Hi, I’m Nicola from The People Mentor. In today’s podcast, I want to discuss how to have a successful, difficult conversation with your boss.
Nobody enjoys having difficult conversations, but when you need to have one with your boss, it can intensify the anxiety and dread you have around it.
Whether you disagree on how a project should move forward or you need to discuss their management style’s negative impact on you, these types of conversations are never easy, but they are necessary.
So, how do you successfully have a conversation like this with your boss? I’d like to share some tips and techniques I’ve picked up in my decades in management.
Tips to Help With The Challenging Conversations
The first is that when it comes to difficult conversations, it’s all in the preparation. If you aren’t sure how to broach the subject with your boss, try this: write down your thoughts in the form of a letter. That letter can then be your framework for the conversation. Turn your thoughts into bullet points that address the main things you want to get across and organise them in order of importance.
If you want to, you can share the points with your boss via email and request a meeting. If they can see your point of view prior to the meeting, it will give them time to think about what you have said and avoid them feeling blindsided by anything.
Another important tip is to focus on the issue at hand when having the conversation rather than being tempted to make things personal.
You shouldn’t allow any personal feelings you have about your boss to get in the way of you both being able to resolve the situation.
I would recommend telling them about the effect the issue is having on the team or the work, and then propose a solution you think would work.
Of course, we’re only human, and difficult conversations can get heated.
It’s always better to try and stay calm, composed, and respectful.
Give your boss time to speak, listen to their responses, and stay aware of your body language. Keep it open and relaxed, and don’t forget to breathe!
If at any point you feel like things are getting too much, find an excuse to step out of the room or ask to reschedule the meeting. This allows heightened emotions to subside.
When Emotions Run High
Now, I just want to take a moment to address what to do if you break down and cry.
I know that many of you will have had this experience, especially during a difficult conversation. I know I have.
Feelings of anger, frustration, injustice, or anxiety are just some of the things that can make you break down.
If it happens in front of your boss, it can feel embarrassing, and you might worry about how this will affect your professional reputation and how they perceive you.
I would say be kind to yourself. Emotions are completely normal, and your boss is probably not judging you as harshly as you are judging yourself.
If you break down and you feel like you are all over the place, ask your boss if you can take some time to compose yourself.
Step out of the room for a few minutes, get some fresh air or a glass of water, and take some deep breaths. When you feel calmer, resume the conversation. Otherwise, ask if you can reschedule.
When you talk to your boss, don’t apologise for being emotional.
Instead, address the fact that you got upset by saying something like “As you can see from the way I reacted, I am very invested in things going well on this project”, or whatever the reason was for you getting upset.
Then, say you are keen to resolve the issue and find a solution that works for everyone, and you would like to talk about the best way to move forward.
Taking ownership of how you feel and react takes strength and confidence, putting you in a position of strength rather than weakness for future interactions with your boss.
The STAR Method
So getting back to tips for having the actual conversation itself.
You may want to try using the STAR method, which stands for Situation, Task, Action, and Result.
First, discuss the situation, making sure you stick to the facts.
Don’t get personal, blame others, or get defensive.
Sticking to the facts helps keep emotions in check.
Next, describe how the situation or issue affects you, come up with possible ways to resolve it, and talk about the outcomes or results you would like to see.
This may seem simplistic, but it’s a good framework for a brief, positive, and productive conversation.
Finally, an underrated tip, in my opinion, is admitting to your boss that the issue you need to resolve and the conversation you’re having with them is causing you discomfort. You and your boss are only human, and the chances are they feel exactly the same.
Finding common ground and empathising with each other’s feelings can make it much easier for you to agree on a solution that works for both of you.
We’ve examined some tips for having successful difficult conversations with your boss; now, I’d like to share some practical examples of difficult conversations and how you might approach them to achieve a positive outcome.
Practical Examples of Challenging Conversations
The first scenario is when your manager’s management style makes your life harder.
It could be that they can’t help micromanaging.
Or maybe they are indecisive and fluctuate from one thing to the next without keeping you in the loop.
I would approach this conversation with the intention of helping them become better leaders.
It’s not a chance for you to tell them ten things you dislike about them!
Be direct and tell them what you have observed and what you feel isn’t working. Make sure you convey that you genuinely care about their success so that everyone in the business benefits.
The next scenario is when you have to tell your boss that you’ve made a mistake.
I would approach this by being honest.
Tell them what happened and what you have in mind to fix it.
It’s also a good opportunity to share with them anything you have learned and what you will do differently to ensure it doesn’t happen again. Everyone makes mistakes; what sets you apart is how you take ownership, learn from them, and grow.
The third scenario is if you’ve been offered a better job role.
Maybe you love your job, but the raise or promotion you want just doesn’t happen.
Or maybe it doesn’t allow you to have the work-life balance you need if you have family or caring responsibilities.
When you come to have the conversation, be prepared that your boss might try very hard to convince you to stay.
If you know in your heart of hearts that you want to leave, be polite, pleasant, and professional. Say something like, “I’ve decided that accepting this new role is what’s best for me right now, and I just wanted to thank you for the opportunities I’ve had while I’ve been here.”
Offer to help with any transition and be firm about the fact that you are leaving because it is what’s ultimately best for you.
Regardless of the difficult conversation you need to have, know that you’re not alone in finding them daunting, no matter what kind of relationship you have with your boss.
Keep in mind that you want the conversation to be productive, and make sure you have a plan, purpose, and agenda before you start.
Be professional and respectful, and even if the conversation doesn’t go as planned, you’ll be able to say that you were able to engage in it without compromising your professionalism or integrity.
We’re approaching the end of this podcast episode, so I wanted to let you know you can get further help with difficult conversations if you are struggling or want to enhance your skills.
That’s all for this episode. I hope it gave you some helpful tips on having successful, difficult conversations with your boss and even improving your relationship.
See you next time.
