As a business expands, the demands on its leadership inevitably shift. The hands-on, “doing everything for everyone” approach that might have propelled an early-stage venture to success can quickly become a bottleneck, hindering further growth and frustrating the very leaders who built the company. I was recently listening to a Harvard Business Review podcast that tackled this very subject. The podcast was about an entrepreneur, called Flynn, who sought coaching to learn how to transform the leadership she offered as her business grew. This podcast offered valuable insights into how leadership must adapt when a company scales up.

From “Cleaning Up Messes” to Strategic Guidance

Flynn, initially accustomed to “doing people’s work versus leading them,” recognised a crucial need to change when she found herself “cleaning up everyone’s stuff”. This realisation highlighted a common entrepreneurial pitfall: getting stuck “in the trenches” instead of focusing on strategic leadership.

The fundamental shift required is from direct problem-solving and finishing others’ tasks to guiding a team to solve problems themselves. This means moving away from micromanagement and instead setting clear responsibilities, defining success and asking questions to foster team independence and growth. As Flynn discovered, this new approach can reveal greater talent and capabilities within the team, while also exposing areas where individuals may lack the necessary skills.

The Imperative of Clear Expectations and Consistent Accountability

A key area for leadership evolution lies in performance management. Flynn admitted to only holding formal performance discussions when “disaster is starting to occur,” preferring casual feedback for positive performance. This resulted in important conversations becoming “an event” rather than consistent dialogues about expectations.

To counter this, growing businesses must:

• Proactively define success: Leaders need to “spend time really outlining what success looks like in each position” through Key Performance Indicators (KPIs), rather than waiting for problems to emerge. While Flynn initially worried that setting KPIs might seem “overly judgmental” in a creative field, particularly for high performers, she later realised that professionals would likely appreciate knowing their success metrics.
• Implement consistent performance management: Regardless of performance level, consistent meetings and feedback—both positive and constructive—are essential. This creates “equitability” across the team, ensuring that high performers also receive formal recognition and that the leader’s expectations are clear for everyone. Such consistency helps to establish the leader’s management style as an expectation.
• Embrace “hard conversations”: The reluctance to have “hard conversations” leads to issues piling up and becoming more serious meetings. Leaders must view these as regular, necessary dialogues about expectations, progress, and areas for improvement, rather than avoiding discomfort.

Adaptability and Strategic Prioritisation

Effective leadership in a growing company demands adaptability. Flynn learnt that management “formulas” should be written “in pencil, not pen,” meaning leaders must be willing to change approaches if initial or past methods aren’t working. There is no “perfect” system, and focusing on rigid perfection can hinder progress. Trial and error, coupled with reassessment, are integral to successful management.

Furthermore, leaders must cultivate the ability to say “no”. Flynn learned that her tendency to “please a bit too much” led to spending money on requests that didn’t align with company priorities, ultimately being “at the detriment of the company”. A leader’s unique role is to be the “gatekeeper” for the company, proudly standing at the gate and ensuring that decisions align with core values and priorities.

The Crucial Role of Strategic Thinking

Finally, leadership at a higher level demands dedicated time for thinking and reflection. Flynn initially saw “doing” as the primary work, but realised that setting aside time to “really think it through” and process ideas is fundamental to her role as a leader. This strategic thinking allows the leader to focus on guiding the company forward, rather than getting bogged down in day-to-day operations or doing others’ jobs.

In summary, as a business grows, leadership must transform from hands-on execution to strategic guidance. This involves establishing clear expectations and consistent accountability, embracing adaptability and rigorously prioritising the company’s needs. While this evolution can be challenging and uncomfortable, it is essential to free up the leader’s time for higher-level work and propel the organisation to its next level of success.

This important topic on leadership will be covered extensively in the upcoming accredited course for family businesses in Malta – the Award in Leading a Family Business offered by EMCS Academy. Designed specifically for the unique dynamics of family-run enterprises, this course equips both current leaders and next-generation leaders with the tools, frameworks, and strategic insight necessary to ensure long-term business continuity. Click HERE to register your interest to be part of the next cohort that will kick off after summer 2025. We can also assist to gain funding for this course.