20 Years of Leaders helping Leaders

Coaching

Phyl Terry, Founder and CEO of Collaborative Gain, has developed a unique coaching methodology.

Profiled in Marty Cagan’s book Transformed, Phyl’s coaching brings together insights from:

  1. Decades of working helping management teams build great products and companies (as CEO of pioneering firm Creative Good where Phyl built a consulting team and worked with clients like Apple, Microsoft, Facebook and others). Phyl wrote about this in the acclaimed Customers Included;
  2. Pattern matching from helping thousands of leaders in Silicon Valley over the last 25 years (through the CG Executive Councils programs). Phyl’s work with the Councils led to the development of Positive Politics, a key coaching program Phyl has used with CEOs, management teams and others (and is explained in the forthcoming Never Lead Alone – expected in 2026);
  3. Deep reading across a range of disciplines – psychology, biology, statistics, philosophy, literature, and others. Phyl is founder of Reading Odyssey, a partnership with scholars and has hosted events with Harvard, Cambridge and others celebrating, among other things, the 150th anniversary of Darwin’s Origin of Species, and the 2,500 year anniversary of the Battle of Marathon;
  4. Profound experience of beauty and art through founding Slow Art Day, a groundbreaking global program inspired by Steve Jobs, running in 1,500 museums around the world, and covered by major press;
  5. Warren Buffett and Charlie Munger – Phyl started the high school business literacy program, WBRG, inspired by these two leaders and refers to these them as their “Dead or Distant” (DOD) Mentors (and teaches and writes about cultivating DOD Mentors).

Phyl has written for the Harvard Business Review, published several books including Customers Included, Never Search Alone, and the forthcoming Never Lead Alone. As mentioned, Phyl and their work has also been written about in books by Marty Cagan and others.

Three Tiers of CG Coaching

  1. PEER COACHING
    This is the heart of our Executive Councils and Associate Councils programs where we have built a Republic of Leaders for Product, GM, CEO (at the Executive Level) and rising starts (at the Associate Level).
  2. CONCIERGE COACHING
    Run by CG Coaches trained by Phyl Terry, this service is for VP/SVP level
    leaders who want to increase their impact and get promoted.
  3. EXECUTIVE COACHING
    This tier is provided only by Phyl and is reserved for two specific kinds of
    clients: 1) EVP+ executives at Big Tech/financial services firms; and 2) CEOs
    of private-equity backed firms.

    Phyl helps smart talented executives play at the highest level – building
    value for their shareholders, customers, teams, and themselves. As noted above, when working with Phyl, clients know they are getting custom, unique insights
    that come from Phyl’s blend of strategic, customer, investor, and psychog-
    ical expertise, plus pattern recognition from coaching and helping more
    than 2,000 leaders over the last 25 years.

Testimonials for CG Coaching

I loved working with Phyl – they know the PE world and the challenges that CEOs face – from working with the board and executive team, to managing M&A, etc. They worked with me every step of the way as I grew the company through multiple exits. Even better, Phyl is independent – i.e., not sponsored by the PE firm so you know they are always working for you.
Amy Kadomatsu, CEO, ComplySci

Phyl is a great coach. They combine business, product, and AI/technology insights, with great psychological insights. They help me play Positive Politics and avoid internal and external potholes as a I build this high-growth AI tech company. Highly recommend.
Rob Pettman, President, Tiffin (former EVP, LPL)

As I work in the midst of the AI revolution, I find myself turning to Phyl more and more for their unique combination of political savviness, AI understanding, and uncanny intuition into what makes me and everyone else here tick. I recommend them to every senior leader I know.
Ron Pessner, Corporate Vice President, Microsoft

I am consistently amazed (and grateful) at Phyl’s ability to help me see things I often don’t see on my own, especially when it comes to working through complex relationships at the highest levels of the company. Can’t recommend enough.
David Rabkin, EVP, Capital One

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