Understory Advising

Clear perspective when it’s hard to see the forest for the trees

When you’re deep inside a business, it’s hard to see the forest for the trees.

Teams carry context, incentives, and risk. Leaders carry responsibility and consequences. Even capable organizations can struggle to name the real issue clearly, ask the uncomfortable questions, or turn complexity into decisions that actually stick.

Understory Advising exists to provide calm, independent perspective when proximity makes clarity difficult.

Why an outside perspective helps

I come in from the outside to ask the questions that haven’t been asked, surface patterns that are hard to see from within, and help leadership teams boil complexity down into clear decision points and well-defined goals.

I work directly with a small group of core decision-makers and a broader stakeholder set as needed. The focus is structural, not cosmetic, and practical rather than theoretical.

This work is direct by design. I’m hired for clarity, not comfort.

What I do

  • Founder-led or investor-backed businesses

  • A small group of clear decision-makers

  • Organizations facing repeating or unresolved problems

  • Leaders who want an honest outside view, not validation

  • Teams ready to make decisions and stand behind them

This is not coaching or implementation work.

Who this work is for

The Decision Sprint

A focused engagement designed to bring clarity to complex or high-stakes decisions.

  1. Intake with 2–3 core decision-makers

  2. Select stakeholder conversations as needed

  3. Independent analysis of operations, risk, and constraints

  4. Clear articulation of the real problem beneath the symptoms

  5. A concise written decision memo outlining options and tradeoff

What it includes

Format

4–6 weeks. Highly focused. Minimal lift for your team.

Investment

Most Decision Sprints range from $8,000–$15,000, depending on scope and complexity.

Making decisions stick

Good decisions don’t always survive execution. Priorities shift, interpretations soften, and original intent can quietly erode.

Understory Advising offers two follow-on options for leaders who want support without handing over implementation.

Decision Integration
A short engagement focused on translating decisions into ownership, sequencing, and guardrails.

Implementation Oversight
Ongoing advisory support to help leaders maintain clarity, notice drift early, and navigate resistance as decisions are carried forward.