My Companies
21st Century Leadership Institute
The leadership operating system that saved a Fortune 150 company $600 million.
Built for the company that's done plateauing.
Executive coaching, team development, and leadership acceleration programs, built for leaders who want to operate at the next level, not just talk about it.
Our Mission
Why This Institute Exists
Because smart, capable leaders deserve a system, not just inspiration
After 30 years operating inside Fortune 150 & 500 boardrooms, five Presidential administrations, and the highest levels of government, Cicely kept seeing the same pattern.
Leaders who were excellent. Undeniable in their capability. And still stuck.
Not because they lacked talent. Not because they lacked drive.
Because the skills that made them exceptional at one level were the same ones quietly holding them back at the next.
The 21st Century Leadership Institute exists to solve that specific problem, with a proven, structured leadership system, not another generic workshop or framework you'll never use.
The foundation is the C.H.A.I.R. framework, Cicely's proprietary model built from three decades of leading, coaching, and transforming leaders at every level, from director to C-suite to world stage.
Featured On:
The Gap Is Growing, And Most Organizations Are Playing Catch-Up.
The market is moving. AI is reshaping every industry.
Your strategy has already changed.
Your leaders are still developing at the pace of yesterday.
If any of these feel familiar, you are in the right place.
The Gap Is Growing, And Most Organizations Are Playing Catch-Up.
The market is moving. AI is reshaping every industry.
Your strategy has already changed.
Your leaders are still developing at the pace of yesterday.
If any of these feel familiar, you are in the right place.
The Urgency Gap
Your C-suite sees what is coming. Your senior leaders are still processing the last transformation.
The window to close that gap is narrowing.
The Readiness Gap
AI and advanced technology are exposing leadership gaps that were always there. Your leaders need more than change management.
They need to lead the change.
The Alignment Gap
Your talent strategy and your business priorities are moving in parallel, not together.
Leadership development is not wired to where the business is actually going.
The Adoption Gap
You are deploying new tools, platforms, and strategies.
Without leaders who can bring their teams through the change, adoption stalls and trust erodes.
The Capability Gap
Your senior leaders are high performers in yesterday's environment.
The capabilities tomorrow requires demand a deliberate, accelerated pathway.
The Coaching Gap
Generic programs do not fit your culture, your leaders, or your goals.
You need development built for your specific leadership population.
Complimentary · No commitment required
This Isn't A Training Program. It's An Enterprise Leadership Strategy
We do not deliver a curriculum and walk away.
We embed as a strategic partner, co-designing a solution that ties your talent strategy directly to your business priorities and builds leadership capability that scales.
This Isn't A Training Program. It's An Enterprise Leadership Strategy
We do not deliver a curriculum and walk away.
We embed as a strategic partner, co-designing a solution that ties your talent strategy directly to your business priorities and builds leadership capability that scales.
Executive Leadership Coaching.
One-on-one and group coaching for senior leaders and executives who need a trusted partner outside
the organization.
Work directly with Cicely to identify what’s holding you back, build the leadership system that moves you forward, and implement it in real time.
Enterprise Leadership Development & Performance.
Custom leadership development programs built for your organization, from individual contributor tracks to executive leadership pipelines.
Not off-the-shelf. Built for your team, your culture, and your specific allow great leaders to perform.
Performance Assessments & Transformation
Before we build anything, we diagnose what’s actually broken. Cicely conducts team and leadership performance assessments that cut through
assumptions and produce a clear, actionable roadmap for transformation.
Organization Development & Design.
Leadership challenges are rarely individual. When the structure, culture, or operating model is misaligned, even exceptional leaders struggle.
We help design the systems, structures, and leadership culture that allow great leaders to perform.
People Management & Talent Strategy.
How you select, develop, and position your leadership talent determines your ceiling as an organization.
We advise on talent strategy, succession planning, and building the people systems that create high-performing teams.
Strategic Communication & Media Training.
How your leaders communicate is either building or quietly undermining your organization’s credibility.
From executive communication coaching to full media training, we equip leaders to be heard at the level they deserve.
AI Transformation & Leadership.
AI is already reshaping how organizations operate.
Leaders who understand how to lead through transformation, not just react to it, will define the next decade.
We advise on leadership strategy, change leadership (not change management), and organizational readiness for AI integration.
Keynote Speaker, Workshops & Meeting Facilitation
Cicely delivers keynotes, half-day workshops, and full-day intensives built on the C.H.A.I.R. Leadership framework and 10 leadership systems for corporate events, leadership retreats, and ERG conferences.
Every session ends with tools your leaders implement the next day.
Executive Leadership Coaching.
One-on-one and group coaching for senior leaders
and executives who need a trusted partner outside
the organization.
Work directly with Cicely to identify what’s holding you back, build the leadership system that moves you forward, and implement it in real time.
