Welcome to Musings—
A space where I cut through the noise and get to the heart of effective leadership and strategy execution. Here, I share hard-earned insights, practical frameworks, and candid reflections to help you navigate the complexities of leading teams and driving change. Each post is designed to be a quick, impactful read—something you can digest between meetings and apply immediately. Whether you're refining your leadership approach, tackling execution challenges, or seeking to foster a more cohesive team, you'll find valuable takeaways here.
Dive in, reflect, and let's grow together.
Every Strategy Needs a From and a To
The first time I saw a From/To staement at Nike, I was blown away that two short lists could make it so clear why we needed a new strategy and what it needed to accomplish. They’ve since become one of my go-to tools when I help clients work through their strategy.
The setup is about as simple as it gets. The “from” list describes the current state of the business, including what needs to change. The “to” list describes what the business will look like and how it will act once the strategy is working.
Everyone’s Busy. The Work Is Waiting.
“We need more people!”
When a new strategic initiative is proposed, the first response is often a request for more people, more budget, or more time. Maybe that’s needed. But before adding resources, take a look at where your team’s hours already go.
With clients I work with, I often find that a healthy (or should I say, unhealthy) share of those hours go to meetings that end without a decision, a next step, or much reason to have met at all. Getting those hours back creates valuable time for the new work.
How Much Guesswork Is Hidden in Your Plan?
I'm sure I considered it a solid plan at the time.
Looking at it from my perspective today, I asked myself about each step, “When this is done, what will exist that didn’t before?” For a lot of them, I couldn’t answer. A line item like “Solicit initial recommendations” could have meant fifty approved picks ready to post or a few emails sent asking for participation. And “Conference call with Directors” could have meant almost anything.
The program never really took off. And I can see now how the ambiguity in my plan could have been a key contributor.
It’s fairly easy to see how plans like these get written. Whoever writes a step probably has a result in mind, and I’m sure I did. I failed to articulate that result, though, so the people doing the work had to guess what success looked like. Different people could have finished the same activity with very different results.
You Can’t Wordsmith Your Way to an Executable Strategy
It’s entirely possible I’m bald now because of all the hair I pulled out during executive wordsmithing sessions.
I remember one time I sat in a meeting with 12 executives who spent three hours debating a single bullet point, and at the end of those three hours, the decision was to revisit it the following week. Seriously. Add up the salaries of everyone at that table across that meeting and the ones that followed, and I think I finally understand where the phrase “$64,000 question” came from.
Why Going Faster Can Make You Slower
If you don’t prepare your company for the changes a strategy brings, that strategy is almost certain to fail. A new strategy puts a new load on an organization. You’re asking people to take on different work, make different decisions, and often stop doing things they’ve been doing for years. If you haven’t prepared for that load, something is likely to break.
Something’s Not Adding Up
Metrics are the language of business, and when the metrics aren't clear, it's hard to plan or execute effectively. Teams have to know what they're working on and how it connects to what the organization cares about most. When those connections aren't clear, every function can feel successful in its own lane without the company actually succeeding.
What You Meant Isn't Always What You Said
We're often not as clear as we think we are.
What's clear in our head, shaped by our own background, biases, and experience, doesn't always translate into the words we actually use with our team.
The good news is you can get better at this, and AI is actually a pretty useful partner to practice with.
The Complexity Trap
The villain is the assumption. Specifically, the assumption that because those in the room understood it, the organization would, too.
But the leadership team developed that understanding through extensive debates. They absorbed the context and internalized the shorthand. So when someone says "drive customer-centric innovation across our core verticals," they know exactly what it means. But that same phrase hits someone two levels down with no shared context, no backstory, and a to-do list already full of urgent work, and it means almost nothing. Or worse, it means something different to everyone who hears it.
Strip It Down
All too often, strategies are filled with complicated business jargon that doesn't translate well to the general population of a business. I don't think people do that just to sound smart. I think they actually believe they're being more precise. Words like "leverage," "ecosystem," "holistic," and "stakeholder value" feel specific to the person who wrote them. The problem is the curse of knowledge—once you know what you mean, it's almost impossible to hear how it sounds to everyone else.
The Empire That Couldn’t Execute: All-Time Strategy Trap Fail #1
In 1775, British Empire was the mightiest force on earth.
Its navy ruled the seas. Its army was professional, disciplined, and well-equipped. Across the Atlantic stood a loose collection of farmers and merchants. No standing army. Little money. Fewer weapons.
From London’s perspective, the outcome seemed inevitable.
Yet six years later, Britain surrendered at Yorktown.
A Fair and Square Disaster: All-Time Strategy Trap Fail #2
In 2011, JCPenney brought in Ron Johnson, the retail star who had built Apple’s iconic stores. His mission was bold: stop playing the endless coupon game and replace it with “Fair and Square” everyday low pricing.
It was simple. It was elegant. It was revolutionary.
And it was a catastrophe.
When a Deadline Becomes the Strategy: All Time Strategy Trap Fail #3
October 1, 2013, was supposed to be a historic day.
Healthcare.gov would open its digital doors and allow millions of Americans to enroll in affordable health plans.
The policy was law. The demand was real. The deadline was immovable.
The site went live.
And it crashed almost immediately.
The Fastest $2 Billion Failure in Entertainment History: All-Time Strategy Trap Fail #6
It launched with nearly $2 billion in funding. It was backed by some of the most powerful names in Hollywood and Silicon Valley.
And there’s a good chance you barely remember it.
That’s the first clue.
In just six months, the company burned through its capital and shut down, becoming the fastest $2 billion failure in entertainment history.
This is the story of Quibi.
Stop Mistaking Financial Targets for Objectives
The Problem: Scoreboards don’t create clarity
A target tells you what outcome you want, but not what you must become or improve to achieve it.
Yes, teams can act on “grow revenue.” But those actions will fragment—each group doing what makes sense in their lane. One team discounts. Another raises prices. Marketing adds promos. Ops tightens costs.
Everyone’s rowing, but not in the same direction.
Clarity Drives Execution
Clarity is the difference between strategy that moves and strategy that stalls. If your team doesn’t “get” the strategy, you have no chance of executing it. Yet, clarity doesn’t happen by accident. It requires discipline: cutting through ambiguity, prioritizing what matters most, and ensuring that every person understands not just the what, but the why behind the strategy.
Start with Why—Then Make It Theirs
Simon Sinek famously calls on us to “start with why.” But for strategy to truly stick, we also need to explain “why me?”
People commit when they see how their work matters—when the strategy doesn’t just make sense, but feels personal. That’s when execution takes off.
And behavioral science backs this up.
To Be and Not to Be
The key to a successful strategy often lies in what you decide not to do. While it might seem counterintuitive, defining what you won't pursue can be more impactful than defining what you will. By spelling out these "why nots" and "what nots," you sharpen your focus and reinforce your distinct position in the market. This process helps both leaders and teams clarify what the organization stands for, ultimately bringing sharper focus and resilience to strategic decisions.
The Surprising Power of Limits
Let’s face it: nobody likes constraints at first. We all want freedom—more resources, more budget, more tools. But here’s the twist: constraints are actually our friend. Knowing what you can’t do helps you laser-focus on what you can do. Instead of chasing every possibility, you zero in on what really matters.
When a new strategy is on the table, there’s often a push for “more”—more money, more people, more time. But guess what? Adding more tends to makes things messier. More complexity, more decisions, more things to manage. The real magic happens when it’s clear that more isn’t coming. That’s when everyone rolls up their sleeves and figures out how to make it work with what they’ve got.