Who’s Actually in This Room?

• Please list the names, titles, and primary reporting lines of the people who will evaluate and approve this transformation (include board liaisons or external advisors).
• Which of those individuals are operational owners, which are executive sponsors, and which are influencers/advisors? Options: Operational owner, Executive sponsor, Influencer/advisor, External consultant, Board liaison, Other
• Who among them will be the visible, regular champion of the program in executive forums? Options: CEO, COO, CHRO, CFO, Business unit leader, No sponsor identified yet, Other
• How confident are you that the named sponsor will actively and visibly advocate for this work over the next 12 months? Options: Very confident, Somewhat confident, Neutral/Unsure, Not confident
• How does the sponsor’s current level of engagement feel to you and the team—energizing, cautious, or a potential risk?

Are We Mistaking Agreement for Alignment?

• When the leadership team says 'we’re aligned,' how often is that genuine agreement versus polite acquiescence or trade-offs kept private? Options: Mostly genuine, Often mixed, Frequently polite agreement, Rarely aligned
• Can you describe a recent decision that looked aligned in the room but fell apart later—what warning signs did you miss?
• Which stakeholders are most likely to privately disagree with the proposed direction, and why? Options: Business unit leaders, Functional leaders (HR/IT/Finance), Long-tenured managers, Board members, External partners, Other
• What incentives or governance quirks cause people to say 'yes' publicly but resist in practice (e.g., budget protection, headcount anxiety, political capital)?
• If we had to surface and resolve those private disagreements, how long and what forum would be required? Options: A single workshop, Several focused meetings over weeks, Executive offsite, Requires board discussion, Unsure

Who Holds the Real Decision Rights?

• If this work became contentious, where would people go for the final say—who actually makes the call? Options: CEO, Board, COO, CHRO, CFO, Consensus of SLT, Business unit leader, Other
• For these decision types—strategy, org design, headcount changes, budget reallocation, vendor selection—who do you expect to own the primary decision for each?
• Are there formal approval thresholds (e.g., budget limits, signoff levels) or informal veto points we should map now? Options: Formal thresholds exist—documented, Formal thresholds exist—partially documented, No clear thresholds, Unsure
• Which individuals or informal powerholders (networks, long-tenured leaders) influence outcomes outside formal governance? Give an example.
• How should we balance centralized decision rights with local autonomy to reduce pushback?

Who's Quietly Cheering — or Sabotaging?

• Who stands to lose the most if this transformation succeeds—and why might they prefer the current state? Options: Status-quo leaders, Owners of legacy systems, Certain vendors/outsourcers, Roles at risk of headcount reduction, Other
• Who stands to gain most from success (identify specific stakeholders and gains—e.g., faster go-to-market, lower cost base, clearer career paths)?
• Which groups have a track record of blocking change in this company, and how did they do it (e.g., delaying, questioning data, public messaging)?
• Which people or teams are likely to resist openly, and which are likely to resist quietly—how will those behaviors show up? Options: Open resistance (public objections), Quiet resistance (non-compliance), Both, Neither/Unsure
• What tangible steps have you seen that successfully converted a resister into a supporter here?

What 'Good' Really Means to Them

• If you asked each key stakeholder to define 'success' in one sentence, how different would those definitions be? Options: Very aligned, Some overlap with differences, Mostly different, Completely divergent
• What is the CEO’s primary measurable outcome (e.g., revenue growth, cost reduction, integration milestones) that this program must deliver? Options: Revenue growth, Cost reduction, Integration / synergy capture, Speed to market, Customer retention, Other
• What is the CHRO’s primary success metric (e.g., retention of top talent, cultural adoption, reduced span of control)? Options: Retention of key talent, Faster hiring/ redeployment, Clear career paths, Improved engagement scores, Other
• What short-term performance dips would stakeholders accept, and what is absolutely off-limits? Options: Acceptable short-term dip in productivity, Acceptable short-term cost increase, No acceptable dips, Depends on stakeholder
• How will we visibly measure and report progress so each stakeholder sees their own version of 'good' being addressed?

