From Start-Up to Grown-Up

In her book "From Start-Up to Grown-Up," Alisa Cohn provides valuable insights and practical advice for founders and CEOs looking to scale their leadership skills alongside their growing businesses. Drawing from her extensive experience as an executive coach, Cohn offers a roadmap for navigating the challenges of leading a start-up through various stages of growth.

Introduction

Starting your own company is an exhilarating experience. As a founder, you're free from the constraints of having a boss, but this freedom comes with the responsibility of learning how to be an effective leader yourself. As your start-up grows, you'll need to develop new skills to keep pace with the expanding demands of your business.

Cohn's book is designed to help entrepreneurs hone their leadership abilities at every stage of their start-up journey. She provides tried-and-tested tools for improving leadership skills and offers guidance on keeping everyone motivated – including yourself, your employees, and even your cofounders.

Cultivating Self-Awareness

One of the most crucial aspects of effective leadership is self-awareness. As the CEO of a start-up, your words and actions carry significant weight. Your employees are constantly looking to you for cues and direction, even when you're just thinking out loud. This amplified impact makes it essential to have a strong grasp on how you communicate.

To become a better communicator and leader, you need to embody the culture you want to see in your company. This starts with self-regulation – the ability to motivate your team and hold them accountable without losing your cool. It's important to be aware of any blind spots in your behavior, as these can hinder your effectiveness as a leader.

Cohn shares the example of Charlie, a fintech CEO who struggled to convince his CTO, Jack, to adopt new engineering processes. Charlie didn't realize that his aggressive manner when discussing the proposal was causing Jack to shut down and resist the changes. By becoming more self-aware, Charlie could have identified this issue and adjusted his approach to be more effective.

To improve your self-awareness, start by reflecting on your communication style. Ask yourself:

1. Do you ask questions and listen carefully?
2. Do you collaboratively explore solutions?
3. Or do you tend to tell people what to do and shift responsibility?

By understanding your natural communication patterns and triggers, you can begin to make conscious improvements in your leadership style.

Overcoming Self-Doubt

Self-doubt is a common challenge for many founders, especially when facing rejection or setbacks. Cohn introduces us to Jake, a founder struggling to secure additional funding from his investors. The uncertainty of the situation led Jake into a spiral of negative self-talk, convinced that his inability to raise funds would be seen as a sign of poor leadership.

To counteract self-doubt, Cohn suggests focusing on past successes rather than dwelling on current challenges. She recommends creating a "highlight reel" of your achievements that you can refer to when feeling unsure of yourself. This practice helps provide a more balanced and accurate picture of your competencies.

For Jake, recalling times when he had successfully secured investment in the past helped him manage his anxiety. With a clearer mindset, he was able to persist through rejections and eventually land his funding round.

To build an ongoing confident mindset, make it a habit to review your highlight reel regularly. Consider starting each day by recalling one or two past successes to boost your confidence and set a positive tone for the day ahead.

Establishing Routines and Rituals

Just as athletes use rituals to center themselves before a competition, leaders can benefit from establishing routines to boost motivation and performance. Cohn suggests thinking of leadership as a sport that requires you to show up and perform your best each day.

To get your day off to a strong start, consider implementing the following morning routine:

1. Use a traditional alarm clock instead of your phone.
2. Keep a pen and paper nearby.
3. Upon waking, take five deep breaths.
4. Write down five things you're grateful for before getting out of bed.
5. Once at your desk, write down three things you want to accomplish that day.
6. Write down one thing you want to let go of (e.g., negative self-talk or a specific worry).

Cohn shares the story of Joyce, an overwhelmed founder and mother of two, who found that implementing this routine helped her handle daily challenges more effectively and maintain a positive outlook.

In addition to a morning routine, consider incorporating energy-boosting activities throughout the day, such as doing jumping jacks during the mid-afternoon slump. End your day with a wind-down ritual, like journaling, to encourage self-reflection and prepare for a fresh start the next day.

By proactively incorporating positive habits into your routine, you'll cultivate the motivation and resilience needed to navigate the ups and downs of growing your start-up.

Hiring for Skills and Values

As your start-up grows, you'll need to expand your team. However, it's crucial to hire not just for skills but also for values that align with your company culture. Cohn illustrates this point with the story of Jocelyn, a health-care start-up founder who hired many doctors based solely on their medical expertise. She soon found that while they were knowledgeable, they struggled with leadership and teamwork, causing frustration and confusion within the company.

To avoid similar mistakes, follow these steps when hiring:

1. Identify the specific jobs that need to be done, rather than relying on common start-up job titles.
2. Consider whether you actually need to hire someone or if a software solution might be more appropriate.
3. Determine the hard skills required for the role.
4. Think about the soft skills and values that align with your company culture.
5. Ask candidates about their problem-solving approaches to gauge their fit with your desired work style.
6. Visualize how the candidate will fit into your team and what specific successes you'd like them to achieve within six months.

By hiring for both skills and values, you'll build a team that not only has the necessary expertise but also works well together and contributes positively to your company culture.