Enterprise Leadership Development & Performance.
Custom leadership development programs built for your organization, from individual contributor tracks to executive leadership pipelines.
Not off-the-shelf. Built for your team, your culture, and your specific allow great leaders to perform.
Performance Assessments & Transformation
Before we build anything, we diagnose what’s actually broken. Cicely conducts team and leadership
performance assessments that cut through
assumptions and produce a clear, actionable
roadmap for transformation.
Organization Development & Design.
Leadership challenges are rarely individual. When the structure, culture, or operating model is misaligned, even exceptional leaders struggle.
We help design the systems, structures, and leadership culture that allow great leaders to perform.
People Management & Talent Strategy.
How you select, develop, and position your leadership talent determines your ceiling as an organization.
We advise on talent strategy, succession planning, and building the people systems that create high-performing teams.
Strategic Communication & Media Training.
How your leaders communicate is either building or
quietly undermining your organization’s credibility.
From executive communication coaching to full media training, we equip leaders to be heard at the level they deserve.
AI Transformation & Leadership.
AI is already reshaping how organizations operate.
Leaders who understand how to lead through
transformation, not just react to it, will define the next decade.
We advise on leadership strategy, change leadership (not change management), and organizational readiness for AI integration.
Keynote Speaker, Workshops & Meeting Facilitation
Cicely delivers keynotes, half-day workshops, and full-day intensives built on the C.H.A.I.R. Leadership framework and 10 leadership systems for corporate events, leadership retreats, and ERG conferences.
Every session ends with tools your leaders implement the next day.
Complimentary · No commitment required
The Future Didn't Wait. Neither Can Your Leaders.
Every organization we work with is navigating the same tension: the business is moving faster than the leaders charged with executing it.
Not because those leaders aren't capable, but because no one has given them a deliberate pathway to develop the specific competencies this moment demands.
"If we're not proactive, the change will determine what our fate looks like."
The organizations that win the next decade won't be the ones that reacted the fastest.
They'll be the ones that invested in their leaders before the market demanded it, that built a leadership culture so strong every change, every disruption, every new strategy lands with execution capability behind it.
That's what the Leadership Accelerator is designed to do.
Complimentary · No commitment required
One leadership operating system. Ten competencies. Ten weeks.
The Leadership Accelerator is a co-created, accelerated development pathway built for your mid-to-senior leaders.
It doesn't just teach leadership.
It installs a leadership operating system that equips your leaders to lead with clarity, capability, and capacity in a world that won't slow down.
That operating system is C.H.A.I.R. Leadership, the proprietary model Cicely built across thirty years advising five U.S. Presidents and the CEOs of Fortune 150 and Fortune 500 companies.
What your leaders walk out able to do:
- Strategic leadership and systems thinking
- Change leadership and transformation
- Communication and executive presence
- Decision-making under uncertainty
- Building and leading high-performance teams
- Organizational influence and stakeholder alignment
- AI readiness and technology leadership
- Performance management and accountability
- Adaptive leadership and resilience
- Culture building and leadership legacy
Complimentary · No commitment required
Your Leaders Are Ready
To Be Built For Tomorrow.
Start with a complimentary discovery conversation.
We'll identify your most critical leadership gaps and co-design what the right solution looks like for your organization, no commitment required.
Complimentary · No commitment required
What We Deliver
Every engagement is built around one objective: leaders who produce measurable results at the next level.
Executive Leadership Coaching
One-on-one coaching for senior leaders and executives who need a trusted partner outside the organization.
Work directly with Cicely to identify what's holding you back, build the leadership system that moves you forward, and implement it in real time.
Enterprise Leadership Development & Performance
Custom leadership development programs built for your organization, from individual contributor tracks to executive leadership pipelines.
Not off-the-shelf. Built for your team, your culture, and your specific performance gaps.
Performance Assessments & Transformation
Before we build anything, we diagnose what's actually broken.
Cicely conducts team and leadership performance assessments that cut through assumptions, and produce a clear, actionable roadmap for transformation.
Organization Development & Design
Leadership challenges are rarely individual. When the structure, culture, or operating model is misaligned, even exceptional leaders struggle.
We help design the systems, structures, and leadership culture that allow great leaders to perform.
People Management & Talent Strategy
How you select, develop, and position your leadership talent determines your ceiling as an organization.
We advise on talent strategy, succession planning, and building the people systems that create high-performing teams.
Strategic Communication & Media Training
How your leaders communicate is either building or quietly undermining your organization's credibility.
From executive communication coaching to full media training, we equip leaders to be heard at the level they deserve.
AI Transformation & Leadership
AI is already reshaping how organizations operate. Leaders who understand how to lead through AI transformation, not just react to it, will define the next decade.
We advise on leadership strategy, change management, and organizational readiness for AI integration.