Timing, Windows, and Political Calendars

• Are there hard external or internal dates (board reviews, merger milestones, fiscal close, compensation cycles) that make alignment non-negotiable by a certain date? Options: Board presentation, Merger/Integration milestone, Fiscal year planning, Compensation cycle, Regulatory deadline, No firm date, Other
• What critical windows should we avoid for major change (e.g., annual performance review, peak customer season)?
• Are there upcoming leadership transitions or reorganizations that could reset alignment? If yes, who and when? Options: Yes—executive level, Yes—business units, No, Unsure
• If alignment takes longer than planned, what is the realistic flexibility in your timeline and budget? Options: Very flexible, Somewhat flexible, Tight—minor slippage only, No flexibility
• How should we prioritize alignment work against delivery urgency—front-load alignment activities or run design in parallel with alignment? Options: Front-load alignment, Run in parallel, Hybrid—align critical decisions first, Unsure

What We Learned From Past Attempts

• When previous transformations in your organization failed or stalled, what was the single most common root cause? Options: Leadership drift, Misaligned incentives, Insufficient change management, Unclear decisions, Technology/data failures, Other
• Tell the story of the last initiative that didn’t stick—what early signals we should watch for now?
• Which parts of the organization show the highest change fatigue today? Options: Frontline teams, Middle managers, Senior leaders, Support functions (HR/IT/Finance), No notable fatigue, Other
• How does change fatigue typically express itself here—delayed decision-making, passive compliance, increased turnover, or something else?
• What specific tactics have successfully rebuilt momentum after a stalled change (e.g., quick wins, targeted coaching, incentive realignment)?

Governance That Actually Works

• Where does your current governance process create honest trade-offs rather than theatrical sign-offs—and where does it break down? Options: Strong—regular, candid reviews, Inconsistent—depends on forum, Weak—sign-off only, No formal governance
• What cadence do you prefer for governance during discovery, design, and deployment phases? Options: Weekly, Biweekly, Monthly, Quarterly, Ad hoc as needed
• Who should chair governance meetings and be accountable for action items—role rather than name? Options: CEO, COO, CHRO, Program sponsor, PMO lead, Other
• What escalation path would you want if critical leaders disagree—who steps in and how quickly?
• How will we know governance is enabling progress (list 3 observable indicators we should track)?

Real Commitments: What We Need From You

• If the CEO had to make one non-negotiable commitment right now to de-risk this program, what should it be? Options: Attend/lead steering meetings, Provide visible sponsorship in town halls, Authorize dedicated budget, Empower decision rights, Allocate senior leader time, Other
• How much leadership time per week/month can be realistically dedicated to sponsorship and governance? Options: <2 hours/week, 2–5 hours/week, 5–10 hours/week, 10+ hours/week, Monthly touchpoints only
• Which roles must be explicitly empowered to make trade-offs without re-opening every decision to the full leadership team? Options: Program sponsor, Business unit leaders, Function leads, PMO, Steering committee, Other
• What commercial or political red lines must we avoid (non-starters) so recommendations are practicable?
• If misalignment emerges mid-program, what immediate actions would you expect leadership to take? Options: Emergency alignment workshop, Executive mediation, Pause and reassess, Escalate to board, Other

Readiness & Next Steps — Where We Go From Here

• On a 1–10 scale, how confident are you we can secure the alignment needed to move to design within your current timeline? Options: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10
• What specific evidence or changes would move that confidence score up by two points?
• Who should we meet next to validate this stakeholder map and surface any missing influencers (name or role)?
• Which immediate alignment actions are you willing to commit to in the next 14 days? Options: Confirm visible sponsor, Schedule steering cadence, Clarify decision rights, Secure initial budget, Assign dedicated PM/PMO, Other
• Are there any questions, concerns, or sensitive political dynamics you'd like us to treat as confidential as we proceed?

Start Here: What Brought You to This Door?

