Some of the Rooted crew on a 120-ton crane removal, from left: Matt Bronakowski, Max Jarvis, Jones, Houston Johnson, Alex DeWan and, front row, Dom Ward. Photo courtesy of Andy Jones.

I almost cried in a tree once.

Not because of the tree. The tree was a massive dead Pinner – the kind of job that reminds you why you got into this business. We had a 120-ton crane on the ground. The job was worth $20,000. The crane alone cost $8,800 for the day.

I should have been locked in.

Instead, my phones wouldn’t stop. Clients wanting bids. Annual insurance audits. A news reporter wanting an interview. My other crew lead needing advice. Brand partners needing travel confirmations. Existing clients looking for their renewal programs. All of it, at once, pouring through two phones while I was trying to focus on one of the most technical removals we’d ever attempted.

At some point, I stuffed both phones into a rope bag and threw them out of the tree. Calls be damned. I had to climb.

I wish I could tell you that was a rock-bottom moment – that I came down from that tree, made some hard decisions and everything changed. The truth is, it was just a Tuesday. That kind of chaos had become so normal I’d stopped recognizing it as a problem. I thought it was just what running a growing business felt like.

It took me longer than I’d like to admit to understand what was actually happening.

I wasn’t just busy. I had become the bottleneck.

A note on the systems

Before we talk about hiring, we need to talk about software – because, in my experience, the answer to administrative chaos begins with systems long before it begins with people.

One of the earliest investments we made at Rooted Arbor Care was a customer relationship management (CRM) system. In those first several years, it helped us organize customer information, scheduling, proposals and job history in a way that handwritten notes and spreadsheets never could. More important, it forced us to start building systems – and systems, not employees, are the real foundation of a scalable business.

Today, there are many excellent software options available to tree care companies, and the platform you choose matters less than whether you’re actually using the one you’ve chosen. Before you conclude that you need another person, ask yourself honestly whether you’ve fully implemented the software you’re already paying for.

Are proposals going out efficiently? Is customer communication organized? Is scheduling centralized? Are invoices being generated promptly? Is your whole team working from the same information?

Many owners believe they need another employee when what they actually need is better implementation of the tools they already own.

We eventually moved to a different software platform, drawn by its integrations, field accessibility and growing suite of AI-driven tools. As we added crew members, the platform proved highly scalable. Over time, it stopped feeling like software and started functioning more like an operational partner. Once it was fully implemented, it changed how the entire organization communicated.

Still, even the best software has limits. Ours became clear around year four.

Sign #1: When systems aren’t enough

Here’s a sign many owners miss, because it feels like the wrong kind of problem to have.

When your software is working, your systems are solid and you’re still running out of hours in the day – that’s not a software problem anymore. That’s a capacity problem.

At Rooted, we went from just under $400,000 in our first year to $560,000, then $690,000, then $1.1 million. This year we’re on track for $1.5 million. We scaled our production team well. Our income-to-debt ratios were actually improving with growth, not moving in the wrong direction – which doesn’t always happen, and we don’t take it for granted. We purchased commercial property to grow into.

By most measures, things were going right.

But we waited until the middle of year four to bring on part-time administrative support. And I can tell you with complete honesty that we waited too long.

The warning signs were there. Estimates sitting unsent. Customer follow-up becoming inconsistent. Invoices getting delayed. Employee development getting pushed to the back burner. Administrative work didn’t just bleed into some evenings – it consumed the majority of them and much of my weekends. And occasionally, a tree-company owner found himself stuffing two phones into a rope bag because he couldn’t figure out any other way to do his actual job.

If that sounds familiar, keep reading.

Sign #2: You’re the bottleneck

One of the easiest traps for a growing-business owner to fall into is becoming the bottleneck – and the insidious part is that it feels responsible at first.

You’re protecting quality. You’re making sure things get done correctly. You’re answering every call, scheduling every job, approving every invoice and personally managing every customer interaction.

Then something shifts.

The person with the most experience, the most industry knowledge and the greatest ability to generate revenue is no longer generating revenue. They’re spending most of their time moving information from one place to another.

When the highest-skilled person in the company becomes the bottleneck, administrative support is no longer a luxury. It’s a necessity.

My high-school baseball coach, Chris Robbins, used to tell us that the best ability is availability. He was talking about showing up for your team. Years later, I’ve realized it applies equally well to running a business. If I’m buried in scheduling conflicts and invoice follow-ups, I’m less available to my clients, my employees and the work that actually moves the company forward.

The goal of administrative support isn’t just to save time. It’s to restore availability.

Sign #3: A part-time solution

The first step doesn’t have to be a full-time hire. For us it wasn’t even close.

