I Had 5 Months to Onboard an Operations Manager. Then My Plan Blew Up.

Earlier this year, I very publicly shared my seemingly responsible, sound, strategic approach to finding and onboarding a new Operations Manager.

I gave myself a five-month runway to get them up to speed before my family and I flew out to Europe.

Five months!

That's pleentttyy of time, I thought.

Plenty of time to transition things off my plate. Update processes. Get someone comfortable with our team and clients. Work out all the inevitable kinks of bringing someone into a small business where, admittedly, quite a lot of information still lived inside my head.

I was being proactive.

Responsible, even.

Well, about two months into that five-month plan, the person I hired got a full-time job offer.

Well, shit-a-doodles.

My nice, well-paced plan suddenly had a very real ticking clock.

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This was also not exactly a calm season of business.

While figuring out what the heck I was going to do about my Operations Manager situation, I was also:

  • launching an internal app

  • selling my house and bouncing between our in-laws' house and hotels

  • navigating a client project I definitely should have turned down

  • keeping up with my 4-year-old still being home with me full-time

  • preparing to move my family to another continent

Talk about a full-freaking plate.

This is approximately the point where conventional delegation advice would tell me to stop.

Don't hire right now.

Get through the busy season.

Document your processes.

Clean everything up.

Get your SOPs in order.

Then, once the business is organized and you have enough time to properly train someone, you can think about delegating again.

Except I had one fairly significant problem with that plan.

I was leaving.

And I 100% planned to unplug when I did.

I had zero interest in trying to solve business problems from Europe while simultaneously figuring out international travel with jet-lagged kids.

Waiting until things “calmed down” wasn't actually an option.

So I hired Sonia.

We had about 90 days.

Sonia wasn't entirely new to Auxo.

She had already been working with us on a project and helping with some of our processes, so she had a head start.

But knowing the business and being responsible for helping it run are two very different things.

We had roughly 90 days to get her comfortable with all things Auxo, including the clients, assistants, systems, decisions, weird nuances and, perhaps most importantly, my particular way of serving our clients and assistants.

And we did not have the pristine operational playbook you're supposedly supposed to create before hiring someone.

Some of our processes were outdated.

Others were actively changing.

We were launching a new internal system while she was learning the old one.

There were absolutely things still living in my head.

So we didn't spend the next three months frantically trying to document every possible thing Sonia might encounter.

We talked.

A lot.

Our onboarding strategy was basically aggressive communication.

We had an hour blocked every Monday.

Initially, we had another 30 to 45-minute block available in the middle of the week.

We talked on Slack basically every day.

And Sonia had full permission to bother me.

That last part matters more than it sounds.

Founders often want someone who can “just run with things.”

I understand why.

The whole reason you're hiring is because you want fewer things requiring your attention.

But you can't expect someone who has been inside your business for seven days to understand decisions you've been making for seven years.

So in the beginning, Sonia asked questions.

I explained why I did things a certain way.

We talked about what I cared about, where she had room to make her own call and when I wanted to stay involved.

She saw the messy parts.

And gradually, she needed less from me.

Within about a month, we stopped needing that midweek meeting.

Not because we'd finished some giant onboarding curriculum.

Because she was learning how the business worked.

Then came the actual test.

Before I left, Sonia sent me what was essentially an “everything currently happening inside Auxo” roll-up.

Clients.

Emails.

Calls.

Pending issues.

Things she was watching.

Things I needed to know.

I could look through it, fill in anything she had missed and know that we were both operating from the same picture of the business.

Then I left.

And I took about 10 days mostly off.

Was everything perfect?

Absolutely not.

At one point, Sonia discovered she didn't have permission to issue a refund.

We'd missed it.

The world did not end.

She flagged it, we dealt with it, and now our process is better for the next time I leave.

More importantly, she handled significantly more than I expected her to be ready for after such a compressed onboarding period.

That's what changed my thinking about being “ready” to delegate.

I am a huge believer in processes.

I literally make money helping businesses operate better.

But I think we've turned “get your systems in order” into another way for founders to postpone getting help.

There is a difference between having enough clarity to delegate well and making your business perfectly delegatable.

The second one may never happen.

Businesses change.

People change.

Roles change when you finally put the right person in them.

The process you created when you were doing something yourself may not even make sense once another person owns it.

So yes, give someone structure.

Set expectations.

Give them access.

Document the things that need to be documented.

But don't spend six months preparing your business for a person who hasn't even joined it yet.

The Simple Take

You don't need to make your business perfectly delegatable before you delegate.

You need to know where you're going.

You need to communicate the context that's stuck in your head.

You need to give the person enough access and information to actually help.

And then you have to let them help.

Sonia and I unpack the entire 90-day experiment from both sides in this week's Can We Not?, including what helped her ramp up quickly, what we didn't bother documenting, what we completely missed and what actually mattered when it came time for me to leave.

Listen to: Can We Not Pretend You Need Perfect SOPs Before You Delegate?



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How to Onboard a New Remote Team Member in a Small Business

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