Startup Leadership

Bay Bridge by Jason Jenkins jdub1980 8487414779 EDIT

Although I work with clients in a wide range of leadership positions, the most common role in my practice is startup CEO. And while every client engagement is unique, I do see patterns and themes in my practice as a result of working with this particular group of leaders so intensively. The resources below have grown out of my coaching practice and my teaching at Stanford over the last decade. To learn more about me and how I work, start here.


1. Effectiveness

Don’t Wait

Early-Stage Survival and Later-Stage Success

Glass, Metal, Rubber

Happy Workaholics Need Boundaries, Not Balance

How to Scale: Do Less, Lead More

Importance vs. Urgency

The Importance of Slowing Down

“Work Hard or Work Smart?” Is the Wrong Question

Three Buckets (On CEO Job Descriptions)


2. Interpersonal Issues

Better Working Relationships

How to Deliver Critical Feedback

Merciful Exits (On Underperforming Executives)

Brené Brown, Vulnerability, Empathy and Leadership

Coaching and Feedback Tools for Leaders

How Leaders Create Safety (and Danger)

Learning to Yield (Navigating Tough Conversations)

On Firing a Senior Team Member

Risk Management (The Importance of Speaking Up)


3. Leadership Challenges

Leading in Four Dimensions

Leadership as a Performing Art

Leadership, Decision-Making and Emotion Management

The Cognitive Dissonance of the CEO

Watch That Next Step (CEO Problems)

What Do Great Leaders Do?

Three Buckets (On Transparency and Truth)

Hammering Eggs (Leadership and Problem-Solving)

CEOs and Celebrations

The Ruling Out of Possibilities (On Failure)


4. Self-Management

Investments, Not Indulgences

Open Space, Deep Work and Self-Care

How to Think (More on Open Space and Deep Work)

Leadership as Professional Practice

Don’t Just Do Something, Sit There! (Mindfulness for Busy People)

Get Moving! (Exercise for Busy People)

Ignoring Bandits and Building Resilience

Dysfunction Isn’t Heroism


5. Organizational Development

The Judicious Imposition of Structure

Pirates in the Navy

Startups As Human Systems

Startup Leadership 1: Are We Video-Gaming or Ditch-Digging?

Startup Leadership 2: Are We Rowing or Rafting?

Startup Leadership 3: A Greater Us

The Fine Art of Levelling

Rules Aren’t Norms (On Better Meeting Hygiene)

Accountability and Empathy (Aren’t Mutually Exclusive)

Role Clarity and Role Confusion

The Truly Strategic People Leader

Three Stages of Executive Assistance

Hail to the Chief (of Staff)

Capacity, Methodology, Innovation (On Hiring)

Daniel Kahneman on Conducting Better Interviews


Updated April 2021.

Photo by Jason Jenkins.