Flying the Plane While Building It?

Linda Carlisle • September 30, 2026

Why It May Be Time for a Better Metaphor for Organizational Transformation

Over the years, I've heard countless leaders describe organizational transformation as "flying the plane while building it."



It has become one of the most recognizable metaphors in business. Whether an organization is integrating an acquisition, implementing new technology, navigating a leadership transition, restructuring operations, or pursuing an ambitious growth strategy, the phrase inevitably surfaces. It captures an undeniable reality: organizations rarely have the luxury of stopping while they evolve. Customers still expect excellent service. Products still need to ship. Quarterly targets don't pause simply because a transformation is underway.

For a long time, I accepted the metaphor without giving it much thought.


Today, I'm no longer convinced it's serving leaders -- or their organizations -- as well as we think.

Not because it's inaccurate. In many respects, it reflects the operational complexity of leading change.


But because metaphors do more than describe reality...they shape it.

The language leaders choose influences how employees interpret uncertainty, competence, risk, and ultimately, trust. Over time, I've come to believe that the phrase "flying the plane while building it" unintentionally normalizes a leadership mindset that is inconsistent with successful transformation.

Imagine hearing that phrase not as an executive discussing strategy, but as an employee trying to make sense of another major organizational change. Or better yet, imagine hearing it as a passenger boarding a commercial flight!


The image is unsettling because it suggests an unfinished aircraft, unnecessary risk, and a crew making critical decisions after takeoff rather than before it. Even when leaders use the metaphor casually, employees may hear something entirely different:


 "We're making this up as we go."


That isn't the message most leaders intend to send. Unfortunately, intention and interpretation are rarely the same thing.


Leadership's Challenge Isn't Navigating Change. It's Building Confidence.


One of the greatest misconceptions about transformation is that organizations fail because people resist change.


In my experience, resistance is rarely the root cause.


People are remarkably adaptable. They learn new technologies, adopt new processes, embrace new leaders, and navigate mergers, restructures, and strategic pivots every day. Most employees understand that change is part of organizational life. What they struggle with is uncertainty and risk that appears avoidable.


When leaders communicate conflicting priorities, managers lack the information they need to answer basic questions, or decisions seem to change without explanation, employees begin to wonder whether anyone is truly steering the organization with confidence. It isn't the presence of change that erodes trust. It's the perception that the organization is creating uncertainty it could have prevented.


Successful transformation has never been about eliminating uncertainty altogether. Markets shift.


Competitors respond. Technology evolves. Unexpected obstacles emerge. Those realities are part of doing business.


The responsibility of leadership isn't to eliminate these uncertainties entirely. It is to eliminate the unnecessary uncertainties.


Great leaders don't ask employees to tolerate unnecessary uncertainty....They reduce it.

They reduce it through thoughtful preparation, consistent communication, visible leadership, disciplined execution, and a willingness to address confusion before it becomes frustration. They help people understand not only what is changing, but why it matters, what success looks like, and the role each individual plays in creating that future.


That distinction changes everything.


Five Warning Lights Leaders Should Never Ignore

Confidence rarely disappears overnight.


Instead, it erodes gradually through a series of warning lights that leaders often overlook while focusing on project plans, budgets, governance, and implementation milestones.


The first warning light is leadership misalignment. Employees can tolerate uncertainty; what they struggle to tolerate is inconsistency. When leaders communicate different priorities, offer conflicting interpretations, or answer similar questions in different ways, employees begin questioning whether leadership is truly united.


The second warning light is cumulative change. Organizations divide transformation into work streams because that's how projects are managed. Employees experience something entirely different. Every initiative competes for the same managerial attention, subject matter expertise, and employee capacity. Individually, each request appears reasonable. Collectively, they become exhausting.


The third warning light appears when communication becomes one-directional. Most organizations invest heavily in explaining change. Far fewer invest the same discipline in listening. Without meaningful feedback loops, leaders lose visibility into confusion, resistance, misinformation, and emerging risks long before they appear on a dashboard.


The fourth warning light is mistaking project readiness for workforce readiness. Technology can be tested. Budgets can be approved. Governance can be established. None of those milestones guarantee that managers are prepared to lead or that employees understand what is expected of them.


