Extreme Mentoring 101 · One-on-one

A seat next to someone who has already done it.

One executive. Complete access. The room where you think out loud, test the strategy before you commit the company to it, and change momentum without performing certainty you don’t feel yet. I’ve mentored leaders for more than twenty years. This is the closest version of that work.

What this is

Most executives have no one they can fully open up to.

The board wants confidence. The team wants direction. Your peers are competitors for the same budget and the same next role. So the hardest thinking, the part where you’re not sure yet, happens alone. That is the most expensive place to make a decision.

Executive mentoring gives you the one thing the org chart can’t. A single person with no agenda inside your company, complete access to what you’re actually weighing, and twenty-five years of having sat where you sit. We go through the strategy, the politics, the people, the doubt. You leave each session with the next move clear and the reasoning sound.

This is built for the moments that decide a chapter. Changing momentum when the team has stopped believing the plan. Shifting culture when the old one is in the way. Standing up a new go-to-market motion and selling the whole company on it before the market gets a vote.

“You don’t need motivation. You need mechanics, and someone who has run them before.”
How you use me

Public to your team, or private to you alone.

Same access, same depth. The difference is who knows I’m in the picture. You pick the one that fits the change you’re leading.

Mode 01 · Public figure

In the open, so the change has a face.

Your team knows you’re working with me. I show up in the rooms that matter, the kickoff, the off-site, the hard all-hands, and the mentoring is visible. This works when you want the organization to feel the shift, not just hear about it. A leader who is openly being coached gives everyone else permission to learn out loud too. It sets the culture you’re trying to build.

Mode 02 · Private figure

Behind the curtain, known only to you.

No one in the company knows I exist. We work entirely off-stage, and every move that comes out of it is yours. This works when visibility would cost you, or when the work is about you before it’s about the team. The new CEO finding their feet. The founder who can’t look uncertain in front of the people they hired. The leader walking into a decision they can’t pre-socialize. You get the counsel without the optics.

The shape of it

Deep enough to matter. Scoped to your week.

This is real bandwidth, not a monthly check-in that fades into the calendar. On average it runs fifteen to twenty hours a month, five to six hours a week, shaped around what the moment needs.

Typical depth
15–20 hrs per month
Weekly rhythm
5–6 hrs per week, on average
Access between
Direct for the calls that can’t wait
Format A
Half-day intensives

We block a half-day and go deep on one thing. The new GTM plan. The reorg. The board narrative. The kind of work that doesn’t resolve in a forty-five-minute slot between two other meetings. We finish with the decision made and the next steps written down.

Format B
Weekly check-ins

A standing session once a week to work through the exercises, pressure-test the week’s decisions, and keep the change moving when it would otherwise stall. Smaller footprint, steady compounding. For leaders who want a consistent thinking partner rather than an occasional intervention.

How the sessions run

Every session moves through HELP.

The mentoring isn’t a venting session with a smart person. It’s a method. The same operating system I install in leadership teams, run one-on-one, on whatever you walked in carrying.

  • Hear.  We get the whole situation on the table before we touch it. What’s actually happening, in your words, including the part you haven’t said to anyone.
  • Evidence.  We separate fact from interpretation. The thing you’re sure is true and the thing you’re assuming are rarely the same. This is where most bad decisions get caught.
  • Learn.  We find the pattern. Twenty-five years of these situations means most of what feels unprecedented to you, I’ve seen a version of. We name what’s really going on.
  • Proceed.  We end on a decision and a move. Not a framework to think about later. The next action, owned, with the reasoning you can defend to your board or your team.
Why me

Twenty years a professional mentor. Twenty-five in the seat.

I’ve been mentoring leaders for over two decades, the whole time I was operating, not after I stopped. I helped scale NetSuite from roughly $30M to over $1B through IPO and the $9.3B Oracle acquisition. I led an 18-month transformation at ImportGenius that delivered the largest revenue quarter in the company’s history.

That matters here for one reason. When you bring me a problem, you’re not getting theory. You’re getting someone who has made the call you’re about to make, with real money and real people on the line, and lived with the result.

20+ yrs
Mentoring executives while operating, not from the sidelines
$30M→$1B+
NetSuite, through IPO and the $9.3B Oracle acquisition
18 mo
ImportGenius transformation to its largest revenue quarter
Co-author
The H.E.L.P. Operating System, the method every session runs on
Get started

Ready for a pro mentor in your corner?

It starts with a 30-minute call. You tell me what you’re walking into, I tell you whether I’m the right person for it, and we both find out fast. If we’re a fit, we scope the cadence and the mode that works for you.