CEO Transition: Founder to Professional CEO

90-min 1:1 with each of 8 direct reports

Run a 90-min 1:1 with each of 8 direct reports as Listening Tour Phase 1, internal. Use the customized 40-question bank. Take notes by hand to signal presence (per First Round on emotional authenticity); codify into shared synthesis tool after each. Per Spencer Stuart's 8-point plan (https://www.spencerstuart.com/research-and-insight/now-youre-in-charge-the-first-100-days): 'meet with top management.' This is the foundation conversation set - the M3 topgrading 9-box scoring is built off this dataset. Aim to complete all 8 by Day 14 so synthesis can begin.

16 skip-level conversations (60 min each)

Run 16 skip-level conversations (60 min each) two levels deep into the org. Skip-levels surface a different angle than the direct-report view - they reveal whether the senior leaders' narratives match the experience of the people doing the work. Per Vistage CEO First-100-Days research (https://www.vistage.com/research-center/business-leadership/ceo-first-100-days/), the facilitator-room option (CEO leaves the room, employees compile anonymous Qs, CEO returns) is optional for 1 of 16 conversations to surface harder truths. Schedule across days 7-21 to overlap with completing direct-report 1:1s.

16 senior IC / manager interviews (90 min x 16)

Run 16 senior IC / manager interviews (90 min each) below the VP line. This is often where the institutional memory lives - the people who have been at the company longest, know the customer deepest, or have unique technical / market knowledge. Per Spencer Stuart 'Now You're In Charge' (https://www.spencerstuart.com/research-and-insight/now-youre-in-charge-the-first-100-days) and Bossidy/Charan 'Execution', operational truth lives below the VP layer. Schedule across days 14-30 to complete the 40-internal target by Day 30.

Weekly listening-tour synthesis check-in (coach + CoS + CEO)

Run the weekly listening-tour synthesis check-in: coach + chief of staff + CEO. What's emerging? What surprised you? What to ask next? Repeats weekly through week 8 (8 sessions x 1h = 8h tracked). Per Bossidy/Charan 'Execution' (https://www.amazon.com/Execution-Discipline-Getting-Things-Done/dp/0609610570), the discipline of synthesis-as-you-go is what converts a listening tour from passive note-taking into active pattern-recognition. The weekly check-in also surfaces whether the question bank needs adjustment - if the same answer keeps coming back, refine the question.

5 customer ride-alongs with sales

Run 5 customer ride-alongs with sales: strategic accounts + 1 churn-risk. Per Bossidy / Charan 'Execution' (https://www.amazon.com/Execution-Discipline-Getting-Things-Done/dp/0609610570) - 'the operations process aligns to deliver' - the CEO needs operational truth, not the CRO's curated narrative. The ride-along is the unfiltered customer signal: what they actually buy on, what frustrates them, where they would expand. Schedule across days 7-21 to overlap with internal listening tour.

5 CSM call shadowing on at-risk accounts

Shadow 5 CSM calls on at-risk accounts. Per Spencer Stuart on customer-truth in CEO transitions (https://www.spencerstuart.com/research-and-insight/now-youre-in-charge-the-first-100-days), at-risk accounts surface both customer signal AND team capability - you learn whether the CSM has the judgment + tools + authority to retain the account. NRR-protective: the conversations also surface concrete intervention asks. Schedule across days 14-21 alongside the customer ride-alongs.

Observe 4 standing meetings (watch don't lead)

Observe 4 standing meetings: watch, don't lead. Note: who speaks, who decides, who codifies, what gets resolved vs punted. Per Tribal Leadership stage diagnosis (Logan / King / Fischer-Wright, https://www.triballeadership.net/), meeting dynamics expose the dominant tribal stage and where the org is stuck. Schedule across days 1-30; choose 4 meetings spanning execution (weekly forecast), planning (sprint retro), customer-facing (CS standup), and decision (any standing exec meeting).

Attend 2 all-hands as a participant

Attend 2 all-hands as a participant. Sit in the audience, take notes on engagement, do not speak. Per First Round Review on culture diagnosis (https://review.firstround.com/i-asked-100-founders-ceos-and-vcs-about-career-transitions-heres-what-i-learned/), the founder-led all-hands is the single highest-bandwidth cultural data point - tone, vulnerability, Q&A density, founder energy, and audience reaction reveal more in 60 minutes than any survey. The Day-30 listening-tour interim talk (T2.5.4) is informed by this observation.

Map current operating cadence (catalogue all rituals)

Map current operating cadence: catalogue every weekly / biweekly / monthly / quarterly ritual, owner, duration, attendees, outputs, decisions made. Per McKinsey 'Starting Strong' (https://www.mckinsey.com/capabilities/strategy-and-corporate-finance/our-insights/starting-strong-making-your-ceo-transition-a-catalyst-for-renewal): 'ask what to delay or terminate - initiatives, meetings, process steps, reports, rituals.' This is the precondition for M4 cadence v1 - you cannot redesign the cadence without first knowing what's there. Output: a single grid with all rituals scored on value-vs-cost.

Document current decision-rights map (top-30 decisions)

Document the current decision-rights map: top-30 decisions x 4 columns (founder Decides / CEO+founder / CEO / functional leader). Captures the as-is, not the to-be. Per McKinsey 'The limits of RACI' (https://www.mckinsey.com/capabilities/people-and-organizational-performance/our-insights/the-organization-blog/the-limits-of-raci-and-a-better-way-to-make-decisions), the RACI critique is that no single person is accountable - the rights map fixes this by naming a single Decide-rights holder per decision. The current-state version is what M4/S4.3 then migrates from.

Author 'no major decisions' charter (1-pager)

Author the 'no major decisions' charter: 1-page note for the new CEO posted in their notes app: no firings, no reorgs, no strategy pivots, no comp changes during first 30 days. Per Kellogg + McKinsey on first-100-days discipline (https://www.mckinsey.com/capabilities/strategy-and-corporate-finance/our-insights/starting-strong-making-your-ceo-transition-a-catalyst-for-renewal), the no-decisions discipline is the single highest-leverage gate for top-team retention - premature decisions in days 0-30 are the leading cause of regrettable exits in months 2-4. The charter is a personal commitment the CEO references when temptation arises.

