by Robyn Bolton | Sep 7, 2026 | Leadership, Strategy
“We had OKRs until 8 months ago when new ELT members came in and decided to abandon them.”
The VP sighed and shook her head. Her company, a mid-sized, multi-million-dollar business, was maturing. Growth had slowed from its heady startup days and was going through the usual growing pains: the founding CEO had stepped down, external hires joined the leadership team, and new processes were making their way into daily work.
The new rigor of building and rolling out a strategy was welcomed and the organization was learning how to operate in a more “streamlined” (and less “entrepreneurial”) manner.
The company’s evolution was going as well as could be expected, until everything changed.
And she was left holding the bag.
She’s not alone amongst her peers
In research conducted using Cascade’s Strategic Maturity Assessment, VPs scored their companies lowest in four of the five pillars studied
On Focus, the first pillar, two-thirds of both the VPs and the C-Suite gave feel their companies are able to identify and clarify strategic priorities and goals.
That’s the good news.
The bad news is everything else
- Alignment (transparency and involvement across the organization): Only 38% of VPs believe their companies are performing well, half the score the C-suite gives this pillar (66%).
- Visibility (communication of, and access to, data and insights): The gap shrinks, but VPs still rate Visibility lower (59%) than any other cohort (C-Suite rates at 70% “mature”).
- Accountability (sense of ownership and commitment): A 22-percentage point gap exists between VP perception and C-Suite (49% vs. 71%)
- Speed (ability to adapt and evolve): This is the single biggest gap of any pillar (30-percentage points) between VPs (42% rate their companies’ speed as good) and the C-Suite (72%)
She is alone in the organization
What’s shocking is that the Directors and Managers that report up to VPs are genuinely more positive and optimistic. In fact, Directors are more positive about Focus, Visibility, and Accountability, than the C-Suite!
In a world where everything seems to roll downhill, why are things getting caught so close to the top?
Another VP, from a multi-billion-dollar company, offered an answer:
“Priorities tend to shift and are often vague or confusing. Resources, people, systems, and processes are severely lacking.” (VP, $10B+, under 1,000 employees)
VPs know what to do, they gave input on the strategy, and agree with it. But they don’t have the authority to get it resourced.
As if that weren’t tough enough, based on the perceptions reflected in the survey data, they’re putting on a brave face and shielding their teams from the futility of the quest.
She doesn’t have to be
“Do more with less” is hitting everyone. The absurdity of immediate AI-driven time (and cost) savings is obvious to everyone with a chatbot. The mandates to beat earnings and deliver record profit are relentless.
And in the middle of it all are the VPs who agree with strategic priorities but lack the resources to deliver them at the pace and scale demanded.
And that’s before a new ELT arrives or the business has a down quarter.
If your VPs sound tired, don’t assume they don’t believe in the strategy or that they’re trying to sandbag their goals.
Ask what they need to deliver the strategy and goals. The answer will be headcount, budget, or a promise that outlasts the next reorg.
You won’t be able to give them everything they ask for but you can (and must) give them more than a promise. Help them creatively problem-solve, connect them to non-traditional sources of talent (e.g. freelancers, temp hires, interns), critically evaluate your budget to ensure spending aligns with strategy.
Your VPs believe in the strategy as much as you do. The only question is whether you’ve given them what they need to deliver it before the next new executive walks in and abandons it.
If you would like to see how your organization scores, click here to take the Strategy Maturity Assessment. Your results will be sent directly to me, not to Cascade, and you will not be added to a mailing list. Please note that some people have had trouble using Gmail and other free e-mail accounts.
Methodology note: The Strategy Maturity Assessment was designed by Cascade and administered by MileZero as a self-serve survey to a sample of MileZero’s own clients: 18 self-selected respondents from 18 different companies, varying in role, revenue, and size. Findings are directional and should not be interpreted as scientific, random, or representative sample. Scores come from a proprietary scoring of Yes / Somewhat / No answers and show relative patterns, not precise measurements. All findings are the opinions of individual participants as of the date they responded, not statements of fact.
by Robyn Bolton | Sep 1, 2026 | Leadership, Strategy
It always amused me that the most “prestigious” consulting firms positioned themselves as specialists in strategy. Because if you believe the research that says that 67% to 90% of strategies fail, that means that McBainCG are really bad at their jobs!
