by Robyn Bolton | Sep 23, 2026 | Leadership, Strategy
“Happy New Year!”
Every July 1, this is how one of my P&G colleagues greeted me as I walked into the office. We’d spent the past three months writing the strategic plan. On July 1, the start of the new fiscal, we finally got to start doing everything we had been planning.
That list of activities survived about as long as the average resolution.
- End of Week 1, 23% were “on hold” or canceled
- End of July, about 50% of the plan was changed or abandoned
- End of August, 80% of it was irrelevant because of “new strategic priorities.”
And this was in the late 1990s when things were measured in months and quarters.
If it’s an event, it’s a waste of time
In the 1990s, change was largely linear, so a linear strategic planning process that ran consecutively with business planning not only made sense, but it also worked. Today, the pace of change is exponential, which means that linear, step-by-step processes no longer work. As Dave Chappelle said, “Modern problems require modern solutions.”
Unfortunately, companies are struggling to create modern solutions for strategic planning. In research conducted using the Cascade Maturity Assessment, most respondents stated that their company’s cadence of strategic meetings and updates is somewhat or completely ineffective.
Many of the executives I’ve spoken with are nervous about switching from a calendar-based annual planning process to something that’s more ongoing. After all, they explain, “strategic planning” is a huge “time suck” for the organization and distracts from the “real work” of running the business.
Except that strategic planning is an essential part of running the business.
If it’s a habit, it happens.
“We’ve built muscle and improved how we approach strategy…doing this repeatedly over the last few years.” – Director at a $10B+ revenue corporation with 10-50k employees (one of the top two scorers in the research)
If strategy is to be an automatic, ongoing, almost intuitive part of running a business, it needs to become a habit. Luckily, the same things that build personal habits – learning, repetition, sensory cues, goal pursuit – also build business habits.
SparkCraft Strategies (who did not work with the executive quoted above) helps organizations build both their strategies and their habits. MileZero and SparkCraft often partner on this type of work and, for over a year, SparkCraft has been working with a client to develop the organization’s strategic planning process and capability.
Defining the process was the “easy” part (not easy, just easy relative to everything else). The hard part is building tools that drive actions and decisions that require the critical thinking and creative problem solving necessary to be strategic. Over the course of a year (or more), SparkCraft works with the client to build a strategic thinking and planning habit, ensuring that strategy is inextricably linked with operations, not just bolted on.
If it’s the culture, it’s the gold standard
“It has worked because we grounded it (strategy) in culture and employees are growing and driving the change” – CEO of a $1-50M startup (the other top scoring company from the research)
Culture is the result of the values and tools an organization consistently uses. Culture, like habit, is implicit, more sensed than spoken. Unlike a habit, it’s shared, pervasive, and enduring. That means that (most) everyone senses, thinks about, talks about, and acts on it simply because they are part of that organization.
The CEO quoted above started by making strategy a habit. Monthly, the leadership team discussed, debated, and updated it. Quarterly, all-hands meetings shared it and invited questions, feedback, and dissent. And performance reviews and incentive plans made it part of how people were measured and paid. Over time, through consistent, repeated, and reinforced activity, strategy became part of the culture and the identity of the company. It is who they are and what they do.
Strategy only works when it is part of the work, repeated until it is who you are.
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 12, 2026 | Leadership, Strategy
The is the third article exploring the strategy-execution gap. You can read the first and seond ones by clicking the links.
“He who is silent is taken to agree” – Latin proverb
“Speak now or forever hold your peace.” – The Book of Common Prayer
“My level of silence is often mistaken for agreement. It’s the caffeine deciding if this conversation is worth the effort.” – coffee mug
Every manager and executive says they agree with the strategy and its goals. And they mean it.
It’s what they’re NOT saying that makes all the difference.
“I know what you want me to do but how do you expect me to do it?”
This isn’t a plea or request for micro-management. After all, two-thirds of Directors have access to a centralized system for tracking performance metrics and KPIs.
But knowing what is expected and delivering it are two different things. Less than one-third of respondents are prepared for change (including only 13% of C-Suite execs!) and not a single VP, Director, or Manager has the resources to execute and deliver their goals.
“Actions speak louder than words, and we’re speaking two different languages.”
Every single survey respondent said their organization has well-defined company values. But only 50% of VPs and 33% of Directors see those values reflected in their colleagues’ behaviors.
“If you want the team to deliver X, why are you rewarding us for different things unrelated to X?”
