Bridging the Culture Gap in the Messy Middle of Growth

Growth is exciting. It’s a sign that your company is thriving, expanding its reach, and moving toward bigger opportunities. But there’s an often-overlooked phase of growth that brings its own challenges: the awkward transition between being a small company and becoming a medium-sized one. This stage is where many organizations experience what feels like a culture vortex—a point where identity, communication, and processes start to falter under the weight of scaling up.

During this phase, the tight-knit culture that defined your small team can feel stretched to its limits. Communication becomes more complicated, decision-making slows down, and employees start to sense that the company they loved is evolving into something different. These shifts are natural, but they also create a risk of losing what made your organization special in the first place.

This messy middle, while uncomfortable, is also an opportunity. It’s a chance to redefine your company’s culture and build a stronger foundation for the next phase of growth. According to research by Harvard Business School, over 50% of U.S. companies fail within five years, with scaling challenges being a significant factor.

The Culture Vortex: What Is It?

As companies grow, they inevitably pass through a transitional phase—too large to maintain the informal, flexible structure of a small business but not yet established enough to operate like a medium-sized company. This phase is what many experience as a culture vortex, where the organization’s identity and communication begin to strain under the pressure of rapid growth.

In this phase, the challenges extend beyond operations—they are profoundly cultural. Processes that once worked seamlessly in a tight-knit team suddenly create bottlenecks. Employees accustomed to wearing multiple hats find themselves questioning roles and responsibilities as new hires bring fresh perspectives but also different expectations. Communication starts to break down, leading to silos and confusion about what’s happening across teams. Longtime employees might feel nostalgic for the “good old days,” while newer ones wonder why the organization isn’t more structured or clear.

What makes this vortex so uncomfortable is the lack of clarity. Everyone feels the change, but no one is quite sure how to address it. The business is no longer small enough for culture to evolve naturally, and it hasn’t yet built the systems and leadership needed to foster a thriving, scalable identity.

This in-between space can leave employees disengaged, frustrated, or unsure about their future with the company. Without careful attention, the culture risks becoming fragmented, eroding trust and morale. But with intention and strategy, this messy middle can also be a turning point—a chance to define who you are as a growing organization and set the tone for the next phase of your journey.

Why Culture Suffers in the Messy Middle

The messy middle magnifies the challenges that arise when a company transitions from a small, close-knit team to a more complex organization. Growth often exposes the tension between where a company started and where it needs to go, creating cultural strain.

1. Small-Company Habits Don’t Scale

In the early stages, culture evolves organically. Decisions happen quickly, and communication flows easily because everyone is closely connected. But as the organization grows, these informal systems can become a source of inefficiency. What once felt natural begins to create confusion and bottlenecks.

2. The Risk of Identity Loss

Early on, a company’s identity is shaped by shared purpose and personal relationships. Growth introduces layers of complexity, and the sense of closeness that defined the culture can start to fade. Longtime employees may feel like the company they joined is becoming unrecognizable.

3. Communication Breakdowns

As teams expand, communication becomes more difficult to manage. Information that once spread effortlessly now gets stuck in silos or fails to reach the right people. Employees may feel disconnected from leadership and unsure about the company’s direction.

4. Leadership Growing Pains

Growth also changes the role of leadership. Founders and senior leaders need to focus on strategy, which pulls them away from the day-to-day visibility they once had. This shift can leave employees feeling distanced from leadership, and leaders may struggle to adjust to their evolving responsibilities. According to SHRM, these growing pains frequently necessitate leadership training to assist managers in adapting, making leadership development essential during periods of growth. Initiatives such as #GirlsClub offer aspiring women leaders mentorship, skills training, and a supportive community, equipping them to successfully tackle these challenges.

5. Culture Clashes Between Old and New Employees

New hires bring fresh perspectives and energy, but they also bring expectations for structure and clarity. This can create friction with longtime employees who are used to the informal ways of the past. Without intentional effort, this clash can create a divide within the workforce.

These challenges are common, but they don’t have to define a company’s culture. By recognizing these growing pains and addressing them head-on, leaders can turn the messy middle into a period of cultural transformation instead of cultural loss. Furthermore, by fostering intentional, authentic relationships, communities like Legacy can help leaders bring together diverse perspectives and bridge cultural divides. 

