Where Calling Meets the Corner Office™
We help newly appointed CEOs, presidents, founder-CEOs and executive teams lead through transition, growth and high-stakes decisions, with commercial rigor and values-based discipline.
For founder-led, family-owned, PE-backed, closely held and growth-stage companies. Serving leaders globally.
A focused, no-pressure conversation about the transition, priority or decision in front of you.
You may be in the right place if:
For newly appointed or recently elevated CEOs, presidents and founder-CEOs who need to establish credibility, clarify priorities and lead from the enterprise level.
You leave with: a leadership identity statement, stakeholder map, three enterprise priorities, CEO operating rhythm, decision-rights grid and 90-day plan.
For CEOs and leadership teams that need to move from repeated discussion to decisions, ownership and coordinated execution.
You leave with: a team charter, decision-rights clarity, TARGET plans, accountability grids and a 30/60/90-day review rhythm.
For consequential decisions involving succession, sale, restructuring, acquisition, leadership exits, family-business tension or competing stakeholder expectations.
You leave with: an options analysis, non-negotiables charter, decision record, communication cascade and evaluation plan.
Every engagement is measured on three layers: leadership behavior, organizational performance and business value.
01
ON TARGET 7 I's
“Who do I need to become in this role, and how will that affect the business?”
02
TARGET Model™
“How do we move from an ambiguous, recurring problem to an executed result?”
03
C.H.A.N.G.E. Framework™
“How do we decide when outcomes, values and stakeholders are in tension?”
The 7 I's develop the leader. TARGET organizes the work. C.H.A.N.G.E. governs the moment when a decision carries real human, financial and reputational consequences.
Reginald M. Holiday brings 30+ years of leading organizations, boards and leadership teams in the United States and East Africa. His work sits where leadership identity, strategic execution, organizational culture and high-stakes decisions meet.
“I don't bring generic advice or a one-size-fits-all personality model. I help leaders think clearly, address what is true, make the hard decision and build the systems that let the organization carry the work forward.”
Founder & Executive Coach
30+ years leading organizations; ICF Associate Certified Coach (ACC) – in progress; Doctor of Strategic Leadership candidate (Regent University).
About Reggie →
Senior Advisor
16 years as Senior Faculty, Center for Creative Leadership; leaders trained in 7+ countries.
Director of Operational Intelligence & Risk Advisory
10+ years across federal, enterprise and AI environments; operations and logistics experience in 73 countries.
“It takes a special leader to lead leaders.”
I really did not understand AI and AI agents until I sat down with my executive coach, Reggie Holiday. When he unpacked how fast things were changing and how far behind I was, I knew I needed his help to navigate this new business world.
Since then, my business has skyrocketed, and others are taking notice. Interest has increased, and so have revenue and profits. His push stirred excitement in me, and CalTee has really taken off thanks to Coach Reggie giving me a 'kick in the butt' to lead with AI as a thought partner.
It takes a special leader to lead leaders, and Reggie Holiday is one of those who can. I encourage other CEOs to schedule a discovery session with Reggie today. You will not regret it!
“Before working with Reggie, my professional life lacked the structure I knew it needed. He helped me build a clear plan, move from thinking to action, and truly understand how coaching could unlock my full potential.”
— Corporate Executive, Uganda
“Coaching with Reggie and On Target gave me something I didn't expect: a real sense of my own agency. In just two weeks, I had a concrete action plan and was already moving toward goals I'd been circling for months.”
— Real Estate Professional
“On Target Coaching helped me stop drowning in overwhelm. I came in stuck — and left with a clear blueprint to launch my business and practical ways to actually maintain balance between my work and my life.”
— Ministry Executive
Experience coaching C-suite and senior executives in corporate, public housing, nonprofit and faith-based organizations.
For Boards, Owners & Sponsors
Every engagement uses three-way contracting. The executive, the sponsor and the coach agree on confidentiality, success measures and reporting boundaries up front, with progress reviews at 30, 60 and 90 days.
Our engagements are designed to reduce transition risk, improve executive-team alignment, accelerate execution and strengthen high-stakes decisions.
Talk with us about sponsoring an executiveTwo ways to get clarity — no commitment required.
Free Diagnostic
A 25-minute diagnostic across 7 leadership domains — identity, intention, insight, innovation, influence, implementation, and impact. Get a personalized profile with no strings attached.
Take the Free Assessment →Free Resource
Five phases. One arc. From confusion to consequential impact. Enter your email and we'll send you the one-page framework.
We give Kingdom-minded CEOs and marketplace leaders a coaching experience that integrates their faith and their leadership — so they build businesses of lasting character, culture, and community impact. The pathway also prepares leaders for what faithful stewardship will require next.
Enter the Pathway →We give high-potential leaders the identity-based framework and coaching partnership they need to step confidently into greater responsibility — so they stop performing leadership and start living it. That formation includes the AI fluency fast becoming a baseline leadership competency.
Enter the Pipeline →We give nonprofit leaders a practical, facilitated process for aligning their board, staff, and community around a clear strategic plan — so their mission stops running on passion alone and starts building on strategy. AI tools and foresight help resource-constrained organizations multiply that impact.
Enter the ELEVATE Track →