Enrollment Is the Missing Link in Strategic Planning
Your strategy failed because nobody was enrolled.
Why do strategies fail? It’s a popular business question with endless theories—frameworks, business models, competitive positioning, value creation.
I’ll leave that to HBR.
Here’s my thesis: companies minimize the need to enroll employees and stakeholders during the strategic process. So implementation falls short.
Enrollment isn’t a soft skill or HR buzzword. It’s the art of facilitating the behavioral, cultural, and human elements that need to be in place for people to make decisions and take action toward desired outcomes.
Without enrollment, you get a beautiful deck that sits on a shelf while everyone goes back to doing what they were doing before.
Strategy Isn't a Product
Most strategic planning processes optimize for speed and polish—consultants build the deck, executives present to the board, then announce the new strategy. Six months later, nobody can tell you what it is because they were never enrolled.
Your strategy failed because nobody was enrolled.
Why do strategies fail? It’s a popular business question with endless theories—frameworks, business models, competitive positioning, value creation.
I’ll leave that to HBR.
Here’s my thesis: companies minimize the need to enroll employees and stakeholders during the strategic process. So implementation falls short.
Enrollment isn’t a soft skill or HR buzzword. It’s the art of facilitating the behavioral, cultural, and human elements that need to be in place for people to make decisions and take action toward desired outcomes.
Without enrollment, you get a beautiful deck that sits on a shelf while everyone goes back to doing what they were doing before.
Work backward from success.
Let me visualize what success looks like and reverse-engineer it.
A successful strategy is executed by an accountable team with autonomy to experiment and make choices to achieve outcomes.
For a team to feel accountable, they need to be enrolled.
To be enrolled, they need to participate in strategic planning—or at minimum, the communication of the plan.
For teams to participate meaningfully, there needs to be executive commitment and a thoughtful strategic process design.
The chain looks like this:
Executive Commitment → Participation/Communication → Enrollment → Accountability
Break any link, and the strategy dies in PowerPoint.
The best strategies are narratives.
Great strategies are stories. They take stakeholders on a journey—historical perspective, present environment, future state—where humans execute choreographed tactics to achieve specific outcomes.
The operative word: human.
Management consultancies are incredibly competent at building strategic narratives. McKinsey can craft a story that makes your board weep with inspiration.
The challenge is turning that story into reality. And that requires enrollment from the people who actually have to execute it.
Embed internal teams early.
I advocate embedding an internal cross-functional, high-performance team with strategic leaders or third-party consultancies throughout the entire strategic process.
Short term, this adds complexity. It slows things down. It creates discomfort.
But that discomfort is where the magic happens. Suffering during the planning process is critical for enrollment.
Suffering forces cross-functional problem-solving among the practitioners within the organization—the people who will actually do the work. Without doers involved, strategy becomes academic. It becomes consultant theater that looks impressive but has no connection to operational reality.
Design the process intentionally.
Here’s my checklist for any strategic planning project:
1. Find and build a balanced internal team.
I identify this team during early stakeholder interviews. I probe: who are the high-potential employees? Who does everyone go to with questions?
Planning processes are excellent opportunities for people searching for stretch assignments. Find your A-players who want visibility and give them meaningful roles.
2. Keep everything visually in one place.
Ideally, a war room—an actual conference room where work lives on the walls. Or a virtual whiteboard like Miro.
Seeing the work develop enables strategic themes to emerge naturally. When everything is scattered across email threads and individual laptops, connections get missed.
3. Divide up the workstreams.
Create mini-teams to investigate and execute questions or issues derived from the planning group. Have them own and present their work.
Ownership creates accountability. If someone is responsible for customer segmentation analysis and has to present it to leadership, they’ll do better work than if they’re just “helping out.”
4. Facilitate and provide tools, knowledge, and coaching.
I embed myself on these teams as a player-coach. I help teams discover answers and provide guidance on executing workstreams.
For example, if a team has a customer segmentation workstream and struggles to get started, I offer methodologies and resources. But they do the work. They own the insights.
5. Over-communicate, especially with leadership.
Invite leaders into the war room—virtually or physically—and regularly walk through completed workstreams and learnings.
Be open to feedback. Make adjustments in real-time. This prevents the “big reveal” moment where leadership sees the strategy for the first time and hates it. By then, you’ve invested months and burned credibility.
