Create reliability
Manage communication, priorities, meetings, follow-through, and the details that keep the executive office moving.
A Special, Limited Advisory Opportunity
Chief of Staff Coaching & Advisory
An experienced operating partner in your corner as you navigate one of the most ambiguous, cross-functional roles in the organization.
Strengthen your partnership with the CEO, align cross-functional teams, build accountability and operating rhythm, develop executive judgment, and grow into a higher-impact version of the role.
Work directly with Jeff James Martin · $3,000/month · Three-month initial commitment · Very limited availability
30 years of experienceWorking through growth, change, complexity, leadership, and execution
Hundreds of CEOs and Chiefs of StaffPattern recognition from both sides of the relationship
Organizations at many stagesHigh-growth, venture-backed, mission-critical, nonprofit, ESOP, and more
Across diverse industriesHealthcare, technology, space, professional services, and beyond
What the role really is
One title. Very different roles.
The Chief of Staff role can range from administrative coordination and executive support to cross-functional operator, integrator, proxy, and strategic advisor.
A Chief of Staff is a trusted operating partner to a CEO or senior executive who increases that leader’s effectiveness and helps translate priorities into coordinated organizational execution.
Link the organization
Connect leaders, information, priorities, dependencies, decisions, and work that crosses functional boundaries.
Drive execution
Build alignment, ownership, accountability, decision flow, and the operating rhythm that keeps priorities moving.
Increase CEO leverage
Bring judgment, perspective, organizational insight, and trusted counsel to the CEO and executive team.
The goal is not to force every Chief of Staff toward the same job. It is to understand what your organization needs and help you grow toward the highest-value version of that role.
Where the role gets hard
The job often asks you to create outcomes without owning the people or the functions.
You may be accountable for cross-functional execution, alignment, and follow-through while carrying limited formal authority. That tension is at the center of many Chief of Staff challenges.
What it feels like
Your role keeps changing.
Priorities, boundaries, and expectations evolve with the CEO’s needs and the problems no one else clearly owns.
What we buildClarity around the role.
Clarify your mandate, priorities, decision rights, boundaries, and where you can create the most leverage.
What it feels like
You are accountable without authority.
You need executives and cross-functional teams to align, own commitments, and move work forward—even when they do not report to you.
What we buildInfluence, alignment, and accountability.
Lead through credibility, shared context, clear ownership, strong relationships, and operating mechanisms rather than hierarchy.
What it feels like
Your CEO needs more leverage from you.
You are constantly deciding what to own, what to filter, what to solve, what to challenge, and what must be escalated.
What we buildA stronger CEO partnership.
Develop the trust, judgment, communication, decision boundaries, and rhythm that let you operate with greater independence.
What it feels like
You are reacting instead of building.
Meetings, priorities, metrics, decisions, ownership, and follow-through can become disconnected—and you become the person chasing everything.
What we buildAn effective operating rhythm.
Connect planning, leadership meetings, decisions, metrics, accountability, visibility, and learning into a system that creates follow-through.
What it feels like
The skills that make you invaluable can also keep you stuck.
If you become the person who fixes everything, coordinates everything, and carries every loose end, the organization can become dependent on your effort rather than your leadership.
What we buildGrowth from doer to builder and advisor.
Develop executive judgment, strategic perspective, systems thinking, cross-functional influence, and readiness for broader operating leadership.
An experienced partner in your corner
Bring the real situation you are working through.
A difficult executive-team dynamic. A cross-functional priority that is not moving. An accountability problem. A CEO relationship that needs to evolve. A decision you are unsure how to navigate. Or simply the question, “What should I be focusing on right now?”
These are not theoretical coaching conversations. Jeff has worked through these kinds of situations repeatedly—from different seats, across different stages of organizations, industries, ownership structures, and levels of complexity.
The work is to help you see the situation more clearly, understand the dynamics around it, think through your options, and determine the best way forward.
You still lead. But you do not have to navigate the role by yourself. And when something important or time-sensitive comes up between scheduled conversations, reach out.
A cross-functional priority is stuck.Leaders agree it matters, but ownership, dependencies, or accountability are breaking down.
Two executives are not aligned.You are in the middle and need to move the issue forward without becoming political.
You are not sure whether to act or escalate.The judgment call matters, and the answer is not obvious from your org chart.
The CEO relationship needs to evolve.You need clearer delegation, better communication, more trust, or a different operating cadence.
You are chasing follow-through.The organization needs a stronger system for priorities, decisions, ownership, and accountability.
