3 Signs It’s Time to Bring in Outside Help for Your Business

Early-stage business growth is a wonderful thing, but it can also be misleading. It can also be addictive. Given both of those things, it’s easy to see why some founders assume they can keep running their company forever without ever bringing in new talent. But my career has taught me otherwise.

When my brother Todd and I started Roof Maxx to provide a cost-effective roof restoration alternative to homeowners whose shingles didn’t yet need replacement, we were in charge of every major executive decision. We wore multiple hats because that’s what it usually takes to be successful in the early days. Everything has to run lean in order to get things moving.

But once things do start moving — and picking up speed — it often becomes impossible for one or two people to keep tabs on every aspect of running a company. That’s when you need to bring some extra help on board.

So here are three signs that you’re reaching that critical point, backed up by my personal experience. If any of the following feels familiar to you, it might be time to start headhunting.

Sign #1: Your growth is outpacing your confidence

I certainly hope that anyone who starts a business does so with a certain degree of confidence. You should start a business because you’ve clearly identified a problem no one else is solving — or solving properly — and you believe you’ve found the best way to solve it.

That’s what we did with Roof Maxx. Nobody was offering roof restoration in the residential space when we started out. Most of the industry just focused on selling replacements that homeowners didn’t always need. The product we discovered and brought to market helped those homeowners get years of additional life from the shingles they already had, for up to 80% less money than a roof replacement would have cost them. Needless to say, we believed in the value of what we were doing unequivocally.

But as you grow, your internal voice starts to sound different. You eventually stop thinking “I know what I’m doing” and start asking yourself, “Am I still doing things the right way?”

When Todd and I started the business, our team was small and agile. We knew everybody who worked with us, so it was easy to keep a bird’s eye view of what was happening and take quick action to solve challenges. But the more customers we served and the larger our dealer network became, the longer we noticed it was taking us to make strategic decisions. There were just more moving parts to consider.

So if you notice that your ability to call the shots is taking longer, that’s your first signal. It means you’re starting to second-guess yourself, and you might need an outsider’s perspective.

Sign #2: You develop leadership needs outside your skillset

Every founder eventually learns to function in a chaotic environment, because that’s what every startup is. But to go from being a startup to being a national brand, you need to be able to organize that chaos. Sometimes, that requires skills or experience you don’t have.

In our case, we realized that Roof Maxx needed more than our passion and determination. It even needed more than the decades of roofing industry experience we had between us. With a dealer network spread across the country, it became clear that we needed a way to share and standardize information for them. That was a technology problem, and we were roofers. We didn’t know the answer, but we knew it had to come from someone who understood data better than we did.

That person ended up being Matt Ferguson, who we eventually brought on as our CTO. He wasn’t a roofer, and he wasn’t part of the Feazel family. But he was a data engineering expert. He’s currently spearheading our development of an AI-empowered training system that supports our dealers by connecting them with learning modules tailored to their individual needs. This has been instrumental in standardizing the experience our network delivers to homeowners across North America.

Sign #3: Pride is impacting your progress

If you use the steps above, identifying your need for outside help is a lot easier. But admitting someone else might be able to do part of your job better than you can be a lot harder.

A lot of founders can see the signs that it’s time to bring in new talent, but they still wait too long to do it because they’re afraid it will make them less valuable to the enterprise they’ve created. They don’t want to feel replaced.

We’re all human, and we all get emotionally attached to the things we’ve invested serious time and effort into making from time to time. In those moments, I find it helpful to remind myself that the ability to let other people in is a strength, not a weakness. We should talk about the value of vulnerability in business as much as we talk about the value of vision. Because in the end, you need both to make it.

Welcoming fresh talent to your C-suite doesn’t weaken you and your co-founders. It protects you by keeping you and your business from burning out. You can read more about that in this article about how we’ve managed to keep Roof Maxx a family-owned business without letting those dynamics impact our growth over the years.

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Early-stage business growth is a wonderful thing, but it can also be misleading. It can also be addictive. Given both of those things, it’s easy to see why some founders assume they can keep running their company forever without ever bringing in new talent. But my career has taught me otherwise.

When my brother Todd and I started Roof Maxx to provide a cost-effective roof restoration alternative to homeowners whose shingles didn’t yet need replacement, we were in charge of every major executive decision. We wore multiple hats because that’s what it usually takes to be successful in the early days. Everything has to run lean in order to get things moving.