseline, and expand if we hit 85% satisfaction.

See what happened? We went from a vague aspiration ("use AI for customer service") to something you could actually execute next Monday morning. Each "how" forced us to get more specific until we hit actions someone could own.

Now try a career example:

Goal: Get promoted to VP within 18 months.

• How #1: Deliver a visible, high-impact project that execs will remember.
• How #2: Take ownership of the supply chain optimization initiative that's been stalled for six months.
• How #3: This week, load your company's 10K, last two investor calls, your top competitor's investor calls, and a couple relevant frameworks (ISO standards, McKinsey's operations research) into NotebookLM. Have it generate a 20-minute podcast you can listen to on your commute. That's 30 minutes of setup for a crash course in what actually matters to leadership.
• How #4: Spend tomorrow mapping what your company is already doing against what you learned. Document the gaps. Add your real constraints: budget, team capacity, political dynamics. Feed that back into NotebookLM and ask for a month-by-month plan, broken into this month, this week, and tomorrow.
• How #5: Execute tomorrow's action. Then the next day's. Track what you ship, not what you plan.

That's a strategy. Not "network more" or "raise my visibility." An hour of focused work with a free tool, followed by action. You now know more about your company's strategic priorities than most of your peers, and you have a plan that fits your actual situation.

The 5-How test isn't about having a perfect plan. It's about discovering where your thinking stops being strategic and starts being wishful.

Where I Learned This the Hard Way

At PwC, I audited Fortune 500 companies on their internal controls. Here's what I learned: every company has beautiful strategy documents. Slide decks with arrows and boxes. Initiatives with names.

But when you dig into the controls? The actual "how do you make sure this happens?" layer? That's where you find chaos.

The strategy said "maintain financial integrity and protect company assets." Five layers down, that becomes a control called segregation of duties. And the reality of that was Dave in accounting who had access to everything because someone gave him permissions in 2019 and nobody took them away.

Strategy that hasn't survived the 5-How test isn't strategy. It's hope with a PowerPoint deck.

My Own 5-How Test

When I decided to go all-in on AI, I had to run this test on myself.

What: Build a world-class one-person company with tools and systems using my experience while learning AI to build things I couldn't build before.

Why: Because the gap between idea and execution just collapsed. Anyone who moves fast enough can now build what used to require significant resources.

Who: Mid-career professionals who are smart enough to see the shift but don't know how to make it real.

When: Now. Not "when I have time." Now.

Then came the hard part:

• How #1: Learn to build production-quality software using AI tools.
• How #2: Start with Claude Code. Ship something real, not tutorials.
• How #3: Put my hands on the keyboard and rapidly learn and apply lessons for using AI. "Do" not "Research"
• How #4: Create frameworks to go faster, share good ones that other people can use. Turn my experience into something teachable.
• How #5: Measure by what ships. Not by what I learn, but by what goes live.

Each "how" revealed the next decision. Each decision made the strategy more real. I'm not where I want to be yet. But I know exactly what "Monday morning" looks like at each level. That's the difference.

The Wishful Thinking Trap

Here's how you know your strategy is actually a wish:

Vague verbs. "We'll leverage AI." "We'll optimize our processes." "We'll align the team." These are non-commitments dressed as plans.

Missing actors. "It will get done." Who? By when? With what resources?

Infinite timelines. "Ongoing." "As resources allow." "Eventually." These are tombstone inscriptions for initiatives that never happen.

Single-layer "how." "How will we do it? We'll figure it out." That's not a strategy. That's a prayer.

Try It Yourself

Run this on whatever you're working on right now. Whether it's a Q1 objective, a career move, or a business you want to build.

If you can fill in all five levels and answer "how" five times deep, you have a strategy.

If you get stuck at the third "how," you now know exactly where to focus your thinking.

The Data Behind This

McKinsey's research on transformations found that roughly 70% of change initiatives fail to achieve their goals. The primary reason isn't bad strategy. It's the gap between strategic intent and operational reality.

In other words: the "how" layer.

Their research also found that organizations with leadership that clearly defined roles, responsibilities, and communicated progress were 8x more likely to succeed. Translation: they answered more "how" questions upfront.

The Monday Morning Test

Next time someone presents you with a strategy, or next time you're building one yourself, ask this:

"If we agree this is the plan, what happens Monday morning?"

If the answer is vague, you don't have a strategy. You have a direction.

Directions are fine. But they don't create results. Results come from answering "how" until you hit something you can actually do.

The Bottom Line

Strategy isn't about vision. Vision is cheap. Everyone has vision.

Strategy is about the disciplined conversion of "what" into "how," repeated until you reach something specific enough to execute.

The 5-How test isn't complicated. But it's ruthless. It exposes every gap between ambition and action.

And that's exactly why it works.

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FAQ

How is the 5-How test different from the "5 Whys" technique?

The 5 Whys drills backward into root causes. The 5-How test drills forward into execution. Both are useful, but they solve different problems. 5 Whys helps you understand why something failed. 5 Hows helps you make sure something succeeds.

What if I genuinely don't know the answer to one of the "how" questions?

That's the point. The question you can't answer is the question you need to research, test, or get help with. A strategy isn't about knowing everything upfront. It's about knowing where your gaps are before you start.

Can this work for personal goals, not just business?

Absolutely. "Get healthier" is a goal. Running it through What → Why → Who → When → 5 Hows turns it into: "Walk 30 minutes every morning before checking email, tracked on my watch, reviewed weekly." That's a strategy.