They’re not (and I’m not writing that just because I used to be employed by one of them).
It’s because strategy development is only the first step on the path to execution.
The problem of a “Strategy-Execution Gap” isn’t new. But it oversimplifies the issue, rendering it unsolvable.
Believing that developing and communicating is sufficient to turn it into execution, then getting mad when that doesn’t happen, establishes and “us vs. them” mentality. Conversely, receiving a strategy that feels divorced from the reality of on-the-ground resources, constraints, and operations, engenders resentment amongst the rank and file.
The answer falls somewhere between strategy development and strategy execution.
In partnership with Cascade, an AI-powered strategy execution platform, I set off to find that somewhere.
5 steps from strategy to execution
There are five pillars of a “strategically mature” company (one that consistently translates strategy into execution:
- Focus: Ability to proactively develop clear plan that anticipates trends and sets goals
- Alignment: Transparency and involvement across the organization and with external stakeholders
- Visibility: Communication of, and access to, data and insights that empower decision-making at every level
- Accountability: Ability foster ownership and commitment across teams and individuals
- Speed: Ability adapt to evolving conditions and make decisions in a timely manner
5 levels of “Strategic Maturity”
In Cascade’s Strategic Maturity Assessments, organizations are evaluated against each of these five pillars and then scored on a level of one to five, with one being the least mature and five being fully mature. Not surprisingly, most organizations fall in the middle:
- Level 2: A basic annual strategic planning process that sets defined goals but there is limited alignment with broader business objective
- Level 3: A formal strategy process produces clearly articulated goals, resources, and responsibilities and are integrated with business objectives with rudimentary measurement and success metrics
- Level 4: Strategy is fully integrated in all business functions and cross-functional teams with continuous means to ensure alignment between strategic and operational goals.
1 Glaring Gap
Everything falls apart at Alignment.
Between 63% and 67% of respondents agreed with statements indicating strong focuses on Focus (a clear plan), Visibility (access to insights), Accountability (ownership of results), and Speed (adaptability). But Alignment? That was a 10-percentage point drop.
And the news gets worse the deeper you go:
- 38% of VPs feel their organization have strong alignment compared to 66% of C-Suite executives
- Only 1 respondent (a C-suite exec) feels they have adequate resources to implement initiatives and 67% of VPs and Directors disagree that they have what they need
- 25% of C-suite execs, 17% of VPs, and 0% of Directors and Managers feel strongly there is cross-functional alignment to executing the strategy
Yikes!
Root causes for this failure were consistent across company sizes (revenue, number of employees):
- “We are a highly fragmented and siloed org that has gone through several mergers recently” (C-Suite · $10B+ · 10–50k employees)
- “Organization siloes, conflicting priorities, protecting the legacy” (VP · $1–10B · 10–50k employees)
1 glimmer of hope
The solution isn’t a better strategy or process. It’s a habit and culture of empowerment
One startup CEO explained: “It (strategy) has worked because we grounded it in culture and employees are growing and driving the change.” A director at a Fortune 500 company described the same pattern from a different angle: “We’ve built muscle and improved how we approach strategy, doing this repeatedly over the last few years.”
The highest scorers built Alignment into the process, not as data-gathering “involvement” and head-nodding but as genuine engagement, buy-in, and empowerment. Does your strategic planning process do that?
If you would like to see how your organization scores, click here to take the Strategy Maturity Assessment. Your results will be sent directly to me, not to Cascade, and you will not be added to a mailing list. Please note that some people have had trouble using Gmail and other free e-mail accounts.
