Madonna’s Mystery

December 01, 2021

Madonna begins her 1989 song, Like A Prayer with the line “Life is a mystery.”

Then she sings, “Everyone must stand alone.”


We can and should stand and walk together.

But those two lines raise an important question: Why is not standing alone so powerful? 

That is a mystery.

I have spent decades thinking and working on this mystery. I have figured out some things as you know from past newsletters.

Yet, with all the thinking I’ve done, however, it’s still a mystery.

Let’s explore it.

Yesterday, I had a 1:1 call with a longtime member, we’ll call him Frank, whose job has rapidly expanded over the last year. He now manages thousands. 

Last year, when Frank was first promoted into this expanded role, we decided to run a Peer Coaching Call (PCC) with a small group of Presidents to help coach him in his first 90 days. 

Each of the “coaches” (the other Presidents) talked about their career journey, their challenges running large companies, and how they have learned to manage from 50,000 feet.

One shared how she had convinced the CFO to invest in the customer experience and rebuild their antiquated technology (she had the CFO shadow customer service representatives).

That technique is well-understood. You could read blog posts, articles, and books (including my own Customers Included).

Yet, hearing it from a real person with the real challenges she faced was much more powerful. In fact, it motivated Frank to act in a new way.

Here’s what Frank wrote in a thank you note after the session:

I was truly impressed with how you each handled similar situations. It was inspiring and changed my approach.  I have reread my notes a few times already. You challenged and energized me.  

Note what Frank said: “inspired”, “challenged”, and “energized”, and, importantly, “changed.”

What’s going on here?

Especially that last part — why did Frank leave changed?

One of the big challenges for leaders is bridging what I call the “knowing-doing gap” – i.e., you know what to do, but don’t act on it.


The mystery came up again yesterday on yet another PCC. 

A member, Sarah, who has been managing 10 people just received a promotion and is now managing 50 product, design, and analytics people. 

Like with Frank’s PCC, no brilliant solutions were offered. 

No counter-intuitive genius insights were revealed to Sarah.

Then I asked: what did you do wrong when you were first promoted to managing 50 or so people? 

The coaches poured out their answers.

You could feel their excitement to learn about each other’s fumbles and foibles.

One member shared how, after her promotion, she was being “too smart.”

I was being too smart. I needed to not be smartest person in room. Instead, I had to get comfortable with managing from this level and giving room to my leaders to lead. You will never have same detailed info that you had when managing 10 people. So, you have to have confidence in the individuals working with you – that they have the same guideposts that you have and that you can trust and get out of their way.

Again, like with Frank this advice was not revolutionary.

You can pick it up in any book or blog post about learning to manage.

Yet, Sarah, like Frank, didn’t just get advice, she got the motivation to actually act and do something different.


We run about 150 of these PCCs a year (in addition to the hundreds of council meetings). We do a post-call analysis with every member and I get to read every one of those reports. 

Here’s the remarkable thing: nearly all are stellar. 

In the Foreword for my next book, Marty Cagan talks about the magic of community. 

I think that’s the right word. This often feels like magic.

What do you think? 

Why is not walking alone so powerful?



Winter Series

  • Elder Fraud, Financial Mistakes and Caregiving  – Thu, Dec 2 @3pm ET
    Howard Tischler, Co-Founder and CEO, and Liz Loewy, Co-Founder and COO, EverSafe

    To registerClick here to email Britany Chism (register your teams to join too!)
     Many members are facing challenges with aging parents (and managing employees facing challenges with aging parents) and asked us to bring in experts from time to time who can help.  

    We found two amazing people (through one of our longtime members).

    Liz Loewy, co-founder of EverSafe, was the founder of the Manhattan District Attorney’s first Elder Abuse Unit, and served as trial counsel in the prosecution involving elder abuse of the late philanthropist, Brooke Astor. In addition, Liz has served as a caregiver for her parents and grandparents.

    Howard Tischler, co-founded EverSafe after his mother was financially exploited and lost her life savings. Howard will discuss what happened to his mother and how he managed his joint corporate and caregiving responsibilities while serving as a Group President and Lead Director in public companies. 

    There will be a robust Q&A session.  Come ready with your own stories or stories from your workforce (and invite your colleagues to join as well, if you like).

Fall Keynotes

  • The What & Why of Continuous Discovery
    Teresa Torres, Author, Speaker, and Product Discovery Coach

    Most product teams are starting to adopt discovery best practices (e.g. interviewing customers, usability testing, experimenting). However, many of us are still stuck in a project world. We do research to kick off a project, we usability test right before we hand off to engineers, and our primary means for experimenting is a/b testing. These methods are better than nothing, but the best product teams are shifting from a project mindset to a continuous mindset. In this talk, we’ll explore the key differences between project-based discovery and continuous discovery and give your team a clear benchmark to aspire to.

