If at first you don’t succeed…Try, Try, then Fly!

My first job post-college was at a recruitment agency in Boston. It had a small “product” division, which was where I worked. One of my main responsibilities was to evaluate and “buy” media for my technology clients. I soon noticed that the other media buyers were 1) all men, and 2) didn’t work particularly hard to get the sale; they basically took us “buyers” out to lunch and expected, and generally received, a contract.

It didn’t take me long to realize that I worked harder and smarter than they did, so much so that the one female rep I knew encouraged me to become a media sales rep myself, and despite a lack of enthusiasm from my friends and family, I took the leap towards a new career. After a few rounds of interviews and some dead ends, I landed my first sales job! 

I was green, but determined.

I loved the product I represented, and ditto for the company. I passionately believed that our product was better than our competitors, and I worked tirelessly to demonstrate to my clients that “buying space” in our magazine was the best use of their media dollars. This hard work paid off and I was able to convert the vast majority of companies running in my competitors’ magazine to ours – with one big, important, and potentially intimidating exception – the biggest software company in Boston at that time.


I uncovered who THEIR top customers were, and demonstrated that those customers were big fans of my magazine. Despite months of effort and meetings I still hadn’t gotten a bite, but I was moving the needle, and making an impression on some employees! Whenever I showed up at their offices, the security guard would ask, “Have you gotten the business yet”? And I would always confidently reply,  “Not yet, my friend… not yet!”

Persistence Pays

A few folks in the client’s marketing team also took notice of my persistence and alerted me to an executive meeting taking place later in the month. I asked if I could I do something to get the executives’ attention, and hopefully persuade them to reconsider working with my magazine. The head of marketing agreed to help me (no small win in itself), and at a pre-determined time she took the executive team to a conference room. It had a huge window, one where everyone there could see the small plane I hired to fly around the building, pulling a banner with both companies logos and a request for us to “fly together” by advertising in my magazine.

Gutsy move? A certain win? Clearly, I won their business, right? Well… actually no. They never did buy from me. But, I didn’t quit. I applied the same passion to other accounts which propelled me to being named Salesperson of the Year for three years in a row!

Looking back, I could have viewed this as a loss, which from a short-term perspective it was.   But in the long term, it wasn’t. I reframed the “loss” into a win!

How to Reframe Losses into Wins:

• While I didn’t get that account’s business, my efforts made it possible for future reps to sell advertising to that company and to many others.

• My actions caught the attention of senior management in my company, and of our competitors. 

• These competitors made me offers to head up their sales team. 

• Determination? I discovered I had much more than I’d ever imagined. 

• I focused on positive outcomes and incremental wins, and was proud of my tenacity, passion, and overall success.

• I established a reputation as hard working, passionate about my product, and a tireless advocate for my customers.

If you are struggling with reframing a “loss” at work, or are missing the passion in your job, home, school, or community, let’s talk. Contact me through email at Anne@MakeYourNowWOW.com, or through the form below. Let’s spend 30 minutes and focus completely on your situation and what you can do to Make Your Now… WOW!!