Methodology note: The Strategy Maturity Assessment was designed by Cascade and administered by MileZero as a self-serve survey to a sample of MileZero’s own clients: 18 self-selected respondents from 18 different companies, varying in role, revenue, and size. Findings are directional and should not be interpreted as scientific, random, or representative sample. Scores come from a proprietary scoring of Yes / Somewhat / No answers and show relative patterns, not precise measurements. All findings are the opinions of individual participants as of the date they responded, not statements of fact.
Why do most strategic plans fail?
Not because the strategy was wrong. Research puts strategy failure between 67% and 90%, and that’s not because those firms can’t develop a strategy. It’s because strategy development is only the first step. In Mile Zero’s Strategic Maturity data, four of five execution pillars scored strong. The one that collapsed: Alignment. That gap, not a bad plan, is where most strategies actually die.
What causes strategic decisions to stall inside a corporation?
Same root causes, regardless of company size. One executive summed it up: “We are a highly fragmented and siloed org that has gone through several mergers recently.” Another named “organization siloes, conflicting priorities, protecting the legacy.” Add in resources: 67% of VPs and Directors say they don’t have what they need to execute. Silos plus scarcity stall even a good decision.
What does a real strategy execution framework look like?
Five pillars, not one silver bullet: Focus, Alignment, Visibility, Accountability, and Speed. Cascade’s Strategic Maturity Assessment scores a company one to five on each, from a basic annual planning process with little follow-through to strategy fully built into every function and cross-functional team. Score all five pillars, and you find out exactly where execution actually breaks.
How do you overcome internal resistance to a strategy everyone already agreed to?
Not with a better deck. The highest scorers in Mile Zero’s Strategic Maturity data didn’t treat Alignment as a data-gathering exercise, checking a box for “involvement” then nodding along. They built genuine engagement, buy-in, and empowerment into the process itself. One founder put it simply: it worked because they grounded the strategy in culture, and let employees drive the change.
by Robyn Bolton | Aug 4, 2026 | AI, Leadership
“Try AI. It will make you more efficient,” every executive at least once in the past three months.
And it always makes me laugh.
Yes, AI will make save you time and effort. Eventually. But not on the timeline you, or your boss, is comfortable with.
A story that proves the rule
A few days ago, I spent 4 hours building a single AI tool for one research task.
Some context: I use AI Daily and have built prompts, tools and agents to streamline regular tasks. The idea came from a Whop site that I use regularly, which outlined the specific tools, prompts, and steps required to successfully build an AEO (answer engine optimization) scanning tool.
That’s why I only blocked four hours for the build.
To build the tool, I created new accounts on four different websites, worked in Terminal, Claude Cowork, and Claude Code, and referred to instructions from both the originating website and Claude.
If I had a boss or an IT department, neither would be happy with me.
Why? After all, I built a tool for a task that was too complicated and time-consuming to do previously, will run automatically every week, recommends practical fixes, and measures impact against meaningful business metrics.
I’ve also had bosses that, if I told them I spent 10% of my week on this, would say, “that’s nice but where do we stand on (fill in the blank).”
The cost of efficiency
“Lean is the enemy of learning,” according to MIT professor, Ben Armstrong. That’s as true for AI in the office as it is on the manufacturing floor.
Learning is inherently inefficient. Baked into the experience are user mistakes, unexpected outcomes, and dead ends. But those mistakes, outcomes, and dead ends generate the insights required to increase the odds the next attempt will succeed.
As Thomas Edison said, “I have not failed. I’ve just found 10,000 ways that don’t work.”
When we do ultimately succeed, we almost immediately forget time, money, and effort the learning cost us. But forgetting is what makes harder to keep learning. And it results in nonsense like, “try AI. It will make you more efficient.”
The value of waste
Next time you’re tempted to say, “try AI,” stop and ask yourself these five questions:
- “Why am I saying this?” Do you really believe that AI is a solution to the problem you’re hearing or are you just saying it because the company is pushing AI? If it’s the latter, just provide a solution to the problem. If it’s the former, keep reading.
- “What does ‘efficiency’ look like?” As with all experiments, define success first. Do you expect time to completion to be cut in half? Or for it to take just as long, with fewer people? Or maybe it simply costs less. Without a goal, AI is just a toy.
