Strategy Session + Brief

When a decision benefits from real-time dialogue and clear written judgment.

The Strategy Session + Brief is designed for complex decisions where written analysis alone is not enough. You need space to talk things through with an expert, pressure-test assumptions in real time, and then walk away with a clear written plan you can act on.

This is not about urgency. It is about depth, clarity, and informed judgment.

chess pieces on board
chess pieces on board
What You Walk Away With

You walk away with both clarity from real-time conversation and a structured written plan you can return to.

The live session allows us to surface assumptions, challenge framing, and work through complexity together. The written brief that follows translates that discussion into a clear recommendation, decision logic, and concrete next steps.

This is not brainstorming. It is judgment, informed by dialogue, then captured in writing.

Time commitment (you): 30 min prep + 90 min session + 30 min follow-up

When Is This The Right Tool

Choose this if you:

  • Want both real-time conversation AND written analysis

  • Have a complex situation that benefits from dialogue

  • Need to talk through options with an expert

  • Want a reference document after the conversation

This is not a good fit if:

  • You want a purely written recommendation with no live conversation

  • Your decision can be resolved without dialogue

  • You prefer to reflect privately rather than talk things through

  • You need ongoing support or access over several weeks

If this sounds like you, the Strategic Brief (Async) or High-Stakes Advisory may be a better fit.

What's included:

• 90-minute intensive strategy session (Zoom or in person)
• Real-time analysis and strategic thinking
• Comprehensive written analysis (8–10 pages) delivered after the session
• Decision framework with a clear recommendation
• Conversation scripts and next steps
• One 30-minute follow-up call (within 3 weeks)

Perfect for:
  • Complex situations with multiple factors

  • Major career crossroads requiring dialogue

  • Situations where you need to "think out loud"

  • Anyone who wants both conversation and written reference

What Makes This Different?

This is not coaching, and it is not therapy. It is also not generic AI advice or facilitated reflection.

What makes this different is the combination of live strategic dialogue and decisive written judgment. We use the conversation to get to the truth faster, then translate that clarity into a written plan you can execute without ambiguity.

The value is not in talking more. It is in leaving with direction.

black pen on white printer paper
black pen on white printer paper
Why this is an investment, not a cost:

For senior professionals, a single misjudged decision at a career crossroads can cost far more than the price of this engagement.

The Strategy Session + Brief pays for itself if it helps you avoid a stalled move, choose the right path earlier, negotiate from a stronger position, or prevent you from committing to the wrong role or direction.

a football field with the words start written on it
a football field with the words start written on it
Ready to work through a complex decision properly?

If you want both real-time strategic dialogue and a clear written recommendation you can act on, this is the right place to start.