When Your Boss Is The Same Age As Your Former Teenage Babysitter

Ellen Lubin-Sherman
CareerSelf Improvement 4 Comments

By Ellen Lubin-Sherman
Personal Branding Expert, Executive Coach, Author & WYSK Special Guest Contributor

After a hiatus of more than one year, you have decided to return to work. At the time you took the hiatus, you were a senior level executive. You were on the “fast track” given your stellar credentials and your reputation for producing high-quality work under pressure. Nevertheless, you decided to take a short hiatus when your child was born. When you considered returning to work, the jobs that were available didn’t appeal to you and you rationalized the cost of childcare against your paycheck. You decided to pack it in and raise your children.

Now your youngest is in kindergarten and you feel a burst of energy – a thirst for the intellectual stimulations of the past. Luckily, you’ve kept your relationships with your former colleagues and you’re able to get an interview with the senior partners of the firm. You’re hired and now you’re about to meet your new supervisor. GULP. She’s twenty-two years younger than you with the swagger and confidence you once emitted. Game on – you’re about to tackle one of the most common challenges for women returning to the workforce: How do you manage a relationship where you are junior to your boss?

Do Not Mother Your Boss

It may be tempting to console and advise your supervisor when he or she is clearly upset by either a business or social issue but that is not your concern. You are an employee, not your boss’s mother.

All Communication is Now Virtual

The old days of knocking on doors to have a chat with a colleague are over. Most communications are virtual with email and text messaging taking the place of one-to-one conversations. You do not have to mimic the brusque bottom-line, all-business communiqués nor should you. Make sure your messages are well written, comprehensive, warm, and have a touch of personality. Do not take umbrage if your boss’s emails are terse and to the point. Your boss is probably doing the jobs of three individuals. Companies no longer have layers – they’re lean and mean.

Never Say The Words “That’s Not How We Used To Do It”

Don’t undermine your opportunity to gain traction by telling your boss that back in the ol’ days you did things differently (and better). No one cares and frankly, it brands you as hypercritical and old. Your job is to master the details of today’s workplace and play on the boss’s team.

Get With The Program But Don’t Lose Your Sense of Style
Twenty or even ten years ago, you dressed more formally for work. You wore “important” jewelry such as pearls and diamond necklaces to indicate your seniority. Your new job has no dress code so everyone wears casual clothes including your boss, who may show up for work in jeans.

Your job is to quickly figure out the dress culture of your company. While you cannot compete with a boss that can rock a pair of jeans tucked into boots, you should avoid fussy suits and certainly leave the gold and pave diamond jewelry back home. If you have the figure and choose to wear jeans, make sure you wear a pair of “trouser” jeans that are less casual and wear them with a crisp shirt and a great sweater or jacket. Make sure your personal grooming is terrific and if you wear glasses, find a pair that makes a fashion statement.

Respect Your Boss’s Acumen and Learn From Him/Her
You’ve re-entered a workforce that’s different from the one you left behind. Your boss has things to teach you – multi-tasking skills, computer applications, branding, leveraging, social media, et al. Do not let hubris stand in the way of acquiring a new skill-set. Re-frame the job as an opportunity to grow and to close the gap on the hiatus. Hopefully, you will find that a younger boss can be a sensational teacher who can bring out the best in you and offer an environment where a fabulous attitude trumps age.

ABOUT THE AUTHOR: Ellen Lubin-Sherman worked for some of New York’s top communications firms, advising top-tier brands including The Gap, Perrier Water, and Martha Stewart. For more than 30 years, she has flexed her “fabulous” muscles, guiding leaders and luxury brands to infuse their identities with flair. In 2003, she founded LAUNCH, an executive coaching firm for business leaders who wish to break out of the pack and lead with charisma. In addition to writing books, Ellen is a sought-after speaker renowned for her witticisms on society, culture, manners and style. For more about Ellen, please visit her website at www.essentialsoffabulous.com.

We are grateful to Ellen for sharing her expertise and writing this insightful and witty post for Women You Should Know.
  • Anne

    It certainly is a challenge to go back to the workforce and find that your boss, and most other employees, are younger than you. But it is something that most of us who returned to business after raising our children found. When I returned to the business world, I was the oldest out of about 35 people. Ellen’s tips are certainly on-point, especially the one about not being your boss’s mother!! On the other hand, working with younger people can give you a much younger perspective on life.

  • KT

    “That’s Not How We Used To Do It”… That is the kiss of death!… Especially with how quickly technology changes and how it has altered the way business is done.
    Great article.

  • Alice

    Wow, this is a topic that most women don’t discuss. Thanks for bringing it to the forefront – there’s something here for all of us to learn from, whether back to the workplace or still riding the wave.

  • Guy from Hells Kitchen

    Boy did this ring a bell. Shortly before I retired, I was attending meetings with men and women who were younger than my children. Don’t get me wrong, they were all very bright but they were not my peers. I recall during a coffee break one of them asked, ” is there any chocolate milk?” I knew then it was time to go.