The fifth warning light is declining trust. During periods of transformation, trust becomes one of the organization's most valuable assets. Once employees begin questioning leadership's competence, consistency, or credibility, every subsequent initiative becomes more difficult than the last.

These warning lights rarely appear in isolation...they compound.


Misalignment creates confusion, confusion increases anxiety, anxiety erodes trust, and diminished trust slows adoption. What leaders often interpret as resistance is frequently the cumulative effect of uncertainty that has been allowed to build over time.


Reducing Unnecessary Uncertainty

If reducing unnecessary uncertainty is one of leadership's most important responsibilities, then transformation requires far more than effective project management.


It requires leadership disciplines that intentionally build confidence.


Those disciplines begin with aligning leaders before communicating broadly so employees hear one coherent message rather than several competing interpretations. They continue with explaining the purpose behind change instead of focusing exclusively on timelines, helping people understand why the journey matters as much as where it leads.


They require leaders to think beyond individual initiatives and consider the cumulative experience of employees, recognizing that people rarely experience transformation one project at a time. They require investing in managers before expecting them to lead others, because managers remain the organization's most influential communicators during periods of uncertainty.


They also require listening with the same discipline used to communicate. Pulse surveys, focus groups, skip-level conversations, and manager feedback aren't simply engagement activities; they're early-warning systems that surface confusion while leaders still have time to respond.


Finally, they require measuring workforce readiness alongside project readiness. Organizations do not transform because a project plan reaches completion. They transform because people choose to adopt new ways of working. Technology, process, and governance make change possible. People make it successful.


Taken together, these leadership disciplines reduce unnecessary uncertainty while creating the conditions that allow organizational resilience to grow.


A Better Metaphor

If metaphors influence leadership thinking, then perhaps it's time to choose one that reinforces the behaviors successful transformation actually requires.


Rather than asking employees to imagine boarding an unfinished airplane, I'd invite leaders to picture a mountain expedition.


Every successful expedition begins long before the first step is taken. The destination is clear. The route has been studied. Equipment has been tested. The team has trained together. Experienced guides understand both the terrain ahead and the capabilities of the people making the journey.


Then reality intervenes.

 ...Weather changes.

 ...Conditions deteriorate.

 ...Progress slows.

 ...Some climbers require more time to acclimate.

 ...The route may need to adjust.


These realities don't suggest poor leadership, but they do represent predictable uncertainties that leaders should prepare their team to face.


Great expedition leaders don't pretend they can eliminate uncertainty. They prepare people to navigate it. They communicate constantly, monitor conditions, adjust the pace when necessary, and make decisions that keep the team moving toward the summit without losing sight of the people making the climb.


The difference between these two metaphors is more than literary. They reinforce two fundamentally different philosophies of leadership.



The role of leadership during transformation isn't to promise a smooth journey.


 ...Markets will shift.

 ...Technology will evolve.

 ...Unexpected obstacles will emerge.


The future has always contained uncertainty, and it always will.


The responsibility of leadership is something different.

It is to reduce the uncertainty that can be reduced, prepare people for the uncertainty that cannot, and create the conditions that allow individuals and teams to succeed despite it.


For that reason, I believe it's time to retire the phrase "flying the plane while building it."


Not because transformation has become easier. But because the metaphor normalizes a leadership mindset that is inconsistent with successful transformation.


The mountain expedition offers a better model. It reminds us that great leaders prepare thoroughly, communicate honestly, adapt thoughtfully, paint a picture of what success looks like, support one another, and continue moving toward the summit together. Most importantly, it reinforces the kind of leadership organizations need when the path ahead is demanding but the destination remains worth pursuing.


The metaphors leaders choose should reinforce the behaviors they expect across the organization -- starting with themselves.

