Tips for working with a younger boss

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By Phyllis Weiss Haserot

This is part of a series of regular columns by generational expert and internationally known consultant, coach, writer, and speaker Phyllis Weiss Haserot on intergenerational relations and navigating the challenges of the multi-generational workplace for better productivity, retention, succession planning, and business development results.

With the Boomers generally in no hurry to leave the workforce for both personal and economic reasons, and the younger generations positioning for greater responsibility, the occurrence of older workers reporting to younger ones is proliferating and will continue for some time. That could bring tensions as reporting relationships deviate from the usual order...but it doesn't have to.

A new survey by job Web site Career Builders shows that many workers are older than their bosses, and it's not a problem arrangement for a lot of them. In this survey of more than 5,000 workers: 43% ages 35 and older currently work for someone younger than they are; 53% of workers age 45 and up say they have a boss younger than they are; and 69% of those age 55 and over say they do.

Although it's not a widespread problem (yet?), this atypical reporting situation can create challenges. The degree of difficulty seems to differ depending on age group. Career Builder reported that 16% of age 25-34 workers said they find it difficult to take direction from a younger boss; 13% of workers age 35-44 find it difficult. Interestingly only 7% of age 45-54 workers and 5% of workers 55 and older indicated that was a difficulty for them.

Do you find that last set of data surprising? (We are limited by the study's data, which don't indicate the size of the age difference between worker and boss in each category; that could be a significant variable.) What the study found seems to suggest that it is easier for Boomers to work for younger managers than it is for the younger generations, and it is hardest for Gen Y/Millennials.

Here are the reasons given by those respondents who have trouble working with their younger bosses:

Generational DefinitionsHere are some quick definitions. Generations are defined by the similar formative influences – social, cultural, political, economic – that existed as the individuals of particular birth cohorts were growing up. Given that premise, the age breakdowns for each of the four generations currently in the workplace are approximately:

Traditionalists born 1925-1942
Baby Boomers born 1943-1962
Generation X born 1963-1978
Generation Y/Millennials born 1979-1998 (under age 30 today)

  • “They act like they know more than I do, but they don't.”
  • “They act like they are entitled – they didn't earn their position.”
  • “They micromanage.”
  • “They don't give me enough direction.”
  • “They play favorites with younger workers.”

So here are my tips for succeeding in these increasingly common reporting and team relationships, many of which apply whether you are the older or younger person.


  • Support and show respect for the younger manager.
  • Learn how to manage up so you will be valued.
  • Be open to new ideas, even if untested.
  • Look for mutual mentoring opportunities.
  • Be tactful and sensitive in making constructive suggestions for improvement.
  • Learn the manager’s communication style – and flex yours if necessary.


  • Talk about how things used to be, the good old days.
  • Put down ideas.
  • Adapt a communication style or interests that seem inauthentic to seem cool.
  • Overvalue years of experience.
  • Withhold information that will help the younger manager succeed or reject a collaborative style.

© Phyllis Weiss Haserot, 2010. All rights reserved.

Phyllis Weiss Haserot is the president of Practice Development Counsel, a business development and organizational effectiveness consulting and coaching firm she founded over 20 years ago, A special focus is on the profitability of improving inter-generational relations and transitioning planning for baby boomer senior partners ( Phyllis is the author of “The Rainmaking Machine" and “The Marketer’s Handbook of Tips & Checklists” (both West 2009). [email protected]. URL:

See all of the articles in this series. 

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