Weekly CEO + coach 1:1 reviewing temptations to act

Run the weekly CEO + coach 1:1 reviewing temptations to act. The coach surfaces 'what did you almost decide this week, and what did you decide instead?' 1h x 4 weeks tracked = 4h. Per coaching standard for new CEOs (Tandem Coach, https://tandemcoach.co/executive-coaching-cost/), the temptation-to-act review is what converts the no-decisions charter from a slogan into a protected discipline. The coach's role is the neutral third party who can name the pattern when CEO doesn't see it.

Conduct 20 strategic customer interviews (60 min x 20)

Conduct 20 strategic customer interviews (60 min x 20): 10 strategic + 5 churn-risk + 2 lost-deal + 3 won-deal. Per Spencer Stuart and First Round (https://www.spencerstuart.com/research-and-insight/now-youre-in-charge-the-first-100-days), customer truth is the foundation of the operating thesis. The 20-customer split spans the full lifecycle: strategic accounts validate the existing strategy, churn-risk surfaces where it breaks, lost-deal reveals competitive weakness, won-deal isolates the differentiator. Schedule across days 31-50 to leave 10 days for synthesis.

10 partner interviews (45 min x 10)

Run 10 partner interviews (45 min x 10): top integration partners, channel partners, advisor relationships. Per Spencer Stuart 'Now You're In Charge' (https://www.spencerstuart.com/research-and-insight/now-youre-in-charge-the-first-100-days), partners surface a market-level view that customers don't have - they see your win/loss patterns vs competitors, your sales-org maturity vs peers, your product-positioning clarity vs the noise. Schedule across days 45-55.

Listening-tour final synthesis (1-pager for thesis draft)

Run the listening-tour final synthesis: coach-facilitated, with chief of staff. What did we learn (themes, tensions, surprises). Output: a 1-pager that feeds the operating-thesis draft. Per Bossidy/Charan 'Execution' on synthesis discipline (https://www.amazon.com/Execution-Discipline-Getting-Things-Done/dp/0609610570), the final synthesis is where the listening-tour data becomes a thesis - patterns are named, tensions made explicit, the 'bets' begin to crystallize. The 1-pager is the bridge artifact between data and decisions.

ghSMART-style structured interview per direct report

Run ghSMART-style structured interview per direct report. Per Smart & Smart, 'Who: The A Method for Hiring' (https://geoffsmart.com/books/who-the-a-method-for-hiring/who-the-book-excerpt/) - chronological career walk, scorecard against next-stage role outcomes, 'go many levels deep.' 4h x 8 = 32h scheduled across 2 weeks; this slug captures 16h direct + 16h prep. The topgrading interview is far deeper than the Day-7 1:1 - it produces the empirical data to score the 9-box (T3.2.3) and write the decision memo (T3.2.4). Schedule across days 35-50.

360-feedback collection per direct report (coach-administered)

Run 360-feedback collection per direct report (peer + reports + customer-facing). Coach-administered. 8-12 raters per direct report. Confidential summaries to CEO. Per coaching standard (Tandem Coach, https://tandemcoach.co/executive-coaching-cost/) the 360 is the second empirical input to the 9-box - it surfaces the 'how' (peer / report / customer experience of working with this person) that complements the 'what' (outcomes hit/missed) from the topgrading interview. Schedule data collection across days 35-50.

Design 2-day exec offsite (Lencioni-style)

Design a 2-day exec offsite (Lencioni-style). Per 'The Five Dysfunctions of a Team' (https://www.amazon.com/Five-Dysfunctions-Team-Leadership-Fable/dp/0787960756): vulnerability-based personal-history exchange + conflict-norm agreement + commitment exercise. Pre-readings, agenda, facilitator. The offsite is where the new CEO and the top-team-going-forward (post-9-box decisions) build trust as a team - it cannot happen before the topgrading because team membership has to be settled. Schedule for days 55-58.

Run 2-day exec offsite

Run the 2-day exec offsite. 4h scheduled prep + 16h exec time = 4h tracked here + 16h captured under exec-team. Per 'The Five Dysfunctions of a Team' (https://www.amazon.com/Five-Dysfunctions-Team-Leadership-Fable/dp/0787960756) and First Round Review on team-formation (https://review.firstround.com/i-asked-100-founders-ceos-and-vcs-about-career-transitions-heres-what-i-learned/), the offsite is where 'this is the team going forward' becomes lived experience - vulnerability shared, conflict norms agreed, commitments made publicly.

Draft 4-page operating thesis v1

Draft the 4-page operating thesis v1: Page 1 Where we are. Page 2 What's working. Page 3 What's not. Page 4 The bets (3-5). Per HBR Guide to CEO Transitions and McKinsey 'Starting Strong' (https://www.mckinsey.com/capabilities/strategy-and-corporate-finance/our-insights/starting-strong-making-your-ceo-transition-a-catalyst-for-renewal). Reviewed with chair, then with CFO + product + sales lead. Positioned as v1 != final. The thesis v1 is the first articulation of where the company is going - it must be specific enough to provoke board feedback but loose enough to absorb it.

Operating thesis review with board chair (1:1)

Run the operating thesis v1 review with the board chair: 1:1, candid, no-decisions, just feedback. Per Harvard CorpGov 'facilitated chair-CEO sessions' (https://corpgov.law.harvard.edu/2025/12/02/beyond-the-first-100-days-rhetoric-how-to-ensure-the-long-term-success-of-new-ceos/), the chair review is the protected space where the CEO can hear hard feedback without it becoming a board-level event. Output: a refined v1.1 draft incorporating chair feedback, ready for the day-60 board pre-read.

Author day-60 board pre-read

Author the day-60 board pre-read: listening-tour findings, top-team grid (anonymized for non-management board), draft thesis bets. No decisions yet - the board signals concerns. Per Spencer Stuart 'Now You're In Charge' (https://www.spencerstuart.com/research-and-insight/now-youre-in-charge-the-first-100-days), the day-60 check-in is the calibration moment between CEO and board - if the board's reaction surprises the CEO, the next 30 days have to be spent re-aligning before the day-100 thesis publish.