• Briefly describe the immediate trigger or moment that made you consider an operating model redesign now.
• Which of the following best captures that trigger? Options: New corporate strategy, Post-merger integration, Board-mandated turnaround / cost directive, Digital/technology transformation, Regulatory or compliance pressure, Other
• How long has this been an explicit priority on the executive agenda? Options: Weeks, 1–3 months, 3–6 months, 6–12 months, Over a year
• Who is the visible executive sponsor (the person whose credibility this most affects)? Options: CEO, COO, CHRO, CFO, Business Unit Leader, Board Sponsor, Other
• If you had to describe success in one sentence for this effort, what would it say?

Who Really Pulls the Strings?

• If I asked five leaders who ‘owns’ how work gets done, would they point to the same person or three different teams—and which is it? Options: One clear owner, Two aligned owners, Multiple competing owners, Unclear / nobody owns it
• List the roles or groups that regularly influence structural or process decisions in practice (select all that apply). Options: CEO / Office of the CEO, Business Unit Heads / GMs, CHRO / People Team, Finance / CFO, IT / CTO, Legal / Compliance, Board, Middle Management, HR Business Partners, Other
• Which of those groups has final veto power over organizational design or resource moves? Options: CEO, Board, CHRO, CFO, Business Unit Heads, Consortium / Steering Committee, None clearly
• How often do frontline managers adjust processes without formal approval because the formal route is too slow? Options: Daily, Weekly, Monthly, Rarely, Never
• Give one recent example when decision ambiguity caused delay or rework—what happened and what was the cost?

Where the Work Actually Gets Done (Not the Org Chart)

• What are your top 4–6 end-to-end value flows (e.g., product development, order-to-cash, workforce planning)? Please name them in priority order.
• For those flows, how clearly defined is end-to-end ownership? Options: Clearly owned and documented, Mostly defined but overlaps exist, Fragmented across teams, Not defined / unknown
• Which capabilities are currently under-resourced or stretched relative to the new strategy? (select all that apply) Options: Talent / succession, Leadership coaching, Data & analytics, Process design / ops, Technology integration, Change management, Governance / portfolio management, Other
• How frequently do cross-functional handoffs miss expectations or SLAs today? Options: Very frequently, Often, Occasionally, Rarely, Never
• Tell us about one failed handoff that still matters—what broke, who was impacted, and how long the ripple lasted?

What Keeps Promises from Sticking?

• Why do past transformations in your organization tend to lose momentum within 12–18 months? Options: Leadership turnover, Unaligned incentives, Insufficient capability build, IT or data bottlenecks, Change fatigue among employees, Governance gaps, Other
• Which single failure mode has cost you the most in previous efforts—and can you briefly describe the impact?
• How do people typically feel on the ground during and after a redesign (select all that apply)? Options: Exhausted, Burned by broken promises, Skeptical but hopeful, Energized and engaged, Confused about next steps, Relieved
• How long did the last major change take to show measurable improvement, and what was the signal you used? Options: <3 months, 3–6 months, 6–12 months, 12–18 months, >18 months, No measurable improvement
• Do you have documented post-project reviews or ‘lessons learned’ from prior transformations and how were they used? Options: Yes—routinely used, Yes—partially used, Yes—but rarely used, No formal reviews

Hidden Incentives and Everyday Trade-offs

• What perverse incentives are quietly steering decisions away from the strategy you say you want? Options: Quarterly sales targets, Utilization / billable hours, Local P&L metrics, Cost-cutting KPIs, Headcount protection targets, Project completion speed over quality, Other
• How transparent are those rewards and metrics across the organisation? Options: Fully transparent, Mostly transparent, Partially transparent, Opaque / hidden
• Describe one everyday trade-off someone makes because their incentives reward short-term wins over strategic outcomes.
• Who currently owns incentive, bonus, and performance metric design? Options: HR / Compensation, Finance, Business Unit Leaders, CEO office, Shared working group, No clear owner
• On a scale of 1–5, how difficult would it be politically to change the most misaligned incentives? Options: 1 - Not difficult, 2, 3 - Moderately difficult, 4, 5 - Very difficult

Governance: Who Sees, Who Signs, Who Owns?

