Developer to CTO: Leadership Skills for Scaling Startups

Learn essential technology leadership skills to transition from individual contributor to leader, master time and calendar management, prioritize backlog, and balance reactive and proactive work.

Master time management for leaders with the Eisenhower matrix, the Pomodoro technique, and the two-minute rule to prioritize backlogs and calendar planning.

Learn to take ownership of your calendar by time boxing, defragging your week, and applying the Eisenhower Matrix to protect deep focus and energy as a leader.

Learn when and how to say no using the Eisenhower matrix to protect creative time and focus. Prioritize high-impact work, explain decisions clearly, and balance team needs with business goals.

Balance proactive and reactive work by prioritizing long-term impact within the Eisenhower matrix. Use time blocking, weekly reviews, and delegation to protect focus and increase organizational impact.

Develop personal productivity by actively controlling your calendar, choosing proactive work over reactive tasks, and practicing prioritization and reflective planning to become an effectual leader.

Develop leadership skills by transitioning from individual contributor to a team leader, balancing team success with accountability and responsibility, embracing ownership, and mastering effective delegation.

Understand how leadership shifts success from individual contributions to team outcomes, and apply Spotify-inspired squad autonomy, mentoring, and collective success to foster high-performing software teams.

Learn the distinction between accountability and responsibility in leadership, shifting from doing work to owning outcomes, illustrated by Amazon's two pizza teams and tips like a team charter and stand-ups.

Own your leadership by immersing in the squad’s work, communicating a shared vision, fostering autonomy, and recognizing contributions to align the team with larger goals and achieve collective success.

Learn to delegate effectively using the Eisenhower matrix to separate important and urgent tasks, shifting ownership from leaders to squads while maintaining accountability for outcomes.

Explore how to lead and collaborate effectively by differentiating accountability from responsibility, fostering ownership, and using the Eisenhower matrix to delegate tasks by importance and urgency.

Reflect on a past project as both contributor and leader to define success metrics, accountability, and ownership; outline delegation and strategies, then apply to a current project.

Lead tech teams by prioritizing people, building trust, and turning outputs into outcomes while mastering difficult conversations and feedback to accelerate startup growth.

Navigate the shift from peer to leader with transparency and open communication. Establish clear boundaries and a guiding leadership philosophy to sustain consistency as the team changes.

Learn to tackle difficult conversations with preparation and a constructive mindset, building trust and better outcomes for your team and projects.

Use a three-page worksheet to plan difficult conversations by neutrally describing the what and who, deciding when and where, adopting a constructive mindset, and detailing preparation and contingencies.

Frame feedback as a gift to improve performance, and prepare for difficult conversations using the SBI framework, data, and private one-to-one discussions to protect client trust.

Learn to navigate late-project conversations with a data-driven mindset, capture blockers and timelines, and use a worksheet to inform the project manager and unblock the team.

Apply the SBI model (situation, behavior, impact) and discuss alternative behavior, delivering specific, timely feedback across a positive-negative, general-specific spectrum to drive change.

Discover how the actionable feedback worksheet uses the sbi model to turn difficult feedback into specific, observable behavior and impact, with actionable alternatives and a narrative approach for team growth.

Learn to use an actionable feedback worksheet to prepare your mindset, assess situations, and deliver constructive feedback with the SBB model (situation, behavior, impact) and alternatives.

Learn how to give actionable feedback to help a team member take ownership and drive projects using the SBB and SBI feedback frameworks.

Lead with honesty to build trust by being open about flaws, saying 'I don't know' when needed, and modeling credibility, transparency, and accountability for a high-trust team.

Use this two-page trust worksheet to proactively build trust using the course's trust framework, focusing on truth, respect, unbiased skill, and transparency with examples.

Develop leaders can build trust with a new team by starting with honesty about not knowing, showing respect, avoiding bias, demonstrating competence, coaching, and transparent vulnerability.

Apply the trust framework—truth, respect, skill, and transparency—to build trust with a new boss, demonstrate competence quickly, acknowledge cognitive biases, and share motives to avoid distrust.

Reflect on transitioning from peer to leader, master difficult conversations, deliver and receive feedback, and build trust to lead with the human side of technology leadership.

Create a relationship map centered on you to map connections, label lines as team member, peer, or boss, and answer questions on interactions, feedback, trust, and history to reveal patterns.

Develop leaders by cultivating peer relationships and mentors across disciplines, communicating clearly, and influencing outcomes by aligning teams, building trust, and embracing healthy conflict.

Develop strong peer relationships to balance your two leadership teams, fostering collaboration, trust, and psychological safety that enable high-performing, innovative problem solving.

