One-on-One Guidance
for the Hardest Job in Business
Strategic advice and real-world support for experienced leaders dealing with the complexity, politics, and pressure of senior roles.
What I Offer
I work one-on-one with leaders — directors, VPs, functional heads — who’ve been promoted for their ability to execute, and now find themselves facing bigger decisions, broader mandates, and fewer people they can talk to.
We meet privately, every one to four weeks. We talk through the challenges you’re facing: cross-functional conflicts, team issues, executive pressure, organizational politics. And together, we work through how to handle them.
No frameworks. No fluff. Just smart, relevant conversations with someone who’s been there.
What To Expect
Every session is:
Focused on a real issue you’re facing right now
Confidential and grounded in your specific context
Designed to build your executive thinking over time
Structured around clarity, not complexity
Followed up with detailed notes for later reference
You leave with better decisions, not more homework.
Who It’s For
You lead managers or cross-functional teams
You’ve been promoted 2–3 times and now work at the director or VP level
You’re running part of the business, but want to influence the whole
You’re tired of vague advice and ready for grounded clarity
Why It Works
There’s no generic playbook for leadership at this level. Every problem is contextual, with a complex mix of culture, people, market, history, timing. That’s why books and courses fall flat.
What works is experienced, personalized guidance. Conversations that make you sharper over time.
Not just more informed. More effective.
Common Issues I Help With
Navigating organizational politics
Handling pressure from above and across
Managing peer conflict or cross-functional misalignment
Shifting from tactical problem-solver to strategic leader
Building executive-level thinking and presence
“Chris’s experience in dynamic, technology-driven environments often means he immediately understands the challenges I face and can provide practical, relevant solutions.”
Let’s Talk
Start with one conversation. No pitch, no pressure — just a short call to see if this would be helpful to you.
Have More Questions?
Visit the FAQ to learn more about how it works, what to expect, and much more.
Ready to Book?
Already know this is what you need? Buy sessions here.