Day-60 board check-in (90-min, no decisions)

Run the day-60 board check-in: 90-min board meeting, 30 min CEO presentation, 60 min board feedback. Output: 1-page 'board signals' doc capturing themes from board feedback. Per Harvard CorpGov 'Beyond the First 100 Days' (https://corpgov.law.harvard.edu/2025/12/02/beyond-the-first-100-days-rhetoric-how-to-ensure-the-long-term-success-of-new-ceos/), the day-60 check-in is the gate between Listen-Synthesize and Decide-Communicate phases. Board concerns surfaced here are absorbed into the day-100 thesis; concerns not surfaced are landmines for months 4-6.

Execute 1-3 exec exits per decision memos

Execute 1-3 exec exits per decision memos. Per Horowitz a16z 'The Sad Truth About Developing Executives' (https://a16z.com/the-sad-truth-about-developing-executives/): 'doesn't show competence immediately ... will never recover.' Move quickly but cleanly: severance package, NDA, public framing, internal comms. Per Spencer Stuart 'Now You're In Charge' (https://www.spencerstuart.com/research-and-insight/now-youre-in-charge-the-first-100-days), the exec-exits are the single most-watched signal in the first 100 days - employees calibrate the new CEO's judgment, courage, and care from how the exits are handled.

Initiate <=2 concurrent exec searches

Initiate <=2 concurrent exec searches. Per a16z 'First Principles of Executive Hiring' (https://a16z.com/the-first-principles-of-executive-hiring/), <=2 concurrent searches is the cap - more in-flight diverts CEO attention and degrades calibration. Define scorecard, brief retained search firm, set interview team. The scorecard is built off the 9-box (T3.2.3) + decision memo (T3.2.4) - it specifies the next-stage role outcomes that the new exec must hit in 90 days.

Announce internal promotions (keep-and-invest cells)

Announce internal promotions for keep-and-invest cells in the 9-box. Formal promotion + comp adjustment. Per First Round Review on team formation (https://review.firstround.com/i-asked-100-founders-ceos-and-vcs-about-career-transitions-heres-what-i-learned/), internal promotions in days 60-100 are the counter-balance signal to exec exits - the org sees the new CEO is investing in talent, not just trimming. Output: announcements made same week as exec exits, not weeks later, to balance the narrative.

Operating thesis v2 finalized (PCG-integrated)

Finalize operating thesis v2: integrate board feedback, exec offsite signals, top-team decisions. Apply Pain-Claim-Gain structure: P = where the company hurts, C = the bets (3-5), G = what changes for customers / employees / shareholders. Per HBR Guide and McKinsey 'Starting Strong' (https://www.mckinsey.com/capabilities/strategy-and-corporate-finance/our-insights/starting-strong-making-your-ceo-transition-a-catalyst-for-renewal), the thesis is the *why* + *what*; the companion deck is the *how*. Thesis v2 is the artifact the board approves and the all-hands sees - it must hold up to scrutiny without sliding into operational detail.

Publish thesis to board (formal vote of confidence)

Publish thesis to the board (formal). Day 95: signed board memo, formal vote of confidence captured. Per Harvard CorpGov 'Beyond the First 100 Days' (https://corpgov.law.harvard.edu/2025/12/02/beyond-the-first-100-days-rhetoric-how-to-ensure-the-long-term-success-of-new-ceos/), the formal board vote at day 95 is the governance gate - without it, the day-100 all-hands and customer comms have no board-blessed mandate. The vote is captured in board minutes and referenced in the M5 quarterly board reviews.

Author decision-rights map v1 (top-30 decisions, migration columns)

Author the decision-rights map v1 (top-30 decisions). Per McKinsey 'The limits of RACI' (https://www.mckinsey.com/capabilities/people-and-organizational-performance/our-insights/the-organization-blog/the-limits-of-raci-and-a-better-way-to-make-decisions): name a single Decide-rights holder for each decision. T2D3-proprietary 4-column format: Day 0 (current) / Day 30 / Day 60 / Day 100+. All Decide rights move from founder -> CEO + named functional owner by day 100. The v1 map is the executable plan that the M7 founder letting-go track operates against.

Publish decision-rights map to exec team + founder

Publish the decision-rights map to the exec team + founder. Walk-through with each function. Founder co-signs map. Per Spencer Stuart 'Founder-Led to Founder-Inspired' (https://www.spencerstuart.com/research-and-insight/transitioning-from-founder-led-to-founder-inspired), the founder co-sign is the load-bearing acknowledgment - without it, the founder shadow continues to operate, and the M7 letting-go track has no contract anchor.

Design operating cadence v1 (cross-playbook composite)

Design operating cadence v1. Cross-playbook composite: weekly forecast review (per sales-methodology M3 forecast cadence), weekly trio interviews (per continuous-discovery M1), monthly MBR, monthly Triple-A growth (per plg-transformation M7), quarterly board pack (per board-governance M4), marketing rhythm (per duct-tape-marketing M7), PMM/Launch/Win-Loss/Roadmap councils (per pragmatic-framework M8). Per McKinsey 'Starting Strong' (https://www.mckinsey.com/capabilities/strategy-and-corporate-finance/our-insights/starting-strong-making-your-ceo-transition-a-catalyst-for-renewal). Engineer-led: each ritual has owner, attendees, agenda, decision rights, output template.

Launch first week of cadence v1

Launch first week of cadence v1. CEO + functional leads run the first week of all new rituals. Per First Round Review on operating discipline (https://review.firstround.com/i-asked-100-founders-ceos-and-vcs-about-career-transitions-heres-what-i-learned/), launching all rituals in the same week creates a 'before / after' marker for the org - the new operating model has a visible start date. Capture launch-week friction for cadence-tuning iteration in M5/S5.1.

First customer / partner town hall as CEO

Run the first customer / partner town hall as CEO. Personal open letter + recorded video. Continuity reassurance + bets preview. Per Edelman / TeamHighwire research (https://www.teamhighwire.com/insights/your-ceo-transition-needs-a-reliable-narrator.-make-sure-its-you), customers calibrate the new CEO from a single high-bandwidth event - the open letter signed by the chair + recorded video from the new CEO is the canonical format. Schedule 1-2 days after day-100 all-hands to maintain narrative consistency.

