7 most dignified ways for midlifers to handle a big company "baby boss" (a new boss who's your child's age)

A friend of mine, let's call him Johnny, recently joined a high-profile, super successful, early-stage technology company.  He is the oldest employee by far at the ripe old age of 49. 

Johnny has been tasked with growing their global sales enormously to turn this mega-successful company (on paper) into the sustainably profitable giant it intends to be.   To do this he must develop deep relationships with MDs and CEOs of giant, mature tech businesses across the globe.    How old are these MDs and CEOs?  You guessed it – 45yrs+.  

This experienced group of midlife CEOs/MDs appear to be almost incomprehensible to the leaders of this early-stage, but huge tech business.   These midlife board members possess lives, personality attributes and interests which have exposed a huge generational crevasse in the relationship building skills of the owners and senior leadership within this early-stage tech business.     

Not only are these midlife CEOs/MDs older than many young tech executives can ever imagine being, they also possess memories that are older than these future board members.  These midlifers have faces that sag into fascinating folds.  They have hair that is greying – either proudly or hairdresser-enhanced.  Their slowing metabolism manifests itself sometimes in a thin layer of belly fat.  They remember a time when smart coffee-machines were not considered an essential in the average home.  They grew up reading books…printed on paper.  They learned to communicate with humans using their voices, their eyes and their gestures before communicating with their on-line personality.  These midlifers can remember a time when bottled water didn’t exist!  They are completely different animals.

Selling global technology contracts involves connecting deeply with human beings behind your potential or existing customers.

Enter Johnny.

In order to create or cement long-term relationships, Johnny entertains his midlife counterparts in other companies a great deal.   He goes to baseball games in US, West End shows in London, comedy clubs in New York, stunning spa days in Middle East and Michelin starred restaurants all over Europe.   On the face of it, this sounds fantastic, but can you imagine spending up to 8hrs with a potential customer with whom you have little in common?  No?  Neither can they.  They simply wouldn't.

Johnny forms real relationships with his customers – genuinely.  These relationships are edging towards friendship but they are not friendship.  At all of these events, he spends evenings or whole days with them, and sometimes even invites their children along for the day.  He spends this time easily and appears to enjoy it.  Why? For him, it’s easy.  They have lived in similar eras, through similar economic cycles and are in similar life phases.  There is plenty to discuss.  

But this will not always be the case. 

These older board members are being slowly replaced by younger board members who are, as I've said, a different animals.   It is not inconceivable that in the near future many successful big company senior leaders will be reporting into much younger people – at a stretch - potentially to a boss as young as our children.   

Don't believe me?  If you are 50 today and started your family at 20, your high-flying child could have had a decade-long career so far.  While their career is on its way up, yours is flattening.   The reality of reporting into someone who is as old as your child is racing towards us at full pelt.

Uncomfortable as that sounds, you might need some strategies to help you cope should it happen to you:

1.    Pause and zip your lips

When you hear the news about your new boss – pause and breathe.  If you are known for forthright communication, this might be a good time to...pop out for lunch.  A disparaging comment like “How old is she – twelve?!” could be very career damaging. 

Any sort of derogatory, ageist comment is exactly what you are trying to avoid.  By the way, yes the policemen are getting younger every day.

2.    Don’t stereotype (out loud in the office, at least)

Stereotyping is a natural human failing - the privacy of our own private worlds.  I know, I know.  You are completely different to all the other mature, big company leaders out there.  Being clumped into a stereotype is incredibly insulting, isn’t it? 

Does it annoy you when you feel stereotyped with all those mature people who don’t want to learn (the research says the opposite, by the way) and who are not open to change?  Yes? So, try not to stereotype that all earlier generations are self-absorbed and only out for themselves.  

You worked hard to get where you are, so did they.  If they are in senior management at a young age, it isn’t because they “slept their way to the top” or “brown-nosed” all the right people.   It’s likely to be because they are smarter than their competition, have amazing technical skills or are great early leaders with promise.  Their skills have been rewarded. 

