Michael Connolly | Crain's Orlando

In this ongoing series, we ask executives, entrepreneurs and business leaders about mistakes that have shaped their business philosophy.

Michael Connolly


Winter Park, Florida-based Sonobi is an independent technology developer that designs digital advertising tools and solutions for the industry's leading media publishers, brand advertisers, media agencies, demand-side platforms, and media technology providers. They are also known for their bro-bot YouTube video series.

The Mistake:

Failing to "systemize" before you delegate.

In a fast-growing company, you have to do what we call "systemize" before delegation. Failing that first step, what you end up with is someone [coming] in on a system that doesn’t exist. And you end up wasting a lot of time.

We’re basically an engineering company, and this concept applies to engineering as much as any other [discipline]. As we were standing up our engineering team, we didn’t have specific processes for software development. So what was our system? Were we using two-week sprints? Were we using four-week sprints? It was a very freestyle environment.

And if you try to "verticalize" that – if you try to add leadership, directors and VPs to that environment – without a defined system, what you end up with is a lot of wasted cycles that aren’t as productive as they could be.

What we had to do is go back and really define the system: “This is how we’re going to develop software; this is going to be our process; this is going to be our sprint-length.” And then move people into leadership roles to execute those systems.

[Before we did that], we would end up rebuilding things that we had already built because the process wasn’t in place to catch things like quality control or to make sure things were documented properly. You can add all the leadership you want to that environment and you’ll still continue to be unproductive. Expecting someone to stand up a system where one doesn’t exist, particularly in engineering, will ultimately result in wasted hours.

"I don’t think everyone was working from the same song sheet."

The Lesson:

Especially with entrepreneurs and CEOs of early-stage companies, when you’re standing up a new team, they’re moving so fast. There are so many different things to do and there’s an assumption that, by hiring someone new, they are good at both standing up a system and executing that system.

And the reality is that most people are not good at both. They’re generally good at one or the other. A good example of that is Tom Brady and Bill Belichick. Belichick establishes the system, Tom Brady executes it. And they don’t do each other’s job.

And you can make that mistake of assuming that because I hired this person, they’re going to be able to create this system. And they’re going to be able to execute it. And what you really need to do is to "systemize" and create that process. And then you hire someone and delegate the execution of it.

[Before], I don’t think everyone was working from the same song sheet. Every fast-growing technology company suddenly has lots of different people, lots of different ways of doing things, but hasn’t quite defined the culture of how they do things "here." In that type of environment, people can be running in a lot of different directions.

Imagine the football game has already started. And then you say, “Okay wait a minute, I want to create an offensive system in the middle of the game.” You basically stop what you’re doing and go back, establish the system, and delegate people to operate within it. Then suddenly you may see things clicking, and you say, "Okay, let’s make an adjustment." But that has to happen from the top down. It can’t happen within.

Follow Sonobi on Twitter at @sonobi.

Photo courtesy of Michael Connolly                                                                                                                                                                               

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