Strategy Archives - Mile Zero

Strategy Execution: What to Do When Your Plans Are Already Obsolete

by Robyn Bolton | Jan 11, 2026 | Leading Through Uncertainty, Strategy

We’re two full weeks into the new year and I’m curious, how is the strategy and operating plan you spent all Q3 and Q4 working on progressing? You nailed it, right? Everything is just as you expected and things are moving forward just as you planned.

I didn’t think so.

So, like many others, you feel tempted to double down on what worked before or chase every opportunity with the hope that it will “future-proof” your business.

Stop.

Remember the Cheshire Cat, “If you don’t know where you’re going, any road will get you there.”

You DO know where you’re going because your goals didn’t change. You still need to grow revenue and cut costs with fewer resources than last year.

The map changed. So you need to find a new road.

You’re not going to find it by looking at old playbooks or by following every path available.

You will find it by following these three steps (and don’t require months or millions to complete).

Return to First Principles

When old maps fail and new roads are uncertain, the most successful leaders return to first principles, the fundamental, irreducible truths of a subject:

Organizations are systems
Systems seek equilibrium and resist change when elements are misaligned
People in the system do what the system allows, models, and rewards

Returning to these principles is the root of success because it forces you to pause and ask the right questions before (re)acting.

Ask Questions to Find the Root Cause

Based on the first principles, think of your organization as a lock. All the tumblers need to align to unlock the organization’s potential to get to where you need to go. When the tumblers don’t align, you stay stuck in the dying status quo.

Every organization has three tumblers – Architecture (how you’re organized), Behavior (what leaders actually do), and Culture (what gets rewarded) – that must align to develop and execute a strategy in an environment of uncertainty and constant change.

But ensuring that you’ve aligned all three tumblers, and not just one or two, requires asking questions to get to the root cause of the challenges.

Is your leadership team struggling to align on a decision because they don’t have enough data or can’t agree on what it means? The Behavior and Culture tumblers are misaligned with the structure and incentives of Architecture

Are people resisting the new AI tools you rolled out? Architectural incentives and metrics, and leadership communications and behaviors are preventing buy-in.

Struggling to squeeze growth out of a stagnant business? Structures and systems combined with organization culture are reinforcing safety and a fixed mindset rather than encouraging curiosity and learning.

Align the Tumblers

When you diagnose the root causes you find the misaligned tumbler. And, in the process of bringing it into alignment, it will likely pull the others in, too.

By role modeling leadership behaviors that encourage transparent communication (no hiding behind buzzwords), quantifying confidence, and smart risk taking, you’ll also influence culture and may reveal a needed change in Architecture.

Modifying the metrics and rewards in Architecture and making sure that your communications and behavior encourage buy-in to new AI tools, will start to establish an AI-friendly culture.

Overhauling Architecture to encourage and reward actions that expand that stagnant business into new markets or brings new solutions to your existing customers, will build new leadership Behaviors will drive culture change.

Get to your Goals

It’s a VUCA/BANI world AND It’s only going to accelerate. That means that the strategy you developed last quarter and the operational plans you set last month will be obsolete by the end of the week.

But the strategy and the plan were never the goal. They were the road you planned based on the map you had. When the map changes, the road does, too. But you can still get to the goal if you’re willing to fiddle with a lock.

The “Not So Obvious or Easy” Answer to Surviving the Next Decade

by Robyn Bolton | Oct 28, 2025 | Leadership, Strategy

Last week, I shared that 74% of executives believe that their organizations will cease to exist in ten years. They believe that strategic transformation is required, but cite the obvious problem of organizational inertia and the easy scapegoat of people’s resistance to change.

Great. Now we know the problem. What’s the solution?

