Finding someone to run your biz when its outgrown your skillset

Wil Reynolds
Sep 6 · 9 min read

Finding someone who can run your biz when your business outgrows your abilities can go great or horrific but its highly likely to be one of the two.
I want to share anecdotal stories that all occurred recently between me and my #2 (And the company’s #1), Crystal O’Neill.

Before we do, lets take a step back and have some perspective. If you business grows enough to where your “problems” are “how do I find someone to help me run and manage it?” Take a second in your crazy whirlwind to reflect on the fact that you got to that point. Good work, now lets get into it.

How replaceable are you?

You’ve got to take an inventory of yourself. If you run the business by the book (Max value of the asset), you actually are making it easier for someone to come in and take over.
If you are more quirky and find yourself waking up some days wanting to do stuff that isn’t “hit margins” & “grow 40% YoY” then you gotta have someone who “gets you” and can help you see how you arrive at your decisions.
Examples for me, are I’ll tank margins to place bets on the future. We’ve given several people 2–3 raises in a year (Crystal got 3–4 double digit raises in her first year with me).
That means at any time, Crystal could get a “hey I’m thinking we grind margins to zero but triple R&D this year” kind of thoughts.

What’s your number & when do you want it?

The more you can paint a specific target at a specific time, the easier it is for a new operator to come in and build a plan to back into that. If you can say 5 years from now I want to sell the business & get a 5x EBIDTA, that’s much easier for an operator to come in and do. When you tell an operator that their job is to be “good to the team” & “do what’s right” & “grow the business” well those are HIGHLY subjective, making their job much harder. Crystal knows my 5 year goal is to love the work, the people we get to work with, and the clients we get to do it for every day. That is a REALLY hard target to hit.

I don’t have advice, I have stories of how I knew I had the right person

I hope for every founder out there who thinks, hmmmmm maybe I should get someone else to come in and run this company, that these examples give you some “sights and sounds” of what has transpired that helped me to identify someone who could take over for me, and can balance running the business operationally and culturally.

Here’s 5 small things I noticed in the last 3–4 months that are daily reminders I got the right person running this business.

Keep an eye out for these kinds of small things as people are coming up in your company, the stories here are just recent examples of things Crystal has been doing for 12 years at Seer. I’ve seen a lot of founders crash and burn on bringing in a “grown up” to help run the business, and it’s worked so well for me that I feel I owe it to share what helped me to feel confident in having someone come in and run the business.

Cleaning coffee spills in the fire exit
Crystal and I finished our 1 on 1 on the seventh floor of the Seerplex. She told me whats happening in the business and I listened, she told me where she thought my time investment would be most helpful and I committed to focusing. She filled me in on some legal updates and some people leaving Seer. With my update and marching orders our meeting was over.
As we opened the door to rush to our next meeting and walked down the emergency stairs we bumped into a newer employee (less than 1 year and pretty entry level), the employee spilled a few drops of her coffee in the fire exit.
Literally 5–10 drops worth, in a concrete and cinder block emergency exit, Crystal told the team member (who was apologetic) to go make their meeting and Crystal grabbed a roll of paper towels to clean up 5 drops of coffee in a rarely used an emergency exit floor. In her 12th year at Seer, she still sees her role the way I do… We’re not above anything to help. To me this matters as much as knowing how to manage a P&L.

Raises / Trust in Me
I began doing my annual check on our wage gap discrepancy and saw it got worse year over year. I was like WTF. Then it all made sense, we had some high ranking women execs/managers who weren’t at Seer anymore. Those few moves moved the average enough to get me a bit uncomfortable. But then I noticed something…Crystal has also given raises to 2 men in our company, 2 people who were stepping way up, so she gave them raises (and didn’t clear it with me), which is a GOOD thing.

But what caused our wage gap to be askew was that she gave some people raises above her salary.

So lets just back up a second, the person who runs the whole company, just gave 2 people raises that put them over her salary, and I didn’t know.
She is running a company and was the 3rd highest paid employee, WTF!
So I made sure that she and I would always make the same going forward. The moral of the story is humility and trust. Crystal knew that when I found out I would do right by her and when I confronted her, she said that was only salary and that she has a profit share so her overall was greater I was like yeah whatever.

