
LeaderOS™
The Complete Leadership Accelerator
Build the Leadership System That Scales Teams — and the Leader Who Guides Them.
The Complete Leadership Accelerator your leadership depends on in just 9 weeks.
A NEW and world-class leadership development program by internationally-recognized author, speaker, and leadership expert Cicely Simpson
Next cohort starts June 4
Please pick a day and time to meet with us.
What Leaders Are Saying About LeaderOS™ — The Complete Leadership Accelerator

Sarah T., Sr. Manager

James K., Sr. Vice President

Jessica S., Marketing Director
"Once I got promoted, I needed to improve how I showed up in rooms with my peers. This coaching is exactly what I needed."
LeaderOS™ —
The Complete Leadership Accelerator
Your Path to Becoming an Exceptional Leader
This isn’t just a leadership program. It’s an accelerator designed to give you the tools, mindset, and presence to lead at the level your results deserve — all in 9 weeks.
We don’t teach leadership theory.
We build high-impact leaders who can scale with speed, consistency, and clarity.
The statistics tell a sobering story:
60% of new leaders report feeling unprepared for their leadership roles.
Nearly 40% of internal promotions fail within the first 18 months.
Only 1 in 4 organizations report having a strong leadership bench.
You’ve spent years building experience.
Now it’s time to scale your leadership in weeks.
This is where high-performing leaders become high-impact transformers.
You're Here Beause You're Tired Of...
The Challenges You Face
- Team Depends on You for Everything
- Leadership Inconsistency: You show flashes of greatness, but lack structure in you lead daily.
- Stalled Growth: Perhaps you have plateaued despite hard work and strong performance.
- Decision Paralysis: You second-guess yourself in complex or high-stakes decisions.
- Struggling to Influence Across the Org: You can lead your team but can’t move senior stakeholders
- Lack of Executive Presence: You are capable, but not yet trusted with the “next level”.
- Leading in Uncertainty: You get stuck when navigating change, politics, or power dynamics.
- Reactive Leadership and Burnout: You're stuck in the weeds, pulled into fires, and can't focus on strategy or growth.
- Meetings That Waste Time: Your 1:1s, standups, or strategy sessions are vague, repetitive, or avoid real problems.
- Communication Breakdowns Across the Team: You repeat yourself constantly. Messages don’t land. Initiatives lose momentum.
- You've Outgrown Mindset-Only Coaching You’ve done the self-work. Now you need the structure to lead others — fast.
The Leadership Accelerator Solution
- Installs decision ownership frameworks
- Learn repeatable leadership systems so they can show up with clarity, consistency, and confidence — regardless of the pressure.
- Map out their next promotion pathway and teach them how to advocate for advancement without waiting for permission.
- Our decision-making frameworks help you act with speed and certainty, even in uncertainty.
- Through our communication tools and office politics strategies, you gain the tools to lead up, across, and externally.
- Help you build leadership presence — how they speak, think, decide, and show up — so you are seen as ready now.
- The Accelerator prepares you to lead with agility and influence, even when the path forward isn’t clear.
- This is the list itemShifts your identity from doer to designer and leader.
- Provides plug-and-play meeting blueprints for 1:1s, team syncs, reviews. Teaches high-leverage agendas and async updates
- Installs your Strategic Communication OS: Teaches message discipline (What to say, when, to whom).
- Phase 1 builds your internal leadership identity (influence, presence, EQ). Phase 2 installs the external systems (communication, decisions, execution).
Hi, I'm Cicely,
Your Leadership Coach
I am a leadership expert, keynote speaker, ForbesBooks best-selling author of the book: Pull Up Your Chair: 5 Strategies to Change the Trajectory of Your Career, Forbes Contributor, Founder of 21st Century Leadership Institute, and Creator of C.H.A.I.R. Leadership, a unique leadership model for modern leaders.
My best-selling book has been featured in Times Square, Apple News, Forbes, podcasts, and too many places to name!
I have been blessed to lead in rooms where real leadership happens:
- 4 U.S. Presidents & Their Administrations
- Foreign Leaders & Global CEOs
- Led Global Teams for World's Most Recognizable Brands
- Advised and coached CEOs, C-Suite Leaders, Senior Leaders and new leaders in Fortune 500 & Fortune 150 companies


My Leadership Journey
Where I Started
This is where I started my leadership journey as a Director. Getting results at all costs without the necessary leadership skills almost cost me.


How I Scaled My Leadership Impact & Income
Once I focused on accelerating my growth and leadership skills, my income and impact grew exponentially.
I cannot guarantee these results for you. What can I say is that I'm turning all my knowledge from my journey into an
9-week accelerator - just for you.'ve turned all my learnings from building & monetizing my audience into an 8-week accelerator.

