61: What Diana Ross Taught Me

61: What Diana Ross Taught Me

From Chicken Soup for the Soul: Time to Thrive

What Diana Ross Taught Me

You know, you do need mentors, but in the end, you really just need to believe in yourself.

~Diana Ross

My first real, paying job was at Bloomingdale’s in Stamford, Connecticut. It was 1980, the height of the disco era, and I was a high school student. It seemed like my destiny to work there. My grandparents and other family lived near the store, and my mother had been a shopper there since it opened in the 1950s. My mother even joked that she went into labor with me there — at the time, the store had psychedelic sixties rugs that made her dizzy — and she headed right to the hospital to have me!

I worked during school breaks and such. It was a part-time sales job and I moved from department to department as needed. Some of my co-workers were pretty amazing, including a survivor of the Titanic. Marvin Traub, President of Bloomingdale’s, maintained an office there. And the famed Kal Ruttenstein — the man many credit with making Bloomies exciting in that era — was often there as well.

But not only were the workers amazing, so were the customers. I met dozens of celebrities and great designers, including Carol Burnett, Lucille Ball, Ralph Lauren, Willi Smith, Paul Newman, Joanne Woodward, Jack Paar, Phil Donahue, Donna Karan — and Diana Ross.

One day, I was asked to assist the personal shopping office. This was the team that handled shopping (mostly) for the rich and famous. Clients would have a salesperson assigned to them, and we would help customers make their shopping dreams come true. The head of personal shopping pulled me aside and asked how I was around celebrities. “Fine, no problem,” I told her. Which was true. I always remained calm, no matter what was going on. I was (and still am) pretty laid-back. She then asked, “Can you handle difficult customers?” Again, I said, “Fine, no problem.” This was tested many times over during my years in retail, and in astounding ways, yet I maintained a Zen calm. After taking a deep breath, she said, “Okay, I’d like to introduce you to Ms. Diana Ross.”

There she was. I resisted the impulse to babble about how wonderful she looked, or how amazing her songs were. I was sure she knew all that already! I got right to work. After getting lots of clothing and accessories together from around the store, on rolling racks and in carts, and getting everything to the fitting rooms, Ms. Ross and her two young daughters proceeded to try things on. As was the standard then, the salesperson would go into the fitting room too, helping customers in and out of their fashions, taking dresses over their heads, etc. Much like dressing people in the theater or for the movies, there were no boundaries. You had to get over any awkwardness fast. I probably saw dozens of celebs in their scanties (as my grandmother would have delicately put it) and it was all business all the time.

Ms. Ross tried on one dress and asked what I thought. I said something like, “It makes your butt look huge, don’t get it!” She asked my opinion again when she tried on the next outfit. I told her, “Nope, your bosom is all wrong in that.” I continued to bring her more and different things, until she looked as amazing as possible — and I told her so. She spent hours trying on clothes and ended up buying an enormous pile of clothing.

I didn’t understand why anyone would have said that she was difficult. But it turned out that I was the first personal shopper to treat her properly. To the shock of everyone in the department, she hugged me and said, “You’re the first person who actually told me how I looked. Everyone else was so scared of me they just said ‘You look great!’ no matter what. Tim, I want to work with you again!”

So as I worked on and off at Bloomingdale’s through my teen years, I’d pull together outfits for Ms. Ross. Not a bad gig. Other people were sent my way, too. The sales relationship worked beautifully, for everyone. I learned a lot about myself then, about being true to myself and my customers, about creating lasting relationships through honesty, and about making the sale — when the product is truly good for my customer.

Here’s what I learned from Diana Ross:

1. Treat people like people. They are not to be oohed and ahhed over. You can’t get nervous because a person is a celebrity (or rich). The customer has a goal. You have to remember what your job is and do it.

2. Be honest. If your butt looks awful in a pair of jeans, don’t you want to know that before you buy them? I do. Find a way to make the selling experience real, and true, no matter what. I am not saying to be mean — far from it. In sales, you are building a relationship, and good relationships are based on honesty. If it’s a difficult topic you have to bring up, put it out there. They will appreciate the honesty. Just like Ms. Ross.

3. Ask questions, show the products, ask for the sale, repeat. Overall, the story has never changed from my early days in retail, through my post-college years as a manager at Macy’s, Pottery Barn, Old Navy, and Guess, to my years selling data products and services for two companies eventually acquired by Merkle, or to more recent times as a digital marketer and e-commerce leader. (I’m a start-up co-founder and CMO, a consultant, and a head of e-commerce right now.)

~Timothy Peterson

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