First investor letter as CEO (sets quarterly pattern)

Author the first investor letter as CEO. Sets pattern for quarterly investor comms going forward. Per Harvard CorpGov 'Beyond the First 100 Days' (https://corpgov.law.harvard.edu/2025/12/02/beyond-the-first-100-days-rhetoric-how-to-ensure-the-long-term-success-of-new-ceos/), the first investor letter is the public-record artifact - it's referenced in future letters as the 'thesis baseline' for measuring progress. Format: 4-6 pages, thesis Pain-Claim-Gain + early-quarter operating signals + bets-progress preview.

Weekly forecast review running end-to-end (cross-ref sales-methodology)

Run the weekly forecast review end-to-end. Per `sales-methodology` M3/M5/M7 forecast-accuracy cadence + manager coaching layer. CEO attends first 4 weeks, then samples 1-of-4 thereafter. Forecast attainment >=95% target. Per Bossidy / Charan 'Execution: The Discipline of Getting Things Done' (https://www.amazon.com/Execution-Discipline-Getting-Things-Done/dp/0609610570) - 'the operations process aligns to deliver.' The forecast review is the single highest-leverage operating cadence the new CEO inherits + tunes - the discipline calibrates the entire sales org's signal-to-noise ratio.

Monthly Business Review (MBR) cadence

Run the Monthly Business Review (MBR) cadence. Functional leaders present; CEO chairs. Standing agenda: KPI scorecard, forecast vs actual, top risks, resource asks. Per McKinsey on operating discipline (https://www.mckinsey.com/capabilities/strategy-and-corporate-finance/our-insights/starting-strong-making-your-ceo-transition-a-catalyst-for-renewal), the MBR is the monthly truth-telling forum - if it becomes performative or skipped, the operating system loses its primary feedback loop. CFO owns; CEO chairs.

Monthly Triple-A growth sprint (cross-ref plg-transformation)

Run the Monthly Triple-A growth sprint (PLG-shaped). Per `plg-transformation` M7 Tiger Team & Operating Cadence (https://www.producttalk.org/) - cross-functional growth sprint, monthly cycle, OKR-aligned. CEO attends quarterly, samples monthly. The Triple-A is the experimentation layer - it's how the company maintains a steady pace of test-and-learn against bets in the operating thesis without polluting the MBR. Inherited only if PLG motion exists.

Weekly trio interview cadence preserved (cross-ref continuous-discovery)

Preserve the weekly trio interview cadence. Per `continuous-discovery` M1 Trio Formation + M7 Stakeholder Co-Creation Cadence (https://www.producttalk.org/product-trios/) - PM/Eng/Designer trio runs >=1 weekly customer interview per trio. CEO samples 1-of-4 monthly. The weekly trio cadence is the discovery rhythm that produces leading indicators of product-market fit; if the new CEO does not protect it, it collapses within 6 months under sprint pressure.

Marketing rhythm + measurement cadence (cross-ref duct-tape-marketing)

Run the marketing rhythm + measurement cadence. Per `duct-tape-marketing` M7 - weekly marketing standup + monthly content review + quarterly campaign retro. CEO samples quarterly retro. The marketing rhythm is what keeps the marketing function from drifting into output-counting (campaigns shipped, content posted) and back into outcome-tracking (pipeline contribution, content engagement, brand metrics). https://ducttapemarketing.com/

PMM / Launch / Win-Loss / Roadmap councils (cross-ref pragmatic-framework)

Run the PMM / Launch / Win-Loss / Roadmap councils per `pragmatic-framework` M8 Operating Cadence (https://www.pragmaticinstitute.com/). CEO attends Roadmap council quarterly, samples Launch council semi-annually, samples PMM and Win-Loss annually. The councils are the product-marketing operating system - they prevent the company from drifting into either feature-factory mode (no PMM oversight) or perpetual-deliberation mode (Roadmap council with no decisions).

360-feedback round 1 on new CEO (month 6)

Run 360-feedback round 1 on the new CEO. Coach-administered, board + peers + reports + 5 select customers. Per Harvard CorpGov 'Beyond the First 100 Days' (https://corpgov.law.harvard.edu/2025/12/02/beyond-the-first-100-days-rhetoric-how-to-ensure-the-long-term-success-of-new-ceos/): 'reflection checkpoints around months 6, 12, and 18.' The month-6 360 is the first empirical signal on KR1.4 (>=4.0/5.0 360 rating). Outputs: aggregate score per dimension, qualitative themes, action items for CEO + coach + chair.

Operating thesis v2 -> v2.1 refinement

Refine operating thesis v2 -> v2.1. Refinement, not pivot. Apply 6-month learnings to bets. Per HBR Guide and McKinsey 'Starting Strong' (https://www.mckinsey.com/capabilities/strategy-and-corporate-finance/our-insights/starting-strong-making-your-ceo-transition-a-catalyst-for-renewal), the month-6 refinement is the calibration point - bets that are working get amplified, bets that are not working get de-scoped (not killed - killing is a strategy v2 decision in S5.3). The v2.1 is the bridge artifact between the inherited thesis and a self-authored strategy v2.

Author strategy v2 (months 7-9)

Author strategy v2. A stretch beyond what the founder shipped. Co-built with exec team. Pricing or packaging revisit (per `pricing-packaging` M5). One outbound or PLG motion deepening (per `outbound-sdr-engine` M2 or `plg-transformation` M5). Per HBR Guide and McKinsey 'Starting Strong' (https://www.mckinsey.com/capabilities/strategy-and-corporate-finance/our-insights/starting-strong-making-your-ceo-transition-a-catalyst-for-renewal), strategy v2 at months 7-9 is the new CEO's first strategic-imprint moment - the thesis was inherited, but strategy v2 is authored. It signals the org what the next 12-24 months will look like.

Board approval of strategy v2 (quarterly board meeting at month 9)

Run board approval of strategy v2. Quarterly board meeting at month 9. Per Harvard CorpGov on board governance of strategy (https://corpgov.law.harvard.edu/2025/12/02/beyond-the-first-100-days-rhetoric-how-to-ensure-the-long-term-success-of-new-ceos/), the month-9 strategy approval is the formal mandate-extension - the board moves from approving the thesis (day 95) to approving the CEO's authored strategy. Without it, the strategy lives only in the operating layer and lacks board cover for the harder commitments (resource shifts, M&A bets, new geographies).