By Linda Carlisle • September 30, 2026
In the Trust Economy, even a sound strategy can crash and burn when the tank runs dry.
By Linda Carlisle • August 31, 2026
This article in CHRO Daily explores Change Fatigue
By Linda Carlisle • August 21, 2026
When a company appears on a “Fastest-growing” list, most people see success. I see a series of leadership moments quietly approaching. Don’t get me wrong -- rapid growth is wonderful. It means customers are buying. New people are joining your ranks. Opportunities are expanding. It means your organization is doing something right. But accelerated growth changes far more than the size of the organization.  Everything from your leadership practices and communication habits to the cultural norms that helped a company succeed at 50 or 100 employees doesn’t necessarily work when you need to reach 300, 500, or 1,000 people. Yet companies often invest heavily in preparing the business for its next stage of growth – bringing in new systems, facilities, technology, financing… and even talent, while investing far less in preparing for how they will help their people navigate the changes that growth brings with them. And that's where success can unexpectedly create risk. When I think about the companies that do this right, I think of the giant redwoods. Redwoods can grow more than 90 meters tall, yet their root systems are surprisingly shallow. Rather than growing deep, their roots spread widely and intertwine with those of neighboring trees, helping these enormous trees support one another. And beneath the forest floor, those roots connect with networks of mycorrhizal fungi that enable the exchange of nutrients and information across the forest. Growing organizations need their own version of that interconnected system. As companies become larger and more complex, they need strong, adaptive communication systems and cultures that allow information to travel, people to remain connected, and the organization to respond collectively to change. The taller the organization grows, the more intentional those connections need to become. The Founder Can't Know Everyone Anymore In smaller organizations with 2 to 50 or 100 people, communication often happens through relationships built by proximity and ‘management by walking around’ (MWA). You’ve undoubtedly seen it. The founder walks through the building, stopping to greet individual employees by name. People hear what’s happening because they sit near someone who has the inside scoop. New employees learn about the culture by observing the people on their team. In the startup and early growth stages, there may not be much of a formal communication infrastructure in the business, because the company doesn’t need one. Then the company grows. Suddenly, the founder can’t talk to everyone. In addition to the greater demands that face the leader of a high-growth company, there may also be multiple locations, functions or shifts. New employees may never even meet the people who established the company’s earliest traditions. Decisions move through several layers of leadership before reaching the people expected to execute them. Consider a 75-person manufacturer that grows to 300 employees and opens a second facility. Employees at the original plant still hear news directly from leaders they know, while employees at the new location depend on supervisors and word of mouth. Without intending to, the company has created two very different communication experiences. The organization has crossed an important threshold: It can no longer rely primarily on relationships to keep people connected. It needs systems. Establishing and implementing communication systems and protocols, and documenting cultural norms, doesn’t mean replacing human connection with corporate bureaucracy. It simply means intentionally creating communication channels, leadership practices, and cultural mechanisms that allow information to keep flowing, transparency and inclusion to continue, and critical connections to survive as the organization becomes more complex. The Middle Management Gap Growth also creates another challenge: more managers -- many of whom are promoted because they were exceptional individual contributors. They know the business, understand the customers – and they get results. But suddenly, their job isn't simply to perform the work. As managers, they’re expected to explain strategy and translate leadership decisions into meaningful guidance for their functional team. Whereas they were once accountable for doing their own work exceptionally well, they are now expected to coach other employees and help them succeed – both professionally and inter-personally. They are now responsible for helping their teams navigate uncertainty, interpret cultural norms, and handle difficult conversations. In other words, they become one of the organization’s most important communication channels. Yet few companies intentionally prepare them for that role…and this is where communication often begins to fracture. Managers are also expected to answer questions they may never have anticipated being asked -- sometimes questions leadership hasn’t fully answered for them. Without talking points, FAQs, or a clear feedback loop for unanswered questions, managers are left to punt, avoid the question, or offer their “best guess.” That’s how inconsistent messages -- and rumors -- begin. Imagine a company where the CEO has just announced a new growth strategy at the town hall and assume managers will carry the message forward to their teams. Despite there being no detailed talking points, FAQ documents, or other tools to explain how the strategy will impact each individual business function, one manager soldiers through to explain what it means for the team; another forwards the slides the CEO used in the town hall; a third admits, “I’m not really sure what this means for us.” One announcement has suddenly become three different employee experiences. Senior leaders believe they’ve communicated something because they