The Obvious: Put the Right People in Leadership Roles

Flipping through the report, the obvious answers (especially from an executive search firm) were front and center:

Build a top team with relevant experience, competencies, and diverse backgrounds
Develop the team and don’t be afraid to make changes along the way
Set a common purpose and clear objectives, then actively manage the team

The Easy: Do Your Job as a Leader

OK, these may not be easy but it’s not that hard, either:

Relentlessly and clearly communicate the why behind the change
Change one thing at a time
Align incentives to desired outcomes and behaviors
Be a role model
Understand and manage culture (remember, it’s reflected in the worst behaviors you tolerate)

The Not-Obvious-or-Easy-But-Still-Make-or-Break: Deputize the Next Generation

Buried amongst the obvious and easy was a rarely discussed, let alone implemented, choice – actively engaging the next generation of leaders.

But this isn’t the usual “invite a bunch of Hi-Pos (high potentials) to preview and upcoming announcement or participate in a focus group to share their opinions” performance most companies engage in.

This is something much different.

Step 1: Align on WHY an “extended leadership team” of Next Gen talent is mission critical

The C-Suite doesn’t see what happens on the front lines. It doesn’t know or understand the details of what’s working and what’s not. Instead, it receives information filtered through dozens of layers, all worried about positioning things just right.

Building a Next Gen extended leadership team puts the day-to-day realities front and center. It brings together capabilities that the C-Suite team may lack and creates the space for people to point out what looks good on paper but will be disastrous in practice.

Instead, leaders must commit to the purpose and value of engaging the next generation, not merely as “sensing mechanisms” (though that’s important, too) but as colleagues with different and equally valuable experiences and insights.

Step 2: Pick WHO is on the team without using the org chart

High-potentials are high potential because they know how to succeed in the current state. But transformation isn’t about replicating the current state. It requires creating a new state. For that, you need new perspectives:

Super connecters who have wide, diverse, and trusted relationships across the organization so they can tap into a range of perspectives and connect the dots that most can barely see
Credible experts who are trusted for their knowledge and experience and are known to be genuinely supportive of the changes being made
Influencers who can rally the troops at the beginning and keep them motivated throughout

Step 3: Give them a clear mandate (WHAT) but don’t dictate HOW to fulfill it

During times of great change, it’s normal to want to control everything possible, including a team of brilliant, creative, and committed leaders. Don’t involve them in the following steps and be open to being surprised by their approaches and insights:

At the beginning, involve them in understanding and defining the problem and opportunity.
Throughout, engage them as advisors and influencers in decision-making (
During and after implementation, empower them to continue to educate and motivate others and to make adaptations in real-time when needed.

Co-creation is the key to survival

Transforming your organization to survive, even thrive, in the future is hard work. Why not increase your odds of success by inviting the people who will inherit what you create to be part of the transformation?

Decision Making in Uncertainty? This 25-Year-Old Tool Actually Works

by Robyn Bolton | Sep 30, 2025 | Leading Through Uncertainty, Strategy, Tips, Tricks, & Tools

Just as we got used to VUCA (volatile, uncertain, complex, ambiguous) futurists now claim “the world is BANI now.” BANI (brittle, anxious, nonlinear, incomprehensible) is much worse than VUCA and reflects “the fractured, unpredictable state of the modern world.”

Not to get too Gen X on the futurists who coined and are spreading this term but…shut up.

Is the world fractured and unpredictable? Yes.

Does it feel brittle? Are we more anxious than ever? Are things changing at exponential speed, requiring nonlinear responses? Does the world feel incomprehensible? Yes, to all.

Naming a problem is the first step in solving it. The second step is falling in love with the problem so that we become laser focused on solving it. BANI does the first but fails at the second. It wallows in the problem without proposing a path forward. And as the sign says, “Ain’t nobody got time for this.”

(Re)Introducing the Cynefin Framework

The Cynefin framework recognizes that leadership and problem-solving must be contextual to be effective. Using the Welsh word for “habitat,” the framework is a tool to understand and name the context of a situation and identify the approaches best suited for managing or solving the situation.

It’s grounded in the idea that every context – situation, challenge, problem, opportunity – exists somewhere on a spectrum between Ordered and Unordered. At the Ordered end of the spectrum, cause and affect are obvious and immediate and the path forward is based on objective, immutable facts. Unordered contexts, however, have no obvious or immediate relationship between cause and effect and moving forward requires people to recognize patterns as they emerge.

