by Robyn Bolton | Feb 23, 2026 | Leadership, Stories & Examples, Strategy
Congratulations, you’ve done the hard part required to get buy-in! You asked instead of told, said “I don’t know” out loud, and got genuine buy-in. Your team believes, is engaged, and ready to go. And yet execution is stalling.
What gives?
Activity without Achievement
There’s no doubt that people are working hard. You can see it in their schedules and you hear it in your one-on-ones. But projects are moving slower than they should, decisions that seem straightforward take weeks, and agreements made in meetings are quietly undone. Strategies, buy-in, timelines are powerless against an invisible and unnamed force.
So, you consider your options. A team offsite can provide a helpful rest but there’s no guarantee it sticks when you’re back in the office. Training can help shore up skill gaps, but your team is already capable, so this doesn’t feel like a skill problem. You could reorg but that creates new problems.
Your People Aren’t the Problem
The problem isn’t your people, your team, or even your culture. The problem is the hidden seams between people, teams, and cultures, that create friction.
Because of friction, people hesitate to share information across functional or hierarchical seams. They make assumptions about other generations. They work to achieve individual or functional, rather than collective, goals.
These friction points have been part of your organization for so long that they are accepted as normal. As immoveable and unchangeable as your company’s mission and vision. And because they’re so ingrained, you shift your efforts to things that feel changeable: skills, org charts, and communication plans.
You’re addressing symptoms because the root cause seems impossible to fix.
It’s not impossible.
How One Company Resolved the Friction and Tightened the Seams Without Extra Work
When a K-5 curriculum company decided to expand into the Middle School market, they knew they were asking the project team to do something new that was complex, ambiguous, and fraught with high-stakes decisions.
Six months in, the project was breaking down. Decisions that should have taken a day took weeks or months. Work got stuck as different functions weighed in at different times with different mandatory requirements. People hid problems and gave optimistic updates.
The executive who owned the project had seen this before. In fact, she was seeing it in every project team across the entire company. So, she knew that the problem wasn’t the project or the people, it was something much deeper, something that was such a part of the company’s standard operating process that it had become invisible.
So, she brought in someone (me) who could see things differently and together we sought out the seams, naming the moments when friction occurred, and engaging the team in developing and experimenting with solutions.
And we did it all as part of the daily work.
We redesigned hand-offs in real time, experimented with decision-making rules until we found what worked for multiple decision types, and rewarded people for saying “I don’t know.”
Within six months, the project was back on track and engagement and morale were sky-high. Other teams took notice and asked for advice. New products began shipping on time, on budget, and to rave reviews.
Now the Real Work Begins
Where are your seams showing up? A cross-functional initiative that’s losing momentum? A decision that never seems to stick? A team that’s aligned on paper but stuck in execution?
That friction has a name. And it’s findable.
If you’re ready to find the seams and resolve the friction, set up a SeamSpotter Session. It’s a 60 to 90-minute conversation, no prep required, and you’ll receive a written summary and recommended next steps within 48 hours.
If your team is bought in, but execution keeps stuttering, you can fix it. Email me at robyn@milezero.io to get started.
by Robyn Bolton | Feb 16, 2026 | Leadership, Leading Through Uncertainty, Strategy
“None of it worked. When I pulled the executive team back together and asked what went wrong, these executives said, ‘You told us what to do. You never asked us what to do.
“What I should have done is just said, ‘I don’t know.’ And when you say those words, what happens is everybody wants to help you.”
That is how Josh D’Amaro, the newly named CEO of the Walt Disney Company, characterized his defining leadership development moment.
Sound familiar?
Every executive, at some point in their career, has faced this moment. The business is doing poorly, the future is uncertain, and everyone is looking to you for answers.
But few of us learn the lesson that Mr. D’Amaro did. So, we keep telling and wondering why compliance isn’t generating the results we expected.
Compliance and Buy-In are not the same
In our world of “using positive words to describe uncomfortable realities,” we often characterize compliance as buy-in. And that’s a dangerous mistake.
“Compliance,” explains innovation expert Tendayi Viki, “comes from external pressures to follow rules and policies due to fear of consequences. In contrast, buy-in comes from internal motivation where people genuinely view the initiative as valuable and legitimate.”
Compliance is what happened when D’Amaro convened the market and sales executives of Hong Kong Disneyland together and told them “to adjust, build, and set ourselves up for the future.”
