The leadership obligations nobody taught you

A newsletter for mid-career product professionals on the human work of leading teams.

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What you'll get

Focused writing on the human side of leading product teams.

  • Practical frameworks drawn from 20+ years leading teams
  • Honest takes on conflict, trust, and difficult conversations
  • The discipline of becoming the leader your team deserves
  • Systems thinking for people who build products and lead people

Why trust me

I'm Matthew Stublefield. I've spent 20+ years leading product and engineering teams – from scaling CoinDesk through a crypto boom to directing an 80-person team at Stride to running a pilot program at KPMG that touched 20,000 employees.

My background is unconventional for tech. I studied Religious Studies and Poetry in college – not because I couldn't do the technical work, but because I wanted to understand people. That foundation taught me to ask “why” until I reach root causes, and to listen for what's not being said. Later, I became a Certified Grief Counselor to better understand how loss and change impact teams under pressure.

I'm the founder of Fieldway, LLC, where I run diagnostic sprints for product teams, and I'm currently writing What a Leader Owes Their Team – a book about the obligation-based leadership framework I've developed over two decades of practice.