We All Need Some Professional Tough Love

Ben Brooks, Professional Coach and founder of PILOT gives us the advice we all need to hear

We’re back with another Member Spotlight, because our members are FRIGGIN’ AWESOME and always worth bragging about!
Now I know that we normally post our Member Spotlights on weekends, but this week’s feature touches on a subject that feels a little more appropriate to publish during the workweek (…and also we want to see if it gets more reads, ya bunch of slackers).
That’s why today, we reflect on your (our) professional development, courtesy of an insightful — and at times sobering — conversation I had with Ben Brooks, career coach and founder of the management training platform, PILOT.
I know it’s a Wednesday, and this piece isn’t as flashy or as heartwarming as some of our other Spotlights. But, if you’re at all like me, a 20-something New Yorker, working for a promising company, with a penchant for ignoring that little voice in your head that screams “WHAT THE HELL IS YOUR PLAN?!”, then read on, because you will get something out of this.

Can you start by giving us an overview of your background?

People have been asking me for advice since I was twelve; I only realized a few years ago that I should start charging for it.

In between those periods I worked for Enterprise, the rental car company, I helped Lockheed Martin with their classified spy plane programs, did some management consulting to help airlines restructure, and I worked in the insurance industry as the Senior Vice President of HR for a global company. I ended up learning a lot about a lot regarding various industry environments, and effectively received a broad-base on-the-job MBA that put me in position to give a lot of advice.

I have always been a very curious person. If I don’t know something, I generally want to learn more. A lot of my career involved figuring out what sort of skills I wanted to use. I love driving change and I like creating new things working with technology, themes that have resurfaced across the various industries I’ve worked within. The trick was stringing these experiences together and being aware of the definition of luck — preparation meets opportunity—and always focusing on the preparation quotient.

What geared you towards becoming a business coach? Was there a seminal moment?

When I decided to get into coaching, I actually didn’t know if I wanted to have that kind of a business. While in between jobs, I was driving on a bridge in Delaware, coming back from this executive education course I had taken in DC. This was a week-long program for execs to reflect on their own leadership, and my plan before that week was to be the head of HR at a mid-size company. I’m on that bridge, it’s foggy, I had this out of body feeling — ominous even — and I realized I was at this fork in the road. All week long I had this name tag that just said “Entrepreneur”, which wasn’t the case. I thought to myself that I could either be an entrepreneur, or an employee. It was a very binary choice; I didn’t know what I wanted to do, but this was back in 2013, when a lot of startups were on the rise, so I decided to take on this identity and then figure out what I wanted to sell.

What I found was people needed advice for their small businesses and their careers. So I started my company with just a pack of business cards; no website, no marketing materials. I ended up earning my first hundred thousand in revenue from $88 of business cards.

So how did that evolve into the sort of coaching do you provide now?

For entrepreneurs and business owners, I help them work on their business, rather than in their business. So we essentially have the board of directors meeting that they don’t have: we talk about the future of the company, the risks, the strategy, and we always push to make those factors better. I’m not involved in any of the work, but I’m involved in their growth, feedback, and broader decisions.

For individuals, the executive coaching side, we manage their career more like a business, more like a portfolio. Because I’m not worried about heir performance —I’m not their manager — we can talk about their needs and what they can do to take action in their career.

How did you end up founding PILOT?

PILOT, like my first business, was conceived in a car as well. But PILOT came from the thought that “Gosh, the same problems I’m solving for my clients by addressing their professional needs — everyone can benefit from.”

Coaching is expensive, only the top 1% or 2% of people can afford it, the median according to Harvard Business School is $500 per hour. So I wanted to figure out a way to make this sort of professional coaching more affordable. I wanted to make the process more accessible and more modern. It shouldn’t feel like you’re meeting your shrink, it should be something you can do on your phone, at night, on the go. I wanted a much more on-demand model in the era of Uber and Seamless.

So I put my life savings into the company as the sole investor. I hired a team of nine people and launched the company to provide more coaching to more people. It’s 96% cheaper than normal coaching, it’s beautiful, easy, and it’s fun.

The thing that we’ve found that’s really interesting across industries, titles, company sizes, age, etc. the PILOT members that are the most engaged — the superfans — are women. Women are nuts about PILOT. Our brand is very gender-inclusive and gender-neutral; we never built the product to cater to women, but female members love it.It makes them feel like they’re empowered, and that they’re advocating for themselves. Self-advocacy is the number one determinant of a satisfying career, and we’re always trying to develop that further into the software.

That’s especially prescient considering the recent “Google Manifesto”

Those are some of the headwinds women are facing. Not all women want to be moms, we want to help them embrace their own values, preferences, and figure out what they want in a satisfying career. We ask “When you retire, what metrics will you use to evaluate a successful career?” and most of the time, people’s answer is “Fuck, I haven’t thought of that”. It’s working on your career rather than in your career.

This is somewhat of a selfish question, but what sort of advice would you impart on a new generation of 20-something managers?

Three things:

First, invest in yourself. People will pay for college and grad school, but as soon as they get a job, they think their education is over. It’s great to see companies invest in people, but it’s costs time, money, and energy. So always put in more than what your company’s putting into you. That puts you way ahead. Go to a workshop, spend a weekend reading a certain book or attending a certain event. Get feedback from people outside of your company or project. Invest in yourself.

Second, take what I would call a portfolio approach to your career — you have an editorial job for a high growth startup, but who are you outside of that? If your startup closed down or you got fired, who are you independent of that title or brand? That may be who you are in the community, or around the issue you care about. Use your professional skills outside of your work. Think beyond the office and job.

Third, take 100% responsibility for your career. If you ever find yourself blaming your manager, the economy, your company, some piece of software, that’s the losers game. It’s tempting because it lets you off the hook, but you’re powerless. Find the resources you need, ask for the feedback you need. Empower yourself to do the things you have to — even if you don’t like them.

Is there anything else you’d like to mention?

I think that the other thing I’ll just mention is a great TED Talk called ‘Why 30 is not the new 20' by Meg Jay. She’s a clinical psychologist who wrote a book called the “The Defining Decade”.

So many people are postponing major life decisions during their twenties — having a kid, buying a house, etc. Some of that is really good, but in other ways people are really farting around at that age. That doesn’t mean you have to be hugely successful at that age; you can learn, make mistakes, but a lot of young people have this “some day” attitude. And that day comes when they get laid off, or their industry tanks, or they hate their boss. This reminds me of a proverb: “The best time to plant a tree is twenty years ago, the next best is now”.

You have got to make your twenties matter


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