6. Write the narrative before building the deck.
Before any PowerPoint, have the team write the narrative using only words. Walk through analyses, learnings, themes, initiatives, financials, and desired outcomes in prose.
Iterate. Get the entire team to sign off on the story.
Then—and only then—build the deck.
Most teams do this backward. They build slides and retrofit a narrative. The result is disjointed, jargon-heavy presentations that don’t tell a coherent story.
7. Let the team be your advocates.
I love when members of the planning team go back to their functional groups and present the strategy themselves.
If one of their own is enrolled and excited, it engenders commitment faster than any top-down mandate. Peer-to-peer communication is more credible than executive pronouncements.
8. Run a road show.
Review the strategy individually with the board, C-suite, senior leaders, and small intimate groups across the organization.
The goal: get maximum feedback and make adjustments as necessary.
Road shows grease the wheels for final plan approval and capital/resource requests. By the time you’re asking for formal approval, there should be no surprises. Everyone should have seen it, touched it, and influenced it.
Why this matters.
Adding these elements to your strategic planning process catalyzes participation, which enables enrollment, which drives accountability.
Execution succeeds when teams are enrolled and accountable.
Most strategic planning processes optimize for speed and polish. Get the consultants in. Build the deck. Present to the board. Announce the new strategy.
Then nothing changes.
That approach treats strategy like a product you deliver to the organization. “Here’s your new strategy. Now go execute it.”
But strategy isn’t a product. It’s a change in behavior across hundreds or thousands of people. And behavior change requires enrollment—not just communication.
The cost of skipping enrollment.
I’ve seen companies spend millions on strategic planning. Beautiful frameworks. Detailed financial models. Impressive decks with custom illustrations.
Then six months later, nobody can tell you what the strategy is. Teams are still operating under old priorities. Resources are allocated the same way they were before. Initiatives launch and die quietly.
Why? Because nobody was enrolled. The strategy was created in a conference room by executives and consultants, then announced to the organization as a fait accompli.
People don’t resist change. They resist being changed. When you involve teams early, let them suffer through the hard questions, give them ownership of workstreams—they become co-creators, not recipients.
Co-creators fight for the strategy. Recipients ignore it.
The takeaway.
Your strategy failed because it was built in isolation and delivered as a finished product.
Next time, slow down. Embed internal teams early. Let them struggle with the hard questions. Give them ownership. Over-communicate. Write the narrative before the deck. Turn them into advocates.
It’s messier. It’s slower. It’s harder to control.
But the strategy that emerges will be executable—because the people who have to execute it were enrolled from the beginning.
Enrollment isn’t optional. It’s the difference between strategy as theater and strategy as transformation.
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Why Mastery Is Expensive But Competency Scales
Easy to do, hard to master.
I saw this phrase describing a SaaS platform. Simple. Layered. It stuck with me.
So I started applying it elsewhere—skills, workflows, career planning. It turned into a framework for thinking about where to invest time and what mastery actually costs.
Mastery isn’t the only path.
Social media makes it feel like deep expertise is the only winning formula. 10,000 hours. Become world-class. Own your niche.
And sure—mastery can lead to outsized returns. But there are plenty of paths to success that don’t require becoming the best in the world at something. You just need to be strategic about where you go deep and where you stay broad.
That requires thinking about commitment, risk, natural ability, value, and time. Not every skill is worth mastering. Some are worth knowing well enough to be dangerous. Others are worth automating entirely.
Mastery Is Expensive, Competency Scales
Mastery takes time, focus, and obsessive depth most people don’t have. Competency across a dozen high-value skills lets you diagnose fast, connect dots others miss, and know when to bring in experts.
Depth vs. range.
Genetic disposition plays a role here. Some people have the wiring for mastery—the obsessive focus, the tolerance for repetition, the ability to grind on one thing for years.
Others don’t. They consume breadth. They connect dots across domains. They’re competent in twelve things instead of world-class in two.
Neither is better. But you need to know which you are, because the strategy changes.
The framework.
Here’s how I think about skill development across four quadrants:
1. Easy to Do, Hard to Master
This is where I spend most of my time. CRM systems. Coaching. Consulting frameworks. SaaS platforms. Strategy development. Writing. Project management.
