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.
Mind Your P’s and Q’s
“I want people who can think for themselves.”
I hear that from leaders a lot. Then something urgent comes up, and those same leaders start telling everyone exactly what to do.
I understand the temptation, because I’ve done it myself. You probably recognize the situation. Some urgent issue or opportunity comes up, the clock is ticking, you have a solution in mind, and explaining what you want done just seems like the fastest way to get things moving.
But starting quickly isn’t the same as finishing quickly. The team still has to do the work, and your answer probably leaves plenty for them to figure out.
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.
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.
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 Signal Fade Trap
The strategy launch went extremely well. The leadership team spent weeks refining the message, building the deck, and rehearsing the delivery. People applauded at the all-hands meeting, and there were good, thoughtful, and engaged questions. You walked out feeling the organization was primed and ready to go.
Then the day-to-day took over.
Two months later, you looked up and realized not much had changed.
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.
It Wasn’t a Prompting Technique
The skill that separates great AI users from average ones is the same skill that separates great leaders from average ones. It has nothing to do with technology.
I had an idea the other day I wanted to develop, and I went to Claude and said, essentially, "I think there's something here. Help me figure out what it is."
But I didn't just give it a task. I gave it context. I shared my why behind what I was trying to accomplish. I shared my uncertainty — that I wasn't sure exactly where it would land. And I asked it to help me get there rather than just telling it what to produce.
The Interpretation Tax
Silence creates more work than bad decisions.
When leadership communication slows down, people start filling in the blanks. You’ll hear questions like: Is this still a priority? Did something change? Should I move forward, or wait?
Most people don’t want to make the wrong call. So they slow down. They check with others or wait for direction.
I call this the interpretation tax.
Beware the Green Mask
If your team is “on track” every month, you’re being lied to.
My friend Mike Africa calls this green masking. It’s the tendency for everything to get reported as “green” (i.e. all is well) until right before a deadline, when the real problems finally surface and you end up in last-minute chaos.
That’s why I’m a big believer in Red Flag Sessions.
Is Urgency Detouring Your Strategy?
Many leaders say they care about long-term direction. Then the week starts.
You’ve probably seen these happen:
A big customer asks for something special.
A key metric declines.
A senior executive raises a concern.
A competitor makes announces a big move.
And all of the sudden, the planned strategic work slides to the side while the immediate issue takes center stage. Run that pattern enough times and the organization learns what really matters…and it isn’t the strategy.
What Writing “The Strategy Trap” Taught Me
One thing I didn’t expect from writing The Strategy Trap is how much it would force me to question my own thinking and break down assumptions I didn’t even realize I was carrying.
I’ve been using a lot of the ideas in the book for years. They weren’t new to me. And I knew they worked. I trusted them. But writing is different. You can’t skip steps. You can’t rely on tone or context or “you know what I mean.”
You have to explain things cleanly enough that someone else can actually do something with them. You know, exactly like communicating a strategy to a team that has to act on it.
The Luxury Festival That Delivered Cheese Sandwiches: All-Time Strategy Trap Fail #7
It was marketed as the ultimate luxury music experience. Supermodels on yachts. Private jets. Tickets selling for thousands—some packages over $200,000.
But when guests arrived, the reality was a nightmare. A rainstorm had soaked the site. The "luxury villas" were actually disaster relief tents, and the mattresses inside were piled up, soaking wet. The gourmet meals were cheese sandwiches in Styrofoam boxes.
Say Less. Mean More.
The hardest part of communicating anything isn’t deciding what to say. It’s deciding what not to say.
Clear communication is a discipline. It means resisting the urge to add, even when adding feels helpful. It means stripping the message down to the parts that actually guide action and letting the rest go.
The Strategic Power of a Well-Chosen Metaphor
We humans aren’t good at taking in lots of completely new information. Metaphors lighten the load and speed up clarity. They pin new ideas to something people already understand so they can act on them faster.
The Illusion of Alignment
Alignment isn’t everyone nodding in agreement. You can’t determine alignment with a yes or no question. Alignment runs too deep for that.
True alignment is when everyone making the same decision when you’re not in the room.
When alignment isn’t real, the cracks show up fast.
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.
We Experience What We Expect
Did you know the placebo effect is active in your brain every single day, not just in hospitals or clinical trials?
Psychologists call it Expectancy Theory, and it shows that the reality we experience is driven by our expectations.
Squishy Words Are the Death of Clarity
The words that sink execution aren’t the fancy bits of jargon. They’re the everyday shortcuts—the words so common that nobody notices how vague those words are.
Squishy words leave a trail of misunderstandings, false assumptions, and dropped balls.
Clear in Your Head ≠ Clear in Theirs
Why Work Miscommunication Is the Norm
At work, we interact with people far less often than our closest relationships. They have even less context for what’s in our heads. What you say is always filtered through their priors:
Their role and incentives
Their past experiences with similar topics
Whatever else is competing for their attention
That’s why, “But I told them,” isn’t enough. It’s not about what you said. It’s about what they heard and how they interpreted it.