    Bio: Teresa Torres is an internationally acclaimed author, speaker, coach, and longtime friend of the Councils (she was a moderator of one of our Product Councils at one point). She’s coached hundreds of teams at companies of all sizes, from early-stage start-ups to global enterprises, in a variety of industries and has taught more than 7,000 through her Product Talk Academy. She’s the author of the recently published book, Continuous Discovery Habits, and blogs at
  • The Hows and Whys of Hybrid Work
    Jaime Teevan, Chief Scientist for Microsoft’s Experiences and Devices
    with moderator Ron Pessner, Vice President of Product, Microsoft

    Jaime Teevan, Chief Scientist for Microsoft’s Experiences and Devices, is charged with creating the future of productivity at Microsoft and for its customers. As part of that effort, she helps lead the New Future of Work: the largest research initiative in Microsoft’s history with hundreds of researchers from across Microsoft, LinkedIn, and GitHub. Their task is simple (and very hard): make this new future of work – in office, remote, and especially hybrid – possible and productive. Jaime Teevan, and moderator Ron Pessner, will provide an overview of what Microsoft has learned and will offer tips for effective and inclusive hybrid work.
    Jaime Teevan is Chief Scientist for Microsoft’s Experiences and Devices, where she is responsible for driving research-backed innovation in the company’s core products. Previously she was the Technical Advisor to Microsoft CEO Satya Nadella and a Principal Researcher at Microsoft Research, where she led the Productivity team. Dr. Teevan uses AI to help people accomplish their goals, developing the first personalized search algorithm used by Bing and introducing microproductivity into Office. Her groundbreaking research has earned her numerous awards, including the Technology Review TR35 Young Innovator and Karen Spärck Jones awards. She holds a Ph.D. from MIT and a B.S. from Yale, and is an affiliate professor at the University of Washington.
    Ron Pessner, a longtime CG Councils member, is in charge of collaboration across the Microsoft 365 collaboration suite (that span across Word, Excel, PPT, etc). He has spent 18 years at Microsoft and has done a number of things including GM for Games for Windows, senior role at Xbox, led Windows 10 for Window Phone, and multiple roles in the Office organization. Prior to Microsoft he worked with a number of startups in the early days of the web and mobile internet. 
  • Heartwood: The Art of Living With the End in Mind
    Barbara Becker, Author

    To access recording (Council members only)Click here to email Britany Chism
     For our second Fall Meeting keynote, Barbara Becker, author of Heartwood invites us into a conversation about the art of living.Members of our Councils are facing difficult life moments now, as they have in the past and as we each will in the future. With this talk, we help deepen the trust and safe space needed for members to be vulnerable, find support and connection, and, of course, ask for help throughout the meetings and beyond.We also hope to reveal, for your own reflection, the individuals and events in your life that shaped who you have become as a person. In work, and in our daily lives, we aren’t often granted the opportunity to name and to process the people we love, the challenges we face, and the difficulties that become part of us – that become our own Heartwood.Bio: 
    Barbara Becker is an ordained interfaith minister and has sat with hundreds of people at the end of their lives. Barbara speaks on a wide range of topics, including deepening our sense of meaning and spirituality and mid-career pivots.  She has dedicated more than twenty-five years to partnering with human-rights advocates around the world in pursuit of peace and interreligious understanding. She has worked with the United Nations, Human Rights First, the Ms. Foundation for Women, the Grameen Bank of Bangladesh, and teaches at Columbia University

Previous 2021 Talks

  • Battle Buddies – A Way to Support Your Teams
    Craig Hopkins, CIO, City of San Antonio
     Join Craig Hopkins for this short webinar focused on Q&A to introduce an idea that has taken off in Craig’s org, the City of San Antonio, where he is the CIO.It’s called Battle Buddies. So, what is a Battle Buddy?Adapted from the US Army, a battle buddy is a partner assigned to an employee in an organization who is expected to assist his or her partner.Even though we are not in military combat, Craig says our corporate responsibilities can feel just as stressful and overwhelming at times.A battle buddy is not only intended for comradery and support, but also to help reduce stress, provide professional and leadership guidance, and at times, get into the trenches together to get things done. Since we will each be watching each other’s actions, we are all battle buddies to each other, as partners and as a leadership team, driven by our mission while adhering to our Core Values.Craig will talk about how this has worked in his organization and how to set it up in yours.
  • Clubhouse and the Audio Revolution (not recorded)
    Jonathan Ehrlich, Partner, Foundation Capital
     Two things to know about Jonathan Ehrlich:
    1) he co-led the seed round in Clubhouse and was thus the first venture capitalist to spot its potential;
    2) he’s a Councils alum with an interesting career arc.We held an informal conversation with Jonathan about Clubhouse, the future of audio, and Jonathan’s career journey from a mostly offline retailer in Canada to relocating to Silicon Valley and reinventing himself.

    Jonathan Ehrlich is a Partner at Foundation Capital who invests in early early-stage consumer, marketplace, commerce, and SaaS startups and technologies. He joined Foundation Capital in 2013 as a partner after spending nine months with the firm as an entrepreneur-in-residence. Before joining Foundation Capital, Jonathan spent 17 years as an operator during which he founded three companies, built a $100M+ revenue business, and ran marketing for Facebook. He is the first institutional investor in Clubhouse and currently sits on the board of Bulletin and Chord. His Foundation and personal investments include Shelf Engine, Mainstreet, Truepill, Hooked, WayUp, League, Front, and Flexport. When not working, he can be found on his bike or chasing his four kids around.
  • JTBD in Large Distributed Environments
    Jay Haynes, Founder & CEO,

    Jobs To Be Done has proven to be an effective methodology for building much better holistic end-to-end products and customer experiences.

    *But* CG Council member companies with large distributed environments are finding it difficult to apply JTBD in effective ways.

    Jay Haynes, CEO of thrv, and a global expert on JTBD will come and speak to the Councils community on this specific challenge of using the methodology in large, complex technology environments.
  • See talks from the last month and beyond here.​

About the Author

Phyl Terry

Phyl Terry, Founder and CEO of Collaborative Gain, Inc., launched the company’s flagship leadership program – The Councils – in 2002 with a fellow group of Internet pioneers from Amazon, Google, and others. Thousands of leaders from the Internet world have come together in the last 15 years to learn the art of asking for help and to support each other to build better, more customer-centric products, services, and companies.

Post navigation
Scroll to top