3.    Get out of your own head and into theirs

If you think it is hard having a boss who is young enough to be your child, imagine how tricky it could be having someone reporting into you who is old enough to be your mum or dad? 

A little empathy will go a long way.  Your new boss will be delighted to have been promoted but they will have their own inner doubts about whether they are up to the job. 

Your new boss may be young enough to be your child but they will also possess all the normal early-career insecurities – just as you did.    But, they will be busy hiding their insecurities – just as you did.

The whole world is crippled by "imposter syndrome" - when we worry unnecessarily that we will be found out to be not good enough even though we are in the perfect position to make use of our talents.

What your new boss will need is a group of right-handers who can contribute their unique combination of talents to improve the business.   You can choose to be one of those.  Or not.

Figure out what their goals are and support them with your talents.  Or do something different.

4.    Don’t assume she/he will be a bad boss

If you had a magically supportive, cohesive team in your first senior leadership role, boy were you lucky.   If you had dolly mixture of personalities, skills an experience profiles all playing out their own individual game-plans, welcome to your Boss Baby's world.  

Managing someone who is the same age as their Mum/Dad will be awkward for them butif you are as valuable as you think you are, their success will be dependent on the success of your relationship.  Meet them half way by assuming that they will be a good boss for you.

It wouldn't go amiss if you could communicate your congratulations and your optimism about how you can work together to great success.  Perhaps a step too far? Nevertheless, a quick "congratulations" wouldn't go amiss?  

5.    Keep high emotion at bay (or within the 4 walls of your home)

High emotion at work often has its basis in fear.  It is almost always regretful and is best left for your loved ones at home.

Mellow the emotion by talking to friends who might also be experiencing reporting to some younger high-flyers in their businesses.  Ask questions of them around the best way to tackle it or just ask about their experiences.  

Articulate your frustrations at home but at work, figure out what exactly it is that you need so that you can feel that your career still has legs

In my experience, this can often take the form of leading individual, specific parts of projects/processes or being seen as an expert on one area.  

You need to create opportunities to use your experience, to apply it to new situations in new ways thereby expecting even better outcomes. 

6.    Offer them the same respect you expect in return

Just because you have a boss who’s the same age as your child, it doesn’t mean that you have the right to be disrespectful.   Bitterness is not becoming of a midlifer in business.   

We are all in a state of flux as we attempt to re-design the second half of our career.   

This new boss might feel like a mighty blow that has hit you at a weak point but there is no excuse for throwing your toys out of the pram.  Figure out what amazing toys you have in your pram and use them to climb gracefully towards continued career success.

midlife career crisis after boss baby arrives


7.    Point your experience at their problems

You have all this experience under your belt, so point it at problems.  Not in a “Move out of the way, I know how to solve this problem” kind of attitude but in a “We had a similar situation like this before, at the time I considered this idea and this was the result.”  Then explore options with your boss.  It is much more likely that you will become the trusted advisor rather than the grumpy pain in the elbow (not that we are stereotyping here).

If all else fails…

If, despite all your efforts, the relationship still isn't working out after a period of time, work out a way to unstick your career.   Check out my article on starting to re-design your career around your superpowers (https://www.midlifeunstuck.com/new-blog-1/2017/5/27/love-fridays-hate-sunday-night-blues-the-key-to-mid-life-career-happiness). 

You may be as lucky as Johnny whose midlife status and experience were real attraction points for his new company.  You might also like to know that he absolutely appreciates the short-term nature of his fortuitous situation.  He fully expects to be reporting into a “baby boss” in the not-too-distant future.  That said, he has already got his back-up plan ready…just in case.  

No matter what your circumstances, don’t resign without a plan, resign with a great plan.

If you can foresee this situation becoming a reality in your career, it can be helpful to take control by identifying your superpowers and planning of the second half of your career. 

If you'd like a personal guide through that process, please email me at lucia@midlifeunstuck.com to organise a free 30 minute call to discuss your situation and see whether I am the right person to help you.  

If you would prefer to re-design your own midlife career sign-up to my newsletter which includes free tips, book recommendations and transformation stories at www.midlifeunstuck.com.