I've made many mistakes.
I've hired the wrong people. I kept poor performers employed for too long. I've given ambiguous instructions, allocated capital to the wrong projects, and signed off on marketing campaigns that should have never seen the light of day.
But whenever I'm asked if there are any decisions I wish I'd never made, I take a more philosophical view.
The simple answer is no.
Just one decision made differently might have changed where the company ended up and where I ended up, so I think it best not to look back.
Though when I do look back at those mistakes, I can see that I did not have all the data needed to make those decisions. Or did I?
When it comes to entrepreneurship or any leadership role, there is one entrepreneurial trait that stands out from the rest: the ability to deal with ambiguity and make decisions without having all the information.
Here's how entrepreneurs can be better at dealing with ambiguity.
Hire talent who can easily deal with ambiguity
The one thing I've learned from the past 30 years of entrepreneurship is that you never have enough information, but, paradoxically, knowing that you don't have enough, is enough.
An entrepreneur who doesn't embrace ambiguity can be paralyzed by the vague nature of the job. And when your team doesn't deal well with ambiguity, they sit around waiting for someone else to make the first move. So nothing gets done.
Therefore, when hiring, in addition to interviewing for skill set, look for the ability to deal with ambiguity.
Here are a few questions I ask:
What is a specific example of a big decision you had to make when you felt you did not have all the information you needed? Why did you make that decision anyway?
When is the last time you made a big professional decision that turned out to be wrong? Would it have been better to wait until you had all the information?
And after you're done making that decision, stick with it and accept that you made the best decision under the circumstances. And remember, it's not just a career trait. It's also a valuable life trait!
Love the puzzle-solving parts
This might sound weird, but I love not knowing all the answers.
There's something exciting about taking a bunch of unrelated pieces and tying them together to create a new business idea or solve a mystifying dilemma.
When I was the CEO of Blinds.com, there was a radio show on NPR I listened to religiously called Car Talk.
Car Talk was a call-in show with two smart MIT graduates, Tom and Ray Magliozzi, who owned a car repair shop in Boston (their "fair city"). Irreverent and hilarious, the brothers adeptly answered questions about cars, jabbed jokes at each other, and added in playful tidbits of life philosophy.
Each week, Car Talk listeners were asked to solve a puzzle and send their answers to Puzzler Tower. I tried to solve the puzzle every week.
I like to visualize what a puzzle would look like before it's assembled. This skill is my superpower and contributes to a lot of my success.
When you're stymied for a solution, look far beyond your direct competition. You should learn from every business, every ad you see, and every person you meet. Everything is an inspiration. Everyone is your mentor. Together, they often align to create a surprisingly unique picture.
Putting those pieces together requires the help of your team. So turn the box upside down, dump out the pieces you know, ask for new pieces, and then bring in some people with no experience. Voilà; you've created something out of nothing.
To do things you didn't even believe were possible, you must treat everything as one big puzzle waiting to be solved.
And when you can do that, it's certain that you and your team can achieve things you never thought were possible.