Cultivate adaptability as the primary leadership skill, recognizing your capacity for rapid personal and organizational change, as it is crucial for success in fast-paced environments.
To release ego, surround yourself with the right people and repeatedly ask for genuine feedback, demonstrating that you truly want to know for self-awareness and growth.
Avoid putting your self-worth into the PR narratives or origin stories created about yourself, as these are often simplified and public perception is cyclical, leading to potential disappointment.
Maintain long-term relationships with people who knew you before success, invite them to observe your work, and explicitly ask for honest, unfiltered feedback to stay grounded.
As a leader, elevate your perspective to a ‘mountaintop’ view, focusing on market awareness, strategy, and identifying future challenges or opportunities that your team might not see.
Embrace the feeling of having ’time to think’ as a leader, recognizing it as an opportunity for strategic ‘deep work’ and representing your company at exclusive tables, which are crucial, unique responsibilities.
Enlist someone to hold you accountable for scheduling and engaging in deep work periods, as this helps leaders maintain focus on strategic thinking.
Hire the right people carefully, but fire quickly when there’s not a fit, because mistakes in personnel can set back foundational development significantly.
Do not simply move underperforming employees to another role (’transfiring’); instead, make the difficult decision to let them go humanely, as ’transfiring’ only shifts the problem.
Hire individuals who are ’too big for the job’ today, focusing on where you want the company to be, as they will attract other high-quality talent and help the company scale.
Delegate tasks that others can do, even if it costs money, as it frees up your mind space and time, allowing you to focus on tasks only you can do for greater success.
Overcome the mental hurdle of delegation by recognizing that others need growth opportunities and by releasing the anxiety that no one can do it as well as you.
Engage in constant learning, which can include surrounding yourself with diverse, interesting individuals and asking them questions, fostering continuous discovery and growth.
Turn off electronics and the constant desire to optimize, allowing your brain to rest, as it prevents cognitive overload and serves as a form of mental meditation.
Implement ‘cold turkey’ habits and mechanisms, such as choosing routes without cell service or intentionally leaving your phone behind, to combat the huge temptation to stay connected.
Make decisions swiftly in the startup world, but ensure they are informed by a structured process like an ‘Amazon memo’ (situation, 3 solutions, pros/cons, recommendation).
Gather sufficient information, then make a decision and ’let go,’ especially if the decision is reversible, because moving forward is crucial.
Regularly conduct After Action Reviews (AARs) to compare expected outcomes with actual occurrences, identify successes and areas for improvement, and iterate on decision-making processes without assigning blame.
Proactively make decisions and move forward, because inaction will lead to external forces dictating your direction.
Keep a solid focus on your core goals and, critically, on your customers, as this is a reliable strategy that will prevent you from going astray.
As a company grows, transition from doing every job yourself to focusing on your specific role and ‘staying in your lane,’ which is essential for sustainable growth.
Understand that your suitability for a role can change as the company grows and evolves, as this awareness is crucial for personal and organizational adaptation.
After significant growth or change, allow a period for digestion, letting people acclimate and get to know each other, which helps integrate new elements and ensures stability.
Find a fine balance between focusing on company culture and business priorities, as both are critical and neither should be prioritized exclusively for sustained success.
When a person isn’t a fit for a role, make the difficult decision to let them go, understanding it’s ultimately better for them in the long run, while treating them kindly.
Be aware that investor-referred candidates might serve the investor’s broader network interests, not solely your company’s, ensuring you hire for your specific needs.
When implementing well-thought-through changes, explain the rationale behind decisions and actively listen to people’s concerns, helping people move through change more smoothly.
Create intentional opportunities for different departments to interact and understand each other’s roles, breaking down communication barriers and fostering mutual appreciation.
Ensure that individuals proposing solutions or writing decision memos fully understand the context of the situation, as proposals without full context may be easily dismissed.
As a founder, transition your focus from solely creating the product to building the business around it, which requires letting go of the ‘product as baby’ mindset.
Let go of control and allow your people to do their work, embracing the often unnatural and unfamiliar responsibilities of your new leadership position, even if it feels uncomfortable.
Hire the right people, let them do their jobs without micromanagement, and foster collaboration among them, empowering the team and leveraging collective capabilities.
As a chief of staff, proactively identify and prevent problems, taking issues off the leader’s plate before they escalate, ensuring smooth operations.
Cultivate a deep understanding of different departments’ work and people’s motivations across the organization, enabling efficient prioritization, problem-solving, and connection.
Develop high emotional intelligence (EQ) to understand people, read a room, and grasp underlying dynamics, as this skill is crucial for effective leadership.
Always remember that, despite technological advancements, the core of any organizational work is ‘people,’ which guides effective leadership and interaction.
Cultivate humility (death of ego), compassion, empathy, and servant leadership, as these traits are fundamental for effective leadership and positive influence.
Explore things you’re curious about, especially if they are unrelated to your main work, as it frees your mind, helps find parallels, and relieves your brain from persistent problems.
Stay grounded by seeking out things greater than yourself, putting yourself in uncomfortable situations, and exploring unrelated curiosities, fostering humility and broadening perspective.
Implement internal tools or game-like mechanisms (e.g., guessing employee names from pictures) to help employees get to know each other and maintain a sense of community as the company scales.
Inform employees about the inevitable cyclical nature of public perception and company narratives, which helps manage expectations and keeps the team focused on core objectives.