• Where are the blind spots in your governance that regularly let decisions stall, risk accumulate, or accountability evaporate?
• List the governance forums currently active and the primary decisions each is expected to make (e.g., Exec Ops - resource allocation).
• Which forums make binding decisions versus advisory recommendations? Options: Binding, Advisory, Both, Depends on topic, None clearly
• How consistent is leadership attendance and follow-through in those forums? Options: Always consistent, Mostly consistent, Inconsistent, Rarely consistent
• Where is escalation unclear—who gets looped in when things go off-track?

What Would We Be Giving Up If We Changed Everything?

• If you had to keep only three things from your current operating model, what would they be and why?
• Which capabilities, relationships, or institutional knowledge would be catastrophic to lose? Options: Key leaders / bench strength, Customer relationships, Specialized technical skills, Regulatory expertise, Proprietary processes, Other
• What cultural strengths or norms do you rely on to make change stick?
• What fixed constraints must we design around (select all that apply)? Options: Union agreements / labor rules, Regulatory constraints, Legacy technology / interfaces, Long-term vendor contracts, Geographic or legal structure, Budget freezes, Other
• Which small, early wins would matter most to you in the first 90 days to prove momentum?

Risk Checklist: Where This Is Most Likely To Break

• If we fail to address one thing explicitly, what is most likely to cause the transformation to fail? Options: Leadership withdraws, Incentives remain misaligned, Key capabilities not built, IT integration fails, Governance collapses, Change fatigue triggers resistance, Other
• From the list below, select up to three risks you want us to prioritise for mitigation planning. Options: Leadership turnover, Budget shortfalls, IT/data readiness, Union/legal constraints, Talent shortages, Incentive misalignment, Poor governance, Change fatigue
• Which stakeholder groups are most likely to resist and what are their core fears or incentives?
• What mitigation steps have you attempted previously and what was the outcome?
• How much additional investment (time, people, money) is leadership prepared to deploy to de-risk execution? Options: Significantly more, Moderately more, Marginally more, No additional investment

What Would Convince You This Time Is Different?

• What measurable early outcomes in 6 months would make you confident the redesign is working? Options: Revenue uplift, Cost reduction, Faster decision-making, Improved employee engagement, Reduced time-to-market, Retention of key talent, Customer satisfaction
• What governance cadence and executive commitments would you require to proceed (e.g., weekly steering, CEO sponsorship, escalation tiers)?
• Who must be on the core working team and what realistic percent of their time can each commit (please list roles and %where possible)?
• Do you want a partner that stays through implementation (design + run) or one that hands off after design? Options: Design and remain through implementation, Design then hand off, Open to either depending on terms, Undecided
• Are there non-negotiable constraints or deadlines (board meetings, fiscal close, regulatory milestones) we must design to meet? Options: Board meeting date, Fiscal year-end, Regulatory filing, Merger close milestone, Cost-savings deadline, No hard deadlines, Other

Getting Our Bearings — One Honest Snapshot

• What's the single most important change you're being asked to deliver right now?
• Which of these triggered the need for change? Options: New corporate strategy, Post-merger integration, Board-mandated turnaround, Digital/technology shift, Regulatory or market shock, Other
• How urgent is this change from your perspective? Options: Critical—must deliver within 6 months, High—6–12 months, Medium—12–18 months, Low—more than 18 months, Unsure
• Who is the executive sponsor and how visible are they expected to be? Options: CEO—very visible, CEO—delegated visibility, COO/CHRO—visible, Board-level sponsor, Shared sponsorship, Not yet identified
• What keeps you awake about this program—concrete fears or anxieties (e.g., performance dip, attrition, politics)?

Are We Sure the Leadership Is Actually Aligned?

