From Operator to Advisor: What We've Noticed

Lis­ten to the Arti­cle (4:57)

We’ve brought a lot of advi­sors onto our team over the years, and I’ve noticed a pat­tern in the ones who turn out to be great at this work.

Almost all of them ran some­thing first. A CEO, a pres­i­dent, a senior exec­u­tive who grew a real busi­ness. And at some point after they’d done that job well, they start­ed want­i­ng some­thing a lit­tle different.

It’s usu­al­ly not burnout. Most of them still want to work hard. They just want to put that ener­gy some­where new. They’ve been through the growth jour­ney them­selves, and now they want to help oth­er lead­ers through it.

I’m shar­ing this because some of you may know some­one in that spot right now.

The paths peo­ple usu­al­ly look at

Plen­ty of great oper­a­tors take anoth­er CEO or exec­u­tive role. That’s a great choice. Some of the best lead­ers I know have run three or four com­pa­nies, and the world needs more peo­ple like that.

For the ones who decide they want to move into advis­ing, a few paths tend to come up:

• Board seats. Real influ­ence along­side a lead­er­ship team, usu­al­ly four to eight meet­ings a year.
• An oper­at­ing role in pri­vate equi­ty. Hands-on, close to the deal, often with equi­ty upside.
• Solo con­sult­ing or coach­ing. Full inde­pen­dence, built exact­ly your way.
• A coach­ing or advi­so­ry fran­chise. A proven sys­tem and a ter­ri­to­ry to work in.

All good options. We’ve seen great peo­ple do well in every one of them.

One more option

What we’ve built is a bit dif­fer­ent, and a lot of peo­ple don’t know this kind of mod­el exists. It’s a firm with a shared oper­at­ing sys­tem. We bring advi­sors clients, so they’re not spend­ing their time sell­ing. And we invest heav­i­ly in their development.

That last part mat­ters more than peo­ple expect. Run­ning a com­pa­ny well gives you great instincts. But help­ing some­one else’s com­pa­ny grow, quar­ter after quar­ter, is its own craft. Know­ing which lever actu­al­ly moves the num­ber. When to push, and when to let a leader get there on their own. How to earn trust with a team that does­n’t know you yet. We spend 13 days every quar­ter work­ing on our own devel­op­ment, because even with decades of expe­ri­ence, there’s always more to learn.

The three most recent addi­tions to our team

Tim Molek, Chica­go. Tim spent most of his career in con­sumer pack­aged goods, even­tu­al­ly lead­ing a busi­ness across North and South Amer­i­ca and grow­ing it near­ly ten­fold. Now he helps lead­er­ship teams turn strat­e­gy into execution.

Frank Mona­co, Toron­to. Frank spent more than two decades as a CEO, Pres­i­dent and COO, build­ing, scal­ing and trans­form­ing busi­ness­es, includ­ing multi­bil­lion-dol­lar inter­na­tion­al oper­a­tions. Now he works with CEOs run­ning com­plex, mul­ti-mar­ket businesses.

Christi­na Bot­tis, Chica­go. Christi­na has more than 20 years as a com­mer­cial exec­u­tive and has been a CXO four times, across SaaS, logis­tics, staffing and man­u­fac­tur­ing. Now she works with PE-backed and mid-mar­ket B2B CEOs who are scal­ing their go-to-market.

Each of them took what they learned grow­ing com­pa­nies and is now using it to help oth­er CEOs do the same.

To read about the rest of our team, click here.

If you’re think­ing about it

This is a big deci­sion, and it’s hard to think through alone. A few things help:

1. Talk to peo­ple who’ve made dif­fer­ent ver­sions of the move. Ask what they like and what they don’t. You only get the real pic­ture after hear­ing from a few people.
2. Try it in a small way first. Join a board for a project, or take on a cou­ple of con­sult­ing engage­ments. See how the work actu­al­ly feels.
3. Get clear on what you want the next ten years to look like. Not what you’re leav­ing, but what you’re mov­ing toward. Impact, free­dom, income and growth don’t always point the same way, and know­ing which mat­ter most makes the choice a lot easier.

If some­one comes to mind

We add about one great advi­sor a quar­ter. We have plen­ty of client oppor­tu­ni­ties. What we’re always look­ing for is peo­ple who want to spend the next decade doing this work.

If you know some­one at this fork, I’d love to meet them. And if you have ideas on where to find more peo­ple like this, I’d love to hear those too. Our Fifth Door white paper goes deep­er, and we’re always hap­py to con­nect peo­ple with one of our advi­sors who’s made the move.