announced it. Managers interpret it differently. Employees hear different versions depending on which manager they report to. And a message that seemed perfectly clear in the executive meeting becomes increasingly distorted as it travels through the organization. In the absence of communications infrastructure (email, newsletter, intranet, Slack/Teams, regular town halls, etc.), growth makes effective manager communication capability a business requirement. Manager cascade is essential -- but consistently excellent manager cascade is also notoriously difficult to achieve without dedicated support focused on developing communications tools that enable managers to be effective and stay aligned as they announce strategic initiatives. Culture Stops Happening Naturally Culture changes as organizations scale. At 50 employees, culture spreads largely through proximity. People watch how the founder behaves. They learn which behaviors get rewarded. Stories travel quickly. Informal norms are reinforced every day. But at 400 employees, culture can’t depend on proximity. It must spread deliberately, by design. Leaders must become much more deliberate about defining the behaviors that matter to the company’s future success and describing what those behaviors look like in practice. Then they must reinforce them through managers, employee experience, communications, leadership modeling, and recognition. Otherwise, something else happens: Every department, location, or leader begins creating its own version of the culture. That’s how organizations wake up one day and realize the company they built no longer feels like the company they remember. Imagine a company that has doubled its workforce in 18 months, and added a 2nd shift. Half the employees learned “how we do things here” by working alongside the founders and early leaders; the other half joined after that proximity disappeared. Unless the culture has been made explicit, those two groups may be working from very different definitions of what the company values. Culture didn’t disappear. It drifted and decentralized. That’s why I often talk about building Culture by Design...Not by Default. Growth doesn’t make culture less important, but it does make leaving culture to chance much riskier. Today's Growth Often Creates Tomorrow's Moment That Matters™ Fast-growing companies also frequently sustain their momentum through other major transitions. • Private equity investment. • An acquisition. • International expansion. • A new facility. • Founder retirement. • Second-generation leadership. • An outside CEO. • A significant technology implementation. None of these transitions indicate that something has gone wrong…Quite the opposite. In fact, they often occur precisely because the company has been successful. But each one introduces another layer of organizational complexity -- and another test of whether the company’s leadership, communication, and culture infrastructure have grown alongside the business. The best time to focus on building these capabilities isn’t after the next major transition has already begun. It's before you need them. Consider a company receiving a significant capital infusion to acquire a competitor, build a new facility or dramatically expand production. The financial investment may solve the capacity problem, but it doesn't automatically create leadership alignment, strong communications discipline and practices, manager readiness, employee engagement or a unified culture. Those capabilities have to be built, too. And sophisticated growth planning should anticipate those needs before the capital is deployed…not discover them after execution begins. When Communication Becomes a Strategic Capability Eventually, growing organizations reach a point where communication can no longer be something “the leaders do” by walking around and chatting with people, or having more an more meetings. As organizations grow, “we all communicate” is no longer a communications strategy. The organization needs a disciplined approach for understanding what people need to know, which initiatives require coordinated communication, who needs to hear what and when, and which channels and messengers are best suited to the audience and the moment. • Leadership alignment before major announcements. • Manager toolkits that help supervisors translate strategy for their teams. • Internal communication channels that reliably reach employees across locations and functions. • Listening mechanisms that help leaders understand what employees are experiencing. • More intentional onboarding. • A stronger employer brand. • Greater executive visibility. • Clearer connections between business strategy and employees’ everyday work. These communications capabilities are not critical because communication suddenly becomes important. They become more essential as the organization becomes more complex. Because complexity creates distance. Distance between leaders and employees. Between strategy and execution. Between the culture leadership believes exists and the culture employees experience. A company can open its new facility on schedule and still struggle operationally if employees don’t understand why the company is expanding, what the change means for them, how the two locations will work together, or which cultural norms must remain consistent. The building may be ready for business before the organization is ready to operate as one company. And strategic organizational communication capabilities close these gaps in understanding. Growth Itself Is a Moment That Matters™ We tend to think about organizational communication challenges when something dramatic happens -- a merger, restructuring, new technology or strategy, a CEO transition, or another major transformation. And yes, any organization that undergoes these major milestones without addressing gaps in its professional communication capabilities is likely to struggle. But even with that said, some of the most consequential Moments that Matter™ arrive much more quietly, and