How can Assistants work effectively with Millennial Executives?

If your boss is a Millennial… Don’t panic! Jan Jones, expert in Executive Assistants, provides you the solution to manage him.

We have recently discussed on Linkedin about Millennial Managers and the best ways to manage them. Tips and support arrived quickly by many Assistants of the community, but to examine in depth the topic, we’ve interview an expert in Executive Asssistants: Jan Jones.

Here’s what she answered!

We have to look at this problem from two sides. First the Millennial Executive working with an older Assistant and second, a Millennial Executive working with a Millennial Assistant.

The first situation is quite tricky. When I was interviewing executives for my book “The CEO’s Secret Weapon”, younger Executives told me they resist hiring an older Assistant because they don’t want to have their “mother” at work. They don’t want to be seen as “a kid”, they wanted to be respected. They were concerned that an older Assistant would boss them around because they have less business experience than their Assistant. This makes them feel intimidated.

Assistants who are older than their Executives should be sensitive to these issues and be careful that their Executive doesn’t feel like the Assistant is treating them like a kid. If the Executive is inexperienced, it is a good opportunity for the Assistant to prove their value by educating the Executive about corporate structure, how business is conducted efficiently, teaching them how to handle new situations, business etiquette, making sure they are dressing correctly for important meetings, arriving on time, etc. Adam Fidler calls this “reverse mentoring”, where the Assistant is training the boss. In his workshop “Be a better Executive Assistant” he offers excellent examples of his experience teaching a new boss how to quickly raise their standards and expectations.

I wrote in my book about Mark Zuckerberg’s first Assistant Anikka. When she joined Facebook, for the first few months she sat on a different floor to Mark. He had no idea what to do with her. She finally decided that she had to take control of the situation. She moved her office next to Mark and started to get involved, not just with helping him, but all aspects of the company. In those days Facebook was a much smaller organization, but Mark was smart to see the value of an older, experienced Assistant and she was clear about the unique contribution she could make, so she stepped up and took charge.

Helping your Executive to benefit from your experience will make you invaluable to them. They will rely on your wise judgment and counsel and you will be a trusted mentor. Young Executives are no different from young people who need help to grow and mature in life. But remember this is a business environment. Don’t smother them and make them feel like they are not being respected. You have to show them the same respect you would show an older Executive because they are your boss. Like Anikka, I suggest you don’t hesitate to step in and take charge when you see situations that could benefit from your experience and expertise, but make sure you help your boss to understand what you are doing and why you are doing it. Older bosses might not need assurances, but younger bosses may feel you are going around them and they may be offended. Always reassure your Executive that everything you do is in their best interest. It will give them a sense of security.

Work style is another area where older Assistants might have to make an adjustment because Millennials like to work shorter hours than older generations. Working shorter hours doesn’t mean they are lazy, they just have different priorities than previous generations: life style is important to them and technology means they don’t always have to be in the office. Discuss expectations and work styles in advance so you both know what is expected from the relationship. Be flexible enough to make necessary adjustments.

Another issue is that Millennials are known for not staying in jobs too long, so Assistants might have to deal with Executives who are leaving the job, on average in less than three years. While it can be frustrating to have to start all over again with a new Executive, it helps the Assistant to develop their mentoring capabilities by giving the new Executive the benefit of their experience. It also gives the Assistant the opportunity to work independently and develop the job into something worthwhile because they are setting the direction. There needs to be flexibility because of differences in personalities and work style preferences. Always remember that you are there as your Executive’s Assistant. Your job is to be a resource to them. They must be your first priority.

With Executives and Millennials who are the same age, while Executives feel more comfortable with someone of their generation, they run the risk of having an Assistant with less experience than they have. This has actually caused problems for Executives because they need an Assistant who has some level of experience. One Executive told me that because his Assistant didn’t have any experience, he went online and started doing research on what an Assistant is supposed to be doing. He had to educate himself about the Assistant’s job and then he was training his Assistant how to do her job. It made their small company very inefficient.

Millennial Assistants have to make sure they are doing everything possible to develop themselves and be of value to their Executive. We all started with no experience, but we have to learn quickly how to become effective and add value to the company. Don’t be afraid to say you don’t know something, but then you must quickly learn how to do it. Know what the expectations are for your job and make sure you are equipped to deliver. Get yourself a mentor who can help you to learn what is required of an Assistant in business. What is the right way to do things, what are the expectations that you need to meet? When you know these things, you can educate your Millennial boss who will look to you for guidance because neither of you has much experience.

It is important to remember that your boss is always your boss, even if you are the same age and have the same generational experiences. You must be professional at all times. Speak respectfully and remember to get into good habits that will benefit you as you mature and develop into a respected, effective Assistant. One Assistant told me that she got along well with her boss because they are the same age, had children the same age, had the same struggles at home, but when it came time to make business decisions, her boss did not take those things into consideration. She wanted a pay raise and shorter hours, but he did not agree to those requests. She felt betrayed because she thought he would understand her situation. The truth is she didn’t have good judgment about the boss/Assistant relationship and had unrealistic expectations from the relationship. Your boss, no matter their age, is always focused on what is in the best interests of the company and what is going to make the company more successful. Assistants should always be thinking from that same perspective so age will never be a factor in creating a successful relationship with your Executive!