Having difficult conversations with your boss and how to handle them like a pro

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Throughout your working life you’re going to be faced with the challenge of having a difficult and uncomfortable conversation with a colleague or a client and perhaps more frequently, with your boss.

Typical tricky conversations with your boss include:

  • Asking for a raise
  • Challenging a decision
  • Airing a grievance
  • Asking for more support
  • Telling them you’re moving on

Nobody likes having these conversations and a lot of people procrastinate over them and lose sleep worrying about how to avoid them.

So how can you handle these tricky conversations with your boss like a pro? Here’s some top tips for before, during and after your conversation.

Before the conversation

1. Look at the conversation more optimistically

If you approach it as a ‘difficult conversation’, it will be. Try to think of it as an opportunity to voice your concerns or discuss ways to move forwards.

2. Prep your key points

Don’t script your discussion as you’ll likely forget it and get flustered, and it will just seem a bit weird and unnatural. Instead, just write down your key points so you can refer to them throughout the meeting.

3. Remove your emotions and get perspective

Even if you feel strongly about the topic up for discussion, you need to bring your emotions down so they don’t overrun the conversation. A great way to do this is to write out everything you’re feeling. Try to look at each point from your boss’ perspective. Consider each point and ask, ‘is this helpful in resolving the issue?’ If not, leave it out of the conversation.

4. Frame the conversation

Ask your boss if you could meet to discuss something and that you’d like their perspective or help with it. Asking them for help, or their input will frame the conversation in a positive light and prime them to do just that, help you. If you ask for a meeting to raise a complaint, you’ve set them up expecting it to be difficult.

5. What’s the ideal outcome?

Finally, ask yourself, ‘what’s the ideal outcome of this conversation?’ What would resolve this for you and where would you be willing to compromise? Preparing yourself for this will help you to articulate and support your boss in finding the best resolution.

During the conversation

1. Breath deeply and slowly

When we’re nervous or tense, we tend to rush and speak a lot faster. Counteract this natural physiological response by breathing consciously – taking deep breaths and breathing slowly.

2. Tap on your karate chop point

Emotional Freedom Technique (EFT or Tapping) is a great technique for reducing the physical response to anxiety or stress. Tapping your forefingers on your karate chop point of the other hand, under the table whilst you have the conversation, can help you stay level headed and stop any nervous shaking, sweating or physical signs of stress.

3. Raise the issue succinctly

Once you’ve sat down to talk, thank your boss for taking the time to talk with you and tell them briefly why you’re asking for their help or opinion. Keep it brief and stick to the key points you’ve prepared. At the end ask, “I’d like to know your thoughts on how we can move forward from this?” or “How do you think we can best resolve this?”

4. Listen and let them talk

Now you need to let your boss take the floor and listen to everything they say. Feel free to jot down notes or points for further discussion but actively listen to them and try and see their perspective. If they say something that frustrates you, remember to try and keep your emotions separate to the facts.

5. Reflect, share and problem solve

Take a few moments to think, thank them for sharing their input and then share your thoughts about what they’ve said. Aim to problem solve with them to find the best solution for all involved. If it can’t be achieved during this conversation, then agree a date and time, plus action points, to get it resolved.

After the conversation

If it went well, or even if it wasn’t resolved there and then, here’s a few follow up tips:

  1. Thank your boss for taking the time to meet
  2. Drop them a quick email to reiterate what you understood and took from the conversation and any key action points you agreed upon
  3. Schedule a time to address this topic in the future if needed
  4. Shortly after the meeting, write a succinct log of the meeting – time, date, and what was covered. This will help with recall and is useful for HR purposes.

Good luck with your tricky conversation and do let us know in the comments below if this post has been useful at helping you handle issues with your boss.

Hate your job and fancy yourself as a freelancer? You want to say hello to Jen, our guest contributor with a passion for going for your dreams. When Jen isn’t writing for us about starting a biz, she’s hanging out with her tabby cat Monty and coaching women to quit their jobs and take the leap. She likes jigsaws, cheese, books and crafts and loves nothing more than the feeling of sunshine on her face. Has been known to throw Zumba-moves in front of her idols. @_JenSmith 


Jen Smith coaches entrepreneurs in social media.

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