The Devil Wears Nike - 5 Secrets to Success from a CEO's Assistant

For my first job out of college I had the horror privilege of being the executive assistant to a ruthless CEO. We’ll call him Don.

To the average employee, Don was the coolest boss — he’d zoom down the halls on his skateboard, allow company parties to celebrate any and every occasion, ran a soccer club from the office back yard and made humor a part of everyday work life. It was a dream job... for most.

As Don’s personal assistant, my “dream” was more of a nightmare. Don was tough, really tough. He himself compared my position to The Devil Wears Prada (though I like to call it The Devil Wears Nike — he was into soccer, not fashion).

For 2.5 years I poured my heart and soul into this position. I booked helicopters and planned movie premiers. I managed an ever-changing schedule of missed flights and rescheduled meetings. I spent two nights a week for an entire summer at the soccer fields collecting registration forms for his sons’ soccer club.

The words “no” and “I don’t know” were despised and unacceptable. He demanded the impractical and expected the impossible. His schedule was hardly manageable and his criticism was unbearable. Yet the experience was incomparable.

I laughed. I cried. I worked my tail off. But I wouldn’t trade that job for anything. Here's what I learned:

1. Always do your research

When someone would call for Don, he wouldn't let me transfer the call unless I knew who the person was, where they worked and exactly what they wanted. This often meant Googling them while quickly jotting down every detail I could think to ask them. Was it a pain? Yes. But I learned to be very thorough when asking for details so I never had to use those three despised words: "I don't know." Want to come across as having it all together — be thorough in your initial research before discussing projects. Then ask any and all remaining questions in your first inquiry or discussion. This is not only useful with bosses and clients, but even friends & family (when/where is your trip… are you bringing the dog or do you need me to watch him… what hotel can I reach you at). When you ask questions and research ahead of time, it'll save you time going back-and-forth waiting for answers as well as make you stand out as being professional, accurate, and effective.

2. Take Notes for Everything

As Don’s assistant, my notebook was glued to my hand – whether I was on a building tour with investors, or just stepping into Don’s office for a quick question. I never knew when he’d have an idea or request that would need to be taken care of. This way I always had documentation to refer back to when things got crazy (I also have the memory of a goldfish, so note-taking was a must)! I still keep to this system in my current job… the employees who don’t take notes often turn to me with: “What did he say, again?” In my personal life I use an app to keep track of things that come up — gift ideas for my family when they mention they like something, blog post ideas, business marketing plans. It never hurts to have things documented!

3. Stay One Step Ahead

I’ll keep this one short and to the point. Your boss/spouse/clients will love nothing more than to hear “I’ve already taken care of that.” When you stay one step ahead, it proves you’re dependable, efficient and smart. Your proactive approach means less stress for someone else. You’ll leave a positive impression, while giving them a sigh of relief. 

4. Pick Your Battles

I learned real quick that some fights just weren’t worth fighting. Getting defensive around Don only ignited the fire. There was no explaining yourself, even if you knew you were in the right. Some other execs and managers never learned this lesson… and suffered from it over and over. So yes, I took the wrath for things that were out of my control or completely not my doing, but a few days later Don would apologize for taking things out on me, acknowledging that it wasn’t my fault. Had I been defensive (even if it had been my fault) the situation would’ve ended ugly. An apology and learning to hold your tongue go a long way in any relationship.

5. Don’t Let Anyone or Anything Steal Your Joy

For the first six months as Don’s assistant, I was pretty miserable (surprising?). I worked long days full of crazy demands with lots of criticism along the way. If things weren’t perfect, I wouldn't hear the end of it. I was stressed. I was overworked. I had lost my joy. Then one day it hit me: who is Don and what is this job that I should allow it to steal my joy? He doesn’t have the pleasure of taking that from me. From that point on, I had a change in attitude. This is just a job. Did I work any less hard? Not at all. I just didn’t let the pressure, stress and negativity bring me down.

I could go on for pages about all the things I learned from this position – but who has time for that?! The biggest thing, which is reflected through all of the above, is just to work really hard at everything you do. I have Don to thank for teaching me that in my first job. If it weren’t for his extremely high expectations and for pushing me towards perfectionism and competence, I wouldn’t be the same person today.

What keys to success have you learned that help drive you in life?