anderbox.com

Advisory

Clarity first. Then momentum.

Most leaders I work with aren't short on ideas or effort. They're carrying a vision they haven't been able to say cleanly enough for anyone else to run at. My job is to sharpen it, get the right people rallied around it, and build enough momentum that it stops depending on me.

Where this comes from

Thirty years of operating, coaching, and sitting in rooms full of owners.

2010 — 2021

Peer-group facilitator · HTG Peer Groups → ConnectWise IT Nation Evolve

Eleven years in a room with owners twice a year, holding them to what they said they'd do.

2016 — present

Leadership coach · Independent

One-on-one and leadership-team work with owners and executives.

2025 — present

Advisory board · MSPCFO

Financial clarity for managed service providers.

2019 — 2025

Board member · Jack's Caregiver Coalition

Six years of nonprofit board governance, supporting the people who care for everyone else. Term completed in 2025; I continue as an advisor.

2012 — present

CEO · Imagine IT

Cloud and managed IT for small and mid-sized businesses across MN, KS, and MI.

2000 — 2012

Founder & owner · Next Level Cafe

My first outsourced-IT company, and the reason I know what the first ten employees feel like.

1991 — 1996

Auditor → Senior Auditor · Price Waterhouse

Where I learned to ask people to prove it. That lens never switched off.

Along the way: advisory work with MSPCFO, ConnectWise, ConnectStrat, and more than 25 managed service providers across the country.

How engagements have taken shape

Different companies need different rhythms. These are the four that have worked.

A quarterly rhythm

Planning cadence, a real scorecard, and the discipline of revisiting what we agreed to last quarter. EOS-style operating rhythm, adapted to the company rather than the manual.

A standing sounding board

Monthly touch-bases plus the in-between: the call before the hard conversation, the text at 9pm when a decision won't wait. No fixed agenda — the value is someone who already has the context when it matters.

A facilitated room

Peer cohorts and leadership offsites. Getting a group of owners to say the true thing out loud, then leave with a decision instead of a document.

A defined intensive

A strategic offsite or a scoped get-unstuck engagement with a beginning and an end. Often the right answer when the problem is clarity, not capacity.

In practice these rarely stay tidy. Most have run on a monthly cadence with reactive coaching layered in between — the quarterly session sets direction, and the calls and texts in between are where it actually holds.

The tools, and how I use them

I borrow my best ideas from the best — and say so. EOS and Traction, StratOp, Working Genius, Lencioni, Good to Great, Scaling Up, StoryBrand, CliftonStrengths. None of them are mine, and I'll tell you whose they are.

What I bring is knowing which one your situation actually calls for, and being willing to abandon it when it stops being useful. The framework is scaffolding, not the building.

Worth saying plainly

I implement EOS-style operating rhythms, but I am not a licensed or certified EOS Implementer, and I don't present myself as one. If you want the official program delivered by the book, you should hire someone who carries that license — and I'll happily point you toward one.

What you get from me is someone who has run these rhythms inside his own companies and in other people's, and who will adapt them to yours.

This tends to work when

  • You can feel the opportunity but can't yet say it in a sentence
  • Your leadership team is capable and under-aligned
  • Growth has outrun the operating rhythm that got you here
  • You want someone who'll disagree with you early, not politely late

It's a bad fit when

  • You want an operator to own it long-term
  • You want a certification or a licensed methodology delivered by the book
  • The decision is already made and needs endorsing

If something here sounds like your situation.

My focus is Imagine IT, so I take on a small number of advisory conversations a year — when the fit is unusually good. If that might be yours, tell me what you're wrestling with and I'll tell you honestly whether I'm the right person.