M&A readiness assessment (cross-ref ma-integration)

Run an M&A readiness assessment. If acquisitions on horizon. Pre-cursor to running `ma-integration` playbook. IMO governance reviewed. Per McKinsey on CEO-led M&A (https://www.mckinsey.com/capabilities/strategy-and-corporate-finance/our-insights/starting-strong-making-your-ceo-transition-a-catalyst-for-renewal), the new CEO's first acquisition is structurally riskier than subsequent ones - the operating system isn't tuned, the IMO governance isn't tested, and the CFO + GC + CHRO trio hasn't run an integration. The readiness assessment surfaces these gaps before the first deal.

International expansion readiness (cross-ref country-expansion)

Run international expansion readiness. If applicable. Cross-ref `country-expansion` playbook. Per McKinsey on global-scale CEO transitions (https://www.mckinsey.com/capabilities/strategy-and-corporate-finance/our-insights/starting-strong-making-your-ceo-transition-a-catalyst-for-renewal), the new CEO's first international expansion is high-stakes - it tests the operating-cadence + decision-rights system in a multi-time-zone, multi-jurisdiction context. The readiness assessment surfaces the cadence + decision-rights gaps before the first market entry.

360-feedback round 2 (month 12, compare to baseline)

Run 360-feedback round 2. Coach-administered. Compare to month-6 baseline. Per Harvard CorpGov 'Beyond the First 100 Days' (https://corpgov.law.harvard.edu/2025/12/02/beyond-the-first-100-days-rhetoric-how-to-ensure-the-long-term-success-of-new-ceos/), the month-12 360 is the second anchor checkpoint - it surfaces whether the CEO has compounded on month-6 development goals or plateaued. KR1.4 target is >=4.0/5.0; lift from month 6 is the secondary signal.

Board annual evaluation of new CEO (cross-ref board-governance M6)

Run the board annual evaluation of the new CEO. Per `board-governance` M6 framework applied to CEO. Output: comp/equity refresh, multi-year mandate confirmation. Per Harvard CorpGov (https://corpgov.law.harvard.edu/2025/12/02/beyond-the-first-100-days-rhetoric-how-to-ensure-the-long-term-success-of-new-ceos/), the month-12 evaluation is the formal close of the transition - the CEO moves from 'in transition' to 'permanent.' The evaluation is rubric-based, comp-tied, and minuted.

Founder energy + capability audit (coach-led)

Run the founder energy + capability audit (coach-led). Map: what gives energy, what drains; what unique IP does the founder bring (product vision, customer relationships, market story); what does the company genuinely still need from the founder. Per Spencer Stuart 'Founder-Led to Founder-Inspired' (https://www.spencerstuart.com/research-and-insight/transitioning-from-founder-led-to-founder-inspired) + First Round Review on energy as readiness signal. The audit is the foundation for the M6.S2 role canvas - without it, the founder picks a post-CEO role from theory rather than self-knowledge.

Inventory founder's unique IP

Inventory the founder's unique IP. Where is the founder genuinely hard to replace - key customer relationships, product/technical depth, market storytelling, recruiting magnet. Output: 1-page inventory. Per Spencer Stuart 'Founder-Led to Founder-Inspired' (https://www.spencerstuart.com/research-and-insight/transitioning-from-founder-led-to-founder-inspired), the unique-IP inventory is what separates a real post-CEO role from an honorary one - the role must be anchored in something the founder genuinely contributes that the rest of the org cannot.

Fill founder role canvas (6 options)

Fill the founder role canvas (6 options). Six options: Executive Chairman, CTO, Chief Product Officer, EIR, External Evangelist, Board Member only, Full Exit. For each: scope, KPIs, ownership, time commitment, comp/equity, communication rules, conflict-of-interest with new CEO. Per Spencer Stuart 'Founder-Led to Founder-Inspired' (https://www.spencerstuart.com/research-and-insight/transitioning-from-founder-led-to-founder-inspired). T2D3-proprietary canvas. The canvas is the structured-deliberation tool that prevents founders from defaulting to 'Executive Chairman' when a different role would be a better fit for both founder energy and company need.

Founder + chair decision on role

Founder + chair decision on role. 1-of-6 selected; documented; in transition contract (T1.1.2). Per Spencer Stuart 'Founder-Led to Founder-Inspired' (https://www.spencerstuart.com/research-and-insight/transitioning-from-founder-led-to-founder-inspired), the role decision is the load-bearing commitment - once made, it constrains all downstream comms (T6.2.4 / T6.2.5), conflict resolution (T6.3.1), and personal plan (M9). Half-presence (e.g., 'I'll figure it out later') is the failure mode the M6 track explicitly prevents.

Founder/CEO conflict-resolution protocol

Author the founder/CEO conflict-resolution protocol. What happens when founder and CEO disagree publicly? Privately? With customer? Standard: founder defers in public, raises in private 1:1, chair adjudicates if unresolved within 48h. Per Spencer Stuart 'Founder-Led to Founder-Inspired' (https://www.spencerstuart.com/research-and-insight/transitioning-from-founder-led-to-founder-inspired), the conflict protocol is the load-bearing process for the entire founder track - without it, the first significant disagreement breaks the relationship and contaminates the operating system.

Founder/CEO weekly 1:1 cadence

Lock the founder/CEO weekly 1:1 cadence. 30-min weekly, no agenda, just relationship maintenance. Per First Round Review on founder-CEO chemistry (https://review.firstround.com/i-asked-100-founders-ceos-and-vcs-about-career-transitions-heres-what-i-learned/), the weekly 1:1 is the relationship-investment ritual - if the founder and CEO only meet when conflict surfaces, by then it's usually too late. The 30-min weekly with no agenda is the protected space for trust-building.

Month-3 founder role review

Run the month-3 founder role review. Chair + founder + coach. Is the role working? Energy check. Adjustments if needed. Per Spencer Stuart 'Founder-Led to Founder-Inspired' (https://www.spencerstuart.com/research-and-insight/transitioning-from-founder-led-to-founder-inspired), the month-3 review is the early-warning checkpoint - if the role is not working at month 3, course-correct before month-6. The conversation covers energy, fit, scope clarity, and any surfaced tensions with the new CEO.