Both VUCA and BANI point out the obvious – we’re spending more time on the Unordered end of the spectrum than ever. Unlike the acronyms, Cynefin helps leaders decide and act.

5 Contexts. 5 Ways Forward

The Cynefin framework identifies five contexts, each with its own best practices for making decisions and progress.

On the Ordered end of the spectrum:

Simple contexts are characterized by stability and obvious and undisputed right answers. Here, patterns repeat, and events are consistent. This is where leaders rely on best practices to inform decisions and delegation, and direct communication to move their teams forward.
Complicated contexts have many possible right answers and the relationship between cause and effect isn’t known but can be discovered. Here, leaders need to rely on diverse expertise and be particularly attuned to conflicting advice and novel ideas to avoid making decisions based on outdated experience.

On the Unordered end of the spectrum:

Complex contexts are filled with unknown unknowns, many competing ideas, and unpredictable cause and effects. The most effective leadership approach in this context is one that is deeply uncomfortable for most leaders but familiar to innovators – letting patterns emerge. Using small-scale experiments and high levels of collaboration, diversity, and dissent, leaders can accelerate pattern-recognition and place smart bets.
Chaos are contexts fraught with tension. There are no right answers or clear cause and effect. There are too many decisions to make and not enough time. Here, leaders often freeze or make big bold decisions. Neither is wise. Instead, leaders need to think like emergency responders and rapidly response to re-establish order where possible to bring the situation into a Complex state, rather than trying to solve everything at once.

The final context is Disorder. Here leaders argue, multiple perspectives fight for dominance, and the organization is divided into fractions. Resolution requires breaking the context down into smaller parts that fit one of the four previous contexts and addressing them accordingly.

The Only Way Out is Through

Our VUCA/BANI world isn’t going to get any simpler or easier. And fighting it, freezing, or fleeing isn’t going to solve anything. Organizations need leaders with the courage to move forward and the wisdom and flexibility to do so in a way that is contextually appropriate. Cynefin is their map.

We’ve Got Uncertainty & Risk All Wrong (and It’s Killing Our Business)

by Robyn Bolton | Sep 2, 2025 | Leading Through Uncertainty, Strategy

In September 2011, the English language officially died. That was the month that the Oxford English Dictionary, long regarded as the accepted authority on the English language published an update in which “literally” also meant figuratively. By 2016, every other major dictionary had followed suit.

The justification was simple: “literally” has been used to mean “figuratively” since 1769. Citing examples from Louisa May Alcott’s Little Women, Charles Dickens’ David Copperfield, Charlotte Bronte’s Jane Eyre, and F. Scott Fitzgerald’s The Great Gatsby, they claimed they were simply reflecting the evolution of a living language.

What utter twaddle.

Without a common understanding of a word’s meaning, we create our own definitions which lead to secret expectations, and eventually chaos.

And not just interpersonally. It can affect entire economies.

Maybe the state of the US economy is just a misunderstanding

Uncertainty.

We’re hearing and saying that word a lot lately. Whether it’s in reference to tariffs, interest rates, immigration, or customer spending, it’s hard to go a single day without “uncertainty” popping up somewhere in your life.

But are we really talking about “uncertainty?”

Uncertainty and Risk are not the same.

The notion of risk and uncertainty was first formally introduced into economics in 1921 when Frank Knight, one of the founders of the Chicago school of economics, published his dissertation Risk, Uncertainty and Profit. In the 114 since, economists and academics continued to enhance, refine, and debate his definitions and their implications.

Out here in the real world, most businesspeople use them as synonyms meaning “bad things to be avoided at all costs.”

But they’re not synonyms. They have distinct meanings, different paths to resolution, and dramatically different outcomes.

Risk can be measured and/or calculated.

Uncertainty cannot be measured or calculated

The impact of tariffs, interest rates, changes in visa availability, and customer spending can all be modeled and quantified.

So it’s NOT uncertainty that’s “paralyzing” employers. It’s risk!

Not so fast my friend.

Not all Uncertainties are the same

According to Knight, Uncertainty drives profit because it connects “with the exercise of judgment or the formation of those opinions as to the future course of events, which…actually guide most of our conduct.”

