A transformation readiness assessment for executive teams, including AI and the leadership, strategy, people, and structure needed to act on it.
Where Do You Stand Before the Next Major Change?
I help you see where to begin, what to address first, and how quickly to move.
Readout in three to four weeks. A 90-day plan your team owns.
How much work is needed?
What needs attention first?
How quickly can you move?
Across the six areas of my Repeatable Transformation™ Framework
AI is changing what your business can do. Leaders may have different priorities, teams may be stretched, and key decisions may still be unresolved.
I examine those conditions together, showing strengths, constraints, and the decisions needed to move forward.
The result is a picture you can act on.
For leaders, owners, boards and private equity operating partners preparing for major change.
AI initiatives move faster than the strategy that guides them.
There is misalignment about priorities and/or their roadblocks.
Work, roles, or decision rights need to evolve, but it's unclear how.
New initiatives will only compete for capacity that does not exist.I examine each area through five levels of practice, from unresolved questions to habits your company can review and improve.
| Area | Unexamined | Named | Aligned | Operating | Repeatable |
|---|---|---|---|---|---|
| Leadership Alignment | Leadership purpose, authority and expectations remain unresolved. | A leader has proposed a direction or a different way to lead. | Leaders agree on the purpose, decision authority, and expected behaviors. | Agreed expectations guide real decisions and executive follow-through. | Leaders review outcomes, adapt their practice and apply learning to the next change. |
| Corporate Strategy | Priorities and tradeoffs are unresolved or driven by inherited assumptions. | A strategic position exists, but the team has not agreed about its implications. | Leaders agree on priorities, customer value, and what can stop or wait. | Investment, resource and operating decisions follow the agreed strategy. | Leaders revisit strategy against outcomes, new evidence and changing possibilities. |
| AI & Automation | AI use and its consequences lack deliberate oversight. | AI opportunities or boundaries have been named without shared ownership. | Leaders agree on the intended value, human authority, and appropriate usage boundaries. | Actual work tests the agreed human and AI contributions, controls and outcomes. | Owners review results and changing capabilities, then adapt how people and AI work. |
| Workforce & Skills | Capability needs and workforce consequences have not been examined. | Skills gaps or role changes have been identified, but a shared solution does not yet exist. | Leaders agree about needed capabilities, learning priorities, and transition principles. | Role, development and workforce decisions use evidence and examine alternatives. | Owners revisit capabilities and roles, retain expertise and learn from workforce outcomes. |
| Org Design & Ways of Working | Accountability, decision rights and workloads remain unresolved or inherited. | Changes to structure or working practices have been proposed. | Participants agree on accountability, decision rights, and how work flows. | Decisions, handoffs and operating rhythms work in practice; workload is checked. | One person is accountable for every seat and the operating model is reviewed and adapted as work changes. |
| Culture & Employee Experience | Human consequences and barriers to change receive little deliberate attention. | Concerns or desired cultural changes have been named. | Leaders agree how people will contribute, raise concerns and understand change. | Employee evidence informs decisions, responses and changes to working practices. | The organization repeatedly learns from employee experience and adapts through change. |
Different areas may be at different levels. Your priorities, evidence, and capacity determine what to do next.
A missing document does not establish a missing practice. Real decisions and informal practices count as evidence. When evidence is insufficient, I leave the finding uncertain.
Use the findings independently, with existing partners, or with me.
A diagnostic report across all six areas, showing strengths, gaps, meaningful differences and what remains uncertain.
A three-hour working session to examine the findings, make choices and establish the next steps together.
Priorities with owners, first steps, timing and evidence of completion. A practical plan your team can begin carrying out.
A two-page account of the business stakes, key findings, decisions needed and resource implications for your board or owners.
I recommend where to focus, what needs attention first, and how quickly to move.
How I workThree to four weeks, with timing agreed around your team’s availability.
Define
You and I agree on the decisions, participants, and available evidence.
Listen
Executives complete individual questions and focused interviews. Existing records and real examples add context.
Interpret
Findings are reviewed across the six areas, with differences and uncertainty made explicit.
Decide
The executive readout turns findings into agreed priorities, ownership, and a 90-day plan.
Plan for 30-40 minutes for the questionnaire, a 30-minute one-on-one interview, and a 3-hour team readout for each participating executive. Sponsor preparation and evidence coordination require additional time.
Designed for companies with $20 million or more in annual revenue and executive teams of three to twelve.
Smaller teams are welcome. One leader may cover several functions; no particular title structure or polished document library is required.
$15,000
Fixed fee for the standard assessment
Additional business-unit assessments, broad employee research, technical testing or in-person delivery are scoped separately.
Start a ConversationNo. I examine how leadership, strategy, AI, work, and people support the change ahead. Individual responses show different perspectives; deeper discovery can follow where needed.
I can use decision walkthroughs, operating examples, or corroborated accounts. Missing documents do not automatically mean low readiness. Unsupported conclusions remain uncertain.
No. I use stated behavioral criteria and your company’s evidence, not industry rankings, external benchmarks, or a single numerical grade.
You and I agree on confidentiality and evidence access before collection. The sponsor receives aggregated findings. Small teams cannot be promised full anonymity; attributable quotes require permission.
Absolutely. Your team receives the reasoning, priorities, and next steps. You can act internally, use another partner, or continue with me. The assessment does not include full design and implementation across the six areas.
After the assessment, you can continue with me as a fractional or interim executive.
If you continue into a fractional engagement, there’s no second discovery phase. The assessment and 90-day plan are already done, so we start on the work in week one.
Share what changes you're considering, why it's important now, and where the starting point may feel unclear. Or email deidra@thewholeenterprise.com