From Start-Up to Grown-Up

Being a leader means seeing clearly enough to navigate not just your business growth but also your personal growth—because the two go hand in hand.

1. Self-awareness shapes your leadership and communication

Effective leadership starts with understanding how you communicate and how others perceive you. Leaders' words and actions carry weight, whether they mean them to or not. As the CEO, even your smallest decisions or passing thoughts can set the tone for your team.

Self-awareness allows you to identify behaviors or habits that may undermine your leadership. It also gives you the ability to respond, rather than react, in challenging situations—helping you maintain professionalism. Many leaders, like Charlie, may misread their actions as being passionate while others perceive them as aggressive. Identifying these gaps is key to fostering collaboration.

Self-reflection is your first step. Think about how you express opinions. Do you ask questions and engage others? Or do you direct and delegate too quickly? Understanding your natural style and being open to changes can transform how you interact with your team.

Examples

• A fintech CEO, Charlie, misunderstood his aggressive tone, which hurt collaboration with his CTO.
• Acknowledging blind spots in communication increased team trust and cooperation.
• Reflecting on key moments helps leaders align their behavior with their goals.

2. Confidence comes from recalling past wins

Self-doubt is a common struggle among leaders, especially during tough times. But confidence can grow by focusing on cues from your past achievements. Stressful scenarios often trigger negative self-talk, but it’s possible to train your mind to counter those thoughts.

When founder Jake faced rejection from investors, he spiraled into anxiety. By reflecting on past instances where he'd excelled, he shifted his mindset from failure to capability. Creating evidence of your successes gives you tangible reminders of your strengths. It’s not boasting—it's regulating your own belief in your abilities.

Think back to your moments of success and make a habit of documenting them. Use this "highlight reel" as a mental reset whenever doubt creeps in. By embracing positive reinforcement, you create a reservoir of strength to pull from during uncertainty.

Examples

• Jake overcame self-doubt during tough investor meetings by recalling past fundraising victories.
• Founders reduce negative self-talk by consciously collecting success stories.
• Viewing past wins daily tunes your mindset towards positivity and resilience.

3. Daily routines fuel productivity and focus

Small rituals can create big changes when incorporated consistently. From leveraging routines in sports to using morning and evening habits in leadership, these small steps make achieving bigger goals easier and more sustainable.

The author suggests starting your day with gratitude and clear intentions. Writing down three goals for the day—not just at work but also personally—helps you stay aligned and motivated. Joyce, an overwhelmed app founder and mom, used morning rituals to manage her workload and stress better, discovering increased resilience along the way.

Rituals also help when you're in a slump. Use quick but effective tools like a stretch break or a walk. Closing the day with reflections in a journal allows leaders to pause, learn, and recharge. Repeated good habits create a mental framework for enduring progress.

Examples

• Rafael Nadal uses pre-match drink rituals to focus before tennis matches.
• Joyce used morning gratitude writing to reduce stress and improve her focus over a month.
• Evening journaling routines improve resilience and encourage better decision-making.

4. Hiring for skills and values ensures team success

It's tempting to prioritize technical expertise when hiring, but leadership and cultural compatibility matter just as much. Skills may help someone complete tasks, but values dictate whether they thrive in your company environment.

Founder Jocelyn learned the hard way after hiring plenty of professionals based on qualifications but ignoring collaboration and leadership styles. The new hires caused delays and confusion. Future hires should align with what a company values. For example, problem-solvers may not just work hard but should also collaborate well with others.

Visualize your new hire’s role in specific future scenarios. Consider how you'll support their growth and whether their traits align with your company's direction. Remember that recruitment is about more than just hiring—it’s about long-term fit within a team culture.

Examples

• Jocelyn's team of experts floundered because leadership traits were undervalued.
• Strong hires solve challenges while improving collaboration, as evident in team meetings.
• Visualizing six months of an employee’s achievements can guide smarter hires.

