Strategic Thinking & Strategic Action

Fostering strategic thinking and strategic action by organizational leaders since 2007.

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The times they are a-changin’
Strategic planning Lee Crumbaugh Strategic planning Lee Crumbaugh

The times they are a-changin’

In 1964 Bob Dylan wrote the song of my generation, The times they are a-changin'. War was raging and protest and rapid social change ensued. Our society warped and cracked and reformed. A tidal wave of Baby Boomers transformed our economy, bringing greater demand and a shift to the information society.

Dylan’s words have as much meaning today as they did then.

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The Leadership Triangle: Do the work only you can do
Leadership Lee Crumbaugh Leadership Lee Crumbaugh

The Leadership Triangle: Do the work only you can do

In January this year, a team of engineers was camped out in Building 92 on Microsoft's Redmond campus. They were in a race and they were behind. Competing teams at Google, Anthropic, and Meta were moving fast, and Microsoft, despite having taken an early lead in AI, was playing catch-up.

Then their CEO walked in.

He showed up not to deliver a pep talk. Not to review a slide deck. Not to remind them how important their work was. Satya Nadella walked in to show them something he had built.

He opened his laptop and demonstrated an application he called "Chain of Debate,” which is a system for coordinating multiple AI agents working together. He hadn't asked someone to build it for him. He had built it himself, using vibe coding, a method that allows anyone to create working software by describing what they want in plain language and letting an AI tool generate the code. No traditional programming required.¹ (“Anyone” includes me: I am vibe coding our FastTrack™ AI-Enhanced Strategic Planning & Implementation System.)

The room noticed. According to Jacob Andreou, the executive vice president leading Microsoft's Copilot product, the engineers traded the kind of looks that pass between people who suddenly realize the new guy can actually play. "That set the tone for how hard the team was going to push," Andreou recalled. "He was in the room with folks, like over their shoulder, there with his machine out. Watching the boss get such excitement out of building new things inspired the team."¹

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Help is on the way!
Coaching Lee Crumbaugh Coaching Lee Crumbaugh

Help is on the way!

I grew up in a culture that expected you to deal with life and solve the problems thrown at you. No whining, don’t be vulnerable, make things work!

Luckily, societal attitudes evolved and I married a clinical social worker who adjusted my thinking. I personally received clinical and non-clinical guidance from counselors and coaches. Mentors and friends helped keep me on a solid path and accountable for good decisions and execution.

Being a business coach who spends 10 hours or so a week in session with clients is a far cry from the life I would have envisioned for myself when I was playing cowboys and Indians or dealing with teenage angst. But that I am able to be of such ongoing help to business owners and leaders is a real privilege. I am proud of my clients who have taken what once was a taboo step: Opening up their businesses and their minds to let me in so that they can share and get expert third-party insight on how to make their businesess better in the ways that they want them to be better.

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Not having a strategy is not a strategy
Strategy Lee Crumbaugh Strategy Lee Crumbaugh

Not having a strategy is not a strategy

After more than four decades working with organizations on strategy, one pattern still surprises me. Many organizations operate without a current strategic plan. Others technically have one, but it sits somewhere in a document or slide deck and does not meaningfully guide everyday decisions.

From the outside, these organizations often appear quite busy and productive. People are working hard, customers are being served, and problems are being solved. Activity is constant and the organization rarely feels idle.

But something subtle is happening beneath the surface.

Decisions are made without a shared direction. Priorities shift depending on who speaks loudest or which issue appears most urgent. Projects are launched that may be worthwhile on their own but are not clearly connected to a broader future the organization is trying to create.

Over time the organization begins solving the same problems again and again. Leaders expend tremendous energy, but the progress achieved rarely matches the effort invested.

Eventually someone asks a question that experienced leaders recognize immediately:

Why does it feel like we are working harder every year but not moving forward as much as we should?

That question is often the signal that strategy has been neglected.

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The Fake-Out: Your brain thinks you’re winning but you’re already losing
Strategic planning Lee Crumbaugh Strategic planning Lee Crumbaugh

The Fake-Out: Your brain thinks you’re winning but you’re already losing

February is the most dangerous month on the strategic calendar.

In January we are hopped up on adrenaline from the New Year start. March brings the rush of the first quarter end. February? February is when we fake ourselves out.

Odds are you have been feeling productive. Your calendar is full. You are clearing your inbox, at least of the important current stuff. You are "in the swing of things."

But, look closely at what you are doing. You may just find a terrifying reality: Your actions aren't strategic. Most of what you are doing likely does not directly relate to executing your 2026 strategic business plan. You are just managing the rush of business and day-to-day processes. Nothing much has changed since 2025.

I hope this is not the case for you. Too many of us get sucked into (or never escape) the subtle mechanism of what's called the Implementation Gap. It doesn't announce itself with blaring trumpets; it hides behind our mask of "busy-ness."

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Why strategy fails… and how to make it succeed
Strategic planning Lee Crumbaugh Strategic planning Lee Crumbaugh

Why strategy fails… and how to make it succeed

In the quest to achieve our vision, “Every organization and business leader has a strategic plan and they are executing their plan for greater success,” we have cataloged 16 causes of planning failure and suggested remedies. Here's our "watch out for it and what to do about it" list, designed to help leaders, owners, and professionals involved in strategic plan implementation assure that their efforts take the organization to the next level.

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California High Speed Rail to nowhere: Lessons for implementing our plans
Strategic planning Lee Crumbaugh Strategic planning Lee Crumbaugh

California High Speed Rail to nowhere: Lessons for implementing our plans

A New Year has befallen us, ready or not. Hopefully, you are ready. That is, you - and your organization, if you are a business owner or for-profit or non-profit leader - have a plan in place for the New Year.

Now your challenge it to execute your plan for greater success. Execution, or, as we strategists call it, plan implementation, should be your mantra.

Execution, or better said, lack of it, is where it all falls apart. While the exact percentage is unclear, it’s safe to say that more than half and up to three quarters of plans are either poorly executed or not executed at all. That’s shame! A plan which is not executed is worthless.

Achieving timely and effective plan implementation is critical to success.

To bring the point home, reflect on this true tale that illustrates the perils of poor planning and, especially, poor execution.

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Why New Year’s resolutions fail: The problem of implementation
Strategic planning Lee Crumbaugh Strategic planning Lee Crumbaugh

Why New Year’s resolutions fail: The problem of implementation

Yesterday, New Year’s resolutions came to mind as I was writing year-end reports to my coaching clients.

A blog post on goal-setting and achievement that I wrote earlier this year, Don’t waste your time planning, unless…, cited research showing that 92% of people who make New Year’s resolutions never actually achieve them. While I recognize that what we resolve to achieve in the New Year can be a casual goal without a lot of commitment behind it, to me it seems silly to put a marker out there and then ignore it or only half-heartedly go after it.

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Bridge the strategy gap
Strategic planning Lee Crumbaugh Strategic planning Lee Crumbaugh

Bridge the strategy gap

With the recent collapse of the Francis Scott Key Bridge in nearby Baltimore, bridges are on my mind.

Given my romance with epic bridges, it is no surprise that I have often likened creating a strategic plan to building a bridge to the future.

I have used the bridge analogy for years. As president of the Association for Strategic Planning (now the International Association for Strategy Professionals), more than a decade ago I started my quest to bridge what I (and others) called “the strategy gap.”

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