So while we can model, calculate, and measure tariffs, interest rates, and other market dynamics, the probability of each outcome is unknown. Thus, our response requires judgment.

Sometimes.

Because not all uncertainties are the same.

The Unknown (also known as “uncertainty based on ignorance”) exists when there is a “lack of information which would be necessary to make decisions with certain outcomes.”

The Unknowable (“uncertainty based on ambiguity”) exists when “an ongoing stream [of information] supports several different meanings at the same time.”

Put simply, if getting more data makes the answer obvious, we’re facing the Unknown and waiting, learning, or modeling different outcomes can move us closer to resolution. If more data isn’t helpful because it will continue to point to different, equally plausible, solutions, you’re facing the Unknowable.

So what (and why did you drag us through your literally/figuratively rant)?

If you want to get unstuck – whether it’s a project, a proposal, a team, or an entire business, you first need to be clear about what you’re facing.

If it’s a Risk, model it, measure it, make a decision, move forward.

If it’s an uncertainty, what kind is it?

If it’s Unknown, decide when to decide, ask questions, gather data, then, when the time comes, decide and move forward

If it’s Unknowable, decide how to decide then put your big kid pants on, have the honest and tough conversations, negotiate, make a decision, and move on.

I mean that literally.

Why Creative Confidence Beats Market Signals (And How Johnny Cash Used It to Resurrect His Career)

by Robyn Bolton | Aug 4, 2025 | Leadership, Leading Through Uncertainty, Stories & Examples, Strategy

The best business advice can destroy your business. Especially when you follow it perfectly.

Just ask Johnny Cash.

After bursting onto the scene in the mid-1950s with “Folsom Prison Blues”, Cash enjoyed twenty years of tremendous success. By the 1970s, his authentic, minimalist approach had fallen out of favor.

Eager to sell records, he pivoted to songs backed by lush string arrangements, then to “country pop” to attract mainstream audiences and feed the relentless appetite of 900 radio stations programming country pop full-time.

By late 1992, Johnny Cash’s career was roadkill. Country radio had stopped playing his records, and Columbia Records, his home for 25 years, had shown him the door. At 60, he was marooned in faded casinos, playing to crowds preferring slot machines to songs.

Then he took the stage at Madison Square Garden for Bob Dylan’s 30th anniversary concert.

In the audience sat Rick Rubin, co-founder of Def Jam Recordings and uber producer behind Public Enemy, Run-DMC, and Slayer, amongst others. He watched in awe as Cash performed, seeing not a relic but raw power diluted by smart decisions.

The Stare-Down that Saved a Career

Four months later, Rubin attended Cash’s concert at The Rhythm Café in Santa Anna, California. According to Cash’s son, “When they sat down at the table, they said: ‘Hello.’ But then my dad and Rick just sat there and stared at each other for about two minutes without saying anything, as if they were sizing each other up.”

Eventually, Cash broke the silence, “What’re you gonna do with me that nobody else has done to sell records for me?”

What happened next resurrected his career.

Rubin didn’t promise record sales. He promised something more valuable: creative control and a return to Cash’s roots.

Ten years later, Cash had a Grammy, his first gold record in thirty years, and CMA Single of the Year for his cover of Nine Inch Nails’ “Hurt,” and millions in record sales.

When Smart Decisions Become Fatal

Executives do exactly what Cash did. You respond to market signals. You pivot your offering when customer preferences shift and invest in emerging technologies.

All logical. All defensible to your board. All potentially fatal.

Because you risk losing what made you unique and valuable. Just as Cash lost his minimalist authenticity and became a casualty of his effort to stay relevant, your business risks losing sight of its purpose and unique value proposition.

Three Beliefs at the Core of a Comeback

So how do you avoid Cash’s initial mistake while replicating his comeback? The difference lies in three beliefs that determine whether you’ll have the creative courage to double down on what makes you valuable instead of diluting it.