Key Program Components
Weekly Masterclass
LIVE 60-90 Minute Masterclass Every Week
Live Masterclass on Tuesdays, starting at 5:00pm Eastern. Live attendance will ensure you get the most out of the program.
Replays will be available.
Weekly Q&A/Coaching
LIVE Coaching and Q&A Calls
Weekly coaching and Q&A calls to ensure your questions are answered and you are implementing the strategies in your daily leadership.
Replays will be available.
Community & Accountability
Your Most Valuable Network
Private access to an exclusive community with like-minded leaders who share your passion for growth and success.
Templates & Resources
Practical Systems, Tools, and Resources
Downloadable manuals, worksheets, diagnostics, assessments, and action guides to support your journey.
9-Week Program Content
Outcome: Build identity, presence, and EQ fluency
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Develop value proposition as a leader; shift from doer to leader
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Lead through empathy, regulate energy, stay calm under chaos.
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Storytelling, executive clarity and concise messages.
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Lead hard conversations, build safety, coach with compassion.
Outcome: Install your systems of decision-making, communication, and execution.
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Move from reactive to Strat-a-tactical and connecting the dots.
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Build weekly cadence of meetings, scorecards, and reviews.
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Design how messages + influence cascade and align across the org
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Be a high performing leader with our Sunday Success Planning System to reclaim hours in your week
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Apply full OS and debrief on next steps.
PLUS THESE EXCLUSIVE BONUSES
SO YOU CAN SCALE YOUR LEADERSHIP

Bonus #1:
LeaderOS
Dashboard

Bonus #2:
Cicely's Best Selling Book

BONUS #3:
Success Planning System

Bonus #4:
Confident Communication Blueprint

Bonus #5:
Collection of Leadership Cheat Sheets

Bonus #6:
How to Monetize Your Experience
(Video Training)
What Smart Successful Leaders Love About This Program
1
Get Answers to Tough Leadership Questions
Imagine having decades of leadership strategies, successes, and tactics at your disposal. Ask your toughest questions and implement the guidance you receive. This alone has been a game-changer for our members.
2
Leverage Tested Strategies in Real Time
Access a library of playbooks, guides, eBooks, success strategies, and roadmaps that your team can use immediately.
3
Impactful Leadership Discoveries
Gain access to an on-demand library of leadership training and recorded mentorship. This treasure trove of knowledge is yours to apply to your most complex initiatives.
4
Collaborate and Contribute with Privacy
Join a global private community of leaders where you can connect with like-minded individuals and get additional support beyond the program.
5
Be a Part of a Leadership Success Network
Get to know other leaders on the same journey. Network, collaborate, and find potential business partners in our exclusive member area.
6
Solve Problems with Experienced Leaders
Your organization and team are unique. A Membership Concierge will help plan your course, solving problems and correcting issues with leaders who have been there before.
Get the support & accountability you need to accelerate your business growth.
Cohort Only
Core Program
Core Offering
- Weekly strategic sessions designed to upgrade how you lead, decide, and communicate at the next level.
- Proprietary LeaderOS Dashboard + toolkits to support execution, reflection, and visibility.
- Decision-Making & Influence Frameworks Templates and systems used by top leaders to create alignment and drive results.
- Communication Scripts so you can speak with power and clarity in high-stakes meetings.
- Implementation Sprint Weeks Built-in support and accountability to turn insight into immediate application.
Cohort + 1:1 Coaching
Executive Program
Everything in Core, plus:
- Everything in the Core Tier
- 2 Private Executive Coaching Sessions (with Cicely) - 1:1 deep dives customized to your leadership context, goals, and barriers.
- Personalized Visibility & Influence Strategy - Tactical guidance to expand your internal/external executive presence.
- Strategic Leadership Review - 360° review of your leadership narrative, gaps, and advancement map.
- Private Messenger Access (with Cicely) Direct access for Q&A and support between sessions.
Cohort + 1:1 Coach + Cicely
Elite Program
Everything in Core & Executive, plus:
- Everything in Core & Executive Tiers
- Full Access to Cicely for 9 Weeks - VIP-level coaching, strategic counsel, and custom feedback.
- Leadership Brand Audit - Deep review of your leadership brand, communication patterns, and promotion path.
- Executive Briefing Labs - Sessions to rehearse and refine high-stakes communication or decision-making scenarios.
- Extended Post-Program Support - Continued access to support implementation beyond the accelerator.