Fifty percent of VPs and two-thirds of directors have clear functional or team plans with explicit KPIs. What nearly 60% don’t have are functional plans aligned with the organization’s goals and clear ownership for delivering SMART objectives.
When functional strategies don’t tie to organizational ones, it’s no surprise that only 25% of the C-Suite, 15% of VPs, and 0% of Directors and Managers see cross-functional alignment on execution.
Resistance rarely looks like rebellion
“Change is always met with resistance,” explained one Manager.
Usually, resistance looks reasonable. A request for “one more set of eyes.” A call to one more person. One more run through the committee to make sure everyone’s comfortable.
In fact, most people don’t even know they’re resisting change. They’re simply following rules and processes set up years before this year’s strategy existed. And while it slows strategic execution, isn’t it worth it to keep the company safe?
This type of resistance is solvable. Change a process, introduce an incentive, “flatten the org.”
But that’s not the resistance the data shows. That kind is silent and deadly.
You must ask for what they won’t say
Speaking up to say the strategy won’t work or the goal can’t be achieved costs a relationship, a reputation, maybe a promotion. So, your team stays silent, and you see it as agreement.
But that silence is preventing you from getting the information and perspective you need to build a strategy that can succeed because people genuinely agree and are able to execute it.
It’s not enough to ask people to speak up or play devil’s advocate. You must eliminate the cost of doing so:
Go first. Call out the weakest part of your own plan before you ask them to poke holes in it. Every company claims humility and candor as a value, yet half your VPs and two-thirds of your directors don’t see it.
Ask for how, not yes. “Are you with me?” gets silent nods. “What would have to be true for this to work in your group?” draws out the constraints they keep to themselves.
Reward the challenge. If incentives still reward last year’s behaviors and goals, you’ll never get execution of this year’s strategy. And while updating incentives is a start, you won’t hear the hard truth until people have incentives to speak it.
Your team already knows how the strategy will fail. Ask them to tell you. Then fix it together.
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 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.
Why do VPs agree with a strategy but still can't execute it?
The VPs surveyed gave input on the strategy and agree with it. What stalls execution is authority. They can’t get it resourced. One VP said it plainly: priorities tend to shift and are often vague or confusing, and resources, people, systems, and processes are severely lacking.
Why do strategic plans keep failing even when everyone agrees with them?
Often it isn’t the plan. One VP watched her company’s OKRs get scrapped eight months in when new leadership arrived and decided to abandon them. VPs believe in the strategy as much as the C-suite does. Plans fail when a leadership change wipes out the work before it gets resourced, not because the strategy was wrong.
Is there a framework for diagnosing why a good decision never gets implemented?
Use Cascade’s Maturity Assessment to score your company on five pillars: Focus, Alignment, Visibility, Accountability, and Speed. Most agree on Focus, two thirds of VPs and the C-suite say they can name their priorities. The other four pillars are where decisions actually die. Cascade’s Strategic Maturity Assessment found VPs rate Alignment, Visibility, Accountability, and Speed lower than the C-suite rates them, on every single one.
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 | Jun 3, 2026 | Leadership, Strategy
“How much did your last 1,000 long-distance calls cost you?”
Juan Enríquez Cabot, Mexican-American academic, businessman, author, and speaker.
Strategy requires making choices. It’s an exercise in trade-offs. It requires prioritizing one thing over another and saying “no” to more things than you say “yes.”
The same is true for life. It also requires making choices, setting priorities, saying “no,” and making trade-offs.
But what happens when you no longer need to make trade-offs?
That’s one of the questions that Juan Enriquez, best-selling author and TED All-Star, posed during his speech “An Uncertain, Scary, Exciting Future.” To illustrate his point, he took us back to the late 20th century when we used to pay for long-distance calls. In the 1970s, long-distance (state-to-state) calls cost a minimum of $3.50 per minute (in 2020 dollars). In the 1980s as industry competition increased, phone companies started offering discounted rates for evening and late-night calls.
I remember my mom talking to my grandma in Pennsylvania for an hour each week and my grandma in California for two hours each month. Assuming those were the only interstate calls made (they weren’t), at a discounted rate of $1.25/minute, those five calls cost $450 in 2020 dollars.
That’s more than 3x what I currently pay for unlimited calls and text.
We used to trade off money, frequency, convenience, and quality simply to stay in touch with family and friends. Now we don’t.
But we’re still making trade-offs.
There are ALWAYS trade-offs
No one likes trade-offs. We’d much rather have everything than just one thing. After all, if you have (or do) everything then when things change, you’re prepared. You’re safe.