The Power of Positive Feedback

As a leader, one of your key responsibilities is to create a psychologically safe environment where your employees feel supported and motivated to do their best work. A crucial element in achieving this is providing positive feedback and recognition.

Cohn shares the story of Wilson, a packaging designer who was visibly upset due to a rumor that his boss, Lindsey, didn't like one of his designs. When the author reassured Wilson that Lindsey had actually referred to him as a creative genius, he burst into tears of relief and gratitude. This anecdote highlights the profound impact that positive feedback can have on employee morale and motivation.

To incorporate more positive feedback into your leadership style:

1. Create a spreadsheet of all your executives and key employees.
2. Track when you give each individual some form of praise.
3. Aim to say something positive to each person at least twice a week.

When you need to address mistakes or shortcomings, focus on facts rather than emotions, and frame the situation in a wider context. For example, instead of criticizing a missed sales target, acknowledge that it happens and then guide the team towards finding solutions for improvement.

Remember that company culture starts with you as the leader. By consistently providing positive feedback and creating a supportive environment, you'll foster a motivated and high-performing team.

Implementing Management Structures

As your start-up grows beyond 50 employees, it becomes increasingly challenging to manage everyone personally. At this stage, it's crucial to implement management structures to ensure continued productivity and growth.

While you may have enjoyed the flexibility of a small team, scaling up requires a more organized approach. Consider these steps:

1. Create a hierarchical structure that suits your company's needs. This doesn't have to be traditional – companies like Spotify and Hubspot have developed unique team structures that work for them.
2. Appoint managers to lead teams and serve as your communication line.
3. Provide your managers with a framework for coaching their teams. The GROW model (Goal, Reality Check, Options, Way Forward) is one effective approach.
4. As you continue to grow, consider hiring a Head of People or establishing an HR function to support with onboarding, training, and performance management.

By implementing these structures, you'll ensure that your employees remain effective and happy, while also attracting top talent to your growing company.

Developing Metrics for Progress

As your start-up evolves, it's essential to develop metrics that measure progress and guide your company forward. While the concept of metrics is simple, their implementation can significantly impact your business's growth and efficiency.

Key points to consider when developing metrics:

1. Start with basic measurements like budget tracking to avoid financial surprises.
2. Create a dashboard to monitor projects and milestones. Use a simple color-coding system (green, yellow, red) to indicate the status of each project.
3. Review the dashboard as a team once or twice a week to ensure everyone is aligned on priorities and progress.
4. Understand that the most important metrics will change as your company grows, but the habit of monitoring them should remain constant.

If you're not naturally inclined towards systems and processes, consider hiring someone who excels in this area to help implement and manage these metrics.

Addressing Cofounder Conflicts

Cofounder relationships can be compared to marriages – they often start with a honeymoon period of excitement and agreement, but conflicts can arise as the relationship progresses. To address potential conflicts before they become major issues, Cohn suggests creating a "cofounder prenup."

This prenup should include questions such as:

1. Why do you want to create this start-up?
2. What are your most important values?
3. Why is your cofounder the right partner for you?
4. What three words describe the culture you strive for?
5. How will you make decisions when you strongly disagree on something?
6. What does success look like to you?

Review these questions individually and then discuss your answers together. Make it a habit to revisit these questions annually to ensure you're still aligned in your vision and goals.

By creating a structure for open communication with your cofounder, you'll set your venture up for long-term success and be better equipped to handle conflicts when they arise.

Final Thoughts

Leading a start-up through various stages of growth is a challenging but rewarding journey. As Alisa Cohn emphasizes throughout "From Start-Up to Grown-Up," success as a founder and CEO requires continuous personal growth and adaptation.

Key takeaways from the book include:

1. Cultivate self-awareness to improve your communication and leadership skills.
2. Overcome self-doubt by focusing on past successes and maintaining a positive mindset.
3. Establish routines and rituals to boost motivation and performance.
4. Hire for both skills and values to build a strong, cohesive team.
5. Provide regular positive feedback to create a supportive and motivating work environment.
6. Implement management structures as your company grows to maintain efficiency and productivity.
7. Develop metrics to measure progress and guide your start-up forward.
8. Address potential cofounder conflicts proactively by creating a "prenup" and maintaining open communication.

By focusing on these areas and continuously working on your leadership skills, you'll be better equipped to scale your start-up successfully while growing as a leader. Remember that the journey from start-up to grown-up is ongoing, and there's always room for improvement and learning.

As you apply the lessons from Cohn's book, remain flexible and open to adapting your approach as your company evolves. Embrace the challenges that come with growth, and use them as opportunities to refine your leadership skills and build a stronger, more resilient organization.

Ultimately, the success of your start-up depends not only on your innovative ideas and market opportunities but also on your ability to lead and inspire your team through various stages of growth. By investing in your personal development as a leader and implementing the strategies outlined in "From Start-Up to Grown-Up," you'll be well-positioned to guide your company towards long-term success and fulfillment.