Challenge and change are part and parcel of any modern woman’s career path. Our Working Women’s Guides provide practical, expert-led advice pieces that will help you navigate through difficult times and empower you to thrive in an ever-evolving landscape. Here we explore how to deal with a difficult boss...

The tricky boss takes many forms: The micromanager, the out-to-reacher, the people pleaser. Like family, you can’t choose them but, like partners, it’s important to know what to let slide, when you need to talk, and when you’re ready to call it quits.

Think of pop culture’s most iconic managers and you’ll probably picture Meryl in The Devil Wears Prada or smarmy Bill Lumburgh from Office Space. “Tricky” bosses are such a cliche, we basically expect them in life. However, this resigned acceptance could be making us complacent, putting up with more than we should and suffering in silence. It’s probably not surprising to read that nearly half of us have quit our jobs because of a bad boss, with 24% suffering nightmares about them and 26% seeking mental health support as a result of the working relationship. 

Things needn’t get to that point. Just because your boss is in a position of power, that doesn’t mean you have none. We asked global HR leader, non-executive director and executive coach, Patricia Galloway, for some advice on dealing with difficult bosses...

A Place of Understanding

First things first: Whether your “tricky” boss is the CEO, a senior leader or a mid-level line manager, step back and see them as a person. “I have rarely met a truly malicious manager,” says Patricia. “Most are struggling with the pressures they are under personally and professionally and don’t have the skills to manage effectively. If you can start from this place of understanding, it will make dealing with them much easier.”

In some circumstances, understanding the motivation behind their management style may not even require action; you might even be able to use it to your advantage. Take the micromanager, for example. They get comfort and confidence from understanding the detail, so they can manage anything that starts going wrong early. Once you understand this, says Patricia, it becomes easier to give them confidence in you by facilitating their need to know everything. "Preempt their questions and give them details in advance," she suggests. "Eventually, they won't need as much information because this approach over time will help establish trust."

Or maybe your boss is the opposite: Very distant or not particularly headstrong; too much of a people pleaser. While certainly not the worst trait, it quickly becomes irritating and stifles progress. "Most people pleasers are insecure and needy," says Patricia. "To secure the outcome you want, anticipate any push back they will likely get and arm them with the arguments they'll need to make their case." If you’re dealing with a distant boss, Patricia suggests showing the value of having one-to-one catch-ups with you by giving them insights into the office or business they wouldn’t have gained otherwise.

Your Chance to Shine?

Maybe you think they are – let's not sugarcoat it – plain old incompetent. Yes, it can be beyond frustrating when you know more about a subject than your boss or you feel they are out of their depth, but it needn't be all bad. If they're new to your organisation or to management, try to just be patient and supportive. You’ll feel better for taking a more positive approach and they’ll remember you for your kindness.  

If, however, they've been in the role for some time and are still out of their depth, you could work this to your mutual benefit. For example, there may be particular meetings you know they don’t want to attend. Patricia suggests supportively offering to go on their behalf. “This is a chance to be seen, broaden your reputation and ensure that, if your boss fails, you don’t,” she says. “You’re also showing yourself as a key person who is able to stretch and is ready for a greater leadership position elsewhere.” 

While these opportunities might have you feeling empowered and pumped, it’s always important to remain discreet. “No matter how bad you believe them to be,” Patricia reminds us, “never gossip behind their back, publicly call them out or confront them in an aggressive manner. This will only reflect badly on you.”

Having the Talk

So when is the time to have a chat? Well, think about it like any other long-term relationship. We’re all human, with quirks and flaws that grate on each other. If, on balance, your boss is reasonable, be inclined to overlook minor irritating ways. If, however, you’ve looked at the situation as objectively as you can and there are specific aspects of their management style that are impacting how you feel or perform at work, then it needs addressing. “Start by having an honest conversation to see if there’s a way you can work together to rectify the situation,” says Patricia.  

Giving your boss feedback on their management style can be a hellish thought at the best of times, but virtually it’s even harder. Always opt for in-person or a video call, so you can see each other and read their body language. Here are some tips for how to go about it:

It’s also important to have some suggestions for a way forward. You want your feedback to make a practical difference, not to just share it and leave it hanging. Try to agree a change, even if it’s for a fixed period, then you can review to see how the change is working. 

Taking Things Further

If you feel you’ve done everything in your power to resolve things with your boss, to no avail, then it may be time to escalate the issue through the appropriate channels. If you have a trusted mentor, you could discuss it with them first. Otherwise, speak discreetly to someone in your HR team, and remember to remain professional. “Your boss will unlikely be happy with you for going to HR,” says Patricia, “but sometimes that’s what needs to happen, for everyone’s sake.” 

If things don’t improve, and your organisation is unable to resolve the situation, you should consider leaving. It could turn out that the problem isn’t actually your boss, but the entire culture of the company; unfortunately, that is a battle you may never win. 

Looking After Yourself

In the meantime, dealing daily with a difficult boss can be stressful and exhausting, so it’s important to look after yourself. Exercise, eat well and get enough sleep; look at other aspects of your life, like hobbies, interests and side hustles, to compensate for a lack of control in work. Let off steam with a friend (not colleague) or family member; they will help you keep your boss in perspective, remind you how brilliant you are and that this is just a blip in your long and brilliant career.