This Is How to Win With a Boomer Boss

Ok, I’m a boomer and for those out there who are reporting to a boomer and are frustrated with trying to figure out who this dude is and how to achieve satisfaction in your job with them in control, this post is for you.

All I can give you is what I expected in my 33+ year corporate career as an executive leader; what I expected from the young professionals that suddenly found themselves reporting through to a mature leader.

My expectations may not be typical of all boomer bosses — I may be tougher than most — but they represent a good benchmark to have in mind.

If young professionals reporting to a boomer boss practise these 5 things, they will not only find their life easier, they will also suddenly find themselves in a favourable position for future advancement.

Get to know the boomer

You may not enjoy the prospect of reporting to a boomer, but in order to maintain a positive and rewarding experience while you’re putting in the time, it’s important that you gain an understanding of who they are and where they’re coming from. Knowing the boomer will at least explain why they act the way they do.

And if you understand what drives the boomer’s behaviour, you will be in a better position to respond in a manner that builds your currency with them as opposed to reacting negatively and diminishing your position with them.

Trust me: if the boomer sees that you’re interested in understanding them, the act itself will give an advantage over your peers who can’t be bothered.

If you know the boomer, you gain more control over your life and your destiny— Roy, boomer

Honour the past

You will most certainly have new ideas that you feel will change the world, but don’t forget your boomer boss has a record of past achievements that they are proud of.

They worked hard to help move the yardsticks forward in the organization and won’t be thrilled if you want to take a demolition ball to the innovation taken in years gone by and morph to your new revolutionary ideas of the ways things should be done.

I’m not suggesting that you should keep your mouth shut and not advance your change agenda — in fact you must act on your personal vision — but do it in a way that recognizes the wisdom of the past and the benefits derived from decisions made yesterday.

It’s all about how you go about changing things. I respected the young professional that understood the historical context of why things were done a certain way, and gently suggested that the current context was different and therefore required a fresh approach.

Boomers have their frame of reference in the past, but are quite prepared to move forward when options are suggested in a thoughtful respectful way.

But boomers won’t likely be jerked around by someone who has not taken the time to at least acknowledge there are valid reasons the present times look the way they do — Roy, listener of respect

Express a sentiment of loyalty

Your boomer boss has an investment in the organization; they have likely put in a substantial number of years to arrive at their current position. They probably have had only a few employers in their career — in my case only one! — and therefore they believe that loyalty is an important characteristic that an employee should possess.

Young professionals with boomer bosses should put a loyalty face forward even if they don’t really expect to stay with one organization forever. No, it’s not hypocrisy in action; it’s trying to maximize your benefits in the limited time you work for the boomer.

Boomers get that young people will likely move on fairly quickly, but they appreciate the demonstration of loyalty during the time they report to them.

I appreciated these 5 acts performed by highly mobile people that reported to me:

  • Active participation in the culture of the organization; identify with its values that paint a picture of how people work together;
  • Knowing the strategic game plan of the company and how each individual can contribute to long term strategic goals;
  • Engaging in team projects that involve various other functions;
  • Showing interest in career development activities.

Young professionals need to demonstrate ‘loyalty in the moment’ to gain the trust and respect of the boomer boss — Roy, loyalty benefactor

Zip it! when it comes to your personal stress levels

I know there is a huge conversation going on these days about managing stress in the workplace; mental health problems caused by excessive stress are serious and need to be solved.

And I also know that there are organizations investing in solutions to help employees deal with their stress levels.

But be careful — regardless of what you think your employee rights are — of how you present your needs and expectations regarding personal stress management rights to your boomer boss.

Remember they come from a place where stress was a fact of life and it had to be personally dealt with. They didn’t have mental health days and special rooms available to help alleviate their personal stress, so they are not likely to have the level of empathy for your circumstance that you expect.

It doesn’t mean they don’t care, just that they won’t feel they should help you solve your stress problem. They were on their own so they are likely to believe that you need to take personal ownership of your own issues.

And don’t get loose lipped around what your boomer boss should do for you. It’ll get you nowhere but reduce your currency, increase your daily ‘pain’ and potentially impair your future career prospects.

Your boomer boss assumes responsibility for their own issues; they don’t expect third party support — Roy, loner

Ask how you can help

Like it or not, boomers have a perception of young professionals that they feel entitled — to a six figure job in a few years, to time off for personal reasons, to stay away from work when feeling slightly under the weather and a myriad of other benefits the boomer didn’t receive.

So when you ask how you can help, it shows your boomer boss that you want to work hard and help solve the problems they are facing. The question is actually an entitlement neutralizer to the boomer; it helps dispel the notion that millennials are a crowd who feel they should get everything for nothing.

Teach your boomer boss that you’re prepared to give not receive, and watch how you will flourish — Roy, passionate supporter

The question young professionals have to ask themselves when confronted by circumstances that have them working for a boomer is ‘Do I want to stick to my ideals, fight every day and get nowhere or do I want to flex to my boomer boss, possibly learn a thing or two and keep my career moving forward?’

And, in the process, make the kind of change and contribution you really want.

Make the right choice if you have a boomer boss.

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