Keynote Speaker, Workshops & Meeting Facilitation
Cicely delivers keynotes, half-day workshops, and full-day intensives built on the C.H.A.I.R. framework, for corporate events, leadership retreats, and ERG conferences.
Every session ends with tools your leaders implement the next day.
The Leadership Operating System That Scales Your Impact
A 10-Week Intensive Leadership Training Program
THE LEADERSHIP ACCELERATOR
Format: Weekly live sessions (Monday, 60–90 min) + Thursday implementation labs
Cohort size: 10–15 leaders maximum
Delivery: Circle platform + weekly Zoom
This is not a self-paced course.
It is not a motivational program.
It is a structured leadership operating system delivered live, with a cohort of senior leaders who understand exactly what you're navigating.
The Leadership Accelerator is built around the C.H.A.I.R. framework and designed for one outcome: by week 10, you lead differently.
Not in theory. In the rooms that matter to you.
Next Cohort: July 2026
Who This Is NOT For:
- New managers looking for basic leadership fundamentals
- Leaders who aren't personally committed to the work
- Anyone looking for inspiration without implementation
Who This Is For:
- Companies who want private cohort group coaching for their teams
- VPs and senior leaders who have been in their role for years, and feel like they've hit a ceiling they can't explain
- Leaders who have read the books, done the courses, and still can't translate insight into visible change
- Executives who want a private, structured, peer-level environment, without involving HR or their company
- Leaders who are ready to work, not just learn
Leadership Accelerator is designed for:
- Executives leading teams, divisions, or entire organizations
- Emerging leaders building their influence and preparing for bigger roles
- Government officials navigating policy, politics, and public service
- Entrepreneurs scaling their impact and building high-performing teams
- Mid-career professionals ready to step into strategic leadership
Newsletter
Get the Free
5-Minute Leader
5 Minutes a Day. That's All It Takes.
Every morning, join 10,000+ leaders who receive one powerful leadership insight delivered straight to your inbox. No fluff. Just actionable strategies you can apply immediately to lead yourself and your team with more clarity, confidence, and impact.
This is a new era of business. We shape tomorrow's leaders today. Because you don't wait for the future. You lead it.
Signature Leadership Programs
Not every leadership challenge fits a pre-built format
Some organizations need more than a keynote. Some leaders face challenges too specific for a general accelerator.
For those situations, Cicely designs fully custom engagements, built around your organization's exact situation, culture, and objectives.
Custom engagements include:
- Half-day and full-day leadership workshops
- Multi-month organizational leadership transformations
- Team performance assessments followed by embedded implementation
- Custom cohorts for your internal leadership pipeline
Every custom engagement begins with a discovery conversation.
The result is a program built specifically for you, not adapted from a template.
1:1 Executive Coaching
1:1 Executive
Coaching
A trusted advisor outside the org chart. In your corner when it counts.
For senior leaders and C-suite executives who need more than a program, a direct, ongoing working relationship with Cicely.
This is the engagement for leaders who are navigating complexity at the highest level: C-suite transitions, organizational restructuring, high-stakes decisions, or simply the reality of leading at a level where almost no one around you understands what the role actually requires.
Cicely has worked directly with leaders at Fortune 150 and Fortune 500 companies, government agencies, and global organizations.
She brings the rare combination of inside government experience, global strategy, and executive corporate leadership, and she uses both to serve you.
Private, confidential, and completely outside your organization.
Results We've Delivered
Every engagement is built around one objective: leaders who produce measurable results at the next level.
Case Study #1
From Invisible Leader to Trusted Executive Advisor
Challenge:
A high-performing leader delivered results for four years, and was consistently passed over for resources, influence, and advancement. Her work was valued.
Her leadership impact wasn't seen by the people who made promotion decisions.
Strategy & Solution:
We didn't change how hard she worked. We changed how her value was perceived. The focus: executive communication, intentional visibility with senior leadership, strategic thinking at the executive level, and a repositioned leadership value proposition aligned with next-level expectations.
Results:
✔ Promoted with a raise within 5 months
✔ Second raise 3 months later
✔ Now serves as a trusted advisor to the North America CEO and leadership team of a global company, actively sought out for judgment, perspective, and leadership on critical initiatives
Outcome: The leader didn't change roles first, she changed how her leadership was experienced. The promotion followed.
Case Study #2
Breaking a Six-Year Leadership Ceiling, 18% Salary Increase in Six Months
Challenge:
For six years, this leader pursued advancement, applying for roles, working harder, waiting for recognition.
No interviews. No promotions.
Over time: frustration, difficulty articulating experience, emotional responses under pressure, no clear path forward.
He had hit a ceiling and didn't know how to break through it.
Strategy & Solution:
We repositioned him as a credible, next-level leader, not just a candidate.
Four shifts: leadership positioning, executive communication (stop over-explaining, start leading), emotional regulation and executive presence, and a disciplined advancement plan for both internal and external opportunities.
