by Robyn Bolton | Jun 17, 2026 | Leadership, Leading Through Uncertainty, Tips, Tricks, & Tools
Up and down New England’s coastline you’ll find lobster (pronounced “lob-stah”) shacks. These weathered wood structures produce the freshest lobster and crispiest fried seafood anywhere, enjoyed on picnic tables as the sun beats down and the waves crash against the rocky shore.
It was at one of these shacks that, many years ago, I learned priceless lesson.
As my friends and I placed our orders, I asked that the head of my lobster be removed before serving. The waitress looked at me like I had nine heads but wrote down my request and returned to the kitchen. A few minutes later she reappeared and announced that the kitchen refused to decapitate the lobster prior to serving.
“I don’t like making eye contact with my food,” I stammered.
She nodded and walked away.
When she returned with our lobsters, they all had heads but one was noticeably different. It was wearing “sunglasses” made of olives and toothpicks.
“Here,” our waitress said. “Now you don’t have to make eye contact with it.”
A short-term “solution”
As VUCA-ness (volatile, uncertain, complex, ambiguous) accelerates, C-suite executives do everything possible to create certainty and construct safety. After all, if the company doesn’t survive the short-term, even the best long-term plans don’t matter.
Evidence of this approach is everywhere:
When these decisions land on your desk, you sigh, knowing they are short-sighted but understanding the rationale. Then, you go implement them, knowing unintended consequences are coming.
Unintended doesn’t mean unpredictable
In fact, because you are on the frontlines of your business, striving to deliver today and build tomorrow, you can predict what those consequences will be:
It’s frustrating to see the problems coming but feel powerless to avoid them.
But what does any of this have to do with a lobster wearing sunglasses?
When you know the Why, you can choose the How
When directives land on your desk, don’t sigh and roll them out. Ask for the Why behind the What.
- Why are employees being forced back to the office? Did productivity decrease? Are mission-critical operations not occurring? Are top-performers leaving for in-person roles?
- Why are experienced people being let go? Is the work being outsourced or has it genuinely gone? Why are you no longer hiring entry-level people? Are they too expensive to train? Is retention genuinely poor?
- Why are innovation initiatives being cut? Is the core business in that much trouble? Do we lack the talent? Are we pursuing growth through other means?
Each directive’s Why is different which means you have more options than you realize for delivering the How. Understanding the outcomes the company needs, reveals options for delivering it while minimizing the unintended consequences.
Don’t decapitate the lobster. Find opportunities for sunglasses.
The kitchen could have easily removed the head from my lobster, but they foresaw the unintended consequences of a disappointing dining experience. When they understood my why, they created a spectacular how.
You don’t control the system so asking “Why?” feels scary, hostile, even mutinous.
You do control your piece of it. You know it better than anyone, so there’s no one better to determine the how.
by Robyn Bolton | Jun 10, 2026 | Leadership, Tips, Tricks, & Tools
We have entered the “do more with less” era of management edicts.
And, just like the eras of “fail fast,” “synergy,” and “we’re a family,” the phrase is met with eye rolls, silent groans, and a deepening certainty that management is completely out of touch with the reality on the ground.
But what if doing more with less is possible without the extra hours and stress that lead to burnout?
(Re)Define “more.”
When we hear “more,” we naturally think of work. More meetings. More emails. More Slacks, texts, Zooms. For most of my career, I believed the more emails I received, meetings I attended, and documents I wrote, the more valuable I was.
Volume does not equal value.
“More” can’t (and shouldn’t) mean more work. It must mean something else.
More value creation. Less box checking.
More progress. Less process.
More meaningful work. Less meaningless activity.
What is the “more” you want from your team? Define it or you’ll get more emails, meetings, and documents. Name it (value, efficiency, progress), and your team will figure out how to do it.
Experiment with “less.”
A client’s team stopped sending meeting summaries. They didn’t send shorter ones, change the distribution list, or even share the link to the AI note-taker. They just stopped.
No one noticed.
Six months later, a new team member asked if they would send a meeting summary. The team leader said no but offered to recap next steps before everyone left the room. No one argued. Everyone left the meeting with clarity on what they needed to do next.
Activity does not equal achievement.
Our days are filled with BS work, tasks that we do because we’ve always done them, because they feel important, and because we worry what happens if we stop.
Documents don’t ensure that people are informed, aligned, or are ready to act.
Meetings don’t guarantee that everyone has thoughtfully considered and agreed on a decision.
Meeting summaries don’t make people complete their next steps.
It doesn’t mean we don’t need documents, meetings, or meeting summaries. But “less” is possible.