• When someone says “the leadership team is aligned,” what would you point to as the single biggest sign that it isn’t?
• Which senior stakeholders need to be actively aligned for this to succeed? Options: CEO, COO, CHRO, CFO, Business unit heads, Head of Transformation/PMO, Board representatives, Other
• For each named stakeholder, what would ‘good’ look like from their perspective (one-phrase per stakeholder)?
• Who has final decision authority over scope, budget, and timing? Options: CEO, Board, COO/Transformation lead, Joint governance group, Other
• How have previous executive alignments broken down here—can you describe one example and why it failed?

What’s Really Broken Under the Hood?

• How often does the current operating model get in the way of the strategy you’re trying to deliver? Options: Almost always, Often, Sometimes, Rarely, Never
• Which capabilities are weakest relative to the new strategy? Options: Data & analytics, Product development, Commercial go-to-market, Talent mobility & leadership, Technology/platforms, Service delivery/operations, Other
• Where are incentives or KPIs actively pulling people in the wrong direction?
• Describe one governance or decision-making bottleneck that caused a recent missed opportunity or delay.
• Which functions or regions tend to invent local workarounds rather than follow central direction?

How Bad Will the Dip Feel — and to Whom?

• If implementing this change causes a short-term performance dip, whose performance would show the first sign of strain? Options: Business units, Sales/Revenue teams, Operations/delivery, Middle managers, Support functions (HR/IT/Finance), Other
• Which metrics will you watch in the first 3, 6, and 12 months to judge whether recovery is happening?
• What level of temporary performance decline is acceptable—and who will decide that threshold? Options: No tolerance for decline, Up to 5%, 5–10%, 10–20%, Depends on function/metric, Undecided
• Which outcomes are non-negotiable for the CEO/Board versus negotiable for middle managers?
• How worried are you about visible losses of credibility—internally or externally—if early months look rocky? Options: Very worried, Somewhat worried, Neutral, Not worried

If Everything Went Right — Picture the Future

• Imagine six months after rollout, a senior leader says “this is better.” What specifically changed in their day-to-day?
• Which three measurable signals would prove the transformation is working?
• What cultural or behavioral shifts would you expect to see in middle management and frontline teams?
• Who benefits most from the new model—who gains power, budget, or speed—and how will we manage that rebalancing?
• If you had to name one early win that would build credibility with the Board, what would it be?

Where Will Resistance Bite? — The Politics Map

• Who stands to lose the most from this change—and why might they push back?
• How fatigued are employees from change programs over the last 18 months? Options: Extremely fatigued, Somewhat fatigued, Neutral, Energized/optimistic, Unsure
• Which groups will need active coaching or protection to avoid collapse (e.g., middle managers, high-performers, key geographies)? Options: Middle management, Top talent/key contributors, Regional leaders, Unionized/work council groups, Frontline operations, Other
• Have any prior reorganizations left visible scars or trust issues we should know about? Describe one and its lasting impact.
• Who on the current leadership team is most credible as a change champion, and who will need the most convincing?

Do You Have the Muscle to Deliver?

• If we tried to operationalize the target model today, what would fail first?
• Do you have the data and systems access required for tracking adoption and outcomes? Options: Yes—full access, Partial access, with gaps, No—significant barriers, Unsure
• Which roles or teams are already identified to own rollout activities (names/titles), and which are missing?
• What existing change networks, internal communication channels, or HR forums can be activated for adoption (select all that apply)? Options: HR business partners, Town halls/all-hands, Middle-manager forums, Union/works council, Internal social platforms, Local champions network, None
• How would you describe current HR and comp integration readiness on a scale from 1–5 (1 = not ready, 5 = fully ready)? Options: 1, 2, 3, 4, 5

How Will We Know We Succeeded — and Who Signs Off?

• What are the top three acceptance criteria that must be met for leadership to call this deployment a success?
• Who authorizes release-to-production / go-live decisions and who owns post-launch validation? Options: CEO/Executive Committee, Program Steering Committee/Board, COO/Transformation Lead, Joint governance with external partner, Other
• What cadence of governance and reporting is realistic and will be trusted by the Board (e.g., weekly, monthly, quarterly)? Options: Weekly, Bi-weekly, Monthly, Quarterly, Ad hoc
• If early adoption KPI targets are missed, what escalation paths would you expect to see?
• Which commercial constraints (budget, vendor terms, procurement rules) could limit how we design implementation commitments?

