COO in Practice
COO in Practice
A six-week live online course for COOs, chiefs of staff, and senior operators.
Sharpen your judgment. Lead the whole business.
Work through the decisions senior operators face: which fires deserve attention, how to get strong personalities moving together, when to push back on the CEO, and how to lead when you cannot share everything you know. I’ll draw on my experience as a three-time COO to help you build critical operating skills, test your judgment, and understand the consequences of your calls.
No textbooks. No playbooks. Real-life scenarios and the critical skills and judgment to handle them.
- Six weeks
- Live online
- Small group
- All sessions recorded
- Founding cohort $2,495
I personally review every application for experience, goals, and fit with the group. Applying does not commit you to payment.
The course
I wish I’d had.
I’ve been a COO at early-stage, mid-stage, and public companies. The hardest lessons came through decisions that affected the business and the people in it.
I’ll take you inside that work: the information I had, the choices I considered, the calls I made, and what happened afterward. We’ll examine what I missed and what I’d do differently, then apply that thinking to situations you face.
Three-time COO
Bring the responsibility
you’re already carrying.
This course is for COOs, chiefs of staff, and senior operators who already carry significant operating responsibility and want to get better at the decisions, relationships, and tradeoffs that come with it.
You might be navigating your first COO role, helping a CEO lead across the business, or running operations with a broader mandate than your title suggests.
This is for you if
- You make decisions that affect several teams or the whole business.
- You work through competing priorities, unclear authority, or difficult executive relationships.
- You can bring operating experience to the discussion and are willing to examine your own thinking.
Six weeks
inside the role.
Build critical operating skills through real-life scenarios. Make a call, explain your reasoning, and examine what follows.
WEEK 1Understand your mandate.
Clarify your responsibility, authority, strengths, and gaps across the business.
What we’ll cover
- How COO, chief of staff, and senior operating mandates differ.
- What you own, influence, or escalate to the CEO and functional leaders.
- How company stage and CEO expectations change your role.
- Where responsibility exceeds authority and what to do about it.
- What your experience prepares you to handle and where you need more exposure.
The scenario
The CEO expects you to fix a problem involving three departments. Each leader believes the decision belongs to someone else, and none reports to you. What do you clarify before taking responsibility, and how do you move the work forward?Practice outcome
Map your current mandate, decision rights, strengths, and development needs.WEEK 2Decide what matters.
Understand the business, separate symptoms from causes, and choose where to put attention and resources.
What we’ll cover
- Business models, economics, cash, and financial statements, taught through the decisions they inform.
- Understanding the strategy and testing its assumptions.
- Using KPIs without being misled by them.
- Separating symptoms from their causes.
- Deciding which fires need your attention and which can wait.
- Allocating people, money, and attention across competing priorities.
The scenario
Revenue is growing, but cash is tightening. Sales wants more people, a major customer needs attention, and the CEO wants a new initiative launched. What do you investigate before committing resources, and what do you postpone?Practice outcome
Defend a priority decision using evidence, business context, and explicit tradeoffs.WEEK 3Get people moving.
Turn priorities into action when incentives, ownership, and personalities collide.
What we’ll cover
- Translating strategy into priorities, owners, milestones, and measures.
- Establishing decision rights and accountability.
- Building meetings and an operating cadence that surface problems.
- Understanding the incentives behind resistance.
- Handling strong personalities and disagreement.
- Knowing when to influence, intervene, or use authority.
The scenario
Two executives publicly support a priority but privately pursue different outcomes. The work is stalled. How do you uncover the disagreement, get a decision, and establish commitments that hold?Practice outcome
Work through an execution problem with clear ownership and an approach to resistance and dependencies.WEEK 4Partner with the CEO.
Build trust, clarify expectations, and handle disagreement without avoiding the hard conversation.
What we’ll cover
- Understanding what the CEO needs from you.
- Clarifying expectations, responsibilities, and decision rights.
- Raising concerns and making disagreement productive.
- Responding to changing priorities.
- Deciding what needs the CEO’s attention and what you should resolve.
- Recognizing when the partnership or role is a poor fit.
The scenario
The CEO promises a deadline you believe the company cannot meet. The team expects you to deliver. What do you say privately, what do you communicate publicly, and what decision needs to happen next?Practice outcome
Prepare and test an approach to a difficult CEO conversation, including the evidence, options, and boundaries you need.WEEK 5Lead through difficult decisions.
Make and communicate difficult calls when information is incomplete, confidential, or consequential for your team.
What we’ll cover
- Assessing whether the organization has the right roles, capabilities, and capacity.
- Handling performance problems and difficult personnel decisions.
- Preparing with the CEO, People team, and other advisers, and recognizing when specialist advice is needed.
- Communicating within the limits of what you can disclose.
- Avoiding promises you may not be able to keep.
- Leading through change and rebuilding clarity and trust afterward.
