CHALLENGE NO. 1: NAVIGATING FOUNDER LOYALTY

Founders often have deep loyalty to the colleagues who built the company with them in its earliest days. These employees are seen as battle-tested, trusted insiders. The problem?

Their skills may no longer fit the company’s scaling needs—and yet, they hold outsized influence. 

For new managers, this creates a painful reality: You’re not only trying to win the trust of your founder but also fighting for credibility with early employees who may see you as an unnecessary outsider. Trying to confront unhealthy loyalty to the people in power can be like stepping on a landmine, primarily because it is not rational and there is way too much ego and emotion involved. 

Case in point: When Anthony joined a “unicorn” as head of sales, one of his direct reports, Joe, was a founding team member very close to the CEO. Joe openly questioned Anthony’s appointment, asking the CEO why they’d hired “an old man” (Anthony was only in his early 30s). Despite being Anthony’s subordinate, Joe had significant influence due to his loyalty to the CEO. Anthony realized quickly that to succeed, he needed to prove himself to both his boss and his report. Instead of fighting Joe’s power, Anthony respected his achievements, delivered tangible results in new regions, and built a working relationship. Eventually, Joe acknowledged his credibility and the two found a way to work together. 

To manage founder loyalty, you must earn credibility fast through visible results, respect early employees’ contributions while introducing scalable approaches, and avoid direct confrontation. Instead, position yourself as a complement, not a replacement.

CHALLENGE NO. 2: MANAGING BETWEEN INEXPERIENCED TEAMS AND SENIOR LEADERS

In scaleups, you’re often “sandwiched”: managing a team of young, ambitious but inexperienced staff, while reporting to senior leaders who may have big titles but little experience in scaling businesses. Young teams may lack the maturity to handle ambiguity. Senior leaders may lack strategic perspective, having excelled in execution but not in leading at scale. You may find that you need to coach upward too. The key is to do it without damaging egos—by guiding, not exposing.

Case in point: In one company, the operations function was almost entirely staffed by recent graduates. They were bright and eager but had no experience of structured work. Their manager, the only seasoned professional, found herself not only coaching them in professional basics but also managing upward—explaining to senior leaders why some expectations were unrealistic.

If you are a manager in this position, you must become a translator and a coach for your team. Build maturity by mentoring employees, modeling professional behavior, and creating structure where none exists. For your leaders, you need to coach gently, providing data, insights, and context without making them feel undermined. This requires diplomacy—the art of guiding without bruising egos.

CHALLENGE NO. 3: HANDLING C-LEVEL MICROMANAGERS

Micromanagement is rife in scaleups. C-level executives who grew up in the early chaos often struggle to delegate, believing “getting their hands dirty” is still a badge of honor. The result is that managers are undermined, and teams don’t know whose direction to follow. Working for a micromanager can be a serious threat to your mental and physical health. 

Case in point: Paula, a long-serving CMO in an e-commerce scaleup, was so insecure about her lack of executive experience that she micromanaged every detail. She tracked Slack response times, checked on employees while they were on vacation, and judged them daily as heroes or failures. Managers under her found themselves stripped of authority. 

To handle micromanagers, provide proactive transparency through trackers, dashboards, and updates to reduce unnecessary interference. Use Nonviolent Communication (NVC), a framework developed by American psychologist Marshall Rosenberg, to set boundaries respectfully. NVC helps you express observations, feelings, needs, and requests without triggering defensiveness. For example: “When you gave me step-by-step instructions on Project X, I felt disempowered because I need ownership to succeed. Would you be open to me drafting the plan first and then reviewing it with you?” Last but not least, protect your team’s trust by acting as their buffer. Don’t let them be exposed to every overreach from a micromanager.

CHALLENGE NO. 4: LEADING THROUGH HIGH CHURN AND PROMOTION PRESSURE

In some scaleups, promotions are expected frequently. When they don’t come, employees feel like failures and leave. The resulting churn forces managers into a constant cycle of rebuilding teams, onboarding new hires, and trying to preserve momentum. As one leader told me, “At my scaleup, not getting promoted every cycle was seen as failure.” 

Case in point: One scaleup tried to fix retention problems by inventing new job levels and titles every six months. While this satisfied employees temporarily, it created confusion, instability, and resentment over time. 

To lead through churn and promotion pressure, you need to shift the definition of success. Celebrate learning, skills gained, and contributions made, not just promotions. Create stretch opportunities. Give employees chances to lead projects or mentor peers, reframing growth as broadening scope, not just climbing levels. Have open career conversations. Be honest about promotion timelines, and help employees map their progression realistically, even if it means they need to build their skills to move on to a different business. Don’t let your team measure success only by job titles. Growth is equally about learning and impact.

CHALLENGE NO. 5: PROTECTING INTEGRITY AND PSYCHOLOGICAL SAFETY DURING PIVOTS

Scaleups pivot constantly. A market looks promising, until suddenly it doesn’t. A product is the “big bet” one month, then shut down the next. For managers, these shifts create credibility risks: How do you lead with integrity when yesterday’s “must win” is today’s abandoned project? 

Case in point: Sandra, an e-commerce leader, was passionate about her mission. But when the company changed direction repeatedly and failed to deliver promised resources, her team lost trust. Sandra burned out trying to hold everything together. This is where psychological safety becomes critical—it is by far the most critical factor in explaining why one team succeeds over another. To protect integrity during pivots, be transparent, share what you know and don’t know, and avoid sugarcoating.

Acknowledge the impact of unexpected changes by naming the frustration your team feels, as this builds trust. Foster safety by creating space for your team to express doubts, push back, and experiment without fear of blame. In a corporate environment, success often comes from being the smartest, most organized, most polished. In scaleups, that won’t cut it. Success depends on mastering the human skills that allow you to navigate loyalty, coach across levels, buffer micromanagers, reframe growth, and protect psychological safety. 

Scaleups are not ideal environments, but they can be profoundly rewarding ones—if you have the skills to surf the waves rather than drown in them. For managers willing to embrace the discomfort, scaleups offer extraordinary opportunities: faster growth, broader responsibility, and the chance to leave a tangible mark. But to thrive, you must rewrite your playbook. Technical expertise gets you in the door. Human skills keep you in the game.