they can outgrow your organization’s existing communication capabilities and cultural infrastructure without anyone immediately recognizing what’s happening. Consider the following everyday occurrences that quietly break the company’s ability to communicate effectively: • The company adds another 100 employees. • A second location opens. • The founder can’t attend every meeting anymore. • Another layer of management appears. • People who once knew one another personally now recognize only a fraction of their colleagues. In each of these situations, nothing is wrong. In fact, the company is winning. But success itself has fundamentally changed the organization. Fast growth deserves to be celebrated. But leaders shouldn’t wait until the next major transition to strengthen the culture and communication systems that will help their organizations scale. Because companies rarely stumble simply because demand exceeded capacity and the company needed to grow. They stumble when their leadership practices, communication systems, and culture don't evolve as quickly as the business does. If leadership says, “Give us the capital and resources we need, and we’ll grow” -- and someone provides them -- leadership then has an obligation to ensure the organization can convert those resources into performance. When a business struggles after receiving the capital, equipment, technology or acquisition it said it needed to reach the next level, stakeholders are justified in asking whether leadership adequately prepared the organization to capitalize on that investment. If the resources are there but the organization still can’t execute because people aren’t aligned, managers aren’t prepared, cultures aren’t integrating, or employees aren’t engaged, the problem may no longer be resources. It may be organizational readiness. And for a PE investor, board, or other stakeholder, that’s when a communication and culture problem can begin to look like a leadership problem. So yes, prepare the business for growth. Invest in the facility, technology, acquisition, and talent that will take the company to the next level. But invest in the communication and culture infrastructure that will help your people take it there, too. Like the redwoods, extraordinary growth requires an equally strong system of connection and support. The time to build that infrastructure isn't after growth exposes the gaps. It's before. Is your firm growing faster than its communication & culture infrastructure? If growth, expansion, acquisition or another major transition is on your horizon, I’d be happy to compare notes on what your organization may need before the gaps begin to show.
By Linda Carlisle • August 20, 2026
I am SO pleased to be a part of this new Podcast Episode of FUTURE VENTURES - CLARITY AT SCALE During this episode, host Maxim and I discuss 5 Key Topics: ** Communication as organizational infrastructure ** Culture by design, not default ** Turning strategy into a story people can enter ** Communicating through Moments that Matter™ ** Listening, authenticity, and trust ...arriving at three key insights: 1) As companies grow, communication should not depend on the founder being everywhere. What worked in the beginning needs to become a simple, repeatable system that keeps things clear and avoids mixed messages. 2) Culture is expressed through repeated behaviors, not just statements on a wall. Scaling leaders need to decide which behaviors they want to keep, which need to change, and how those expectations shape everyday decisions. 3) Employees are more likely to accept change when they can see themselves in that future. Founders still need to set the direction, but clear communication helps connect that vision to people’s work, growth, and sense of belonging. Hope you enjoy listening as much as I enjoyed guesting! _________________________________________________________ FUTURE VENTURES is the podcast for founders, operators, and investors who are building companies worth owning for the long term -- and who need to think clearly about capital, structure, strategy, and growth to get there. Each episode cuts through the noise around scaling: how to structure a deal, how to position a business for institutional capital, how to build operational leverage without losing control, and how to make the high-stakes decisions that compound in value long after the moment has passed. Hosted by Maxim Atanassov, CPA-CA - a four-time founder and the Managing Partner of Future Ventures Corp. Since 2018, FVC has invested in, incubated, and scaled companies across sectors — with a focus on platform opportunities that compound in value. Maxim's background spans executive leadership inside Canada's largest energy companies and senior advisory at Deloitte and EY. He's a CPA-CA who has sat at the table where capital gets deployed, governance gets built, and hard decisions get made. Now he helps founders get there faster. https://lnkd.in/g8KStgxX
By Linda Carlisle • June 18, 2026
From charisma to credibility: navigating leadership transitions in an era of podcasts, social media, and heightened employee expectations.
By Linda Carlisle • June 10, 2026
Linda Carlisle guests with host John Pezoulas on the ReadySetExec podcast
By Linda Carlisle • May 18, 2026
Comm-ext Launches Communications Toolkit to Help Leaders Navigate Layoffs Without Damaging Trust, Culture or Performance 
Earth Day Reflection text over a sunny park scene with a parked car, trees, and a person near a tree
By Linda Carlisle • April 28, 2026
Understand the shift from childhood environmental awareness to today's climate crisis. Join us in driving impactful change.
Abstract seashell with pearl on sandy background, overlaid with quote: “Great communicators layer messages with care.”
By Linda Carlisle • April 9, 2026
Integrate strategy & culture into daily messages for a stronger employee experience. Contact us for tailored communications solutions.
By Linda Carlisle • April 9, 2026
The case that's launched a thousand questions...
Show More