But “all of the above” is not an option.
My mom would have been stuck on the phone for hours every day talking to my grandmas if long-distance calls were free. But, because we couldn’t afford the financial trade-off required for daily multi-hour, long-distance calls, my mom was free to live her life untethered from the kitchen phone.
Now, the financial and physical trade-offs of long-distance calls have gone away but we’re still tethered to our phones. Instead, we’re trading away our attention and energy, data and privacy, even our mental well-being for the “convenience” of always being connected and accessible.
What trade-offs are you making (because you ARE making them)?
Look at your business strategy, your team, your daily calendar. What are you trading off? What will you stop doing so that you can invest more in starting or accelerating something else?
If you’re like most executives, you can’t answer those two questions because you choose “all of the above.”
But you did make trade-offs. You’re trading off time spent with friends and family and your physical and mental well-being to do more with less. You’re trading off your business’ future to maximize today’s profits.
There are always trade-offs. The ones you proactively and consciously choose are always better than the ones that creep up on you, promising “all of the above” while taking the things you’d never knowingly give up.
by Robyn Bolton | May 5, 2026 | Leadership, Leading Through Uncertainty, Stories & Examples, Strategy
Sunday morning, my phone blew up. Thirty-three text messages. Most mornings, I have zero, so my first thought was “who died?”
The texts were about a death. Sort of.
Sloan Management Review died (ceased publication) and a group chat filled with academics, thought leaders, and consultants were having an absolute meltdown.
Knowing that my husband, an actual Sloan graduate, hadn’t yet seen the news, I broke it to him gently. “Okay,” he shrugged, not even glancing up from his phone.
This was in stark contrast to his reactions to the demise of Spirit Airlines (howling with laughter at the memes) and the resurrection of Allbirds as an AI company (thoughtful and incredibly technical analysis).
Lesson 1: The Race to the Bottom Never Ends Well
CNN’s headline said it all, “Why did Spirit fail? Too many passengers hated flying it.” To prove the point, the article opens,
“Lousy service, not the Iran war, killed Spirit Airlines. Spirit was doomed to fail because of mismanagement, deep financial problems, and – crucially – its reputation for poor customer service. The spike in jet fuel prices during the war just accelerated Spirit’s inevitable demise.”
If that can be written about your business, you don’t deserve to be in business.
It’s only a matter of time until you’re not.
Lesson 2: Be Patient for Growth and Impatient for Profit
Allbirds raised $348 million when it IPOed in 2021 and, at one point, was valued at $4.1 billion despite never turning a profit. Six years later, its stock price had fallen 95% and it sold its business and IP to a brand management company for $39 million.
How did this happen? There are plenty of theories – it expanded too aggressively into bricks and mortar retail, it made ugly shoes but operated like a fashion brand, its Tech Bro image is no longer aspirational for Gen Z customers – but the fact is that it prioritized growth over profit and that ultimately bit them in the balance sheet.
Lesson 3: Some Businesses are Butterflies
While my colleagues’ alarm was understandable, it missed the bigger picture.
Sloan Management Review (SMR) didn’t die. It metamorphosed.
Yes, the SMR brand is going away, but future ideas, research and findings will continue to be shared through digital newsletters, short-form videos, podcasts, and social-first content.
In effect, SMR is metamorphosing to better reflect how its subscribers consume information. Busy executives don’t have the time to read long-form, dense research articles. They grab information in snippets and soundbites. This change ensures the people who need the ideas the most get them.
3 Questions to Find Your Fate
- Do you treat your customers like they exist for your benefit? In other words, are you more focused on value extraction than value creation and delivery? If yes, start planning your business’ funeral and don’t expect anyone to attend.
- Do you have a financially and operationally sustainable business model? If no, start planning your funeral but take comfort in the fact that people will attend and may even say nice things about you.
- Do you know the unique, relevant, valuable, and hard to imitate reason why you exist? Can you articulate the rare and essential Job to be Done you do for your customers? If no, you’re on life support. When you can answer yes, you’ll be ready to be a butterfly.
One quick caveat
When businesses die, people lose their jobs and that is incredibly tragic. The psychological, financial, and relational impacts of job loss are tremendous, impacting people far beyond the individual laid off. It can take months, even years for people and families to recover and, for some, it never happens.
Creative destruction is real and necessary for long-term economic, technological, and societal growth. But the short-term impact has human consequences that should never be ignored.