We started by outsourcing bookkeeping and bringing on part-time administrative support – and the relief was immediate enough that my only real regret was not doing it sooner.

A part-time administrator can handle scheduling, customer communication, invoice management and CRM maintenance while freeing the owner to focus on estimating, production management and employee development. You don’t need to solve the whole problem at once. You just need to start.

The question isn’t whether administrative support costs money. It does. The question is whether your time is being spent where it creates the most value – and whether the math works in your favor when you do the honest accounting.

For most growing tree-care companies, it does.

A throwback photo from 1993 of Jones with his mother, Kate, who came out of retirement to manage key administrative roles for Rooted Arbor Care. Photo courtesy of Andy Jones.

Sign #4: The right people

As we approached the end of year four and headed into year five, administrative support was no longer an expensive luxury. It had become a mandatory sanity saver.

I want to be careful here, because I got genuinely lucky – and I know it.

Our administrative team at Rooted consists of two people who are, in their respective lanes, about as good as it gets.

Luke handles everything CRM-related, phones, our website and our digital marketing – both the Rooted Arborists media content and our client-facing marketing. He is, without exaggeration, the reason our backend runs as smoothly as it does. If you’ve ever interacted with our brand online and thought it felt polished and professional, that’s Luke.

Kate – my mom, who we successfully lured out of retirement – manages our books, handles insurance, coordinates with municipalities and contractors and steps in as our most effective collection agent when an account needs a firm but gracious nudge. She brings a level of precision and institutional knowledge to those functions that I could not replicate and, frankly, have no desire to.

That said, even with great people, the early stages of administrative onboarding are rarely smooth. They won’t immediately understand your processes, your software, your customer expectations or your particular brand of entrepreneurial mania. There will be training. There will be mistakes. There will be moments when you question the whole decision.

It often feels worse before it feels better.

This mirrors field employee development almost exactly. When a talented climber begins taking on greater responsibility, production often dips before it improves. Remember: time, training and teamwork lead to traction. New hires don’t create new problems as much as they shine a spotlight on existing ones – missed follow-ups become visible, scheduling weaknesses surface, processes that only existed inside the owner’s head get forced out into the open.

That’s uncomfortable. It’s also exactly how organizations get better.

Sign #5: Stop doing it all

Here’s the shift that surprised me most.

I expected administrative support to take work off my plate. What I didn’t expect was how much it would multiply what the rest of the plate could hold.

As arborists, we understand production-force multipliers intuitively. We invest in mini-skids, bucket trucks and cranes because they allow us to accomplish more with the same amount of labor. The ROI is obvious, and we don’t hesitate.

Administrative support works the same way – we just don’t always think about it in those terms.

The right administrative professional paired with a fully implemented CRM doesn’t just answer phones and send invoices. They identify inefficiencies. They improve communication. They maximize crew utilization. They strengthen scheduling. They help unlock the full value of the software you’ve already invested in. They become the xylem and phloem of your operation – quietly moving the right resources to the right places so everything above the surface can grow.

They stop performing tasks and start creating capacity.

That’s when a collection of people and software starts functioning like an actual organization.

Restoring autonomy

I still wear a lot of hats. That’s the reality of entrepreneurship, and I don’t expect it to change anytime soon.

Climbing is still one of my primary hats – and honestly, one of my favorites. So is consulting with clients, developing employees, strengthening industry partnerships and growing the business. Those are the hats I was built for.

The difference now is that the hats I wear connect directly to the things I’m uniquely qualified to do – and I spend less time on the things someone else can do more efficiently than me.

You’ve probably heard plenty about work-life balance. If I’m being honest, I’ve always found it to be a bit of a myth for small-business owners. There are seasons when the business demands more than we’d like to give.

But autonomy – spending more time on the things you’re built for, and less time on the things you’re not – that feels achievable.

Administrative support didn’t eliminate my responsibility. It restored my autonomy. And for most tree care business owners, autonomy may be the closest thing we’ll ever find to work-life balance.

Because the goal was never to work less. The goal was always to be available for the things that matter most.

Andy Jones, BCMA, CTSP, TRAQ, is an ISA Board Certified Master Arborist and production climber and co-founder of Rooted Arbor Care, a TCIA member company based in St. Louis. He is a member of TCI Magazine’s Editorial Advisory Committee and an Air Force veteran.

“How Do I Know When It’s Time to Stop Being My Own Office Manager” by Andy Jones, BCMA, CTSP, is one of three articles that make up our How Do I Know When It’s Time To… business feature. The other two are “How Do I Know When It’s Time To Develop an Apprenticeship Program” by Jonathan Perry and “How Do I Know When It’s Time To Train or To Terminate” by Korey Conry, CTSP.