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Executive Coaching for leaders who carry the final decision
Executive coaching with Tony DiSilvestro is private, one-on-one work for CEOs, presidents, and senior executives who have become the point where every decision stops. Tony is a keynote speaker, entrepreneur, author, and systems strategist who has spent 30 years building more than 30 businesses, and he also works directly with the people running companies.
Six Pressures That Land on the Person in Charge
The wheel groups the leadership themes Tony speaks on and brings to his work with companies into six pressures that sit with the person in charge: decisions, delegation, alignment, accountability, systems, and the leaders coming up behind you. Select a segment of the wheel to see how each one shows up at the top of a company.
Every decision still ends up on your desk
How it shows up at the topDeciding everything felt like speed when the company was young. At a larger size it makes the chief executive the slowest step in the business: approvals wait for your signature and your direct reports stop forming opinions.
Tony works through your decision load with you: which calls truly belong at the top, which belong with the leaders who report to you, and what those people need from you before they can take them.
You hand work off and take it back a week later
How it shows up at the topAn executive delegates a project, the result comes back different from the picture in their head, and they quietly finish it themselves. The team learns that handoffs from the top are temporary, and the executive decides again that it is faster to do it personally.
Effective delegation is one of the themes Tony speaks on. One on one, the conversation turns to your own handoffs: where the expectation was never spelled out, and where you are the one pulling the work back.
Your leaders are pulling in slightly different directions
How it shows up at the topEach senior leader heard the strategy, and each one runs a slightly different version of it. The gap shows up as departments competing for resources and a CEO refereeing arguments over an unclear priority.
Tony's work bridges the gap between vision and bottom-line results. One on one, that means checking how clearly the vision in your head reaches the priorities your leadership team acts on.
Nobody inside the company holds you to your word
How it shows up at the topExecutives set expectations for everyone else, yet very few people in the building will tell the person at the top that a commitment slipped. The organization copies whatever standard the leader keeps for themselves.
Working one on one gives you a direct conversation with an operator outside your reporting lines, about the commitments you set for yourself and the ones you expect from the leaders who report to you.
The company grows faster than the way it runs
How it shows up at the topRevenue and headcount climb while the operating habits stay the same as they were at half the size. Critical knowledge sits in a few people's heads, and every new location, product, or hire adds strain that lands back on the executive team to absorb.
As a systems strategist, Tony looks with you at where the business still runs on memory and personal effort, and what needs to be written down and owned before the next stage of growth adds more weight.
Managers wait for direction instead of leading
How it shows up at the topA company can be full of capable managers and still have no one ready to step into a bigger role. When the executive keeps every hard call, the people below never get the reps, and succession becomes a worry instead of a plan.
Tony looks with you at building a leadership team rather than a layer of managers: who is ready for more responsibility, and which parts of your own role you need to release so they can take it on.
When Every Decision Stops at Your Desk
Most senior executives got the job by being the person who could decide fast and fix anything. That habit works while the company is small enough to see from one desk. Past that size, the same habit makes the top of the organization the place where work waits. Approvals stack up, your leaders bring you problems instead of recommendations, and the calendar fills with meetings that exist only because nobody else is cleared to decide.
No one below you can say that out loud, and a board or an owner group rarely has the time to work through it with you. Executive coaching gives you a private place to sort out what only you should be carrying and what your leadership team should own.
Tony has carried that weight himself, as the owner of the Ynot Italian restaurant group and the founder of companies that grew past the size one person can run from a single desk. He has had to hand off his own decisions to other leaders to keep those companies growing, and that is the ground he covers with executives.
Executive Coaching, Business Coaching, or Team Coaching
Tony works with companies in three coaching formats. They share the same operating experience, but each one starts from a different person or group, so it helps to know which conversation you actually need.
Executive Coaching
For CEOs, presidents, and senior executives. The work is private and centers on how you lead from the top: the decisions you carry, what you delegate, how your leadership team stays pointed the same way, and who holds you accountable.
You are hereBusiness Coaching
For business owners and entrepreneurs who are still building the foundation. The focus is on the owner's business itself, including growth constraints and the difference between a business owner and an entrepreneur.
Business Coach → 03Team Coaching
For leadership teams and groups who need to work through the same issues together in one room. It fits when the problem lives between people and departments rather than with a single executive.
Team Coaching →
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Know How Tony Talks Before You Sit Down With Him
Before you commit time to one-on-one work, it helps to hear how Tony thinks through a business problem. Watch the clip and judge the fit for yourself.
Tony also speaks at conferences and leadership events for organizations that want the same operating lessons delivered to a full audience.
Tony's Keynote Speaking →Experience You Can Check Before the First Conversation
His first customers were beachgoers buying bulk candy from an eight-year-old, and he helped his mother sell Mexican pottery. The companies that followed include the Ynot Italian restaurant group, which he owns today, and a home that earned the 2020 Best Home in the World Award.
He is a member of Entrepreneurs' Organization and the author of The Business Scaling Blueprint, a book about avoiding costly mistakes, building strong foundations, and putting systems in place for sustainable growth.
Where Executive Coaching Connects to the Rest of the Business
He is able to tap into both head and heart.
Executive Coaching Questions
Anything not answered here can go in the form below along with your role and company.
Who is one-on-one executive coaching with Tony meant for?
It is meant for CEOs, presidents, and senior executives who lead other leaders. The common thread is responsibility at the top: you carry the final decisions, your choices set the standard for the organization, and you need a private conversation about how you lead rather than training for a group.
How is executive coaching different from business coaching or team coaching?
Executive coaching is private and centers on one senior leader. Business coaching is built for owners and entrepreneurs working on the foundation of their company, and team coaching brings a leadership team or group into the same conversation. If the issue sits with how you lead, start here. If it sits between people on your team, team coaching usually fits better.
Tony is known as a keynote speaker. Why work with him one on one?
The keynotes and the one-on-one work draw on the same operating experience. On stage Tony shares it with a full room. In executive coaching he applies it to the specific decisions, delegation habits, and leadership questions in your company.
How is an executive coaching engagement set up?
Scope depends on your role, your company, and what you want to work on, so it is discussed directly rather than sold as a package. Send the form with those details, and Tony's team will reply about fit and availability.
Does Tony work with executives outside hospitality, franchising, construction, and real estate?
Those four industries are Tony's primary focus, and he has built businesses across multiple industries over his career. Tell his team what industry you lead in when you reach out, and they will let you know whether the fit is right.
Ask Tony About Executive Coaching
Use the form to tell Tony's team about your role and the leadership issue you want to work on. They will reply about fit and availability for one-on-one work.
- Your title and the size of the company you lead
- The decision pattern or leadership issue you want to work on
- Your industry
- Anything your leadership team is already working through
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Prefer to reach out another way? Contact Tony's team →