Widen the frame first
Before a big decision, we work to see the whole field — the second-order effects, the quiet risks and the options not yet on the table.
Working with Me
An outside perspective, in your corner.
I work with a small number of founders and CEOs as an ongoing outside perspective — someone in your corner who isn’t inside the business, the board, or the cap table.
Most of the leaders I work with are already good at what they do. They don’t need another expert with answers. What’s rarer, and more useful, is someone who helps them see the whole field: the second-order effects, the quiet risks, and the questions they haven’t thought to ask. My job is to create the conditions for clear, honest thinking — the same thing I do as chair of the Montreal group of TIGER 21.
It’s a long game, built on trust and genuinely aligned incentives — fewer relationships, each held to a higher standard. I’m most useful where things aren’t straightforward: complex decisions, long timelines, and the moments with real downside.
How I work
A deliberate way of thinking about hard decisions.
Aligned, for the long term
Long-term, selective partnerships built on trust and genuinely aligned incentives. Fewer relationships, held to a higher standard.
Clarity under uncertainty
Clear thinking when timelines are long and information is incomplete — where most of the value, and most of the mistakes, are made.
Is the situation actually complicated, or is it really quite straightforward — but you’re making it complicated because it requires a lot of courage to make the straightforward decision?
Work with me.
If you want an outside perspective in your corner, start a conversation.
Email Randall