The scenario
You know an organizational change will affect jobs. Before the announcement, your team asks whether they should be worried. How do you answer honestly within what you can disclose, and how do you lead afterward?Practice outcome
Develop a decision and communication approach that accounts for people, uncertainty, confidentiality, and consequences.WEEK 6Build your next level.
Turn what you’ve learned into a practical plan for stronger judgment and broader responsibility.
What we’ll cover
- Reassess the strengths and gaps identified in week one.
- Identify decisions you can handle better and experiences you still need.
- Assess opportunities for broader responsibility and the authority they require.
- Explain your operating contribution with evidence.
- Choose what to practice next and how to assess progress.
The scenario
The CEO wants you to take on a broader mandate. What can you responsibly own now, where do you need support, and what must change for the mandate to work?Practice outcome
Leave with a development plan grounded in your responsibilities, experience gaps, and next decisions.What you’ll leave with
- A clearer understanding of the whole business and your responsibility within it.
- Practice making difficult calls and explaining the judgment behind them.
- Decision and communication approaches you can apply to your work.
- An assessment of your strengths and experience gaps, with a practical development plan.
Someone asks in the all-hands
“Should we be worried about our jobs?”
What do you say? What do you avoid promising?
Every scenario works this way: what you know, what stays uncertain, whose incentives matter, the choices you have, and what happens after you decide.
Who’s pulling up
a chair?
I’ll draw on my network to invite leaders around what the cohort wants to learn. Your application helps shape the invitations.
Examples of the kinds of executives who might join: a public company COO, a product leader at an AI company, a Series D CFO, a CEO who has worked with several COOs, and other operators. The chairs on this page rotate through example profiles; none are confirmed speakers.
The COO
Public consumer packaged goods company
The product leader
AI company
The CFO
Series D business
The CEO
Has worked with several COOs
Or someone else entirely.
Who gets invited depends on what the cohort wants to learn.
Illustrative profiles. Guests to be announced.
Learn it. Make the call.
Compare approaches.
Six weekly themes, taught live on video over six consecutive weeks. Each week offers up to four one-hour sessions, and every session is recorded.
One week, proposed
- Tuesday ProposedTeachingDevelop the skills and judgment behind the week’s decisions.
- Wednesday ProposedRoundtableWork through scenarios and compare reasoning with peers.
- Thursday ProposedOffice hoursDiscuss questions and connect the material to your work.
- Friday ProposedGuest conversationExamine how another experienced leader approaches the responsibility.
The proposed format offers up to four one-hour live sessions each week over six weeks. Every session is recorded. You do not need to attend all four live. Choose the live discussions most useful to you and use recordings for sessions you miss.
The final days, frequency, and start date will be confirmed before you decide whether to enroll.
Before you pull up
a chair.
Who is this course for?
COOs, chiefs of staff, and senior operators who already carry significant operating responsibility and want to strengthen their skills and judgment. I personally review applications for experience, goals, and fit with the group.
Do I need the COO title?
No. Chiefs of staff, VPs, heads of operations, and other senior operators can bring relevant experience. What matters is the responsibility you carry and the decisions you want to handle better.
Is this suitable if I’m new to operations?
The course assumes operating experience. Discussions build on responsibilities participants already carry. If you are unsure whether your background fits, explain it in your application and I will review it personally.
How much time does it take?
The proposed format includes up to four one-hour live sessions each week for six weeks. Every session is recorded, and you do not need to attend every session live. The final schedule and frequency will be confirmed before enrollment.
Is this a course or a coaching group?
It is a structured live course. Each week develops critical operating skills through scenarios, teaching, and discussion, with roundtables and office hours to connect the material to your work.
What do you mean by no textbooks or playbooks?
We’ll learn through real-life operating scenarios and the judgment behind the decisions. We’ll examine what you know, what you need to find out, the choices available, and their consequences. You’ll develop your own approaches and plans as you practice.
Will this apply to my company?
We’ll examine how decisions change with company stage, business model, CEO expectations, and operating context. Your application helps me understand your responsibilities and assess whether the course is relevant to you.
Will this help me become a COO?
It can help you develop the skills and judgment for broader responsibility. The focus is improving how you operate and understanding what leading a business requires. It does not promise a title or job placement.
When does it start?
Dates and the final schedule are being finalized. You’ll receive them and the detailed curriculum before deciding whether to enroll.
Does applying commit me to anything?
No. Applying does not commit you to payment or guarantee a place. I review your application first, then share the details so you can decide whether to enroll if offered a place.
Apply for the
founding cohort.
Tell me about the responsibility you carry, the situations you want to handle better, and what you want to develop. I personally review every application for experience, goals, and fit with the group.
I’m building a small cohort where participants bring useful experience and learn from one another’s decisions.
I’m discounting it because this is the founding cohort. You’ll be helping me shape the course as we run it.
- Apply
- Personal review
- Review the details
- Decide whether to enroll
Applying does not commit you to payment or guarantee a place. If offered a place, you’ll receive the detailed curriculum and final schedule before deciding whether to enroll.
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