Coping With Difficult Bosses

Read­ing Time: 4 min­utes

Author Jan­ice Davies said, “dif­fi­cult peo­ple are your key to self empow­er­ment, you need to learn how to cope with them, not let them dom­i­nate and affect you.” But what if the dif­fi­cult per­son is your boss? What then?

In over 20 years of work­ing in my cho­sen career I have large­ly had what I can only sup­pose is the great­est luck in select­ing my boss­es. Most have been more than fair, have taught me along the way as true men­tors, and sev­er­al I still count as friends and advi­sors to this day. A cou­ple, how­ev­er, have tru­ly been night­mares.

Every­one has their own gauge for what makes a boss dif­fi­cult to work with, but mine comes down to more of a feel­ing than a set of con­crete habits. And when I say dif­fi­cult, I’m not refer­ring here to a demand­ing boss, or one who expects results and calls you out for not achiev­ing the results; that’s just the price of admis­sion in the cor­po­rate world. I’m talk­ing about when things reach a lev­el of dif­fi­cul­ty where you begin fear­ing for your job.

The prob­lems in deal­ing with dif­fi­cult peo­ple are, by nature, made even more dif­fi­cult when that per­son is large­ly in charge of your abil­i­ty to pro­vide for your fam­i­ly. Your stress lev­els can increase, you start tak­ing out your frus­tra­tions on the oth­er peo­ple in your life that you work with or care about, and your over­all health and out­look can become marked­ly more neg­a­tive, lead­ing to a decrease in pro­duc­tiv­i­ty.

Below are some strate­gies I have found that have helped me, and I hope that some or all can help you should you find your­self in the posi­tion of hav­ing to deal with a dif­fi­cult boss.

Adjust — As much as pos­si­ble, try to adjust to the new real­i­ty of the sit­u­a­tion. Some­times, as peo­ple are put in new posi­tions they can feel over­whelmed, under pres­sure, and are them­selves deal­ing with dif­fi­cult rela­tion­ships upstream. With any luck, this peri­od of dif­fi­cul­ty will pass and you’ll find that you’re able to cul­ti­vate a strong, trust­ed rela­tion­ship with your new boss.

Be Proac­tive — Try to antic­i­pate your boss­es needs before he or she knows they have a need. If they’re under pres­sure, and you can be the go-to-per­son that hands them reports, deliv­er­ables, etc., ahead of them ask­ing, you’ll have gone a long way towards eas­ing the rela­tion­ship into a bet­ter place.

A lot of times this comes from under­stand­ing your boss’s role in the com­pa­ny. For instance, I report to the CFO at my company–a role which is large­ly con­cerned with bud­get­ing, fore­cast­ing, and gen­er­al­ly deal­ing with the finan­cial health of the com­pa­ny. Every­thing that I do in the tech­ni­cal sphere is couched in terms of impact to the bot­tom line of the com­pa­ny. That’s a gross over-sim­pli­fi­ca­tion, of course, but the point is that you need to under­stand your boss, what their role in the com­pa­ny is, and how you can help to make them look good to their boss.

Don’t React Emo­tion­al­ly — I can’t tell you how many times after read­ing an email I’ve want­ed to walk down the hall to my boss’s office, storm in, and start loud­ly expound­ing on my view of the world and my boss’s place in it. I have seen that hap­pen, and while I some­times get a lit­tle joy in the vic­ar­i­ous­ness of the thing, I nev­er indulge myself in the same behav­ior. I respond even­tu­al­ly, but not quick­ly or emo­tion­al­ly.

I’m not sug­gest­ing you ignore emails, phone calls, mem­os, or ran­dom edicts at all. In fact, I have a gen­er­al rule of try­ing to respond to any­thing that comes my way by the close of busi­ness the same day. If it comes from my boss, I respond with­in two hours even after-hours. That said, you can acknowl­edge some­thing sim­ply, direct­ly, and with­out emo­tion. If, a few hours lat­er you still feel the need to have a con­ver­sa­tion, you’ll have giv­en the heat-of-the-moment emo­tions a chance to sim­mer down.

I have sent some seri­ous flame-throw­er emails in my day–some to ven­dors, some to co-work­ers, and even some to peo­ple I’ve worked for. Do you know the one thing every one of those emails in the last 20 years has had in com­mon? With­in min­utes or hours I regret­ted send­ing them–each and every one. A lit­tle bit of time would go by and I’d increas­ing­ly start feel­ing like the petu­lant child I was act­ing like. Almost inevitably I’d trudge off some­where to make an apology–not because I had to, but because I felt I need­ed to.

Learn from the Expe­ri­ence — Many of us either lead teams today, or will lead teams in the future. Even if lead­er­ship roles aren’t what you per­son­al­ly aspire to, the time will prob­a­bly come where you will find your­self lead­ing a team of some size. The expe­ri­ences you have with your boss­es should be sug­ges­tive of the type of leader you want to be. We all love the good ones, but some­times it’s the bad boss­es that teach us more in the end.

Know When to Walk Away — The rela­tion­ship you have with your boss should nev­er feel per­son­al­ly neg­a­tive. By that I mean that you should nev­er feel as if your boss **hates** you, or wants you to fail, or has no con­fi­dence in you as a per­son. Good boss­es will let you know if you’re not meet­ing expec­ta­tions long before it becomes an issue. If your boss is mak­ing your life mis­er­able with­out any sort of use­ful feed­back, then it’s like­ly one of two things is going on:

  1. They’re a mis­er­able prick, and want every­one who works for them to feel the same way.
  2. They don’t have the self-con­fi­dence to sit down with you and tell you that they have no con­fi­dence in you. So, they walk around with a mas­sive grudge, hop­ing that you’ll leave and they won’t have to deal with the prob­lem any longer.

In either case, this is prob­a­bly the point where you have to con­sid­er that things may not get bet­ter, and per­haps walk away. Work rela­tion­ships should nev­er be per­son­al­ly neg­a­tive, but we’re all human beings and some­times things just don’t work out. It’s irri­tat­ing, often feels unfair, but it’s the way things some­times are and we just have to deal with it as best we can.

What­ev­er you do, don’t fol­low your first instinct, and freak out. Don’t write up a nasty let­ter, or tell the per­son what you real­ly think. Just fol­low the process pro­fes­sion­al­ly, and if you real­ly need to vent a bit, that’s what your Human Resources depart­ment is for. Even then, how­ev­er, nobody likes a whin­er so try to keep your crit­i­cism as con­struc­tive, pro­fes­sion­al, and imper­son­al as pos­si­ble.

Then, do what I do: go home, kick off your shoes, pour a nice drink, and cel­e­brate your unbe­liev­able good for­tune to not have to deal with that boss ever again. Just don’t make a habit of it… after a string of bad boss­es, you might have to con­sid­er that the prob­lem was­n’t with them.