Brian Ballard | Crain's Washington D.C.

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

Brian Ballard


Based in Herndon, Va., Upskill is a tech company that connects hands-on workers with the information, equipment, and people they need to do their jobs more efficiently. Its software platform, Skylight, powers smart glasses and other wearable devices across manufacturing, logistics and field service operations.


The Mistake:

My board and partner still critique me on this: I’m fairly direct, so if I make a statement and everyone nods, I assume everyone’s got it and that’s the end of it.

I remember, specifically, when we were first expanding beyond military intelligence, and we were going to test a couple of different market verticals. At the time, it was logistics, manufacturing, healthcare, and field service all of which have fairly different product marketing needs. But when we began recruiting people for the healthcare vertical, we did a terrible job articulating to the team why we were making these hires, and how product marketing fit into that.

We wasted time and money, and just did not execute in that space at all. This was in deep contrast to our performance in the manufacturing vertical, where we did a better job articulating what was happening and why.

It’s really important to communicate and reinforce your vision often.

The Lesson:

It’s really important to communicate and reinforce your vision often. Just because you say it once whether it’s to the media, your partners, or to your teammates it’s important that everyone internalizes it. Failing to do that wastes so much business energy because you’ll eventually have to go back and course correct. It’s like operating with the head disconnected from the body.

Part of the way we’ve solved this is by moving to a default open communication style. On Slack, for example, we have an entire channel that automatically gives people access to all the information they need, while also allowing them to engage with each other. The information flow is far more proactive that way.

And sometimes, we just have to pick up the phone. If you text or email someone and don’t hear a response back, the communication might not have happened. Having that human-to-human conversation to make sure you’re on the same page is very important. Sometimes, that little investment can make all the difference.

Follow Upskill on Twitter at @upskillio.

​Photo courtesy of Upskill.