Ask your team what you can do less of. Stop doing things and see if people notice. If you can’t stop something completely, ask what less of it looks like. Instead of a meeting summary, send next steps. Instead of a presentation, write a one-page summary. Instead of a spreadsheet build a visual dashboard.
Rethink “indispensable.”
The managers in my client’s training program were in roles that everyone called the most pivotal in the company. They didn’t feel pivotal. They felt reactive and overwhelmed, with no control over their own calendars.
The COO’s fix was simple. Just stop attending.
It surprised him that they wouldn’t. They couldn’t. The fear of missing something kept them in every room, including the ones that ran fine without them.
You’re in every meeting because you’re good at your job. Being good got you invited into every decision, and somewhere along the way no one uninvited you. Now you stay out of habit, not need. The permission to step back is usually there. You just haven’t tested it long enough to know what happens.
Presence does not equal performance.
Look at your calendar for the meetings you sit in out of habit. Pick one this week to not attend. Resist the urge to instructions. Simply tell the team lead you won’t attend and that you trust them to keep things moving.
Your absence isn’t dropping the ball. It’s demonstrating that you trust the team and empowering them to do their jobs. It’s the rare version of less that gives you more time and your team their autonomy.
“Do more with less” isn’t a demand to work harder
The constraint isn’t going anywhere. Volume isn’t value. Activity isn’t achievement. Presence isn’t performance. It’s a reason to finally drop what doesn’t matter.
by Robyn Bolton | Mar 18, 2026 | AI, Customer Centricity, Leadership, Leading Through Uncertainty, Strategy
If you’re uncertain, you’re not alone. According to data from FactSet, 87% of Fortune 500 companies cited “uncertainty” during their 2025 Q1 earnings calls. And while things are definitely a tad chaotic in the world, I’ve started asking my clients, “What would you do if you were certain?”
It’s not an academic thought experiment. It’s a very practical exercise that radically shifts the way the think about and lead their businesses.
An Example That Proves the Rule
Most leaders facing disruption do one of two things: freeze and hope that “this too shall pass” or follow and hope that there is safety in numbers.
Neither is a strategy. Both are knee jerk reactions rooted in fear and communicated in the language and buzzwords of business.
This behavior didn’t start with AI. It happens every time a disruptive technology or philosophy bursts onto the scene. The printing press. The industrial revolution. Microchips. Each time, a new leader and paradigm emerges. How do they do it?
They’re certain.
Not because they’re omniscient. But because they know the answers to three questions
Question 1: Who Are You?
When photography made academic realism obsolete, Picasso didn’t freeze. He didn’t pick up a camera. He created something entirely new. Why? Because he knew exactly who he was. “I don’t seek,” he said. “I find.”
Today’s business icons are no different. Richard Branson describes himself as curious and someone who challenges the status quo. Lou Gerstner, when he arrived at a floundering IBM, declared himself a results man, not a visionary.
These self-definitions aren’t marketing. They’re decisions filters that define what you are and aren’t willing to do, agnostic of events, technologies, and capabilities.
Question 2: What Does Your Organization Actually Do?
Not what you make. Not what you sell. What Job to be Done do customers hire you to do?
Nintendo’s answer has been consistent across 130 years of radical product change: help me have fun with friends and family. From playing cards to the Game Boy, Wii, and Switch, their products changed completely. The Job didn’t.
IBM has done the same. From punch card tabulators to consulting and AI, the Job of helping customers make sense of complex information to run better never change. Amex moved from freight forwarding to credit and debit cards, but it’s commitment to move value securely when direct exchange isn’t an option never wavered.
When you know the Job you do, you stop chasing trends and start making choices.
Question 3: How Do You Move Forward?
You can’t answer this question without answering the first two. When you try, you get caught in the same freeze/follow trap as everyone else.
But when you answer the first two questions, the answer to this one becomes clear. For Picasso and Branson, they create. For Gerstner, he optimized the status quo. For most businesses, the answer is “And, not Or.” They must stabilize today’s business, step into (even follow) the next wave, and invest in creating the new.
Satya Nadella’s transformation of Microsoft is a perfect example. He defined himself as a learner, not a knower. He defined Microsoft’s job as helping people make a difference in their roles. From those two answers, every major move followed logically: maintain Office 365, step into cloud, create quantum computing technology.
None of it was reactive. All of it felt certain.
Your Moment Is Now
Yes, the world is uncertain. You don’t have to be.
Before you close this tab and tell yourself you’ll think about it later, answer the first two questions. You can change your answers later, but you need to start now.
The leaders who navigate this moment won’t be the ones who wait and see or follow the crowd. They’ll be the ones who know themselves and their organizations well enough to be certain.
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 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.
