Critical
Conversations
PHILOSOPHY
Some decisions are too important to make in isolation. Some challenges are too complex to navigate without outside perspective. Some moments require someone who can see both the strategic landscape and the psychological patterns at play.
This is single-session strategic support for pivotal moments. Facing a major decision? Navigating a complex challenge? Need sophisticated outside perspective but not ready for ongoing partnership?
Critical Conversations are single, extended sessions (2-3 hours, in-person or virtual) where we dive deep into whatever complex question you're facing. Business transitions. Major decisions. The moments that will shape your business's future.
THE PROCESS
BEFORE THE SESSION
1-2 weeks beforehand, you'll receive:
Detailed questionnaire about your situation, business, and specific challenge
Request for any relevant materials (business info, financial data, etc.)
Pre-work prompts to help you articulate what you're actually facing
DURING THE SESSION
We start with where you are: What's the decision? What's the challenge? What have you already tried? What's keeping you stuck? Then we go deep:
We examine your business situation from multiple angles. Market dynamics. Revenue implications. Operational considerations. Competitive landscape. Growth scenarios. Risk assessment.
Strategic Analysis
Scenario Explanation
We map out potential paths and outcomes. What happens if you do X? What are the implications of Y? What would Z require of you? We explore possibilities without premature commitment.
Concrete Next Steps
We end with specific, actionable next steps. Not vague recommendations, but actions you can take immediately to move forward with clarity.
AFTER THE SESSION
You’ll leave with:
Clarity on the decision or challenge you're facing
Strategic framework for making the choice
Psychological insight into patterns at play
Multiple scenarios mapped with implications
Concrete next steps and action plan
Recording of our session for reference
Within 2 weeks, I’ll share a follow up:
Written summary of session notes, key insights, frameworks, and recommendations
Any resources or tools discussed during the session
One follow-up email exchange (within 30 days) for questions or clarifications
INVESTMENT AND BOOKING
$1,000-$2,500 PER SESSION
Investment varies based on:
Complexity of decision and preparation required
Session length (2-3 hours intensive)
Materials review and analysis needed
Includes:
Pre-session questionnaire and materials review
2-3 hour intensive session (in-person or virtual)
Written summary and resources within one week
One follow-up email exchange (within 30 days)
Logistics:
Book your session—choose your preferred format (in-person or video)
Schedule & prepare—we'll find a date that allows 1-2 weeks for preparation. You complete detailed questionnaire and provide relevant materials
Session—We meet for intensive deep-dive work on your specific challenge (2-3 hours)
Integration—You receive written summary within one week, and the option for a follow-up email exchange (available for 30 days post-session)
Typical timeline from booking to session: 2-4 weeks (sometimes sooner if urgent)