Again, this is the kind of thing a leader just does. I’m appreciative to have earned her trust over the years for her to know if I ever see something off, I’ll make it right. I thought our maternity leave worked a certain way 6 years ago when Crystal took off, upon her coming back and me finding out that it didn’t work for her how I thought, I ended up paying her the difference (I think it was in the 10’s of thousands) she never brought it up, but by me jumping on it and making it right then, I think it earned her trust that in the end I’ll make things right, and she has done the same for her direct reports.

Volunteering

Working w/ Habitat to clean a warehouse.

I had an open day, 10 or so people had volunteered at habitat for humanity, one by one people dropped off, including me. 3 were left and Crystal was still going to go she made a commitment, she JUST KNOWS that volunteering is a deep part of our culture and that any time she spends doing that she is living out our values and leading by example.. I felt shamed a bit I found an excuse to not go, and here she was living out our values better than I was, so I said eff this, I’m going too.

She leads by example, and that made me follow her, she knows that making our communities better is a real value of ours and in spite of her having 1001 things going on she chose to work in a warehouse cleaning up for habitat knowing full well that in doing so, she was going to go home spend time with the kiddos and be working late that night.

People Matter

Hanging in SD making 1:1 time for pretty much everyone

There’s a theme here, Crystal doesn’t have a ton of free time, but she makes time for the things that matter and is willing to do the work to get it all done.
I was recently blown away when in our 1:1 she said she was going to grab coffee with one of our remote team members who lived about 2 hours away from the office. Crystal’s logic was simple…we had a co worker whom she hadn’t met in person, who lived only 2 hours away, so Crystal decided to drive 1 hour and meet them half way. She worked “remote” for a day with one of our remote co-workers who lived close enough for that to happen.

She just instinctively knows that if I could I would fly to everyone’s house to meet up with our remote team members if I could, but I have limits on how much I travel and its just not possible (She did approve my budget to have 2 apartments in Philly so remote team members could come to the office any time they want and spend time with co workers how ever often they want…we even pay for 2 flights per year for remote peeps to fly to a HQ). Lets take a step back on that too, I ask Crystal for all kinds of shit that financially could be seen as “hurting” our financials, but I just feel are right for culture, what is great is that she finds a way to make those things happen. Apartments in Philly and SD cost us REAL money, hits margins, but we want to make it easy for our team to come visit another office and stay as long as they want.

Here is our Director of Finance’s desk when you walk by:

She’s recently realized that our exec team should have more remote empathy, so she is forcing all of us to work remote for 2 weeks a year, so we can have more empathy for remote team members. That was her idea 100%. Love that she did that.

5 — SQL

All these stories are about culture. This one is about vision…I have been quite pushy about big data if you haven’t noticed 🙂
One day Crystal just mentions in passing that she is taking SQL classes an has passed them. As if she didn’t have enough to do she quietly just got it done. She didn’t tell me what she was going to do, she just did it.

If you are the kind of person that likes working in the business instead of on the business (like me, I love hands on work, client work, etc) don’t let people tell you you shouldn’t. BUUUUUT what you need to realize is that if your company is growing fast the company might end up outgrowing your skills. Holding on too long is dangerous.

I never found it fun to sharpen my saw on getting better at operating the company, I wanted to innovate, work with clients, and help my team members to grow. It was such a drain to learn the differences been net and gross margin trends. If you find yourself like this start looking now in your company for an eventual replacement, Crystal was with me 6–7 years and on that journey kept getting more and more responsibilities. Operationally she was learning and was more of a natural than I was for sure. So when it came time for me to find someone, operations was important, but wasn’t enough, they also had to know how to check what is operationally good for the company and what is good for the culture. I got to see that with each promotion, she never allowed the ops to dominate decision making. It influenced decisions of course but I never had to come in and say “have you thought how that is going to effect the people here???”

How’d I get Crystal? Craigslist. 🙂 A reminder that you can find talent all around you. The bigger of a deal culture is to you, the more you are going to have to start grooming people early to see who might in 4–5 years be able to take more and more operational and cultural responsibilities. You have to see these people in action to know they can represent all the crazy in your head and not lean too far to “operational metrics”. Its’s part of why I really enjoy it 17 years later.

Wil Reynolds

Written by

Serial Underdog @seerinteractive doing SEO, Marketing, & Stuff, I am whatever you say I am.

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