Month-6 founder role review

Run the month-6 founder role review. Same as t6-4-1. Joined to the M5 month-6 reflection cycle. Per Harvard CorpGov 'Beyond the First 100 Days' (https://corpgov.law.harvard.edu/2025/12/02/beyond-the-first-100-days-rhetoric-how-to-ensure-the-long-term-success-of-new-ceos/), the month-6 reviews of both CEO and founder run synchronously - the joint review surfaces dynamics that single-side reviews miss.

Month-12 founder role review (decision point)

Founder walks through decision-rights map with CEO

Founder walks through the decision-rights map with the CEO. Per M4/S4.3 - but from the founder's POV: 'what am I no longer deciding, who decides instead, what's the new escalation path.' T2D3 IP: founder co-signs. Per Spencer Stuart 'Founder-Led to Founder-Inspired' (https://www.spencerstuart.com/research-and-insight/transitioning-from-founder-led-to-founder-inspired), the walkthrough is the load-bearing internalization moment - the founder reads the map aloud and explicitly states 'I no longer decide X' for each decision they previously held.

30-day pilot of new decision rights

Run a 30-day pilot of new decision rights. Founder defers all decisions in their old portfolio for 30 days. Coach + chair check in weekly. Per Crunch Teams 'founder shadow' diagnosis (https://crunchteams.com/blog/founder-shadow), the 30-day pilot is the empirical test of letting-go - the founder either successfully defers or surfaces the patterns that prevent it. Either outcome is valuable.

Design 'letting go' weekly checklist (12 prompts)

Design the 'letting go' weekly checklist (12 prompts). T2D3-proprietary checklist: meetings I will NOT attend this week (list 3); decisions I will defer to the CEO (list 3); Slack channels I will mute (list 3); customer escalations I will route to CEO (list); comments I will NOT make in Slack (list); 1:1s I will skip (list); presentations I will not be in (list); board meetings I will or will not attend (state); media interviews I will refer (state); investor calls I will defer (state); recruiting calls I will defer (state); product reviews I will not lead (state). Per Crunch Teams 'founder shadow' diagnosis (https://crunchteams.com/blog/founder-shadow).

Founder fills checklist week 1

Founder fills the checklist week 1. Setup the rhythm. Per Crunch Teams 'founder shadow' diagnosis (https://crunchteams.com/blog/founder-shadow), the first fill is what converts checklist-as-document into checklist-as-discipline - if week 1 is skipped, weeks 2+ rarely happen.

Founder cuts standing meeting attendance

Founder cuts standing meeting attendance. Per McKinsey 'Starting Strong' on what-to-terminate (https://www.mckinsey.com/capabilities/strategy-and-corporate-finance/our-insights/starting-strong-making-your-ceo-transition-a-catalyst-for-renewal) - applied to the *founder*: identify 5 standing meetings to drop. Without explicit cuts, the founder's calendar continues to look like the CEO's - and the founder shadow operates by default.

Founder mutes Slack/internal channels

Founder mutes Slack / internal channels. 5-10 internal channels muted; founder no longer needs to monitor. Per Crunch Teams 'founder shadow' (https://crunchteams.com/blog/founder-shadow), the Slack-channel mute is the highest-frequency micro-intervention - the founder no longer sees the daily flow of channel activity that previously triggered 'helpful' interventions.

'No tweet from sidelines' pact (12 months)

Day-90 audit: % decisions founder is removed from

Run the day-90 audit: % of decisions founder is removed from. Sample 30 decisions across exec team; how many touched founder. Target >=80% no-touch. Per Crunch Teams 'founder shadow' diagnosis (https://crunchteams.com/blog/founder-shadow), the day-90 audit is the first empirical signal on KR3.2 - whether the letting-go discipline is actually working in the operating system or only in the checklist.

Day-180 audit

Run the day-180 audit. Same sample protocol. Should be >=90%. Per Crunch Teams 'founder shadow' diagnosis (https://crunchteams.com/blog/founder-shadow), the day-180 audit is the mid-cycle check - if the % is stalled or regressing, surfaces the structural blockers that the checklist alone can't fix.

Day-365 audit (final)

Run the day-365 audit. Final audit. >=95% target. Per Crunch Teams 'founder shadow' diagnosis (https://crunchteams.com/blog/founder-shadow), the day-365 audit closes the founder track - it's the empirical evidence that the letting-go discipline has converted from operating overhead into operating norm.

Author 'Why I'm doing this' personal narrative (500 words)

Author the 'Why I'm doing this' personal narrative. 500-word essay/post. Per First Round Review on emotional authenticity (https://review.firstround.com/i-asked-100-founders-ceos-and-vcs-about-career-transitions-heres-what-i-learned/): stoicism is the wrong register; vulnerability is right. Three audiences: employees, customers, broader community. Coach + Comms review. The personal narrative is the founder's emotional anchor for the entire transition - it's referenced in the all-hands script, the customer letters, and the press statement.

Apply Pain-Claim-Gain to founder's transition narrative

Apply Pain-Claim-Gain to the founder's transition narrative. T2D3 IP: P = my own pain (e.g., 'I was the bottleneck'); C = the bet (e.g., 'we hired a CEO to scale us beyond what I'm best at'); G = what changes for the company. Per First Round Review (https://review.firstround.com/i-asked-100-founders-ceos-and-vcs-about-career-transitions-heres-what-i-learned/), the founder-side PCG is the structural backbone of the personal narrative - it converts a vulnerable essay into a leadership artifact.

Author founder all-hands script (Day 0)

Author the founder all-hands script for Day 0. 5-min talk + Q&A. Founder publicly endorses new CEO. Per First Round Review (https://review.firstround.com/i-asked-100-founders-ceos-and-vcs-about-career-transitions-heres-what-i-learned/): 'signal ongoing involvement' (e.g., wear company apparel). The Day-0 talk is the founder's emotional handover moment - it sets the tone for the entire org's calibration of the founder's commitment to the new arrangement.

Rehearse all-hands script with coach

Rehearse the all-hands script with the coach. Live rehearsal; emotional authenticity calibration. Per First Round Review (https://review.firstround.com/i-asked-100-founders-ceos-and-vcs-about-career-transitions-heres-what-i-learned/), the rehearsal is the calibration moment - tone, pacing, vulnerability. Without rehearsal, the founder defaults to over-stoic or over-emotional registers that miss the audience.