Quick Tests & Small Bets — What We Can Try in 30 Days

• What's one small, time-boxed test we could run in the next 30 days that would surface the truest signal about feasibility?
• What minimal resources would that test need (people, data, budget)?
• Who should own the test and who needs to be informed or empowered to stop it if it causes harm?
• What specific metric or qualitative feedback would make you call the test a meaningful success?
• How willing are you to pause or pivot after a failed small test? Options: Very willing—fail fast, Somewhat willing, Prefer to double-down, Unsure

Getting Comfortable — A Quick Snapshot

• In one sentence, what triggered you to consider an operating-model change right now?
• Which of these best describes the immediate trigger for the change? Options: New corporate strategy, Merger / acquisition integration, Board-mandated turnaround / cost program, Digital transformation / technology shift, Leadership change, Other
• What timeline feels realistic for having the new model functioning at an operational level? Options: 0–3 months, 3–6 months, 6–12 months, 12–18 months, 18+ months
• Who is the primary decision-owner for this effort? Options: CEO, COO, CHRO, CFO, Board / Committee, Other
• If you could name the single most important outcome this change must deliver, what would it be?

Are We Really Aligned — Or Just Agreeing To Move Forward?

• Which visible signals make you confident executive alignment exists today (or not)? Options: Public sponsorship from CEO, Regular executive steering meetings, Clear resourcing commitments, Conflicting public messages, No visible sponsor, Other
• Tell a brief example of where two senior leaders’ priorities have already pulled the organization in different directions.
• Which stakeholders would you expect to quietly block or slow the change, and why would they do that?
• How would a lack of true alignment most likely show up six months into rollout (practical, observable signs)?
• What would need to happen in the first 30 days to make you feel alignment isn’t just assumed but real?

Where the Organization Really Breaks — The Hidden Gaps

• What part of your current operating model causes the most daily friction for leaders and teams?
• Which capability gaps are most critical to close for the new strategy to succeed? Options: Talent / leadership capability, Cross-functional delivery, Data & analytics, Technology enablement, Governance & decision rights, Performance management, Other
• Describe a recent example where governance or incentives produced the wrong decision—what happened and what were the costs?
• How have previous reorganizations or change efforts failed here (root causes, not symptoms)?
• Which processes or handoffs do you suspect will create the biggest design-to-execution risk? Options: Budgeting & resource allocation, Performance reviews & rewards, Project prioritization, PMO / Program management, Talent redeployment, Other

What Would ‘Good’ Feel Like for Each Person?

• If the CEO were to call this change a success in 12 months, what would they describe in plain language?
• How would the CHRO know this was working—what three concrete people signals or metrics would they point to?
• What short-term performance dip would be acceptable to the leadership team, and for how long? Options: No dip acceptable, Minor dip (1–3 months), Moderate dip (3–6 months), Longer dip tolerated (6–12 months), Unsure
• Which early wins would meaningfully shift skeptical leaders’ perceptions—specific outcomes or pilots we could deliver fast?
• How will you measure adoption—what KPIs or behaviors would prove the new model is being used as intended? Options: Role occupancy vs plan, Decision cycle time, Cross-functional project throughput, Employee engagement in changed roles, Incentive payout alignment, Other

The Political Weather — Who Wins and Who Loses

• Which political fault-lines inside the company could cause this work to stall or be reshaped away from strategic intent?
• Who are the informal power holders (not necessarily title holders) we should be aware of, and how do they influence decisions?
• Has anyone in leadership a clear incentive to oppose the new model (e.g., loss of span, budget, or status)? Please name roles and motivations.
• When politics have derailed change previously, what tactics helped restore forward motion (or failed to do so)?
• What escalation paths and neutral decision forums would you trust to adjudicate disputes fairly? Options: CEO adjudication, Executive steering committee, Independent sponsor / board liaison, External mediator, HR-led arbitration, Other

What Will People Actually Have To Do Differently (And Will They) ?

