Leadership Transitions That Enable Growth

Evaluating current leadership and orchestrating transitions that enable your business to transform

The Real Question

Businesses transitioning to scale growth face a critical question that has nothing to do with compliance or succession planning:

Can your current leadership take your business where it needs to go?

Not whether someone is leaving. Not whether you need a succession plan on file. The question is strategic: As your business grows, transforms, and scales—do you have the leadership in place to enable that transformation?

Maybe you’re a CEO looking at your VP of Engineering and wondering if they can scale the team 3x. Maybe you’re transitioning from startup to scale-up and questioning whether your Director-level leaders are ready for VP responsibilities. Maybe you’re acquiring companies and need to evaluate leadership across the portfolio.

These aren’t succession planning scenarios. They’re leadership transitions that enable business transformation.

Leadership transitions are among the highest-risk moments for any organization. When a Director steps into a VP role, or a VP assumes CTO responsibilities, the stakes are enormous. Get it right, and you unlock growth. Get it wrong, and you risk team instability, lost momentum, and strategic setbacks.

There’s a better way. Complex, business-critical transitions require a different approach—one that integrates assessment, planning, development, and ongoing support.

What Makes This Different

Consider these common scenarios:

The Scale-Up Question

Your startup is transitioning to a scale-up. The Director who was perfect at 50 people might not be equipped to lead 200. Do you develop them, bring in a VP above them, or make a change?

The Acquisition Integration

You’ve acquired companies and need to evaluate leadership across the portfolio. Who stays? Who develops? What roles need external hiring? How do you orchestrate transitions without losing momentum?

The CEO’s Leadership Audit

You’re a CEO looking across your functional leaders (Product, Engineering, Design) and asking: “Can this team take us where we need to go?” Not because anyone is leaving—because the business is transforming and you need to know if your leadership can transform with it.

The Pre-Emptive Development

Your VP is doing well today, but you’re thinking 2 years ahead. If they need to step into a C-suite role, what development do they need now? How do you de-risk that future transition?

The External Hire + Internal Bench

You’re bringing in external VP talent but want to develop your internal Directors simultaneously. One gets promoted, the others strengthen your bench. How do you orchestrate that?

How This Partnership Works

This isn’t succession planning consulting. It’s not executive search. It’s not standalone coaching. It’s integrated assessment, strategic planning, and sustained development that ensures leadership transitions enable business growth rather than derail it.

Phase 1: Leadership Assessment & Transition Strategy

Timeline: 4-6 weeks
Investment: Fixed fee (contact for details)

What happens:

Working with the executive sponsor (CEO, Transition Leader, or senior executive) and HR Business Partner, we:

Assess your leadership landscape:

  • Surface dynamics, strengths, development needs using the Enneagram for Teams methodology
  • Evaluate current leaders against future business requirements (not just current role performance)
  • Identify who’s ready for next-level responsibilities, who could be ready with development, and where you have gaps
  • Understand team composition and capability gaps

Create the transition strategy:

  • Four strategic consulting sessions with executive sponsor and HRBP
  • Customized development roadmap for Phase 2
  • Clear metrics and timeline for transitions
  • Decision clarity: Develop internally, hire externally, or both?
  • If going external: Job requirements based on actual capability gaps
  • If promoting internally: Development plan to close readiness gaps

Deliverable: Clear transition strategy that positions your business for growth, whether developing internal talent, recruiting externally, or strengthening your overall leadership bench.

Phase 2: Executive Development & Transition Execution

Timeline: 12 months
Investment: Custom (based on scope – contact for details)

This phase develops the leaders you’ve identified and supports the transitions themselves.

For each leader being developed:

  • Bi-weekly 1:1 coaching sessions – Targeted development for next-level leadership
  • Always-on access – Unlimited text/email support between sessions
  • iEQ9 Enneagram assessment – Deep work on patterns that will shape their leadership at the next level
  • Monthly team observations – Real-time feedback in actual work contexts
  • Enneagram for Teams workshop – Once in new role, building team alignment and effectiveness

Optional: Support for the executive sponsor

  • Coaching as they navigate their own next-level role
  • Partnership through the transitions
  • Strategic talent orchestration support

Ongoing partnership:

  • Quarterly check-ins with HRBP and executive sponsor
  • Coaching continues through and after transitions
  • Adjustments based on business needs and leader development

The result: Leadership transitions that enable business growth—developed leaders step up successfully, external hires integrate effectively, the team maintains momentum, and your business unlocks its next phase of growth.

