Is your Strategy a Waste?

"Strategy" has a bad rap in many teams - not because it's a bad thing, but because in most companies, it's disconnected.
Disconnected from reality, from their work, from the situation they are facing.
A team lead recently told me, "We're not involved in strategy. That's someone else's job. We just get told our job, and then we do it."
And that's how strategy goes to die before it's even ready to walk.

Three Signs your Strategy is Failing

Over the years, I have condensed a few leading indicators for strategic failure that help you avoid the pitfalls:

1. Strategy Without Operational Awareness

Don't get me wrong: It's not like I haven't built my own strategy slide decks.
But: most of the time, strategy builds cloud castles - created by folks who don't do the work, for people who don't do the work.
I remember having an executive explain to me their "strategy" in detail, patiently, for over an hour. Finally, I asked four questions:

• How does that relate to the work people are doing?
• What signals do you expect, to tell you whether you're getting there?
• What steering mechanisms will you be using as you drive?
• Do the people doing the work even know about this strategy?

All I got was, "That's Operations, not Strategy."
And that's exactly the kind of cloud castles I'm talking about: there's zero chance that such a strategy survives contact with reality.

2. Your Strategy is a Fixed Plan

Most companies create a strategy in fixed intervals, and then document, file and distribute it.
At the end of the strategic interval, they run a post-mortem to figure out why it didn't work.
Predictably. Every. Single. Time.
Strategy is an abstraction. On purpose. It ignores the details. It needs to - or it deteriorates into tactics.
It's built on assumptions. But these assumptions need to be validated against reality - in real time.
The missing nuances? No problem - until they become a problem. When that happens, you need to catch the signal, and adjust course:

• Without mechanisms to capture whether your understanding of your situation is your situation, you're hallucinating, not strategizing.
• As time progresses, your deck drifts further and further from reality. The answer isn't spending more time on better slides: it's adaptivity.
• When internal and external conditions make your strategy unfeasible, you need to adjust your strategy, not the work.

3. Your Strategy isn't Aligned with Execution

I was amazed when working with a CEO who was so adamant that his strategy was clear - and nobody knew what to do with it!
Yes, his closest circle had seen the slides, but this "strategy" was a mumbojumbo of sloganized buzzwords like "AI-powered innovation empowered with data-driven decision-making" and "Industry leadership with future-proof paradigms."
People simply wanted to know, "Do you want to strengthen existing products, or diversify?" - but none of that was answered: Execution simply drifted mid-air.

The misunderstanding?

• Strategy doesn't need fancy words. It needs to connect: What customers need, what people do, and how people think.
• You're not defining strategy for executives. It's for execution. If you can't tell me how you execute, you're blank.
• If your execs don't know how to talk to workers, and vice versa, your strategy gets "lost in translation."

How to Close the Gap

Closing the Strategy-Execution gap is not optional. If you don't, you'll burn money, drive off your best people, and lose out on market opportunity. A coherent, executable strategy is not a "nice to have" perk - it's necessary to run a sustainable business. Incoherence, however, creates waste and friction - translating into money spent for nothing, and money not earned. So here are a few tips to help you close the gap:

Map the Situation, then the Destination

Of course, you need a vision - but "a vision without a plan is a hallucination." And a plan includes a transition "from here to there." That means:

• Where are we today?
• How will our situation be different?
• What are the key moves we're going to make?
• What is needed in order to make these moves?

Many "strategies" fail as key moves are not realistic based on today's situation, or the preconditions for making a move are out of sync with the available capabilities and resources.

The people who know the situation, and how to change it? These are the execution folks - which is why they need to be at the table when you close the gap.

Build Real-Time Feedback

If your strategy is fire-and-forget - let me tell you: it's forgettable.
Strategy that has a bite connects outcomes with metrics, signals, feedback, and conversations.
Strategic Post-mortems aren't a sign of a healthy strategic process: they're a sign that your process isn't built to succeed.

