The Full Stack Leader

The secret to many leaders’ success is knowing how to ask for help. Asking direct and honest questions in a 1-1 or in a group of peers can lead to surprising insights.

When asked about advancing in my career as a product leader and business executive, I often share two main strategies. First, work with an executive coach and then join a cohort-based executive coaching program.

The accountability of coaching gives me the motivation and a framework to make visible progress on career growth.

I won’t cover executive 1-1 coaching here, so if you want a taste, check out the Learn & Create blog from Automattic: A peak into performance coaching; A peek into mindset coaching; and A peek into non-dual coaching. And for a personal recommendation, I suggest getting in touch with Greg Fraser for a 1-1 consultation.

Executive Coaching Programs

A peer-based program gathers like-minded people to learn and grow together. Being external means the program is neutral and not focused on private details of any given person or company. Instead, you explore situations, best practices, and get peer coaching from people with similar jobs and career tenure.

The best programs follow a cohort-based learning approach with access to the entire organization while invited to a small group for a team feeling, led by a facilitator. Programs avoid assigning competitive companies in the same cohort—though not 100% guaranteed.

How to choose?

Different groups have different flavors and styles. You can find one from a mix of the following factors:

• Geography: NYC or SF/Bay area in-person; or remote & global
• Company size/stage: Startup, scaleup, or enterprise
• Function/role: CX, Product, Engineering, and UX — or a broader mix of people
• Learning styles: Reading and reflection; mastermind sessions; coaching/situational inside the cohort (round-robin); city or industry conference circuit; or a match-making service for lunch, coffee, and “speed rounds”
• Gender or under-represented specific: For example, focused on women executives, like Chief

Compare the programs:

• Price: Does it fit your budget?
• Commitment level: Hours per week / month. Doable? Is travel expected, or 100% remote?
• Current members you’d like to learn from?

My Recommendation

Here are several programs I recommend, with the first two where I am most familiar because I’ve joined them as an active member in the last 5 years.

Collaborative Gain

• Groups form based on industry and role
• Members are open to reading, learning, and asking for help
• Best fit: career-minded, ambitious, yet kind people

Venwise

• Engineering, Product, GM/COO, and CEOs
• Startup and fast-growing small companies
• NYC-based; opened up more widely during the pandemic
• Best fit: Founders of fast-growing companies

Enrich

• Cohort-based learning in peer groups usually functions/roles based (e.g. VP Eng with other Engineering leaders)
• Highly recommended by several coworkers, but I don’t have first-hand experience
• Best fit: Tactical advice and like-minded practitioners

Round

• NYC-based
• From the website: “A curated community and platform for tech’s most thoughtful leaders.”
• Update April, 2024: Round is no longer active (shut down)

The Grand

• Remote, digital-first platform
• Group-coaching platform for individuals and companies
• Includes groups for leadership or navigating transitions

Lunchclub

• Pairs you with like-minded people for short chats
• Best fit: General

There are also more traditional executive training and networking groups, often region-based such as:

1. YPO: Young Presidents Organization
2. EO: Entrepreneurs’ Organization

Executive coaching groups provide valuable ways for leaders to seek guidance, get support, and gain fresh perspectives. It’s also not a bad way to build a professional network.

Embracing the power of collaboration and seeking help when needed can lead to surprising results and accelerate personal and professional growth.