When things are not going well and the future is uncertain (and therefore scary) it’s normal to think that, because you are in a role with authority, that you need to have all the answers. But you don’t. Because you can’t. Because no one has the answers.
You need help.
Why Buy-in, not compliance, is required for success
No one is going to help you when they’re afraid. Instead, they’re going to execute orders regardless of their own experiences or judgment, which may be more informed and likely to result in the desired outcome (as was the case with D’Amaro and his team).
But when you ask for help, people help. They feel ownership of both the problem and the solution and seek out creative ideas and alternatives. They work across traditional organizational boundaries, like functions and levels, and they’re more resilient when faced with adversity. Even better for you, they don’t require constant instruction, surveillance, and micromanagement.
Getting buy-in frees you up to do the very thing you want to do: lead a team to a common goal and better future.
Buy-in is NOT another Change Management initiative
I’m sorry to say that getting buy-in is much harder than running the standard Change Management playbook.
Change management gives leaders a structured playbook of communication plans, training schedules, governance milestones. It’s systematic, observable, and leader-driven. And it’s not wrong. It’s just not sufficient to gain buy-in.
Buy-in is individual, nonlinear, and rooted in belief, not process. It forms one person at a time based on trust, relevance, and whether the individual sees themselves in the future state. It happens when one human being trusts the motives and behaviors of another human being.
How to get Buy-In
Earning buy-in requires you to do what D’Amaro eventually learned: invite dissent, share incomplete thinking, and say “I don’t know.” But that’s just the beginning.
You also have to find where things are breaking down internally, the gaps that allowed the situation to grow ever more concerning and dire. And it’s rarely at the obvious boundaries between silos that everyone can see and org charts try to fix.
It’s at the seams: the hidden disconnects between people, decisions, handoffs, and incentives where functions, levels, and priorities intersect. These seams are where compliance lives and buy-in dies. And until you make them visible, you’ll keep mistaking one for the other. But they can be made visible and that changes everything.
Now that you see the difference, where is compliance masquerading as buy-in in your organization?
by Robyn Bolton | Feb 8, 2026 | AI, Leadership, Leading Through Uncertainty, Strategic Foresight, Strategy
In 2023, Klarna’s CEO proudly announced it had replaced 700 customer service workers with AI and that the chatbot was handling two-thirds of customer queries. Labor costs dropped and victory was declared.
By 2025, Klarna was rehiring. Customer satisfaction had tanked. The CEO admitted they “went too far,” focusing on efficiency over quality.
Like Captain Robert Scott, Klarna misjudged the circumstance it was in, applied the wrong playbook, and lost. It thought it had facts but all it has was technical specs. It made tons of assumptions about chatbots’ ability to replace human judgment and how customers would respond.
Calibrated Decision Design, a process for diagnosing your circumstances before picking a playbook, consistently proves to be a quick and necessary step to ensure success.
When you have the facts and need results ASAP: Go NOW!
General Mills, like its competitors, had been digitizing its supply chain for years and so facts based on experience and a list of the facts it needed.
To close the gap and achieve end-to-end visibility in its supply chain, it worked with Palantir to develop a digital twin of its entire supply chain. Results: 30% waste reduction, $300 million in savings, decisions that took weeks now takes hours. It proves that you don’t need all the answers to make a move, but you need to know more than you don’t.
When you have hypotheses but can’t wait for results: Discovery Planning
Morgan Stanley Wealth Management’s (MSWM) clients expect advisors to bring them bespoke advice based on mountains of analysis, and insights. But it’s impossible for any advisor to process all that data. Confident that AI could help but uncertain whether its would improve relationships or create friction, MSWM partnered with OpenAI.
Within six months, they debuted a GenAI chatbot to help Financial Advisors quickly access the firm’s IP. Document retrieval jumped from 20% to 80% and 98% now use it daily. Two years later, MSWM expanded into a meeting summary tool to summarize meetings into actionable outputs and update the CRM with notes and follow-ups. A perfect example of how a series of experiments leads to a series of successes.
When you have facts and time to achieve results: Patient Planning
Drug discovery requires patience and, while the process may be predictable, the results aren’t. That’s why pharma companies need strategies that are thoughtfully planned as they are responsive.
