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See How PILOT Founder & CEO Ben Brooks Commanded His Career

"You can’t connect the dots looking forward; you can only connect them looking back."
— Steve Jobs

Rather than burdening you with another founder bio, how about I trace my career backwards and give you some insights along the way? 

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1. Put Time On Your Side

It is often said that “the secret of getting ahead is getting started.” I learned early that it’s never too soon to start building the skills and gaining the experience that will someday help me make it big. I launched my first company at the age of 14 — The Lawn Ranger, a yard-care company in my hometown of Fort Collins, CO. From business cards, scheduling, equipment maintenance, customer satisfaction, and securing long-term commitments, it taught me a great deal about business at a young age. In fact, the principle of compounding is not just relevant to money, it also applies to experience and capability. The sooner you get it, the more it can compound, over time, and work on your behalf. Start now!

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2. Play Offense

One of the most prominent problems I see in how people manage their careers is that they are far too passive. Instead of commanding their careers, they conform to them or collapse under them. I have learned to continually push myself to take larger risks, get uncomfortable, and ultimately be bold. Nobody else cares more or benefits more from managing my career smartly than me. Rather than wait for external forces like a layoff, downturn, or re-org to propel me into action, I found the drive from the inside out to take my career to the next level. For instance, once I realized I wanted to work for Oliver Wyman, I identified the person I wanted to work for and FedEx-ed him a pitch to work there. Within two weeks I had had multiple rounds of interviews on the phone, in Chicago and NYC, and he had FedEx-ed me back a job offer to join the firm. Playing offense, before I’m forced to, has continually enhanced my career and life. 

 
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3. Find What Fires You Up

It took me a while to be more targeted and selected in what I got involved in. As I’ve matured, I’ve listened to what gets me really fired up, curious, or passionate. After having a negative experience right after joining my consulting firm in NYC, I turned my anger into action and co-founded our firm’s first employee resource group, GLOW (Gays & Lesbians of Oliver Wyman). Because I was so committed to the cause, it made working on GLOW over weekends or trading in sleep on my 6 A.M. weekly flights worth it. The satisfaction I got from transforming our culture and policies to be LGBTQ inclusive is what got me involved in helping to get the military’s Don’t Ask, Don’t Tell policy repealed as the Development Chair of the Servicemember’s Legal Defense Network (SLDN). 

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4. Find A Meritocracy

While at Lockheed Martin, I learned a tremendous amount and worked with some of the brightest and most dedicated people in business. However, the company was very dated in its human resources thinking and performance played only a small part in when one was promoted or got a raise (based almost exclusively on tenure and education). A mentor worked with me as a de facto career coach to help me find an environment that would enable me to be rewarded (in all respects) for my growing performance and capabilities without artificial restrictions. At Oliver Wyman, I found a fertile environment that encouraged me to take on special projects, take risk, learn, and grow — all of which I was rewarded for. Based on my ability to perform, I eventually landed a talent management role at our parent company working for our Chief HR Officer.

 
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5. Invent The Job You Want

I’ve seen so many friends scour the internet to find the role that’s just right for them magically appear. I opted for a different strategy. When I was just 16 working as a unionized bag boy at my local Safeway grocery store, I looked for ways to enhance and expand my role into things that would teach me something new. I kept doing this while working in retail banking and at Enterprise Rent-A-Car and then at Lockheed I succeeded in getting a job that was of my creation, title included! I continued this at both MMC and Marsh, learning to get good at writing my own job description and negotiating the role I wanted versus what someone else had scoped out.

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6. Create Real Impact

I’ve always been a results-oriented guy. I learned that I get a great deal of satisfaction from meaningfully changing something or creating something from nothing. I would quickly tire in roles that felt like I was turning a proverbial crank and not making a difference. While at MMC, I partnered with Marsh’s Chief HR Officer, Laurie Ledford, and her C-suite to engage in a process that created a new long-term future for the organization (after a devastating decade of loss, in every way imaginable). Out of that work we took the executive team’s commitment to grow and develop colleagues and manifested that into a cutting-edge internal social network. We connected our 25,000 colleagues in 400 offices around the world in a way that had never been done and the feedback from staff and leaders alike was fabulous. Our impact was recognized outside of the firm in many ways and even landed us on the cover of HR Executive Magazine.  

 
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7. Learn Emotional Intelligence

I had never even heard of emotional intelligence (or EQ for short) until my mid-20’s. Perhaps because mine needed some development. Growing up, I never understood why my mom was so patient and courteous with her colleagues, even when they dropped the ball or were out of line. Over time I learned that the quality of my own work or the rigor of my thinking played just a part in my overall success. Equally, if not more important, was how people felt about me in general. It was challenging, but letting go of that last round of revising the slides to instead give colleagues a preview and get feedback and buy-in served me well. As did proactively creating and growing relationships, and having the patience to deal with breakdowns in a very less combative way.

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8. Be The Conductor

I spent a lot of time worrying about what I was going to be good at (sales, operations, etc.). Over time I saw where the economy was going and that one of the most powerful roles, in fact, wasn’t being great at just one thing — a single instrument — rather being able to understand, appreciate, and integrate all of the diverse instruments into beautiful symphony — the conductor. This required entirely different skills and wasn’t about being a star myself, instead making sure everyone was a star by supporting them. I had to get curious and know about things that intimidated me or that I had no interest in. Being able to weave many disciplines, people, and types of work together is a capability that has enabled me to translate innovative ideas into real results. 

 
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9. Have A Business Ownership Mindset

I was disheartened to see a number of my corporate colleagues “mail it in” when it came to their jobs, doing the minimum it took to retain their job. I developed a significant competitive advantage in my career by simply caring and taking ownership of my work. Rather than make excuses, blame other departments, or only think of my own little piece of the puzzle, I took a more expansive view with a larger locus of control. While this sometimes resulted in me stepping on toes, I had far greater impact by taking greater responsibility for the work being planned and executed. Using ingenuity, I was able to flexibly solve problems, keep work moving, and ultimately deliver superb quality work. Now the term “intra-preneur” captures this mindset and is highly coveted by well-run organizations.   

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10. Build A Brand

I didn’t expect to be an entrepreneur when I left my successful corporate career in 2013. I stumbled in explaining who I was or what I did for others. Spending the time to create a clear, pithy (literally one sentence), and compelling explanation of this made all of the difference. Staying consistent to this, while evolving and improving it along the way, required me to be increasingly focused and discerning with the types of clients I would work with and opportunities I would pursue. I had to resist the temptation to chase variety and claim expansive capability, instead doubling down on the narrative of who I was and why I mattered to others. Other’s didn’t define me, I did. And I let my network and beyond know who I was and what to expect from me.