Results:
✔ Secured a new role in a new industry within 6 months
✔ 18% salary increase
✔ Stepped into a formal leadership role managing a team
✔ Remained in coaching for 3 additional years
Outcome: He didn't just change jobs. He changed how he led, communicated, and positioned himself, and the opportunities followed.
Case Study #3
C-Suite Executive Bottleneck to Scalable Leadership Team
Challenge:
A C-suite executive was under pressure from three directions simultaneously.
Upward: not showing up with the impact expected at Board and CEO level. Across: struggling to build credibility with executive peers.
Downward: team relied on her for nearly every decision, she was the bottleneck, stuck in the weeds, unable to operate strategically.
Strategy & Solution:
We approached this as a leadership system problem, not a personality problem.
Coaching ran at two levels simultaneously: the executive and her leadership team.
For her: executive influence with the CEO and Board, peer credibility, stakeholder navigation.
For her team: no-surprises communication discipline, structured manage-up practices, improved decision-making and information flow.
Results:
✔ Improved presence and confidence with CEO and Board
✔ Earned increased respect from executive peers
✔ Direct reports proactively communicated and anticipated needs
✔ The executive shifted from operational management to strategic leadership
✔ Remained in coaching for multiple years, ultimately introduced Cicely to the organization for company-wide leadership coaching
Outcome: By elevating both the leader and the leaders beneath her, the organization moved from dependency on one executive to a scalable leadership system.
Case Study #4
Fortune 200 Culture Reset, From Fragmented Teams to Trusted Strategic Function
Challenge:
A Fortune 200 client needed to stabilize and rebuild after a series of leadership changes. Three teams responsible for U.S. and global strategy. Leaders didn't trust each other.
Information was hoarded.
Newly promoted leaders had never been taught how to lead. Performance stalled. The function had lost credibility inside the business.
Strategy & Solution:
A full leadership and strategy reset, top to bottom.
Unified three competing teams into one operating structure. Replaced likability expectations with respect-based leadership. Built collaborative behaviors, cross-functional communication, and strategic thinking capability. Coached the EVP directly.
Trained newly promoted leaders in core leadership skills.
Shifted leaders from answer-providers to developer of problem-solvers.
Results:
✔ Teams became highly collaborative and consistently delivered on time
✔ One leader who initially resisted the engagement became the top performer within 11 months
✔ Internal credibility and respect significantly increased
✔ Company remains a client, continues to seek leadership and strategy guidance
Outcome: A fragmented, low-trust environment became a respected strategic function. When leaders are taught how to lead, performance and culture improve together.
Built From 30 Years Inside the Rooms That Matter
Not a framework built in a classroom. Built in boardrooms, the White House, and every leadership challenge in between.
Cicely Simpson has spent 30 years at the intersection of leadership, business, and government.
Youngest VP at Dunkin' Brands. Chief Advocacy Officer for an $800 billion industry. Legislative Director on Capitol Hill, helping write legislation signed by four consecutive U.S. Presidents. Advisor to five Presidential administrations.
She has sat in the chair at every level.
The C.H.A.I.R. framework isn't a theory.
It's what she used to lead, advance, and perform at the highest levels, and it's what she installs in every leader who works with her.
Forbes reached out to her to write the book on leadership. The result: Pull Up Your C.H.A.I.R., a 4.9-star Amazon bestseller, featured on the Times Square billboard.
What Leaders Say
Trusted by Five U.S. Presidents & Their Administrations, Fortune 150 & 500 CEOs
She has a gift of finding in each person the skills that they particularly have, and then helping you to see how you can put those forward to other to other people."
The one part that she has brought to light for me is I have been undervaluing myself in my work. Her career experiences, her journeys of what she's done, the different industry sectors that she has served, and again help you think about not only who you are, but what you are and what you want to be."
"I want to express our deep appreciation for the time you invested with our teams. Your presence helped us reach some truly revelatory moments. Our discussion the next day, inspired by your insights, led to some significant breakthrough moments. We are all deeply committed to this new energy and eagerly anticipate how it will positively transform our work and team dynamics."
"I love Cicely. She is a no-nonsense person. Cicely will challenge you. She will confirm your strengths and she will provide you resources and tools to develop the areas that she feels that there are opportunities. Her energy, her experiences and just her attitude really connected with me… The one part that she has brought to light for me is I have been undervaluing myself in my work."
"She has helped me to be able to pinpoint my unique place of value as opposed to being very general. She has not prescribed the path that she thinks each person should be on. Instead, she has been very authentic and tailored, helping me think through what, in fact, it is that I actually want. She has a gift of finding in each person the skills that they particularly have, and then helping you to see how you can put those forward to other people."
Copyright © 2026 Cicely Simpson. All Rights Reserved