• Name the top three roles or groups whose day-to-day work will change most dramatically under the proposed model.
• Which behaviors must leaders adopt to make the new model stick (examples: delegating decision, cross-functional coaching, new performance conversations)?
• How aligned are your incentive structures with the behaviors you just listed? Options: Highly aligned, Partially aligned, Misaligned, Not sure
• What formal training, coaching, or on-the-job supports are already available—and where are the gaps? Options: Leadership coaching, Role-based training, On-the-job shadowing, Digital learning modules, No structured supports, Other
• Who would be the named owners responsible for adoption metrics and behavior change?

Constraints That Kill Beautiful Designs (Call Them Out)

• Which hard constraints are non-negotiable (budget ceiling, headcount limits, regulatory rules, union agreements)? Options: Budget cap, Headcount reduction target, Regulatory / compliance limits, Union contracts, Technology platform lock-in, Other
• Are there data or systems we cannot access that will be required to measure or run the new model? Options: None, Partial / limited access, Significant restrictions, Unsure
• How flexible is HR on compensation and job architecture changes needed to align incentives? Options: Very flexible, Somewhat flexible, Resistant, Unknown
• If we had to deliver a minimal viable operating model within your constraints, what would be the single non-negotiable element to include?
• What procurement, legal, or board approval steps are required before we can begin work in earnest?

Design-To-Delivery — How Fast, How Big, How Phased?

• If you had to choose, would you rather: move quickly with a narrower scope, or move deliberately with a comprehensive scope? Options: Move quickly, narrower scope, Move deliberately, comprehensive scope, Hybrid / phased approach, Unsure
• Which phasing options feel realistic given your organization’s change appetite? Options: Pilot a single function, Roll out by region, Phased by capability, Big bang, Other
• What governance cadence would you commit to during implementation (reviews, steering, executive updates)? Options: Weekly tactical, Bi-weekly, Monthly executive, Quarterly board-level, Ad-hoc as needed
• Which adoption KPIs would you require to green-light phase 2 (examples: role fill rate, decision compliance, performance improvements)? Options: Role fill rate, Decision compliance, Time-to-decision, Project delivery on time, Employee adoption surveys, Other
• Who must sign off at each phase—we should capture names and levels rather than titles only.

What Keeps You Up At Night — Risks, Real And Imagined

• What single event or outcome would cause you to lose faith in this initiative within the first 12 months?
• List the top three execution risks you see today (people, technology, funding, politics, other). Options: People / leadership resistance, Technology integration failure, Insufficient funding, Competing priorities, Regulatory challenge, Other
• What early warning signs would you want us to report immediately—what metrics or behaviors should trigger course correction?
• Reflecting on prior external partners, what behaviors or approaches from consultants undermined your trust?
• What mitigation approaches would you be willing to adopt to reduce the top risk you listed (e.g., staged funding, independent reviews, executive war room)? Options: Staged funding, Independent audits, Executive war room, External change network, Contingency reserves, Other

Decisioning & Practical Next Steps — How We Actually Move Forward

• What would make you implacably committed to choosing a partner now rather than later?
• What does your internal decision process look like (steps, required materials, committee reviews) and target date for a selection? Options: Single executive sign-off, Executive committee, Board approval required, Procurement-led process, Multiple-stage approvals, Other
• Are there reference checks, case studies, or specific proof points you require before engagement? Options: Peer CEO reference, CHRO reference, Industry case study, Metrics-based case study, Implementation reference, Other
• What commercial or contractual terms would be deal-breakers for you (e.g., guaranteed outcomes, fixed-fee, time-and-materials, resource continuity)?
• If we proposed a short diagnostic sprint to validate core assumptions, would you prefer a paid pilot, scoped discovery, or workshop-based approach? Options: Paid diagnostic sprint, Scoped discovery with executive workshop, Free initial discovery workshop, Other
• What would success look like in the first 90 days of our partnership—two or three specific deliverables or decisions?