How to deal with a difficult boss: seven brilliant tips

Sorry to say, but there are plenty of difficult bosses out there! Which makes learning how to deal with a difficult boss an essential career skill.

Don’t let your workplace success and your mental health suffer every time you encounter a difficult manager. Here are 7 brilliant tips to help you regain your mojo.

How to deal with a difficult boss: in summary

Here’s a quick summary of our tips:

  1. Get a little perspective (recognize that they’re not all bad!)
  2. Identify their triggers, knowing what sets them off is half the battle.
  3. Match their social style, sometimes it’s about style, not substance.
  4. Test if they will accept feedback. Do it right and help them to help themselves.
  5. Don’t hide from difficult conversations, turn them into opportunities.
  6. Set boundaries. Discover how to establish yours.
  7. Create FAST Goals. They’ll help you manage expectations and keep your boss on track.

Read on and learn more about how to deal with a difficult boss!

Seven tips for dealing with a difficult boss

You may not be comfortable experimenting with all these tips. However, I recommend you work on tips 1-3 first, these are small steps that get you moving you in the right direction.

Then select from the remaining 4 and see what will work for you.

1. Get a little perspective

We all have systematic errors in our thinking, known as cognitive biases, that occur when we process and interpret the world around us.

Why do I mention this?

Because the halo effect and the horn bias are two of the most common. If we encounter someone with a few positive characteristics, we assume that everything about them is positive. If we encounter someone with some negative characteristics, we can only see the negative.

We can also catastrophize, which makes small problems seem much bigger than they are!

Take a breath, take a step back. Regain your balance. Recognize the positives of your boss as well as what makes them difficult.

2. Identify their triggers

Once you’ve got a little more perspective (and realized that they’re not all bad!), you can identify their triggers.

What sets them off?

I once had a manager who liked instant responses to his requests, even if the deadline he set was a few days away. He’d make the request, set the deadline, and then send me frustrated reminder emails before the deadline.

I’m diligent, reasonably smart, pragmatic, and I get the work done. But I also like a little time to reflect on my work, and I work to deadlines, I don’t get all excited about providing an immediate response.

But I also realized that this manager needed quick responses, regardless of the deadline. So, I adapted. It took a little effort, but it helped me to deal with this boss.

Identify their triggers and manage them.

3. Match their social style

Another way to adapt, to deal with a difficult boss, is to match their social style. The social styles model is a simple and insightful model for understanding people’s natural communications preferences and learning to adjust your style to match.

The four styles are:

  • Driver
  • Analytic
  • Amiable
  • Expressive

We are all a mix of all four styles, but we have natural preferences. Learning to tap into the different styles can help make you a more flexible and effective communicator.

Start by reading more about the social styles model, then observe your manager and recognize their style. Finally, adapt your social style to match. You’ll soon see the benefits!

4. Test if they will accept feedback

There are not many managers who wake up in the morning and say to themselves “let’s see how difficult I can be today! Wooohooo!”.

Most difficult bosses simply do not know they’re difficult bosses. This is where your feedback comes in.

Our effective feedback model will help, but you need to adapt it a little too.

Imagine your boss is giving you too many short-term deadlines, it’s making your work more difficult and stressful than it needs to be. Perhaps you could try something like:

We’ve had a lot of short-term deadlines recently. I’m starting to think there could be a better way of managing these tasks. Would it be OK if we talked about this?

Or maybe they get angry and frustrated without giving you clear guidance:

Yesterday, when I gave you the draft report, it felt like you were quite upset with my work. Have I got that right? I want to do a good job, can we please discuss what I should do next?

These examples show how you can ‘shine a light’ on their behavior, and encourage them to reflect, without being confrontational.

Easy? No. But if you can test whether you’re boss is open to feedback it can have a great impact on your working relationship.

5. Don’t hide from the difficult conversations

Difficult conversations are the ‘crossroads of productivity’. If you hold them, and hold them well, you’ll move the business forward and build relationships. Too often our goal is to simple avoid difficult conversations.

To start a difficult conversation with your boss:

  1. Ask permission (it creates buy-in)
  2. Keep it short (the more you ramble, the higher the tension ratchets)
  3. Keep your tone light, let the message speak for itself

For more, take a look at our article: how to start a difficult conversation.

6. Set boundaries

As work and life becomes increasingly integrated, setting boundaries is becoming more important with any boss, and particularly difficult bosses. It’s not an easy process, will involve trail and error, and won’t always work out.

Caroline Castrillon, is a career and life coach who makes the following points:

  • Prioritize your values
  • Communicate clearly
  • Prepare to negotiate
  • Frame your response
  • Expect pushback

You can find more in her article how to set boundaries with your boss.

7. Create FAST Goals

We’ve all heard of SMART goals, but FAST goals are more help dealing with a difficult boss.

The FAST acronym stands for:

  • Frequently discussed
  • Ambitious
  • Specific
  • Transparent

When exploring how to deal with a difficult boss, it’s the ‘Frequently discussed’ that is most useful. You’ll keep expectations aligned and ensure there are no surprises to derail your relationship.

Take a look at FAST goal setting.

How to deal with a difficult boss: a final thought

There is plenty of research that shows people quit their bosses (rather than quit because of their role, or organizational issues).

If you’re thinking of leaving your boss, stop for a moment. Reflect on the tips above. You owe it to yourself to take action to improve how you work together, before making a final decision.

If you don’t learn how to deal with a difficult boss, and choose to jump ship, the danger is that you’ll move to another organization and find yourself in exactly the same situation.

As I said, there are plenty of difficult bosses out there!

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