One conversation. Direct questioning. A written record of every gap.
If it doesn't produce real clarity, you don't pay.
Five signs your plan needs a stress test before the market gives you one
Nobody Actually Challenged It
You're too close to it. The people around you are too close to it, or worse, they're too polite to ask the questions that break it.
You Feel Sure. You're Not Sure Why
That's usually a sign the plan was never actually tested, just believed. You can't read the label from inside the bottle.
The Gap Always Surfaces Eventually
In a client meeting, an investor pitch, or a bank account. A conversation is a cheaper place for it to show up first.
You've Been Building This Alone
Nobody around you wants to be the one who pokes at it. We do.
Every Plan Hides One Word
A word standing in for a step you never actually worked out. We find it, one question at a time.
The Results Are Real
"I went into Strategic Dissent confident in a system I had built over months. I came out with the same conviction and a much clearer picture of what I would need to defend. Jason is not there to tell you your idea is good or bad. He finds the places where you have been assuming instead of knowing, and asks about them directly, one at a time, until you either have an answer or you do not. Three of his questions changed what I am doing. One of them stopped an entire channel I had been planning to pursue until I resolve it properly. If you are confident in your idea, that is exactly when this is most useful."
"The Strategic Dissent session gave me a valuable thinking partner as I worked through a specific leadership challenge. Jason's thoughtful, step-by-step approach helped me examine the issue from different perspectives, validate my approach, and move from uncertainty to a clearer path forward with concrete next steps."
"Jason guided me through a complicated business case involving movement of resources to a global staffing model. There was high risk to the company--business continuity, client experience and a large up front investment. Jason's agent/tool allowed me to dig deeper into the project plan and the analytics that had been previously prepared. The work proved out that the budget and timelines were solid, and also prodded me to go deeper on the leadership hierarchy resulting in a more effective structure to staff, train and retain globally."
"Strategic Dissent gave us an objective, direct way to work through a brand decision we would likely have debated for hours. It surfaced the assumptions underneath our thinking, helped us separate what we knew from what we were guessing, and gave us real clarity on the path forward."
How The Session Runs
Bring what you're thinking, decided or not
An idea you haven't run past anyone yet, a plan you're about to commit to, or something already in motion. The only requirement is that it's real, not hypothetical.
We have a guided, blunt conversation
Roughly an hour, back-and-forth. Your assumptions get named and pushed on the way a sharp, skeptical peer would — not a coach nodding along.
You leave with a written debrief
What got tested, what changed, what's still open, with gaps identified, with next steps and actions attached — not just notes from a conversation.
Ask a chatbot a question, get an answer. Run a Strategic Dissent session, get cross-examined.
What This Is, And Isn't
Strategic dissent is
A place to think clearly under pressure
A structured way to challenge assumptions
A fast route from ambiguity to next steps
Direct, practical feedback on what may be missing
Strategic dissent isn't
Done-for-you execution
Ongoing accountability coaching
A guarantee that a particular strategy will work
Three Ways To Work Together
Start with the free assessment if you're unsure which fits.
Recommended
Strategic Dissent Sprint
$1,500
Guided Strategic Dissent + two 30-minute check-ins over two weeks
For decisions that need more than one conversation. The full guided session, plus follow-ups to review progress and refine the direction as new information comes in.
You'll receive
—One 60-minute guided strategic dissent session
—Detailed written debrief, gap analysis, open items, and action list
—Two 30-minute refinement sessions over the following two weeks
—Additional stress-testing as the work develops
—Updated priorities and next steps
The check-ins begin only after the guided session has delivered real insight.
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Guided Strategic Dissent
$850
One session
A focused session to stress-test a decision, offer, project, or direction. Bring a deck, notes, a rough idea, or just talk it through live. We provide an intake form to guide you.
You'll receive
—A guided 60-minute working session
—Direct questioning that tests assumptions and surfaces what's missing
—A detailed written debrief including a Gap analysis with open Questions and Actions to resolve
A clearer, evidence-tested direction and a practical path forward.
Insight guarantee — if it doesn't produce real clarity, you don't pay
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Free Assessment
Free
30 minutes
A short call where we'll walk through the process, discuss what you need to stress-test, and decide whether this is right for you.
We'll clarify
—The decision, idea, offer, or project in front of you
—What feels unclear or stuck. Your hypothesis.
—The outcome you need from the process
—Whether this is the right format for the problem
No commitment, no preparation needed.
Insight guarantee
If it doesn't produce real clarity, you don't pay
If the session doesn't produce meaningful new clarity, insight, or a useful next step beyond what you brought in, you don't pay.
Meaningful value includes
—A previously unseen assumption, risk, or gap
—A clearer decision or narrowed set of options
—A question that materially changes what needs validation
—A concrete next action you didn't already have
About Me
During my 25+ years in the corporate world, I was never the one to nod along and agree just for the sake of it. Not so much a contrarian, but always asking the questions that no one else would — poking at why something may not work, why it might not be the best decision, and what could be done differently. "Wow, you ask a lot of questions" was often followed by "we never thought of that," "that's a great idea," or "we should look at that again."
Why this exists
This started years ago as a habit, not a plan - something I would just naturally do with people over a meal or as part of normal conversation. It didn't have a name or a process. It was just Jason being Jason. It helped me build a reputation as being a bit of a "trusted advisor" or "consigliere" to people.
It took some time, some coaching, and self-testing, but I was able to identify a process, a formula and a system for what I was doing. Building a tested and validated AI-assisted process was the goal. Mission accomplished. It's my process with the benefit of a bigger brain :)