My approach: build a broad base of moderate skills with the ability to go deeper when a specific situation demands it. I’m not trying to be the world’s best Salesforce admin. But I can configure it, troubleshoot it, and know when to call in an expert.
Go-to resource: YouTube tutorials, vendor documentation, pattern recognition from repetition.
2. Easy to Do, Easy to Master
I minimize time here. Most manual, stepwise processes fall into this bucket—data entry, basic formatting, repetitive admin tasks.
My goal: automate or outsource anything in this category. If a process can be scripted, documented, or handed off, it should be. These skills don’t differentiate you. They just consume time.
Go-to resources: Scribe for documentation, Zapier for automation, RPA tools, virtual assistants.
3. Hard to Do, Hard to Master
I don’t claim mastery in anything here. Few can. But I maintain competency in several hard skills I’ve developed over my career—programming, sales, lead generation, financial modeling, design thinking, product development.
These require real commitment. If you start down one of these paths without a solid reason, you’ll burn significant energy for minimal gain. But if you choose wisely, competency in hard skills opens doors and commands higher compensation.
Masters in these areas are rare and expensive. Knowing enough to evaluate their work, brief them effectively, and integrate their output is often more valuable than trying to become one yourself.
Go-to resources: Networking, online communities, mentorship, paid courses with real feedback loops.
4. Hard to Do, Easy to Master
I struggled to populate this quadrant. Accounting, maybe? Skills with high barriers to entry but clear paths to competency once you’re in?
Honestly, I don’t invest here. If something is hard to access but easy to master once you do, it’s probably not a leverage point for me.
My personal thesis.
I aim for competency across the value stack of business transformation—enough depth in hard skills to diagnose opportunities, enough breadth to see connections others miss, and enough humility to know when to bring in masters.
The goal isn’t to be the best at any one thing. It’s to be dangerous enough in the right combination of things that I can rapidly assess what’s broken, what’s possible, and who needs to be in the room to execute.
I need to know what mastery looks like so I can help clients stitch together the right resources for ambitious projects. But I don’t need to be the one delivering that mastery in every domain.
The exercise.
Take fifteen minutes and map your own skills across these quadrants:
- Easy to do, hard to master — Where are you building broad competency?
- Easy to do, easy to master — What are you automating or outsourcing?
- Hard to do, hard to master — Where are you committing real energy? Is it worth it?
- Hard to do, easy to master — Does this quadrant even exist for you?
Then ask yourself:
- What’s your commitment level to each category?
- What’s your natural wiring—depth or range?
- What does your skill development thesis look like over the next three years?
This should be unique to you. Don’t copy someone else’s path because it worked for them. Figure out where you have leverage, where you have interest, and where the intersection of those two things creates value.
The takeaway.
Mastery is expensive. It takes time, focus, and often a specific genetic disposition for obsessive depth.
But competency is scalable. You can be competent in a dozen high-value skills and still have time to build a business, stay curious, and avoid burnout.
The trick is knowing which skills are worth going deep on, which are worth staying broad on, and which are worth ignoring entirely.
Most people never ask the question. They just accumulate skills randomly and wonder why nothing compounds.
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How Legacy Infrastructure Kills New Ventures
Why your growth initiatives keep dying.
Most enterprises carve out capital for new ventures. They target high-growth markets that complement the core business. They staff up with smart people. They launch with fanfare.
Then the initiative dies quietly eighteen months later.
You can blame culture. You can blame execution. You can blame market fit. But there’s a deeper pattern: business model coupling. Companies try to run new business models on legacy infrastructure. Round peg, square hole. It doesn’t work.
Legacy Becomes the Liability
Most enterprises believe their infrastructure is an asset for new ventures. In reality, legacy systems create friction, bloated costs, and customer experiences that tank NPS before you hit year two.
The Widget CO problem.
Here’s the pattern. You’re a global construction widget company. Fifty years building market dominance. World-class at manufacturing, distribution, channel partnerships, and service. Strong margins. But growth has flatlined, and the CEO wants “innovation.”
A sharp team builds a cloud-based software stack. Game-changing product. The MVP crushes in early trials. So leadership launches it through the existing channel—leveraging fifty years of distribution muscle.
A year later, software revenue is 10% of plan. Leadership wants to kill it.
