Define the unit of work.
Labels vary between providers. Some coaching engagements emphasize questions and reflection; some advisory engagements also offer an experienced operator’s perspective. Ask how the person actually works and what the engagement includes.
At Proving Ground Advisory, private 1:1 work combines reflection, direct advisory conversations, practical planning, and accountability. Organizational Commercial Performance Advisory has a separate scope. The distinction is who owns the challenge and what work the engagement needs to support.
| Question | Individual leadership engagement | Organizational commercial engagement |
|---|---|---|
| Who is central? | A leader taking on a consequential next move | The organization and stakeholders responsible for a commercial issue |
| Typical focus | Priorities, judgment, delegation, communication, accountability | Commercial leadership, portfolio focus, in-market execution |
| Working material | The leader’s decisions, commitments, and operating plan | Agreed business evidence, stakeholders, and execution constraints |
| Scope at Proving Ground | The 90-day Next Level Engagement | Defined after a conversation about organizational needs |
Use the problem statement to choose.
“I have taken on a larger role and need to stop being the decision bottleneck” is a clear starting point for individual work. “Our teams and partners disagree on portfolio priorities and ownership” points toward an organizational issue.
Some situations contain both. Name them separately so the engagement does not quietly grow beyond what was agreed. A leader’s development plan should not be treated as a substitute for an organizational decision that requires other stakeholders.
Questions to ask before choosing an advisor
Ask for examples the advisor is permitted to discuss. Distinguish the advisor’s prior operating experience from results achieved for advisory clients. Neither a job title nor a testimonial guarantees an outcome for your situation.
- What experience is relevant to this situation, and where are the limits of that experience?
- How much of the work involves reflection, direct advice, analysis, or facilitation?
- What preparation, meetings, and work between sessions are expected?
- What tangible plan or decisions should the engagement help produce?
- Who needs to participate, and who owns decisions after each session?
- How will progress be assessed against the starting situation?
- How will confidentiality, payment, scope changes, and ending the engagement be addressed in the agreement?
Prepare for a useful introductory call.
Write three short statements: what is changing, what decision or execution gap matters most, and what you would want to be different at the end of the work. Add who owns the problem and what you have already tried.
For an individual leader, the Next Level Engagement is 90 days of private 1:1 advisory, beginning with a 75-minute strategy session and continuing through weekly sessions. Organizational work begins with a separate scope discussion. An introductory call helps establish fit before either path begins.