5. Positive feedback drives loyalty and better performance

Employees perform their best when they feel valued and safe. Simple acts of praise can inspire confidence and productivity within your team. Leaders who think appreciation isn’t necessary often miss opportunities to motivate their staff.

When Lindsey’s employee Wilson misunderstood her lack of feedback as disapproval, it hurt his morale. Once reassured how much Lindsey admired his work, his confidence rebounded. Even a spreadsheet to systematically track acknowledgment can help leaders stay intentional.

On the flip side, constructive feedback also matters. Providing fair, factual critiques framed within a larger context makes corrections just as important, keeping employees motivated but also aligned.

Examples

• Wilson in Lindsey’s company was emotionally affected by a lack of praise.
• Google’s research highlighted psychological safety as the driver of team effectiveness.
• Regular acknowledgment motivates employees to stay driven and creative.

6. Manage your growth with structure and HR support

As start-ups grow, leadership must evolve. The early ad-hoc systems that worked with 10 employees won’t handle the complexity of 50 or more. Structures allow you to delegate responsibilities effectively and avoid bottlenecks.

Systems, such as managers supported by HR, are essential. For example, Spotify separated workers into squads and tribes. A framework of expectations, like the GROW coaching model, helps guide teams and employees. Bringing in Heads of People frees up time for the CEO while improving processes like hiring, onboarding, and reviews.

Over time, this approach ensures that teams remain both productive and happy—a key factor for retention and morale.

Examples

• Spotify uses tribes and squads to structure roles while maintaining agility.
• The GROW model improves decision-making by setting clear action plans.
• Onboarding support allows managers to focus on mentoring effectively.

7. Metrics keep the team on track and forward-looking

A good leader measures progress to manage resources and clarify goals. Metrics are essential, whether they involve tracking funds or completing key projects. Without this clarity, growth often stagnates.

Start-ups frequently face financial or operational blind spots. Metrics like dashboards give visual clarity to where things stand—whether green (on track), yellow (issues exist), or red (completely stalled). Weekly reviews of dashboards align priorities and ensure that teams address issues faster.

Monitoring key metrics not only keeps the company running but improves decision-making and motivates teams by giving them a clear picture of problems to solve.

Examples

• Dashboards helped teams visually manage milestones in real-time.
• Financial budgeting prevented overspending in a fast-growing company.
• Visualizing performance created buy-in for team-wide accountability.

8. Handle cofounder conflicts early with clarity and planning

Cofounder relationships determine how well your company weathers challenges. Like a marriage, unresolved tensions lead to misunderstandings and, sometimes, breakups. Planning for disagreements from the start ensures smoother communication.

Raj and Josie’s rising misalignment over work habits was an example of what happens when expectations go unchecked. A "cofounder prenup" clarifies mutual priorities. By regularly aligning on values, goals, and decision-making styles, communication becomes clearer.

Periodic revisits to agreed principles make disagreements less disruptive and partnerships more aligned for the long haul.

Examples

• Josie assumed Raj’s flexible hours reflected a lack of commitment.
• A cofounder prenup structured questions around mutual values and goals.
• Reviewing agreements annually improved transparency between partners.

9. Leadership is both personal and professional growth

Scaling a company requires scaling yourself. Balancing personal development and your leadership approach inspires others to grow, boosting team unity.

Adopting habits like reflection, learning to manage conflict, or even journaling helps leaders stay accountable. Employees mirror what they see, so a CEO invested in their own growth inspires others. Making systems to guide progress and regularly evaluating personal priorities enables leaders to stay agile in evolving contexts.

Balancing self and organizational improvement builds the resilience needed for sustained company success.

Examples

• CEOs who document examples of progress stay adaptable.
• Leaders who plan around personal habits, like journaling, focus more clearly.
• Employees imitate the long-term perspective of reflective leaders.

Takeaways

1. Create a personal operating manual that clarifies how your team can work best with you during onboarding.
2. Develop regular rituals like journaling or morning gratitude to build momentum and manage stress.
3. Construct a metrics dashboard for tracking team-wide milestones visually and addressing delays in real time.