What happened?
You tried to sell SaaS like you sell widgets.
Widget CO is phenomenal at moving hard goods. They’ve optimized heavy tech stacks like SAP. Trained partners to maximize widget market share. Built supply chains that work at scale.
But SaaS is a different business model. Different economics. Different playbook. Different customer expectations.
Widget CO doesn’t know this playbook, so they customize a hybrid Frankenstein solution. The result: terrible customer experience, bloated costs, and unit economics that make no sense compared to benchmarked SaaS businesses.
The legacy becomes the liability.
Widget CO believes they’ll win because they have infrastructure, brand equity, and distribution. And sure—some of those assets help. But most create friction.
The legacy infrastructure was built to support channel partners, not sell directly to end users. Channel partners don’t know how to sell SaaS—they’re widget people. There are no implementation partners. Minimal tech support for customers. The service org can’t answer basic software questions.
NPS craters. The new product threatens the brand. Finger-pointing starts. Before long, the initiative gets shelved.
Fast forward three years: an external startup with an inferior product becomes a unicorn solving the same problem.
How to actually win at this.
Companies that approach new business models with humility can avoid this outcome. Here’s how Widget CO should’ve played it:
1. Use the actual playbook.
SaaS has well-defined business models. Don’t reinvent the wheel. Build from the ground up using proven SaaS economics—CAC, LTV, churn benchmarks, pricing models that work. Use frameworks like the Business Model Canvas to map it out before you build anything.
Don’t retrofit your legacy model and call it innovation.
2. Extract to survive.
New ventures need protection from the mothership. They can’t operate under the same KPIs, approval chains, and quarterly pressures as mature business units.
Create an internal or external venture structure with autonomy. Let them iterate and fail like a startup. Compensate for risk-taking, not for playing it safe. The good news: this can all be virtual. You don’t need a Silicon Valley office.
3. Build a modern tech stack.
Cloud platforms let you stitch together best-in-class capabilities with fewer resources. But don’t force new ventures to use legacy tech stacks designed for mature business models.
Your SAP instance is not the answer. Give new teams autonomy to build lean, proven stacks that match their business model.
4. Cherry-pick the good stuff.
Some legacy assets actually help. Brand recognition. Existing relationships. Distribution muscle—if used correctly.
Figure out which assets create value for the new model. Then structure internal systems to create win-win behaviors. Sales and channel partners can be useful if they’re designed into the business model with the right expectations and training.
Don’t assume everything transfers. Most of it doesn’t.
5. Study what actually worked.
Dig into the ventures that succeeded. What forces enabled those outcomes? What did leadership do differently? What constraints were lifted?
Repeat the elements that worked. Kill the rest.
6. Organize by business model, not business unit.
Some enterprises benefit from organizing around business models instead of traditional structures. Industrial products, retail, ecommerce, SaaS, services—each operates with different economics and different playbooks.
Forcing them under one P&L with shared KPIs creates misalignment and politics.
The takeaway.
Corporate ventures fail for many reasons. But business model incompatibility is the root cause nobody talks about.
Taking time upfront to research the business model and its requirements will save you eighteen months of expensive theater. You’ll either build something that works, or you’ll kill it early before burning capital and credibility.
Stop trying to force new business models into old infrastructure. It’s expensive, demoralizing, and predictable.
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Stop Incrementalizing Yourself to Death
Most people run from chaos. That’s a problem.
There’s a soft skill nobody talks about in transformation work: the ability to sit in disorder without panicking. It’s terrifying. It feels reckless. But it’s one of the fastest ways to cut through years of incremental bullshit.
Take the Twitter saga—whatever you think of Elon, there’s a method worth examining. He laid off half the workforce in one swing. Brutal? Absolutely. Chaotic? By design.
But here’s what happened: the system broke in specific places. Fast. He learned in weeks what would’ve taken consultants eighteen months and millions in discovery fees to figure out. Which 100 roles actually mattered. Which systems were load-bearing. Which processes were theater.
You can hate the approach. But you can’t ignore the speed.
Disorder Uncovers What Matters
Most organizations study problems until the market moves. Controlled chaos cuts through years of planning by spiking the system and watching what actually breaks.
Chaos as a diagnostic tool.