Define communication as transferring ideas between minds, examine encoding and decoding challenges, and apply the feel, think, do model to prompt clear action.

Use a three-page feel, think, do worksheet to prepare for high-stakes conversations, guiding you to define the ask, anticipate objections, manage emotions, and structure an efficient message.

Learn to craft clear, outcome-focused emails that motivate teams to fill timesheets on time, linking pay to submissions, addressing objections, and reducing encoding and decoding challenges with simple language.

Learn to craft high-stakes headcount requests in startups by aligning with investor goals, addressing runway concerns, and presenting a clear, numbers-based case for Project Phoenix.

Explore benevolent influence to align goals and guide teams toward shared outcomes using the influence doorways model, from data and information to emotions, logic, and feedback.

Apply the influence doorway framework to anticipate and influence outcomes by aligning data, information, emotions, and logic with their goals, using a stepwise worksheet.

Use the Influenced Doorways worksheet to align data, information, and a teammate's internal narrative with your project goals, and contextualize it to unblock their backlog.

Articulate a clear vision and use data, burndown charts, and backlog context to influence your boss for additional headcount while highlighting outcomes and building virtuous feedback loops.

Learn to distinguish healthy and unhealthy conflict, align goals with mutual respect and positive intent, and apply the pause model: prepare, actively listen, understand, share, end, to foster safe dialogue.

Learn to move conflicts from unhealthy to healthy using the pause method, preparation, and courageous, composed dialogue, emphasizing active listening, empathy, and alignment toward shared goals.

Turn an unhealthy conflict into a healthy dialogue by preparing, acknowledging the conflict, listening, and empathizing with Jen. End with alignment and action to ensure ongoing collaboration and shared goals.

Apply the pause framework to transform unhealthy conflict into productive dialogue through private one-on-one talks, active listening, open questions, and positive intent, aligning goals and timelines.

View your peers as advisors and mentors, map relationships, and seek lessons across disciplines through respectful conversations to build trust and become a humble, confident leader.

Shift your mindset to view peers as collaborators and partners, not obstacles, and learn from diverse disciplines through open communication. Foster trusting, psychologically safe relationships to learn from others.

Discover how to build and leverage a network of high-value advisor relationships to lead tech teams, scale startups, and transition from developer to CTO.

Leverage mentors and coaches as career advisors to gain experiential guidance, accountability, and outside perspectives, reduce burnout, and confront imposter syndrome.

Find mentors within your organization and seek coaches beyond it to build a diverse network of advisors through networking events and cross-discipline outreach.

Learn how to reach out to potential advisors with clear goals and value for both sides, overcoming imposter syndrome to build effective advising relationships.

Define clear mutual goals and milestones with your advisor, prepare sessions with a list of asks, and leave with actionable items to ensure accountability.

Prepare for a respectful, difficult conversation by recalling why you started the advisor relationship, the goals achieved, value contributed, and then offer to help.

Clarify your advisor goals with the worksheet, assess what you need, what you’ve tried, why this advisor fits, then craft an outreach email or slack message.

Learn to complete an advisor worksheet to attract a mentor and become an executive leader, outlining skills and goals for the board, investors, PNL, and suppliers.

Develop a network of advisors who can amplify your leadership as you scale startups, overcome imposter syndrome, and apply communication and influence skills to initiate advisor conversations.

Explore overwhelm in tech leadership and learn practical strategies to turn challenges into opportunities, boosting resilience, work-life balance, and cultures of innovation.

Define overwhelm as a mental emotional state caused by accumulating pressures in tech leadership, where complexity meets suboptimal decisions, and it harms well-being, decision making, and project quality.

Overwhelm affects leaders and teams by causing decision fatigue, eroding quality, sabotaging communication, and lowering morale, with personal well-being shaping team health and innovation.

Navigate overwhelm in tech leadership by recognizing factors like rapid pace of change, high stakes decisions, team dynamics, information overload, and remote work challenges.

Explore how emotional intelligence helps leaders manage overwhelm, develop emotional awareness and empathy, and balance technology and people for better decision making and resilience in tech teams.

Discover how self-awareness, self-regulation, motivation, empathy, and social skills empower tech leaders to manage overwhelm, lead crises with calm, and inspire cross-team collaboration.

Build resilience to adapt and grow through adversity, using emotional intelligence and self-awareness to manage overwhelm in tech leadership, and apply the four-quadrant model and Yerkes-Dodson insights toward flow.

Develop adaptability as a key leadership skill for scaling startups by embracing uncertainty, learning, flexibility in problem solving, and active listening.

Turn overwhelm into growth, a signal for learning, with emotional intelligence, resilience, and adaptability for tech leaders. Create actionable steps, document triggers, and share your goals to build accountability.