The Leadership Reality
The higher you go, the worse your information gets. People filter what they tell you. Your board, your partners, and your team each want something from you, and the feedback you receive is shaped by it.
Meanwhile the decisions get bigger and the margin for error gets thinner. The person most responsible for the outcome has the fewest people to think out loud with. Most senior leaders don't need motivation. They need a sharp, independent thinking partner who understands the job from the inside.
Where Leaders Get Stuck
- The company outgrew your operating style. What got you here won't get you to the next stage, and you're still the bottleneck on decisions your team should own.
- A key relationship has quietly soured. A co-founder, partner, or investor. Everyone is polite in the meeting, and nothing gets resolved.
- A strong executive in the wrong seat. You know it. You've known it for two quarters. The conversation keeps getting postponed.
- An inflection point with no neutral advisors. A raise, a sale, a succession, or a step back, and everyone around you has a stake in your answer.
Jon's Operating Perspective
Jon founded Admissionado in 2007 and built it from two people to more than 90 team members across 42 offices worldwide. Along the way the firm mentored more than 3,500 professionals, many now at companies like Apple, Google, and Intel, before Jon's exit in 2017. He later served as CEO of a national single-family rental company, scaling it from under 100 homes to more than 2,000 through its acquisition in 2025.
He has made payroll in lean months, hired and let go of senior people, negotiated with debt and equity partners, and taken a company through an acquisition.
That operating history is paired with formal training: a Harvard MBA, a JD from Chicago-Kent, certification as a court mediator, ICF ACC credentialing, and Northwestern's executive coaching certification. The mediation training matters more than it sounds. Much of senior leadership is managing conflict between people who each have a point. Jon helps leaders see the system they're operating in, name what's actually happening, and decide.
Representative Engagements
Founder-CEO, year three of rapid growth.
Biweekly sessions over nine months to rebuild the leadership team, push decisions down, and get the CEO off the critical path.
Partner preparing to lead the firm.
A 360-degree assessment followed by targeted coaching to build credibility with the partnership ahead of a managing-partner transition.
CEO and co-founder at odds over strategy.
Joint and individual sessions, drawing on mediation practice, to reach a decision both can commit to and execute.
Request a Consultation
If you're carrying a decision you can't fully talk through with anyone inside your company, start with a confidential conversation. No pitch. Just a direct discussion of where you are and whether working together makes sense.
Request a Consultation