Diligence

Before you hire me.

These are the ten questions a serious owner should ask before putting an outsider in the seat. Most people spend the first call getting these answers out of me. Here they are in writing so you can spend that call on your business instead.

Two of them are uncomfortable for me to answer. Those are the two I put in full.

The thing you will find on your own

The practice is two and a half years old. The work is not.

The work is not that new. Twenty years leading sales teams and moving company revenue. Close to six of those years spent advising owner-operators from outside their org chart, three of them inside Zillow, where advising real estate business owners was not a side function. It was the job.

So the only thing that changed two and a half years ago is who signs my check. I did not leave a job to start a consulting firm. I left because I would rather be in one business than advise ten.

Do not evaluate me like a firm with a hundred logos. Evaluate me like a hire: what has this person personally carried, what did it produce, and would the people who watched him do it say the same thing. Those three answers are all on this site, with names attached.

Q01

Give me two or three clients whose businesses looked like mine when you started.

I will name them on the call, and I will tell you which ones are not a match for your situation. What I will not do is describe a company in a way that makes it sound closer to yours than it is. The closest analog I have in public: ChuckTown Homes went from 10 to 90 producers in 15 months across five new markets in three states. As their Zillow Growth Advisor, I worked with their leaders on recruiting and ramping new agents. That was a producer-count problem inside a services business. If your problem is producer count, ramp, or retention, that is the same problem wearing different clothes.

Q02

What specifically did you change in their business?

In every case it was the same three things in the same order. First, I named the seat nobody had built, the one above the staff and below the owner. Second, I took the calls the owner had been carrying alone: the hires, the renewals, the pricing conversations, the partner talks. Third, I hired and developed the person who takes those calls from me. The change is not a system I install. It is a set of decisions that start getting made on a cadence instead of getting deferred until the owner has a free Tuesday.

Q03

What was the measurable result?

Zillow: a business line from $0 to $300M over three years, built with the original team that brought Flex, now Preferred, to market. ChuckTown Homes: 10 to 90 producers in 15 months. Lifestyle Family Fitness, later acquired by L.A. Fitness: as Regional Sales Director I built the sales team at the company L.A. Fitness acquired at $20M. A current real estate client: 70 hires in six months, scaling from 60 to 120 producers across five markets and two states. Every one of those is a number I personally carried, not a number I advised on.

Q04

What would those founders say you did poorly?

I move faster than the team is ready for. In month one I have pushed initiatives before people were up to speed, and I have had to learn that bringing the team along is part of the move, not a delay to it. When it goes wrong, it goes wrong the same way: I am three steps ahead, the team is on step one, and the work stalls because I got out in front of the people who have to run it. I now build the ramp into the first thirty days on purpose. It is the correction I have had to make most.

Q05

Can I speak privately with two former or current clients?

Here is the straight answer. I stopped taking W-2 roles two and a half years ago and I have worked with a small number of clients since, so I am not going to hand you a reference list built to look bigger than it is. The only thing that is two and a half years old is who signs my check. Before that, I spent three years inside Zillow in a consulting seat whose entire job was advising real estate business owners on their businesses, which is where most of my advisory reps come from. What I will give you is 16 written recommendations from the executives, peers, and teams who worked beside me from inside the operation, every one public on LinkedIn under a real name with a real date, where you can click through and verify each one yourself. Most of those are colleagues, executives, and teams who worked beside me. Some were clients of the business I was inside at the time, not clients of my own practice. I am telling you that up front so you weight it correctly. On the call, ask me anything you would have asked them.

Q06

What does the first 30 days actually look like?

Week one I am in your meetings, not in a data room. I sit in the ops meeting, the sales meeting, and whatever one-on-one you dread most, and I say very little. Week two I bring you the shortlist: the three moves that are worth making and the one you have been avoiding. Week three I start running one of them, with your team, in the room, on the calendar. By day thirty you should be able to point at a call that got made because I was here and would not have been made otherwise. If you cannot, we have a problem, and I will be the one to say it.

Q07

What decisions will you own versus recommend?

I own execution. I recommend on capital, equity, and anything that changes who owns the company. Inside the operation I carry a revenue target, I run the calls, and your team reports on the work with me in the room. That is the part that makes this different from advice. What I do not do is spend your money or restructure your cap table. Those stay yours. If you want somebody who only recommends, you want a consultant, and I am not one.

Q08

How many other clients will you have while working with me?

Four teams at a time, and that is a hard ceiling, not a marketing line. You can verify it on the call: ask me who the others are and what industries they are in. I will tell you. If I am at capacity when you call, I will say that too, and I will tell you when a seat opens rather than taking your money and thinning myself out.

Q09

What happens if after 90 days we decide this isn't working?

Three-month minimum, then month to month. If we decide to stop after that, we land the plane so the work in flight gets handed off instead of dropped. The month I stop being worth what you pay me, I say it first. I would rather end an engagement cleanly and keep the relationship than ride out a quarter that both of us know is dead.

Q10

What would make you tell me I'm not a good fit for you?

Teams too small to cover the engagement, because the math does not work for either of us. An owner who wants a plan they can file rather than a person who runs it. A business where the real problem is capital, or product, or a partner who needs to be bought out, because none of those are mine to fix. And any situation where I would be the fourth outside person in three years, because that pattern is rarely about the outside people. I turn down more of these than I take, and I will tell you on the first call, not after you have paid for a scorecard.

The fair question

What if the bottleneck isn’t you.

My whole pitch assumes the business has grown around you and the decisions now queue behind you. Sometimes that read is wrong. Here is how I sort it, and I sort it out loud on the first call.

Mine to fix

  • The business routes every decision through you.
  • The team is there but the calls are not getting made.
  • Producer count, ramp, or retention is the ceiling.
  • Revenue is flat and nobody owns why.
  • You need a manager bench before you can step back or sell.

Not mine

  • Product-market fit

    If the market is telling you no, more sales activity makes the no louder. Not my seat.

  • Capital

    If you need a raise or a credit facility to survive the next two quarters, you need a banker before you need me.

  • Unit economics

    If the business loses money on every unit, scaling it is the wrong move and I will say so.

  • A partner problem

    If two owners want different companies, no operator can run between you. That is a lawyer and a hard conversation.

  • One great salesperson

    Sometimes the answer is a hire, not a seat. If that is the read, I will tell you what to look for and you can go hire them.

If the diagnosis comes back as something on the right, I tell you on the call and I do not pitch you. I would rather be the person who told you the truth once than the person who billed you for a year of the wrong work.

Ask me the rest live.

Three-month minimum, then month to month. The month I stop being worth what you pay me, I say it first.

Or read how I run the seat week by week before you book.

Not ready to book

Every week you wait has a number on it. The calculator tells you what it is, in about two minutes.

Show me my number

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