A quiet, softly lit architectural room with upholstered chairs, prepared for a private conversation

Private advisory & coaching

When the way you have been leading is no longer the way forward.

I work privately with CEOs, founders, and owners to make decisions they can stand behind.

Begin a confidential conversation

A place to say what is difficult to say elsewhere

Some questions are difficult to discuss with the people closest to the situation. Your board needs confidence. Your peers may have a stake in the outcome. Your team looks to you for direction. Family relationships may be part of the decision itself.

I bring more than two decades of operating and consulting experience. In our work together, we explore the business question and the assumptions you bring to it.

See what’s influencing your decisions so you have more choice in what you do next.

When this work is useful

  • A decision you can’t discuss openlyYou face difficult decisions that you cannot fully discuss with your board, peers, team, investors, or family.
  • Too much depends on youYou have capable people and have delegated responsibility, but still spend much of your time following up and making sure the work gets done.
  • Work follows you homeYou want to be present with loved ones, but keep thinking about what you have not finished and what needs your attention next.
  • The pressure has not easedYou have more than you once thought you would ever need, but still find yourself wondering whether it is enough.
  • You are preparing to step backA new hire, succession, exit, or change in role is on the way. You are working out how to hand over responsibility and what you want to do next.

If one of these describes you, begin a conversation.

Experience behind the work

My background includes senior leadership roles at Walmart, Procter & Gamble, Indigo, and GoBolt, where I co-led a $115M financing.

I am Founding Partner of Anther, a leadership advisory and development firm, and CEO of Strongpoint Group, a boutique operations consultancy based in Toronto.

I hold an MBA from Cornell University and a Master of Applied Positive Psychology from the University of Pennsylvania, where I am an Assistant Instructor. My work combines operating experience with research on how people make decisions and change established patterns of behavior.

I am also the author of A Guide to Thriving, published by Wiley.

A modernist meeting room with a solid-wood table and a glass wall opening onto a forest

What you want to change

For many of my clients, the goal is greater agency: more choice in how you lead and respond.

You can achieve a great deal and still feel bound to the habits and expectations that got you there. Greater agency helps you recognize options you may have stopped seeing and act on what matters to you now, even when you cannot control the outcome. It gives you more say in how you lead and how you want to live.

What we work on

We examine the assumptions behind the decision, which often changes the question itself. We then work through the options and their consequences.

I bring my operating background to the discussion and challenge your thinking where I see things differently. My own reading of the situation is open to question too. You remain accountable for the final call.

Between conversations, we compare what you intended with what actually happened to inform what you try next.

We examine the gap between what you intend and how others experience your leadership, including what they may find difficult to tell you.

From those I work with

“I was caught in the weeds and doing too much myself. Working with Jon helped me recognize when to step back and give my team the space they needed to take on more responsibility. A big shift for me.”

— Third-generation CEO, family-owned enterprise

Working together

  1. Send a short noteBriefly describe what brings you here. Leave sensitive details for our conversation.
  2. Introductory conversationWe speak one-to-one to understand what’s happening and determine whether working together makes sense.
  3. EngagementIf we proceed, we agree on the focus, the length of the engagement, meeting frequency, and the fee before we begin.

This work asks for a willingness to examine your own role in the situation and try something different.

Praise for A Guide to Thriving

A Guide to Thriving by Jon Rosemberg, hardcover book

Not every situation calls for an active engagement. For those not currently seeking one-to-one or team advisory work, in A Guide to Thriving (Wiley, 2025), I examine how familiar patterns limit our agency and how we can recover more choice.

“Grounded in science, this is a human-centered approach to changing our stories and our actions.”

— Seth Godin, author of The Song of Significance

“A remarkable place to help you expand your options, ground your decisions, and align you with the people you care about.”

— Guy Kawasaki, host of the Remarkable People podcast and chief evangelist of Canva

Begin a conversation

Send me a few lines about what’s on your mind. You don’t need to have a clear question or know exactly what you’re looking for. We’ll speak privately and decide together whether working with me would be useful. There’s no obligation to go further.

If you’d like to refer someone, a brief note is enough. They can share their circumstances with me directly.

A brief outline is enough. Please leave sensitive details for our conversation.

Jon Rosemberg