In the feel-good movie “The Intern,” 70-year-old widower Ben Whittaker (Robert De Niro) takes an internship at an online fashion company. Things get to a rocky start between Ben and his much younger boss Jules Ostin (Anne Hathaway), the CEO and founder of the company. Ben is an old-fashioned rule-follower, while Jules is the typical free-spirited and creative leader. Jules is originally skeptical of Ben and what he can bring to her company, but over the course of the movie, she grows to appreciate his experience and insights, until he eventually becomes her trusted business and life advisor. If only real life was that easy…
The situation of a younger millennial boss managing much older subordinates is very common in today’s corporate world. For example, when students finish the graduate program in Health Care Administration at Trinity University, they often find themselves thrown right away into leadership positions. Typically these positions consist of “Assistant Administrator” or “Associate Administrator” roles and entail responsibility over several departments. The directors of these departments tend to be veterans of their areas, with many having worked in the hospital for a long time. The dynamic of having a young boss in his/her late twenties with subordinates in their 40’s, 50’s and sometime 60’s creates unique challenges for these up-and-coming leaders. While they have the formal formal fancy degree, their subordinates have real like and work experience.
Take the example of Sophia (not her real name), a bright and ambitious 27-yeard old healthcare administration graduate who was appointed Assistant Administrator at a medium-sized community hospital. As part of her role, Sophia had the Directors of Radiology, Environmental Services, and Food & Nutrition departments reporting to her. As she started preparing to take on her new responsibilities, one of the main challenges that Sophia faced was her young age compared to the Directors reporting to her. Some of them had actually been working at the organization longer than she has been alive! What made the situation even harder was that Sophia is a petite woman with a baby face and soft voice. It didn’t take long for the jokes and side remarks to start flying whenever she got introduced at meetings and events. Some would remark “How did someone so young like you get this position?” and others would quip “I have children that are older than you!” Before too long, her nickname became “the kid.”
Sophia didn’t appear to mind the jokes. Most of the time she went along with them and pretended that they didn’t affect her. But deep inside, they made her feel self-conscious and deeply worried about whether she could do the job. In 1:1 meetings and large-group ones, she would find herself torn between staying quiet and saying too much. If she decided to listen and learn, she could hear others thinking: “Why is she so quiet? Maybe she doesn’t know much!” And if she offered her opinion and contributed to the discussion, she could imagine them saying: “You just got here yesterday and now you are telling us what to do!”
When I started coaching Sophia, she was 3 months into her new position and facing a significant confidence crisis: “When I sit down with my Directors, I want them to trust me. But how do I get them to trust me?” She needed to find a balance between being perceived as a wallflower and being seen as a whippersnapper.
One of the first thing that we identified as important for Sophia’s confidence was for her to learn more about how her departments actually functioned. To do that, she committed to rounding on her departments for half-an-hour every morning, and to spending two hours every weekend researching and learning about their technical content. This way, when she had 1:1 meetings with her directors, she knew what the issues were ahead of time and felt comfortable asking specific questions without the risk of appearing stupid. Furthermore, before major meetings, she scheduled time to sit down with the leader of each specific meeting to talk about what would be discussed at the meeting and what the history of the issues was. This way, when the opportunity came, she felt comfortable contributing to the discussion without forcing it.
Once these practices became hardwired in her management approach, she started feeling gradually more confident. Employees loved seeing her on a regular basis in their areas and felt comfortable telling her about what is working and what is not working. Her Directors started sensing her comfort and came to trust her more and more as she explained that she was there to support them rather than to tell them how to do their jobs. While Sophia remained the young-looking executive, her age became less and less of an issue for her and for her subordinates.
In the book “When Generations Collide,” authors Lynne Lancaster and David Stillman offer additional advice to young bosses managing others with plenty of experience. Based on the old-adage “if you want respect, you have to show it first,” they suggest that young bosses have to respect their subordinates experience and incorporate it into their decisions. One other thing that Sophia did based on our coaching conversations was to show her humility when interacting with her Directors. Some of the behaviors that she worked on was to listen intently and demonstrate that she heard the suggestions by saying stuff such as ‘thank you for sharing,’ ‘I didn’t know that’ and “I thought this should be done differently but what you described makes more sense.”
Putting it All Together
Young executives who find themselves managing older subordinates run the risk of appearing too shy or overconfident. Specific behavioral changes that are facilitated by an executive coach can help them find the right balance.
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Dr. Amer Kaissi is a Professional Speaker, Executive Coach and an expert on Leadership, Humility & Ambition, Assuming Positive Intent, Psychological Safety & Accountability, Growth Mindsets & Resilience.