- “How long am I willing to wait for efficiency?” Efficiency doesn’t magically appear the moment a prompt or tool spits out a response. Are you willing to dedicate an hour a week, even if it takes six months to be efficient. Or is success expected in a day, no matter how many hours?
- “Am I willing to pay the cost of learning?” The costs of learning go beyond trainings and tools. It’s the opportunity cost of time spent on another project, calls to customers, conversations with consumers, engagement in meetings. If you’re not willing to pay all those costs, don’t encourage people to “try AI.”
- “How will I reward and spread this learning?” Your “learning waste” can create value for your organization. But only if you reward the people who did the work and spread the learning beyond your team, enabling people to build on what’s known with less “waste.”
“Try AI” is a shortcut to avoid the hard and inefficient work of learning. But paying the cost is the only way to earn the efficiency.
by Robyn Bolton | Jul 21, 2026 | Leadership, Leading Through Uncertainty, Stories & Examples
“Disruption [is] driven by the pursuit of profit. That’s the causal mechanism for these things…”
Clayton Christensen at the 2011 Gartner Symposium ITExpo
When I told a client that peak profit was one of the signs that they were about to be disrupted, his jaw fell open. He didn’t believe me because, like any businessperson, achieving record profit is THE reason to celebrate. His company had just doubled revenue in the past five years and was positioned to double again in the next five. AND they supply mission-critical systems to build out data centers.
Business literally could not be better.
Which is exactly what the CEOs of Big Steel thought in 1968.
It wasn’t too big to fail.
“US Steel posted record profit margins in the years prior to unseating by the minimills; in many ways it was blind to its disruption.”
Clayton Christensen in HBR
Since the mid 1850s, steel was produced in integrated steel mills that performed every function required to produce the material that was building America. The costs to build a mill were high, about $8B in today’s dollars, and, to operate efficiently, mills ran 24/7 to produce at least 2M tons of steel per year.
In 1968, a metallurgist at Nucor invented something called the minimill. It could only perform half of the functions of an integrated mill and produced only rebar, the lowest quality of steel. But the minimill cost only $6M and could be profitable at just 50,000 tons of production.
Christensen called the minimill “not good enough.” He was being nice. The minimill was a joke.
Rebar was a joke, too. At just 4% of the steel market, it had the lowest gross margin of any type of steel. Ceding it to minimills freed up integrated mill capacity to produce more high profit steel. By 1977, Nucor was the leading manufacturer of rebar.
It had also spent 7 years improving the minimill.
The pattern continued:
- 1984: Big steel cedes the angle iron, bars, and rods to Nucor
- 1989: Bethlehem Steel’s market value jumps to $2.4B, from $175M just 3 years earlier
- 1993: Minimills directly compete with integrated mills in all segments of the market.
- 1995: Bethlehem Steel’s primary plant ceases operations
- 2001: Bethlehem Steel files for Chapter 11
- 2003: Minimills production exceeds integrated mills while Bethlehem Steel ceases to exist.
By 2017, only 9 integrated mills were still operating in the US, compared to 111 active minimills. The disruption took 35 years to play out.
You don’t have 35 years
The steel industry isn’t the only example:
| Company |
Time to Disruption |
Peak |
Disruption |
Disruptor |
| Sears |
30 years |
1969: World’s largest retailer |
1999: Removed from Dow Jones Industrial Average |
Walmart, Kmart, Target, Amazon |
| Kodak |
16 years |
1996: Record $16B revenue |
2012: Filed for Chapter 11 bankruptcy protection |
Digital photography |
| Blockbuster |
6 years |
2004: Record revenue: $6B |
2010: Filed for Chapter 11 bankruptcy protection |
Redbox, Netflix |
| Nokia |
7 years |
2007: Record Net Profit $51B, 40% of global handset market |
2014: Handset business sold to Microsoft for $7.2B |
iPhone, Android |
| Intel |
3 years |
2021: Record revenue $79B |
2024: Worst ever stock year as price goes below $18/share |
TSMC, Nvidia |
It’s happening right now. Are you seeing it?
