Philly CEO's career advice: 'Swim in ambiguity'

Miles Wilson, the President/CEO of EducationWorks, a Philadelphia nonprofit with contracts to provide after-school programming, at Grover Cleveland Mastery Charter School on April 4. "To be entrepreneurial, you can’t have everything figured out," he says.

Miles Wilson came to our interview well-prepared, his thoughts neatly spelled out on a tablet set squarely in front of him on a conference room in the headquarters of EducationWorks, a Philadelphia nonprofit with contracts to provide after-school programming, often at distressed schools in Philadelphia and Camden.

And naturally, being a reporter, I took one look at that tablet and read it all immediately, upside down. It’s a skill that comes with the profession.

One phrase jumped out. 

What’s "swim in ambiguity"?  I love that.

If you look at some of my past, all the different things, there were plans, or there were thoughts of a plan.  But, there’s always, like, an ambiguous space that exists in almost everything  we do. I’ve had a couple of speaking engagements at Lincoln University and at St. Joe’s.  One thing I share with the young people there is you have to find comfort in ambiguity. 

Far too often in the world that we live in, especially now, the expectation is that everything is solved and figured out for you.  It’s an execute model.  You just come in and you plug and play.  People who have been walking the earth a little bit longer know things just don’t work that way.  And, you can’t be so impacted by the fact that things have not been fully formed and fleshed out for you that it destroys your drive and has you not being successful in the workplace. 

So, one thing that we talk about here at EducationWorks and that we build into the conversation, even while we’re interviewing, is that we’re looking for individuals who swim in ambiguity.    It’s an entrepreneurial mindset that we’ve introduced here in this organization.  To be entrepreneurial, you can’t have everything figured out. 

There is no such thing as a perfect time and a perfect place.  What we’re looking for is individuals who swim in ambiguity.  They love it.  They backstroke in ambiguity, versus run from it.  You’re going to help us figure out what the high-end goal is, what the endgame is.  Then we have to trust each other.  We’re smart enough to reverse and figure out all the steps we have to take to get to that place.  But, in order to work that way and operate that way, we all have to be willing to swim in ambiguity, enjoy the ambiguity, and look at it as an opportunity to build and craft something.

[Click here to read my Executive Q&A with Miles Wilson, published in Sunday's Philadelphia Inquirer. His message? Don't let racism derail your dream.] 

When I interview people one of the things we talk about is that, given our mindset and who we are, you have to be able to swim in ambiguity.  We’re looking for builders, not maintenance people.  I’m not interested in robots.  I’m not interested in anybody that’s looking for everything to be completely figured out.  I want you to have a voice.  I want you to have a say.  I want you to be able, regardless of the position, to be able to give us feedback on what’s going on so we can craft the next best thing for the kids that we serve.

Interesting. Any other philosophies?

We believe in failing fast here.  I would much rather have an individual that goes after it and fails, versus somebody who will bury themselves in a corner and not move and be active.  One of the things that we’re trying to introduce here in this space is the ability to fail fast.  Go after it.  We’ll give you the parameters to play in and then run wild with your thoughts and opinions.  Like, figure this thing out.  Let’s have an exchange about what the next best thing is.  Don’t be fearful of a misstep.  Recognize the misstep, learn quickly from that misstep and pivot. 

So, this whole thing about swimming in ambiguity also dovetails with this idea of failing fast.  The idea of being dynamic.  Dynamism is something that you’ll see in the walls across the office.  We want dynamic people with dynamic thoughts.  But, we also want people to move with urgency.  You can be thoughtful and be urgent all at the same time.