Signs Your Company Is Stuck in the Messy Middle

Recognizing when your company is stuck in the messy middle is the first step toward making meaningful changes. This phase can feel chaotic, but there are clear warning signs that point to cultural strain:

1. Increased Employee Turnover

When the culture starts to feel fractured, employees are often the first to notice. High turnover—especially among longtime employees—can signal dissatisfaction with the changes growth is bringing, and SHRM research shows that 20% of employees leave their roles due to cultural misalignment.

2. Role Confusion and Lack of Accountability

In the early days, people wore many hats, and responsibilities were fluid. As the company grows, this lack of clarity can lead to inefficiencies, missed deadlines, and frustration. Employees may find themselves unsure of who is responsible for what or how decisions are made.

3. Communication Silos

Teams that used to collaborate effortlessly might now operate in isolation. If employees are frequently left out of key updates or unaware of decisions happening in other parts of the company, it’s a sign that communication channels need to evolve.

4. A Divided Workforce

When there’s a noticeable divide between “old guard” employees who resist change and newer hires who struggle to adapt to the lack of structure, tension can build. This division can erode trust and collaboration.

5. Declining Morale

Subtle changes in morale, like reduced enthusiasm for company initiatives or a drop in participation at events, are often indicators of cultural disconnection. Employees may feel less engaged, less motivated, and more uncertain about the company’s future.

6. Decision-Making Bottlenecks

As leadership adjusts to managing a larger organization, decisions can become slower and less transparent. This creates frustration across the team and can make it harder to maintain momentum.

7. Nostalgia for “The Way Things Were”

If conversations often circle back to how things used to be, it’s a sign that your team is struggling to align with the company’s current identity. Nostalgia can be a red flag that employees don’t feel connected to the culture as it evolves.

Strategies for Bridging the Gap

The messy middle brings challenges, but it also offers the chance to shape your company’s culture in meaningful ways.

1. Revisit and Reinforce Core Values

Your company’s values are the foundation of its culture, but as the organization grows, they can fade into the background. Take time to revisit your core values to ensure they still resonate with your team and align with the company’s future direction. Use these values as a guide for hiring, decision-making, and communication.

2. Invest in Scalable Communication Systems

Clear communication becomes essential as your company grows. Establish tools and practices that ensure everyone stays informed, such as regular all-hands meetings, a shared knowledge hub, or structured updates from leadership. Scalable systems help bridge the gap between teams and reduce miscommunication.

3. Create Simple, Scalable Processes

Processes that worked for a small team often break down as the organization expands. Focus on creating systems that bring structure without adding unnecessary complexity. For example, a lightweight project management tool or a clear onboarding plan for new hires can go a long way in reducing friction.

4. Develop Leaders Across the Organization

In the messy middle, leadership can’t be concentrated at the top. Invest in developing mid-level managers who can embody your culture and lead their teams effectively. Strong leaders at every level ensure that employees feel supported and aligned, even as the company grows.

5. Foster Connection Through Traditions and Celebrations

Growth doesn’t have to mean losing the sense of community that defined your small team. Keep the culture alive by celebrating milestones, maintaining company traditions, and creating opportunities for employees to connect. These moments help employees feel part of something larger than their immediate roles.

6. Address Tension Head-On

Don’t ignore cultural clashes or resistance to change. Create open forums for employees to share feedback, and actively listen to their concerns. Acknowledging and addressing these tensions shows your team that you value their input and are committed to fostering a positive environment.

7. Define Your Evolving Identity

Culture is not static—it evolves with the organization. Use this phase to define what your culture will look like as a larger company. Be intentional about blending the best of your small-company roots with the structure and clarity needed for growth.

Your Path Forward

Navigating the messy middle of growth is one of the most challenging phases for any company. It’s a time when the systems, habits, and culture that carried you through the early stages are no longer enough to support what’s ahead. But it’s also a defining moment—an opportunity to build a culture that not only sustains your organization but propels it forward. SHRM's findings show that 94% of people managers agree a positive workplace culture fosters resilience, further proving culture's critical role in growth. 

By recognizing the signs of cultural strain, addressing tensions with intention, and investing in the systems and leadership that foster connection and clarity, companies can emerge from this phase stronger and more united. Growth will always bring change, but when handled thoughtfully, it can also bring alignment, purpose, and a deeper sense of identity.

The messy middle doesn’t have to be a culture vortex. It can be a turning point—a chance to evolve into a company where both people and purpose thrive.