I'm a very positive, optimistic person. If there's a chance of rain, I'm still bringing my sunglasses and wearing my Techstars t-shirt. In a recent post, I talked about why optimism is bad for business--but this isn't the whole picture.

Quoting Winston Churchill, "an optimist sees the opportunity in every difficulty." This might as well be the motto for every startup in existence. Without seeing the opportunity for disruption, entrepreneurs wouldn't be on a quest to solve the problems that exist today--whether that be in financial technology, or in agriculture.

Startups need a team of optimists to conceptualize an idea. Those optimists see an industry leader and believe they -- the quasi-company with just an inkling of an idea -- can one day build a solution to put that major corporation out of business.

When starting, or even simply running a business, it's best to have plenty of optimists, but you also need a balanced team. You can stack your decision-making team with forward-thinking idealists -- to keep fresh, creative ideas top of mind -- but you best have a least one skeptic around that table to play devil's advocate. Here's why:

Devil in the details

When things are trucking along as usual, optimists see a glass half full. But, there could be trouble lurking around the corner.

Skeptic leaders will push the team to look into issues that may not currently exist, which allows a startup to stay on their toes. Have you thought about a potential user data leak taking place tomorrow? Of course not--because you haven't had one, and why would you?

Having a leader with this mindset will allow your company to prepare for a crisis that could potentially end your business. You don't want someone who is afraid the sky is falling, but you want someone who has a general lack of confidence in humans, or simply the process, to behave the intended way.

Willingness to call a baby ugly

I've heard a lot of startup pitches in my day. The best pitches get you excited about the idea behind the company, but also speaks to the potential factors that could get in the way. Trying to hide these potentials makes it very obvious to investors that you either haven't thought of them, or you're simply trying to skirt around a problem.

For any avid watchers of Shark Tank, you'll see this criticism in motion. Sometimes it comes with kindness, other times with brutal honesty. It's easy for the Sharks, and even the viewers, to spot a team that is too optimistic, with their heads in the clouds.

In some cases, the best business advice founders get is having an outsider tell them they have an ugly baby. Having someone on your team who can speak skeptically will save your company time, and potential embarrassment on prime time TV.

Hire a wolf, not a sheep in wolf's clothes

As humans, we're social animals. It feels wrong to stray from the path, to have the unpopular opinion. No one wants to be a Debby downer when the team is all amped up, but it's necessary to keep the entire team in check.

It may seem more productive, or more smooth, to have someone who can deliver the "compliment sandwich." You've heard it countless times before: "this is a great idea, but I think we need to focus on this. But again, thanks for bringing this to the table."

These people might keep smiles on faces, but look for someone who is blunt, who can tell it like it is. In the long run, you'll appreciate bringing the veracity to your leadership team, even when feathers are ruffled.

Published on: Nov 1, 2018