Make Strategy Responsive, Not Directive

Percolating strategy top-down is the most pervasive disease corporations have, and too many small companies get inspired to adapt it, even though the results are mediocre and failures massive. Strategy is a map and a compass - not the road. The road needs to be built, and that is execution.
The people deciding distance, speed and direction don't even have the information or bandwidth to concern themselves with every rock or tree on the ground. That's okay - but their ability to succeed depends on taking these things into account.
That's why you need a responsive strategy - one that adapts as necessary without losing the way, or the plot.

Co-Create With Execution

The best strategies build momentum from "where we are" by leveraging the strengths that are already there. Ask the people who are executing the work what they see as meaningful steps, and where they believe resources are mis-invested, you'll be amazed.
A good strategy should have clear, actionable goals, and be immediately relatable to people's daily work. If people can't say where they fit in the big picture, you've found the problem already. And it's either that people didn't get connected, or that there is no connection. In either case, you can adjust right there, right then - and don't need to wait for a post-mortem held in an ivory tower among people, none of whom know why the strategy failed again.

tl;dr

Most strategic failures aren't caused by a "bad strategy" or "poor execution." They died in the strategy-execution gap - and when that happens repeatedly, teams lose trust in "strategy." But it's not hopeless. There are a few things you can readily do to improve - starting today Map the situation, wire in real-time feedback, and make strategy responsive and co-created. Close those loops, close the gap.

Story Points answer nothing

It's 2025, more than a decade since Story Points should have been buried. But they still aren't.
Let me tell you why they're a distraction, not a solution.

The purpose of Estimation: Decisions

When Estimates come up, I always ask: "Who needs the estimate, and what decisions will be made based on them?"

Let me give you a few examples when estimation can't be answered by providing a Story Point number:

• "I need to know whether we can afford this. Can you tell me how much it costs?"
• "We need to plan for contingency in case this is late. Can you do it on time?"
• "Would it make sense to distribute the work across multiple teams to get it done faster?"
• "Is this the simplest thing we can do to reach our goal? Does it make sense to take a shortcuts?"
• "How big is the risk of failure to deliver on time, in quality by deadline?"

Did you realize that none of these questions need to be asked inside the team - and none of them relate to "Agile?"

Business-facing, not team-facing

When the only party depending on the estimate is the team, internally - why do you even estimate? There is no criticality, no risk, no dependency, no impediment. Just do it. Best you can do, as soon as you can deliver. That's enough. But - for the business, that is not enough.

None of the questions suggested above are relevant inside the team: their relevance is defined outside the team. With your stakeholders, the people who pay your bills. If they can't make a proper decision, you're alienating them, risking a communication gap that could cost you your credibility.

Stakeholders don't need to know if something is 12 or 49 Story Points. They don't care if something is a Story or an Epic. What they care is, "Do I need to adjust anything? Will I get what I need, when I need it, how I need it - at a price I can afford?"

These questions can not be answered by Story Points, unless you clearly relate Story Points back to team days and money. But if you do that - then why use them to begin with?

Estimation that doesn't drive business decisions is waste.

Customer decisions, not team decisions

What many Scrum teams and Scrum Masters fail to understand: business requires planning, too. Your sales team must give an account to your customers if they get what they signed up for. Your customers must plan their budget, and how they use their resources.

Let me give you an example: If you buy a Mobile phone, you want to know when you can use it. Customers don't accept "You get it when you get it" - they'll most likely leave the shop and take your money elsewhere. And the answer, "We still need 17 Story Points until you can use it" would immediately trigger the question, "And how long is a Story Point, exactly? Minutes, Hours, Weeks?"

Estimation that pushes uncertainty to the customer is an antipattern.

Conclusion

Before you talk about which estimation method to use, try understanding your stakeholders:

• Learn what your answer causes for them. Understand which decisions they will make with the information you provide.
• Use the estimation approach that helps you come to a common understanding with your stakeholders.
• Sometimes, "No problem, you'll have it by the end of next week" is all the information required.

When possible, skip estimation entirely - just make sure you're confident that you can live up to your promises.
But when you need to estimate: find out for whom, what they need, and give them that. And use the approach that makes you confident your answer is trustworthy.

Your job is to make the business successful, not to "do Estimation correctly."