Most organizations incrementalize themselves to death. They pilot programs. They form committees. They study the problem until the market moves and the problem changes.
Controlled chaos does something different—it creates variance fast. You spike the system, watch what breaks, and identify the vital few variables that actually move outcomes. The critical Xs that drive your most important Ys.
In transformation work, we do this deliberately. We dump everything into one space—a war room, a virtual whiteboard, whatever. All the diagnostics, all the analyses, all the conflicting data. It looks like a disaster. Clients panic.
That’s the point.
Ambiguity is a feature, not a bug.
We coach teams to work the chaos. Test hypotheses. Find connections nobody saw when everything was siloed. Build consensus around what success actually looks like—not what the strategic plan from 2019 says it should look like.
Slowly, patterns emerge. The puzzle assembles itself. A strategic path becomes visible that nobody could’ve planned from a conference room.
This is a form of productive suffering. Grinding through disorder hardens the outcomes. The strategy that survives chaos is antifragile—it gets stronger under pressure because it was forged under pressure.
When chaos doesn’t work.
If your business runs well and has solid foundations, don’t inject chaos. Incremental planning works fine when systems are healthy.
But if you’re dysfunctional? If you’re in rapid change and legacy processes are anchors? If every meeting ends with “let’s form a working group to explore this further”?
You don’t need more structure. You need controlled demolition.
The takeaway.
Get comfortable being uncomfortable. Chaos reveals truth faster than consensus ever will. The answers are already in your organization—they’re just buried under process, politics, and the fear of breaking things.
Sometimes you have to break things to find out what matters.
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From 20 Years Experience, 10 Lessons on Financial Forecasting
What twenty years of financial modeling taught me.
Early on, I built credibility through complexity. Multi-tab spreadsheets with hundreds of inputs, sensitivity analyses following statistical distributions, thousands of outputs, and forecasts stretching twenty years out.
I could command a boardroom with the stories these models told. I believed the numbers.
Then I checked the receipts. Short-term? Decent. Long-term? Garbage. Accuracy varied wildly by industry maturity, but the pattern held: complexity didn’t equal precision.
80/20 Rule
Also known as pareto’s principle: roughly 80% of effects come from 20% of causes. Find the vital few, ignore the trivial many.
A decade later, I stripped it all down.
Fewer inputs. Fewer assumptions. Leaned hard into the 80/20 rule—find the variables that actually move the business, ignore the rest.
The 80/20 principle comes from Vilfredo Pareto, an Italian economist who noticed that 80% of Italy’s land belonged to 20% of the population. The pattern showed up everywhere he looked. Today we call it the Pareto Principle: roughly 80% of effects come from 20% of causes. In financial modeling, that means most of your forecast accuracy comes from a handful of key drivers. Nail those, and the rest is noise.
The simpler models weren’t perfect. But they performed better. And teams could actually use them without a decoder ring.
The lesson: less is more. Here are ten things I wish I’d known earlier.
- Understand the goals of the model. Whether revenue, cash flow, market share, P&L, headcount, or volume, design a simple model focused on the core output. And resist the tendency to build the all-in-one model.
- Think modularly, for example, inputs, calculation engine, and outputs.
- Resist complex embedded formulas at first. Further, make it easy for others to edit and understand the logic.
- Use writing as an analogy to modeling. Work quickly to write a first draft, or MVM, a minimal viable model. And then begin an editing process until you create a structured and logical result.
- Subtractive is better than additive. Sculptors start with a block and chisel away until they execute their vision. I attempt to do the same. Start with knowns and chisel away based on confident subtractions. The additive approach, or bottoms-up, can provide a nice check and balance but tends to overshoot reality.
- Start with a shorter duration with realistic assumptions, then expand. Working backward from a target is valuable, but it often leads to disconnected results — so do both. Working the model from the goal also helps to assess input sensitivity.
- Show your results as scenarios; base case, moderate, and aggressive. Don’t fall in love with a single number or scenario.
- Focus on the inputs rather than argue about the outcomes — make it easy for reviewers to challenge inputs and see the results in real time.
- As confidence builds around the model, add new modules or consolidate formulas to reduce the size. Redo the editing step.
- Start from scratch with your models, or at the very least, start with other’s models that you trust and wholly understand.
Modeling anything takes a bit of art and science and most importantly – reps.
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