Deliver day-0 all-hands talk

Top-50 customer 1:1 emails (founder-authored)

Top-50 customer 1:1 emails. Founder authors a personal email to each of the top 50 customers; introduces new CEO; pledges continuity; signals their new role. Per Spencer Stuart 'Founder-Led to Founder-Inspired' (https://www.spencerstuart.com/research-and-insight/transitioning-from-founder-led-to-founder-inspired), the top-50 1:1 emails are the highest-leverage customer-retention intervention in the transition - they prevent the 'I worked with the founder, why are they leaving' narrative from triggering churn or expansion holds.

Partner letter (broad)

Author the partner letter (broad). Single letter to all partners. Per Edelman / TeamHighwire on transition narrative (https://www.teamhighwire.com/insights/your-ceo-transition-needs-a-reliable-narrator.-make-sure-its-you), the partner letter is the lower-effort sibling of the customer letter - it serves the same continuity-reassurance function for the partner ecosystem.

Joint founder/CEO customer tour (5 calls)

Press statement (board chair + new CEO + founder triple quote)

Author the press statement. Standard transition press release; founder quote is brief, generous, specific. Per Edelman / TeamHighwire (https://www.teamhighwire.com/insights/your-ceo-transition-needs-a-reliable-narrator.-make-sure-its-you), the triple-quote format (board chair + new CEO + founder) is the canonical structure - the founder quote is the emotional anchor that signals authentic endorsement.

2-3 founder podcast interviews (first 60 days)

Run 2-3 founder podcast interviews within first 60 days. Tells the founder narrative widely + signals authenticity. Per First Round Review (https://review.firstround.com/i-asked-100-founders-ceos-and-vcs-about-career-transitions-heres-what-i-learned/), the podcast circuit is the medium-bandwidth communication layer between press (one-shot) and customer 1:1 (high-touch). It reaches the broader community + recruiting pipeline + investor pipeline.

Deep energy audit (coach-led, 4-week)

Run the deep energy audit (coach-led, 4-week). Per First Round Review on energy as readiness signal (https://review.firstround.com/i-asked-100-founders-ceos-and-vcs-about-career-transitions-heres-what-i-learned/): 'When you're waking up feeling excited to tackle something new, that's a good indicator you're ready.' Track energy daily for 4 weeks; identify patterns. The deep audit goes beyond M6.S6.1.1 - it's the daily granular tracking that surfaces what specifically energizes vs drains.

Design post-CEO portfolio

Design the post-CEO portfolio. Per Spencer Stuart 'Transitioning from Founder-Led to Founder-Inspired' (https://www.spencerstuart.com/research-and-insight/transitioning-from-founder-led-to-founder-inspired) - portfolio of business + civic + family + learning. Time-allocation %s; 6-month commitment. The portfolio is the structural answer to 'what do you do all day' - without it, the founder defaults to either over-engagement (founder shadow) or drift (depression / aimless venture-creation).

Design 100-day break

Design the 100-day break. Per First Round / Orloff default (https://review.firstround.com/i-asked-100-founders-ceos-and-vcs-about-career-transitions-heres-what-i-learned/): 100 days. 14-day email/phone detox minimum. Per William Bridges 'Transitions' recommendation (https://www.amazon.com/Transitions-Making-Sense-Lifes-Changes/dp/0738211427). Travel, learning, relationships, body. The 100-day break is the structural reset that prevents the founder from rolling directly from CEO into a new venture without the recovery period that converts past into not-past.

Author 'I will not do this for 6 months' list

Author the 'I will not do this for 6 months' list. T2D3 IP: explicit list of 5-10 things the founder will NOT do (start a new company, take board seats, comment on company decisions, give media interviews about company strategy, etc.). Coach + chair witness. Per First Round Review on founder-shadow risks (https://review.firstround.com/i-asked-100-founders-ceos-and-vcs-about-career-transitions-heres-what-i-learned/), the not-doing list is the explicit commitment that prevents the most common founder-after-CEO failure modes - a hasty new venture or board-seat over-load that consumes recovery time.

Identity-work sessions with coach (4 sessions x 4h)

Run identity-work sessions with coach. 4 x 4-hour sessions; 4h captured here. Per First Round Review on identity (https://review.firstround.com/i-asked-100-founders-ceos-and-vcs-about-career-transitions-heres-what-i-learned/): 'you are not your startup.' Coach-led explorations. The identity work is the deepest layer of the founder track - it addresses the question 'who am I if not the CEO of this company.' Without it, founders frequently start new companies within 6 months as an identity-replacement strategy that often fails.

Relationship rebuild (family + friends)

Schedule relationship rebuild (family + friends). 2h structured time. Per First Round Review on holistic wellbeing (https://review.firstround.com/i-asked-100-founders-ceos-and-vcs-about-career-transitions-heres-what-i-learned/): 'Prioritize health, relationships, and beginner's-mind learning.' Founder schedules deliberate time. Most founders' relationships have been deferred for 5-10 years of company-building; the post-CEO period is the rebuild window.

Identify and engage 1-2 accountability partners

Identify and engage 1-2 accountability partners. Often a peer founder who's been through this; or a longtime friend; or a former board member. Bi-weekly check-ins. Per First Round Review (https://review.firstround.com/i-asked-100-founders-ceos-and-vcs-about-career-transitions-heres-what-i-learned/), the accountability partner is the operating mechanism that converts the personal plan from intention into practice - bi-weekly check-ins surface drift before it becomes regression.

Month-6 personal reflection session (full-day retreat)

Run the month-6 personal reflection session. Coach-led full-day retreat. Energy, identity, purpose. Per First Round Review (https://review.firstround.com/i-asked-100-founders-ceos-and-vcs-about-career-transitions-heres-what-i-learned/), the month-6 retreat is the personal counterpart to the M5 month-6 reflection - the founder evaluates whether the post-CEO life is energizing as designed or drifting into one of the failure modes (founder shadow / new-venture-too-soon / depression).