Creative confidence: The belief we can think and act creatively in this moment.
Perceived value of creativity: Our perceived value of thinking and acting in new ways.
Creative risk-taking: The willingness to take the risks necessary for active change.

Cash wanted to sell records, and he:

Believed that he was capable of creativity and change.
Saw the financial and reputational value of change
Was willing to partner with a producer who refused to guarantee record sales but promised creative control and a return to his roots.

Your Answers Determine Your Outcome

Like Cash, what you, your team, and your organization believe determines how you respond to change:

Do I/we believe we can creatively solve this specific challenge we’re facing right now?
Is finding a genuinely new approach to this situation worth the effort versus sticking with proven methods?
Am I/we willing to accept the risks of pursuing a creative solution to our current challenge?”

Where there are “no’s,” there is resistance, even refusal, to change. Acknowledge it. Address it. Do the hard work of turning the No into a Yes because it’s the only way change will happen.

The Comeback Question

Cash proved that authentic change—not frantic pivoting—resurrects careers and disrupts industries. His partnership with Rubin succeeded because he answered “yes” to all three creative beliefs when it mattered most. Where are your “no’s” blocking your comeback?

Three Executive Decisions that Make or Break Strategic Foresight

by Robyn Bolton | Jul 8, 2025 | Strategic Foresight, Strategy

You stand on the brink of an exciting new adventure. Turmoil and uncertainty have convinced you that future success requires more than the short-term strategic and business planning tools you’ve used. You’ve cut through the hype surrounding Strategic Foresight and studied success. You are ready to lead your company into its bold future.

So, where do you start?

Most executives get caught up in all the things that need to happen and are distracted by all the tools, jargon, and pretty pictures that get thrown at them. But you are smarter than that. You know that there are three things you must do at the beginning to ensure ultimate success.

Give Foresight Executive Authority and Access

Foresight without responsibility is intellectual daydreaming.

While the practice of research and scenario design can be delegated to planning offices, the responsibility for debating, deciding, and using Strategic Foresight must rest with P&L owners.

Amy Webb’s research at NYU shows that when a C-Suite executive with the authority to force strategic reviews oversaw foresight activities, the results were more likely to be acted on and integrated into strategic and operational plans. Shell serves as a specific example of this, as its foresight team reported directly to the executive committee, so that when scenarios explored dramatic oil price volatility, Shell executives personally reviewed strategic portfolios and authorized immediate capability building.

Start by asking:

Who can force strategic reviews outside of the traditional planning process?
What triggers a review of Strategic Foresight scenarios?
How do we hold people accountable for acting on insights?

Demand Inputs That Challenge Your Assumptions

If your Strategic Foresight conversations don’t make you uncomfortable, you’re doing them wrong.

Webb’s research also shows that successful foresight systematically explores fundamental changes that could render the existing business obsolete.

Shell’s scenarios went beyond assumptions about oil price stability to explore supply disruptions, geopolitical shifts, and demand transformation. Disney’s foresight set aside traditional assumptions about media consumption and explored how technology could completely reshape content creation, distribution, and consumption.

Start by asking these questions:

Is the team going beyond trend analysis and exploring technology, regulations, social changes, and economic developments that could restructure entire markets?
Who are we talking to in other industries? What unusual, unexpected, and maybe crazy sources are we using to inform our scenarios?
Does at least one scenario feel possible and terrifying?

Integrate Foresight into Existing Planning Processes

Strategic Foresight that doesn’t connect to resource allocation decisions is expensive research.

Your planning processes must connect Strategic Foresight’s long-term scenarios to Strategic Planning’s 3–5-year plans and to your annual budget and resource decisions. No separate foresight exercises. No parallel planning tracks. The cascade from 20-year scenarios to this year’s investments must be explicit and ruthless.

When Shell’s scenarios explored dramatic oil price volatility over decades, Shell didn’t file them away and wait for them to come true. They immediately reviewed their strategic portfolio and developed a 3–5-year plan to build capabilities for multiple oil futures. This was then translated into immediate capital allocation changes.

Disney’s foresight about changing media consumption in the next 20 years informed strategic planning for Disney+ and, ultimately, its operational launch.