You are carrying too much.You want to stop being the human workaround and build the systems that make the organization work better.
The system behind the support
Solve the immediate problem—and build the operating capability to solve more of them yourself.
Peak OS grew from the same challenges Chiefs of Staff confront every day: unclear direction, fragmented priorities, weak alignment, slow decisions, uncertain ownership, inconsistent accountability, and operating rhythms that do not keep pace with complexity.
Create clarity
Translate CEO intent and strategy into priorities, decisions, boundaries, and a shared understanding of what matters now.
Connect leaders
Build shared context, trust, ownership, and cross-functional alignment even when you do not have formal authority.
Build operating rhythm
Connect planning, meetings, metrics, decisions, accountability, visibility, and follow-through into a coherent cadence.
Help the system adapt
Surface friction, identify patterns, learn from results, and help the organization improve as conditions change.
What success starts to look like
The role creates leverage instead of absorbing pressure.
The CEO gets leverage
More can be trusted, filtered, anticipated, delegated, and moved forward without everything returning to the CEO.
Leaders align faster
Priorities, decisions, ownership, and dependencies become clearer across the executive team.
Accountability improves
Follow-through comes from the operating system—not from you personally chasing every commitment.
You operate with judgment
You get better at knowing when to lead, influence, challenge, protect, escalate, or step back.
Your career compounds
You turn unusual organizational exposure into executive capability and readiness for broader leadership.
The advisory relationship
Personal, practical support built around your real role.
The goal is not to give you more work. It is to give you an experienced partner, a structured way to understand the role, and a practical operating system for increasing your impact.
What is included
- A 90-minute opening session to understand your role, CEO, organization, pressures, goals, and what success needs to look like.
- A unique Chief of Staff Assessment covering responsibilities, role clarity, CEO partnership, executive-team relationships, influence, cross-functional execution, accountability, and organizational operating rhythm.
- Two 60-minute advisory conversations each month focused on the most important situations and capabilities in front of you.
- Transcript-supported continuity so each conversation builds on the last without adding administrative work for you.
- Periodic reassessment as your role, relationships, and organization evolve.
- Access for important or time-sensitive situations, if and as needed.
Begin directly with youCEO involvement is not required. Other perspectives can be added later only when useful.
Bring the hard situationsUse the relationship for judgment, dynamics, priorities, accountability, and execution—not routine task support.
Build, do not just copeWork through today’s problem while improving the system that keeps creating it.
Grow beyond the roleTurn your exposure to the CEO and organization into stronger executive capability.
I’ve seen this before
Experience matters most when you are in the middle of a situation that does not have an obvious answer.
Over 30 years, Jeff has worked alongside hundreds of CEOs, Chiefs of Staff, executives, boards, and leadership teams through growth, change, leadership transitions, ownership changes, mission-critical execution, and organizational complexity.
He has been both a Chief of Staff and an executive. So when you bring him a problem, he is not only looking at it through the lens of the Chief of Staff. He can help you think about what the CEO may need, how the executive team may be interpreting the situation, what is happening in the broader organization, and which part of the operating system may actually be breaking down.
His experience spans high-growth and venture-backed companies, nonprofits, employee-owned businesses, mission-critical organizations, and industries including healthcare, technology, space, professional services, and more. Those patterns became part of the foundation for Collective Genius, Peak OS, and Peak Teams.
Pattern recognitionSee the organizational issue underneath the immediate symptom.
Executive-side perspectiveUnderstand the situation from both the Chief of Staff and CEO seats.
A practical way forwardMove from insight to clearer decisions, relationships, accountability, and execution.
Who this is for
For Chiefs of Staff who want to become more valuable to the CEO—and more capable as leaders.
It may be a strong fit if you want to…
- Clarify a role whose scope and expectations continue to evolve.
- Drive cross-functional priorities, alignment, and accountability without relying on formal authority.
- Become a more trusted and independent operating partner to your CEO.
- Stop chasing execution and build the operating rhythm that creates it.
- Navigate executive-team relationships, confidential issues, and difficult judgment calls with an experienced partner.
- Grow from exceptional doer to builder, advisor, and broader executive leader.
It is probably not a fit if you want…
- An outsourced Chief of Staff to complete projects for you.
- Someone to edit decks, documents, or routine meeting materials.
- A standardized curriculum disconnected from your CEO and organization.
- A guaranteed promotion or one prescribed career path.
- Unlimited on-demand tactical support for routine work.
Chief of Staff coaching questions
Frequently asked questions
What does a Chief of Staff do?