Quarterly review of CEO mandate

Run the quarterly review of the CEO mandate. Chair + comp committee + lead independent director. Is the mandate still right? 2h x 4 = 8h tracked. Per Harvard CorpGov 'Beyond the First 100 Days' (https://corpgov.law.harvard.edu/2025/12/02/beyond-the-first-100-days-rhetoric-how-to-ensure-the-long-term-success-of-new-ceos/), the quarterly mandate review is the board's primary stewardship instrument - it prevents the mandate from becoming stale as the company evolves.

Quarterly review of founder transition contract

Run the quarterly review of the founder transition contract. Same cycle. Is the contract honored? Adjustments? 2h x 4 = 4h tracked. Per Spencer Stuart 'Founder-Led to Founder-Inspired' (https://www.spencerstuart.com/research-and-insight/transitioning-from-founder-led-to-founder-inspired), the quarterly contract review is the board's check on whether the founder track is operating per the contract or whether informal patterns have emerged that need formalizing or correcting.

Hand off board pack format from founder to CEO (cross-ref board-governance M4)

Hand off the board pack format from founder to CEO. Per `board-governance` M4 Board Pack & Operating Cadence - the board pack format is one of the few artifacts the founder owned end-to-end; the new CEO needs to inherit + tune. Per Harvard CorpGov 'Beyond the First 100 Days' (https://corpgov.law.harvard.edu/2025/12/02/beyond-the-first-100-days-rhetoric-how-to-ensure-the-long-term-success-of-new-ceos/), the board-pack handoff is structurally tricky - the founder's pack format reflects the founder's narrative emphasis; the new CEO has to preserve continuity while introducing their own emphases.

Board meeting cadence under new CEO (cross-ref board-governance M4)

Confirm board meeting cadence under new CEO. 4x / year + 2 strategic + 2 finance. Per `board-governance` M4 (https://corpgov.law.harvard.edu/2025/12/02/beyond-the-first-100-days-rhetoric-how-to-ensure-the-long-term-success-of-new-ceos/). The cadence inheritance is the structural counterpart to the board-pack handoff - the new CEO inherits the schedule but tunes the standing-agenda items based on the operating thesis emphases.

Executive session at every board meeting (without CEO)

Run an executive session at every board meeting (without CEO). 1h x 6 meetings = 6h captured. Per `board-governance` M5 Executive Sessions & Observer Policy (https://www.spencerstuart.com/research-and-insight/now-youre-in-charge-the-first-100-days) - independent directors meet without CEO. Surfaces concerns early. The exec-session ritual is what keeps the board's check on the new CEO from becoming performative or deferred to formal evaluations - concerns surface in real time.

Monthly chair / CEO 1:1

Run the monthly chair / CEO 1:1. Standing 1-hour. Candid feedback channel per Harvard CorpGov 'facilitated chair-CEO sessions' (https://corpgov.law.harvard.edu/2025/12/02/beyond-the-first-100-days-rhetoric-how-to-ensure-the-long-term-success-of-new-ceos/). 12h captured for year 1. The monthly chair-CEO 1:1 is the operating-tempo counterpart to the quarterly mandate review - it surfaces and resolves concerns at month-tempo rather than quarter-tempo.

Month-6 board-led 360 on new CEO

Run the month-6 board-led 360 on new CEO. T2D3-proprietary board stewardship rubric. Coach administers; chair owns. Compare to mandate letter. Per Harvard CorpGov 'reflection checkpoints around months 6, 12, 18' (https://corpgov.law.harvard.edu/2025/12/02/beyond-the-first-100-days-rhetoric-how-to-ensure-the-long-term-success-of-new-ceos/). The board-led 360 is the formal counterpart to the M5 month-6 reflection - the board independently assesses whether the CEO is on track against the mandate.

Month-12 formal evaluation (cross-ref board-governance M6)

Run the month-12 formal evaluation. Per `board-governance` M6 Annual Evaluation framework. Comp / equity refresh decision. Mandate v2 (or confirmed). Per Harvard CorpGov (https://corpgov.law.harvard.edu/2025/12/02/beyond-the-first-100-days-rhetoric-how-to-ensure-the-long-term-success-of-new-ceos/). The month-12 formal eval is the formal close of the transition - the comp committee + chair + LID make a comp/equity refresh decision and confirm or refresh the mandate.

Review board composition under new CEO (cross-ref board-governance M3)

Review board composition under new CEO. Per `board-governance` M3 Director Recruiting & Onboarding - does the board still match the company's stage? Often a CEO transition triggers a board refresh (1-2 director changes within 12 months). Khurana caution applied: stage-fit not celebrity (https://press.princeton.edu/books/paperback/9780691120393/searching-for-a-corporate-savior). The composition review is the structural counterpart to the CEO's strategy v2 - the board that approved the inherited thesis may not be the board that operates the strategy v2.

Director recruiting (if needed) (cross-ref board-governance M3)

Run director recruiting (if needed). Standard `board-governance` M3 process. Per Khurana on stage-fit director recruiting (https://press.princeton.edu/books/paperback/9780691120393/searching-for-a-corporate-savior), the post-CEO-transition director recruiting is structurally tricky - the new CEO needs board members who challenge appropriately without disrupting the still-forming operating system.

Maintain transition-specific risk register

Maintain the transition-specific risk register. T2D3-proprietary risk register: 10 failure modes (per research): owner, signal, mitigation. Reviewed quarterly. Per McKinsey 'Starting Strong' (https://www.mckinsey.com/capabilities/strategy-and-corporate-finance/our-insights/starting-strong-making-your-ceo-transition-a-catalyst-for-renewal), the transition-risk register is the board's anticipatory instrument - it surfaces failure modes before they detonate (top-team mass exodus, customer churn cascade, founder shadow, board dissatisfaction).

Quarterly comms-pulse review

Run the quarterly comms-pulse review. Are employees, customers, partners, investors hearing what we want them to hear? Pulse survey + Slack monitoring + customer NPS. 4h captured for year 1. Per Edelman / TeamHighwire (https://www.teamhighwire.com/insights/your-ceo-transition-needs-a-reliable-narrator.-make-sure-its-you), the quarterly comms pulse is the operating-tempo check on the transition narrative - if employees, customers, or investors are drifting from the official narrative, the comms team adjusts before the drift becomes a crisis.