By application · Limited members

The Decision Circle

A monthly working relationship with Christopher M. Donaleski for leaders whose decisions carry weight. Four private sessions a month, group and ad-hoc live work, priority access in between, and the full Validated OS platform — every assessment, framework, and tool we ship.

Investment

$4,997/month

Commitment

Three-month minimum, then month-to-month

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What it is

Not a course. Not a cohort. Not a coaching package.

The Decision Circle is the small room where leaders bring the decisions that matter most — and work through them with someone who has spent two decades inside the gap between what gets decided and what eventually shows up in the world.

Every member has direct, personal access to Christopher — four private sessions a month, plus priority email and chat between them. Group sessions and ad-hoc live work extend the conversation when something timely surfaces. The full Validated OS platform is yours to deploy — every assessment, every framework, every tool we ship — and the research reaches you first as it forms.

One quieter benefit worth naming: the Circle puts you in a small, considered group of high-caliber leaders. The room isn't the reason to join — but it is, almost incidentally, one of the better small rooms you'll be in.

This is the room for leaders who want the work, not the noise.

Inside the Circle

What every member receives

Four private 1:1 sessions per month

Weekly working sessions with Christopher — bring the decision, leave with clarity. Forty-five minutes each, scheduled around you.

Priority email and chat access

A direct line for what surfaces between sessions. Members get priority response — same-day where possible, never longer than 24 hours.

Group sessions and ad-hoc live work

Recurring group sessions for collective thinking, plus ad-hoc live conversations when something timely surfaces. Optional but always available.

Full access to the Validated OS platform

Every assessment, every framework, and every tool we ship inside VOS — yours to deploy on the decisions that matter, with new instruments added as the lab releases them.

First access to the research

Working papers, validator findings, instrument updates — before they reach a wider audience. You see the work as it forms.

Member retreats and themed workshops

Periodic in-person retreats and themed workshops for the Circle. Optional, considered, and designed for the kind of unhurried thinking that doesn't happen on Zoom.

Who this is for

The Circle works best for one kind of leader

You make decisions that shape organizations, capital, or careers.
You have the authority to act on what surfaces — not just diagnose what's wrong.
You want a thinking partner. Coaching is part of the work, but only part.
You can name the parts of your judgment you suspect aren't holding up.

The process

What happens after you apply

Submit your application

Eight questions about what you're working on, who you are, and why this is the right next step. Specific is better than polished.

Discovery conversation

If your responses suggest fit, we schedule a 45-minute call. The purpose is mutual fit — not a sales pitch.

Begin (if mutual fit)

First month begins after the discovery conversation. Three-month minimum, then month-to-month. Stop with 30 days' notice.

Application

Apply for The Decision Circle

Eight questions. Christopher reads every application personally. Response within five business days.

Contact

Who you are

So we know how to reach you and which name to use.

First name*Last name*

Email*

OrganizationWebsite

Phone (optional)

The conversation

What you're working on

Specific is better than polished. These answers help us know whether this is the right room for you.

Your role and the decisions it touches*

Title, scope of authority, and the kind of decisions you typically make (strategic, capital, organizational, M&A, etc.).

Company size and stage*

Approximate team count + revenue range, current stage (growing, mid-market, post-acquisition, etc.).

The decision (or class of decisions) you're weighing right now*

Brief is fine — what's actually on your mind? The more specific, the more useful our conversation.

Why now?*

What's prompting you to seek this kind of support today rather than six months ago — or six months from now?

What have you tried so far?

Coaches, advisors, consultants, books, frameworks — anything you've used to get clarity on decisions like this. Be honest; this saves us both time.

What does success look like three months from now?*

If The Decision Circle works for you, what's different about how you decide and what you've decided?

Where do you most want to be challenged?

The Circle is a thinking partnership. The most useful relationships happen when you can name where you suspect you're wrong.

Anything else you'd want me to know before we talk?

Optional. Context, constraints, timing, hopes, hesitations — whatever feels relevant.

Investment

Acknowledgment

I understand The Decision Circle is a $4,997/month engagement with a three-month minimum (~$14,991 upfront commitment), then continues month-to-month.

Reviewed individually. Response within five business days.

Questions

What members ask before joining

Why three months minimum?: Decisions of consequence take time to surface, weigh, and commit to. One month is enough to feel the shift; three is enough for the framework to become the way you think rather than something you reach for.
What's the difference between your offerings?: We try not to think of them as tiers. Christopher likes to say working with us should feel like opening Uber — three quick questions: where are you, where are you going, and how do you want to get there. Your answers point to a path. The $247 Workshop is for leaders who want the framework in hand and the discipline to apply it on their own. The $749 Coaching is monthly working time with Christopher — two sessions, community access, the assessments, and email and chat between. The Decision Circle is for executives whose decisions move enough that priority access, four sessions a month, group and ad-hoc live work, and the full Validated OS platform earn themselves back in a single decision. Same destination either way: clearer judgment, decisions you can stand behind. Different routes depending on where you're starting from and how you want to travel.
What kinds of decisions do members typically bring?: Capital allocation. M&A direction. Leadership transitions. AI and automation strategy. Board and investor positioning. Organizational redesign. The specific question matters less than this: the decision carries weight, and the cost of getting it wrong is real.
What actually happens in a session?: Sessions adapt to what you bring. Christopher has been in this work long enough to know that sometimes you need a coach — someone to help you see what you've been missing — and sometimes you need an advisor, someone to tell you what they'd actually do. Strategy and conversation can take you part of the way; the rest comes down to execution. Every member meets him at a different point on that arc, so no two engagements look quite the same. What stays constant is the goal: a validated mind. Leaders who make decisions today they'd make again tomorrow, and the day after. That's the only measure of the work that actually matters.
How small is small?: Intentionally limited. We don't publish the number — but the rate of acceptance is low and the rate of renewal is high, by design. The relationship only works if Christopher has real bandwidth for each member.
What if I'm not sure I'm ready?: The real question isn't whether you're 'ready' — it's whether you're weighing a decision big enough that getting it right matters more than getting it fast. The Decision Circle is built for leaders contemplating exactly that. In engagements at this level we consistently see 7–12X return on the work, with validation spend typically running 2–7% of the underlying decision's total cost. The math earns itself any time the decision is real. If you're not weighing one of those right now, start with the book, the Decision Clarity Workshop, or the $749 Coaching tier — and apply to the Circle when the question gets bigger.
What if it's not the right fit after we talk?: Then it's not the right fit. You leave with clearer language for what you're working on, no obligation, and the option to apply again later if the situation changes.

If you've read this far, you already know

The Circle is small on purpose, and not every application moves forward. The room exists because the work is real. If that sounds like the right next step, the application is below.

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