A Chief of Staff is a trusted operating partner to a CEO or senior executive who increases that leader’s effectiveness and helps translate priorities into coordinated organizational execution. The scope varies widely—from administrative coordination and executive support to cross-functional execution, strategic alignment, decision support, executive-team integration, operating rhythm, and acting as a trusted advisor or proxy.
Why is the Chief of Staff role so difficult to define?
The role is shaped around the needs of a specific principal and organization rather than a standardized function. Scope can change with company stage, leadership needs, organizational complexity, and the Chief of Staff’s own capability. That flexibility creates opportunity, but it can also create unclear boundaries, authority, and measures of success.
What is Chief of Staff coaching?
Chief of Staff coaching is specialized development for a role that sits between executive support, strategic leadership, cross-functional coordination, and organizational execution. It helps clarify the mandate, strengthen the CEO partnership, build judgment and influence, navigate executive dynamics, improve operating rhythm, and increase organizational impact.
How can a Chief of Staff drive cross-functional execution without formal authority?
The strongest Chiefs of Staff lead through influence rather than hierarchy. That means creating shared context, clarifying priorities and ownership, building credibility with executives, making dependencies visible, establishing accountability mechanisms, and knowing when an issue requires influence, challenge, escalation, or CEO involvement.
How do I stop becoming the person who chases every follow-up?
Move the accountability from yourself into the operating system. Clear priorities, visible ownership, decision records, recurring review cadences, metrics, and leadership-team accountability should create follow-through. The goal is to build a system that works without your personal heroics.
How can a Chief of Staff improve the CEO partnership?
Clarify expectations, decision rights, communication preferences, priorities, delegation, filtering, escalation thresholds, and the purpose of recurring one-to-one conversations. As trust grows, the relationship can evolve from task support toward greater independence, thought partnership, challenge, and executive leverage.
How do I know what to own versus what to escalate?
There is rarely a perfect rule. Strong judgment comes from understanding the CEO’s intent, agreed decision rights, risk, reversibility, stakeholder impact, and how much context the CEO needs. This is one of the areas where an experienced outside perspective can be particularly valuable.
What is an operating rhythm?
An operating rhythm is the connected cadence through which an organization plans, sets priorities, reviews metrics, holds leadership meetings, makes decisions, assigns ownership, follows through, and learns. A strong rhythm reduces noise and gives leaders a shared system for execution.
Can coaching help if my role is still mostly administrative?
Yes. Administrative responsibilities can be essential to the role. The goal is not to dismiss them, but to perform them well while identifying where you can increase leverage through better prioritization, decision support, executive communication, cross-functional ownership, organizational visibility, and operating capability.
How do I grow from a doer into a more strategic Chief of Staff?
Growth usually requires moving from personally completing and coordinating work toward improving the systems through which work gets done. That includes stronger judgment, orchestration, decision support, cross-functional influence, operating rhythm, strategic perspective, and the ability to make the organization less dependent on your individual effort.
What is included in the Chief of Staff Assessment?
The assessment examines role and responsibility clarity, CEO partnership, executive-team relationships, influence without authority, decision support, strategic visibility, cross-functional execution, accountability, organizational operating rhythm, and leadership growth opportunities.
Does my CEO need to participate?
No. The relationship can begin directly with you. CEO or executive-team perspectives may be useful later if they serve the work and everyone agrees, but they are not required to schedule an initial conversation or begin the engagement.
How often do we meet, and can I reach out between sessions?
The standard cadence is two 60-minute advisory sessions each month after a 90-minute opening session. Access is also available for important or time-sensitive situations, if and as needed—especially when another perspective could materially help with an upcoming decision, conversation, or organizational issue.
How much does Chief of Staff coaching cost?
The advisory relationship is $3,000 per month with a three-month initial commitment. It includes the opening session, Chief of Staff Assessment, two monthly advisory conversations, transcript-supported continuity, periodic reassessment, and access for important or time-sensitive situations when needed.
Can this help me advance my career?
No advisor can guarantee a promotion. The work is designed to help you build capabilities that transfer into broader leadership: executive judgment, strategic perspective, influence without authority, systems thinking, cross-functional execution, operating discipline, and the ability to help an organization perform at a higher level.
A limited personal advisory practice
You do not have to navigate one of the organization’s hardest roles alone.
If you are carrying more responsibility, navigating harder cross-functional and executive situations, or trying to grow into a higher-impact version of the Chief of Staff role, let’s have a straightforward conversation.
Very limited availability. No application form required.