Lilly is doing just that by investing in its own capabilities and building an ecosystem of partners. It started by launching TuneLab, a platform offering access to AI-enabled drug discovery models based on data that Lilly spent over $1 billion developing. A month later, the pharma giant announced a partnership with NVIDIA to build the pharmaceutical industry’s most powerful AI supercomputer. Two months later, it committed over $6 billion to a new manufacturing facility in Alabama. These aren’t billion-dollar bets, they’re thoughtful investments in a long-term future that allows Lilly to learn now and stay flexible as needs and technology evolve.
When you’re making assumptions and have time to learn: Resilient Strategy
There’s no way of knowing what the global energy system will look like in 40 years. That’s why Shell’s latest scenario planning efforts resulted in three distinct scenarios, Surge, Archipelagos, and Horizon. Multiple scenarios allows the company to “explore trade-offs between energy security, economic growth and addressing carbon emissions” and build resilient strategies to recognize which one is unfolding and pivot before competitors even spot what’s happening.
Stop benchmarking. Start diagnosing.
It’s easy to feel like you’re behind when it comes to AI. But the rush to act before you know the problem and the circumstances is far more likely to make you a cautionary tale than a poster child for success.
So, stop benchmarking what competitors do and start diagnosing the circumstances you’re in, so you use the playbook you need.
by Robyn Bolton | Feb 2, 2026 | AI, Leadership, Strategic Foresight, Strategy
It was a race. And the whole world was watching.
In 1911, Captain Robert Scott set out to reach the South Pole. He’d been to Antarctica before and because of his past success, he had more funding, more expertise, and more experience. He had all the equipment needed.
Racing him to fame, fortune and glory was Norwegian Roald Amundsen. Originally heading to the North Pole, he turned around when he learned that Robert Peary had beaten him there. He had dogs and skis, equipment perfect for the Arctic but unproven in Antarctica.
Amundsen won the race, by over a month.
Scott and his crew died 11 miles from the South Pole.
When the Playbook Stops Working
Scott wasn’t guessing. He’d tested motor sledges in the Alps. He’d seen ponies work on a previous Antarctic expedition. He built a plan around the best available equipment and the general playbook that had served British expeditions for decades: horses and motors move heavy loads, so use horses and motors.
It just wasn’t right for Antarctica. The motors broke down in the cold. The ponies sank through the ice. The plan that looked solid on paper fell apart the moment it met the actual environment it had to operate in.
The same thing is happening today with AI.
For decades, when new technologies emerge, executives have followed a similarly familiar playbook: assess the opportunity, build a business case, plan the rollout, execute.
And for decades it worked. Cloud migrations and ERP implementations were architectural changes to known processes with predictable outcomes. As time went on, information grew more solid, timelines became better understood, and the playbook solidified.
AI is different. Executives are so focused on picking the right AI tools and building the right infrastructure that they aren’t thinking about what happens when they hit the ice. Even if the technology works as designed, you have no idea whether it will deliver the intended results or create a ripple of unintended consequences that paralyze your business and put egg on your face.
Diagnose Before You Prescribe
The circumstances of AI are different too, and that requires a new playbook. Make that playbooks. Picking the right playbook requires something my clients and I call Calibrated Decision Design.
We start by asking how long it will take to realize the ultimate goals of the investment. Do we need to break even this year, or is this a multi-year bet where results slowly roll in? Most teams have a sense of this, so it allows us to move quickly to the next, much harder question.
What do we know and what do we believe? This is where most teams and AI implementations fail. To seem confident and indispensable, people present hypotheses as if they are facts resulting in decisions based on a single data points or best guesses. The result is a confident decision destined to crumble.
Where you land on these two axes determines your playbook. Apply the wrong one and you’ll either waste money on over-analysis or burn through budget on premature action.
Pick from the Four Playbooks
Go NOW!: You have the facts and need results now. Stop deliberating. Execute.
Predictable Planning: You have confidence in the outcome, but the payoff takes patience. Build a flexible strategy and operational plan to stay responsive as things progress.
Discovery Planning: You need results fast, but you don’t have proof your plan will work. Run small, fast experiments before scaling anything.
Resilient Strategy: The time horizon is long and you’re short on facts. The worst thing you can do is go all in. Instead, envision multiple futures, identify early warning signs, find commonalities and prepare a strategy that can pivot.
Apply it
Which playbook are you using and which one is best for your circumstance?
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.
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?
