4 Top Tips for Challenging a Difficult Boss

I’ve been quite lucky to have really inspiring, talk-the-talk, walk-the-walk managers over the past few years but nothing prepared me for my most recent job post as an executive assistant.

Having a boss who makes you question how they even got the job can be disheartening and even make you question whether you want to stay…They stress everyone out and leave a whirlwind trail of disorganisation everywhere they go…yet somehow still manage to keep just about on top. There’s no point in getting frustrated and angry at them, you have to be proactive- you are going to need a nifty survival tool-kit up your sleeve so you can manage them and not go crazy yourself.

Learn as much as possible about their role

Knowledge is power. When you have more knowledge, you can make informed decisions autonomously and can challenge them whilst having confidence that you understand the entire picture. Understand their exact responsibilities, who their line managers are or people they should work in close communication. Understand timelines and schedules that involve them and when they should be hitting certain project goals.

Avoid asking other colleagues for the dirt on your boss — people gossip and these people are your colleagues, not your friends. It can very easily get back to your boss and damage relations. Stay neutral and just keep an ear open for any comments people make about them.

Understand their behaviour

This can get Very interesting when you start paying attention and you will likely start to see patterns in their behaviours. Think of it like a faulty car that YOU need to drive…the more you take note of the sounds it makes and when it gives you certain signals something is wrong, the quicker you can get to the root of the problem and fix it.

• What did they do?
• Why did they react that way? What was their intention?
• What were the implications?

Here is where you will see patterns. The more you understand the Whats and the Whys, the better you can understand their decision making behaviours.

Influencing their Behaviour

Build on Strengths. Reflect things back that are positive, their good intentions, and what IS working before making a suggestion about what needs to change. This creates that all important non-challenging, ego-stroking dynamic that will help you get a leg up with steering them in the direction you want.

Radical Candor — or being Brutally honest, is the second approach which you can also combine with strength building. Show them that you care personally while you challenge directly, without being aggressive or insincere. This might look like; “That isn’t your responsibility and I think it would really benefit your own capacity if you kept you attention of this project rather than that one.”

Clarification Questions — Requesting Explanation

“Help me to understand”… — style Questions. This approach will make your boss feel like they are helping you which creates a non-challenging dynamic. In explaining out loud, it gives them a change to think through what they are doing, and you a chance to understand their thought process. They may even make clear to themselves that there is not a good rationale for their decisions.

“Help me to understand…

• …How you got to that conclusion.
• What is your rationale for …
• Can you explain why this needs to be done now/is so time sensitive

Even if you just use a few of these tips, they will help you to gain stability at work and make your working environment, and hopefully your relationship with your boss, less stressful.