“Financial results measure how healthy the business was, not how healthy the business is. Financial results are a particularly bad tool to manage disruption, because moving up-market feels good financially.”
Clayton Christensen and Michael E. Raynor, The Innovator’s Solution
Executives and shareholders may feel good right now because, despite supply chain disruptions and high interest rates, earnings are buoyed by “margin expansion” and “revenue beats.” AI feels like an opportunity, not a threat. And there’s no reason to believe that tomorrow’s results will be worse than today’s numbers.
It’s exactly how the CEOs of Big Steel felt in 1968.
You still have time to find the joke.
by Robyn Bolton | Jun 23, 2026 | Leadership, Leading Through Uncertainty, Tips, Tricks, & Tools
For eight days, the Tartan Army filled Boston’s streets with kilts, bagpipes, and the constant refrain of “No Scotland. No Party.” Bars ran out of beer, traffic cones adorned statues, and resident’s souls were healed.
Now, some are saying corporate managers should have the same effect on the people around them (presumably without consuming all the beer in the office).
The possibility of collective effervescence
Collective effervescence is everywhere right now: in New York at the Knicks’ championship parade, the Tarps Off shirtless section at baseball games, at every unexpected draw or win at the World Cup.
It’s the “emotional electricity or excitement that lifts people outside of themselves and makes them feel like they’re connecting to something transcendent,” explains Christina Simko, and associate professor of sociology at William College. “They (members of a crowd) have to have a common focus and a common mood, and through that physical interaction, they generate something … greater than the sum of its parts.”
Greater than the sum of its parts.
Where have a I heard that before?
Could it be in every press release announcing an acquisition, all-hands meeting kicking of a transformation, and email confirming a re-org?
Which explains why I’m reading about the need for executives to create collective effervescence to ensure the success of transformational initiatives.
Seventy percent of transformations fail and one of the leading causes of failure is insufficiently high aspirations. Collective effervescence is sufficiently high but setting that as a metric of success will only drive up the failure rate.
The probability of emotional contagion
Emotional contagion is also everywhere: in the laugh that spreads through a room, the frown that moves around a conference table, the yawns that can’t be suppressed in meetings.
It’s the “phenomenon in which a person unconsciously mirrors or mimics the emotions of those around them” through nonverbal, conversational, or behavioral cues. It can be positive, like smiles and laughs, or negative like frowns or the tension from a tough conversation.
That’s good news for executives.
Leaders are “emotional amplifiers” because team members are more likely to mirror the leader’s tone than their peers. Research out of USC also indicates that, historically, positive emotions are more contagious than negative ones.
It’s also bad news for executives.
The emotional amplifier role cuts both ways and research shows that people tend to “overperceive” negative cues from leaders, even magnifying small emotional cues well beyond what a leader intended.
That means the frown everyone on the company-wide Zoom was most likely interpreted as disagreement, even opposition, to what was being discussed. And not that your shoes are too tight.
The reality of leading humans through change
Leading people through change is hard. It’s even harder when you’re under a microscope and every smile, frown, sigh, cough, and eye roll is scrutinized and interpreted as if it were a secret code foretelling the future of thousands.
It’s not. But your team believes it is.
And perception is reality.
Here’s how to start shaping reality to make the changes happen:
- Start with self-awareness. What is your mood right now? If it’s useful to the team, spend time with them. If it’s not, reschedule the meeting or send a proxy.
- Make direct eye contact with people. According to the research, eye contact during verbal communication activates brain regions that help us understand what someone is saying and what they mean. Just don’t stare. That’s creepy.
- Neutralize the negativity publicly. A bit of skepticism can be healthy for teams going through change but too much easily crosses over into pessimism and even hostility that spreads throughout the team. So stop the spread by publicly and patiently calling out the behavior and seeking to understand the root cause.
You don’t need collective effervescence to successfully lead change.
You do need spread the belief that change is possible and beneficial.
And you can do that without wearing a kilt.
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.