Common Configurations

Evaluating and developing one leader:

  • Phase 1: Assess readiness for next-level role
  • Phase 2: Address capability gaps, 6 to 12 months, can be split into two phases, with the second phase supporting leader in new role

Developing multiple candidates (building the bench):

  • Phase 1: Assess current leadership team capability against business strategy
  • Phase 2: Develop multiple leaders simultaneously, orchestrate transitions as needed

Strategic talent development (12-36 months out):

  • Phase 1: Assess current bench strength against future business needs
  • Phase 2: Long-term development before transitions become urgent

This Is For

By Business Context:

  • Mid-sized companies or business units in large enterprises evaluating whether current leadership can take the business to its next stage
  • Late-stage startups transitioning to scale-up and questioning whether startup-era leaders are equipped for scale
  • Companies on the transition to scale growth orchestrating leadership changes that enable transformation
  • CEOs thinking strategically about leadership 12-36 months ahead

By Complexity & Criticality:

  • Complex, multi-faceted transitions where getting it right is business-critical
  • Director → VP or VP → C-suite transitions, primarily in Product, Engineering, and Design functions
  • While specialized in PED leadership, the fundamental approach applies across functions—reach out to discuss your situation

By Timeline:

  • Imminent transitions – You’re actively making leadership changes now
  • Strategic planning – You’re thinking 12-36 months ahead and want to assess talent early, develop leaders, and de-risk future transitions

By Use Case:

  • Leadership evaluation – Assessing if current leaders can take your business where it needs to go
  • Talent optimization – CEO or senior executive elevating functional leadership capability
  • Transition orchestration – Managing complex changes across multiple leaders or teams
  • Pre-emptive development – Building capability before transitions become urgent

By Commitment:

  • Organizations ready to invest in strategic talent development
  • Senior leadership and HR alignment on the business need
  • Willingness to partner closely throughout the process
  • 4-6 week minimum for proper Phase 1 assessment

This Is NOT For

By Business Context:

  • Organizations treating this as a compliance exercise – This requires genuine commitment to development

By Complexity & Criticality:

  • Simple, straightforward promotions – If the transition is obvious and low-risk, you don’t need this
  • Non-critical transitions – This is for transitions where success is business-critical
  • Single-dimension needs – Just hiring? Work with a recruiter. Just coaching? Consider Professional Growth.

By Level:

By Commitment:

  • Companies not ready to invest in leadership development – Requires meaningful financial commitment
  • Rushed transitions – Phase 1 needs 4-6 weeks minimum for proper assessment
  • “Check the box” succession planning – This requires genuine commitment to development

By Readiness:

  • Organizations without senior leadership/HR alignment – Needs buy-in from the top

Why This Approach Works

It’s strategic, not reactive: You’re not planning for departures. You’re evaluating whether current leadership can enable your business transformation and developing them before the need is urgent.

It’s integrated: Assessment informs planning, planning drives development, development enables successful transitions. Each phase builds on the previous one.

It creates optionality: Not locked into a single path. Develop internal talent while keeping external options open. Coach multiple candidates and see who rises. Make decisions based on actual capability development, not guesswork.

It de-risks business-critical transitions: The most expensive outcome isn’t a failed hire—it’s a failed transition that derails business momentum. This approach dramatically reduces that risk.

It builds lasting capability: Not just filling roles. Developing leaders who will drive your business forward for years.

Who Leads This Work

I bring 20+ years as a technology operator and executive—I’ve lived these transitions from every angle. I’ve been the successor stepping into bigger roles. I’ve been the leader building succession plans. I’ve seen what works and what doesn’t.

Combined with professional coaching expertise (CPCC, ICF-accredited, iEQ9 Enneagram practitioner), I understand both the operational realities and the leadership development required to make transitions succeed.

Learn more about my background.

How to Engage

If you’re a Transition Leader or HR partner thinking about an upcoming leadership transition:

The best time to engage is before the transition becomes urgent. Whether you’re 3 months out or 24 months out, starting with Phase 1 gives you clarity, options, and a plan.

We’ll discuss your specific situation, explore whether this partnership is the right fit, and outline what Phase 1 would look like for your organization.

Let’s start a conversation:

Schedule Initial Consultation →

Frequently Asked Questions

That’s exactly what Phase 1 helps you figure out. The Enneagram for Teams workshop and assessment process surface who’s ready, who could be ready with development, and where you have gaps. You’ll have clarity on the best path forward before committing to Phase 2.

Absolutely. Many organizations use this to strengthen their leadership bench. Coach 2-3 strong candidates—one gets the immediate promotion, the others are ready for future opportunities. It’s a smart talent strategy.

This works perfectly for that scenario. The Transition Leader champions the development of their team, and the partnership focuses on elevating the talent they already have.

Standard executive coaching focuses on the individual. This integrates individual development with team assessment, transition planning, live observation, and organizational support. It’s coaching in the context of a business-critical transition, in support of a clear business outcome: transition to scale business growth.

The 12-month timeline and ongoing observations are designed to catch issues early. We adjust the approach, provide additional support, and work closely with you and HR to ensure success. That’s the value of sustained partnership versus one-off interventions.

Leadership transitions don’t have to derail momentum. With strategic assessment, clear planning, and sustained development, they become the catalysts that enable your business to transform and grow.