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HOW TO HAVE A DIFFICULT CONVERSATION WITH YOUR BOSS

Difficult conversations are challenging and can be uncomfortable and awkward, but are necessary as people aren’t mind readers.

Two young men at a workbench looking frustrated at one another

Even the best manager is likely to be unaware of what is causing a person stress without good communication. 


If problems are left unspoken and unaddressed, change is difficult and the situation can become worse. In the end a little discomfort in the moment can lead to better outcomes and positive working relationships. 


Here are a few tips to help you navigate a difficult but crucial conversation with your boss: 

1. Don't think about it as a difficult conversation


Get into with the mindset that it is just a regular conversation.  


2. Let your supervisor know you want to talk


Let your supervisor know you would like to discuss and issue and request a time to do so.


"I’ve been reviewing the upcoming schedule for the month, and I have a few ideas I would like to discuss with you. Would Thursday be a good day to schedule a time to chat?"


3. Find a time to meet when you are sure you have their full attention


Your supervisor may want to talk to you right then. If you are not ready, or feel they are too rushed to give you their full attention – let them know:

"I need a bit more time to prepare my thoughts and would prefer to discuss it on Thursday".


4. Have a plan, but not a script


Jot down key points.

  • What is the issue?

  • How is this impacting you?

  • What would you like the solution to look like?

It is good to know what you want out of the conversation - it shows initiative.


5. Be honest


It is a lot harder than you think. Don’t throw people under the bus or play the blame game – make the conversation about you, not everyone else. That being said, if an issue with a colleague is bothering you, bring it up with your boss sooner rather than later.

You don’t want to reach your tipping point before going to your boss with an issue.


6. Keep your language, simple, clear, direct and neutral


Stay focussed on the real issue, and try not to get confrontational, aggressive, yell or swear.


7. Acknowledge the others’ point of view


Ask for your boss’ perspective and listen to what they have to say. Go into the conversation with an open mind  - not a 'my-way-or-the-highway' attitude. 

Don’t think that your boss has it out for you because in most cases, they probably don’t.


Finding out their reasoning behind their decisions can help you better understand their thought process. 


8. Reach a resolution


Be constructive in suggesting solutions or alternatives. But don’t feel like you need to give an answer right away – you might need some time to go away and think about it (this goes for your supervisor too, they may need time to think).

But don’t forget about it!

Agree on a time to come back soon to talk about it – otherwise it is too easy to let it slip away.


9. Agree on a way forward


Decide on the next steps, set a time to follow-up. This will help you both be accountable for your agreed actions



Lost for words?


Here are some examples of what to say.


Example 1: Issue with a comment raised in a meeting


“In the toolbox meeting on Monday, I heard you say [xyz]. When I heard it, I felt undermined because of [abc]. I’m wondering if you can understand my point of view?”


Example 2: Cause of work-related stress


“I am finding the last-minute requests and changes to the project schedule frustrating. It is increasing my stress as I now must change tasks at the last minute in order to meet this new deadline. I do not enjoy working like this, I feel that my work quality suffers.


Can you understand how your last-minute changes impact me? Can we look at project scheduling and deadlines in more detail to avoid these last minute requests?”


Example 3: Made a mistake


“I have made a mistake. It is not easy for me to admit that I [insert mistake committed], but I want to be transparent and assume full responsibility for my error. It is my hope and my desire never to make this mistake again. Since it was my mistake, I will also be the one to fix it by [insert how to fix mistake]. I understand how this mistake was made and in future will [insert how you will avoid it in future] .


OR: I would appreciate your advice on what I did wrong and what you would have done in this situation.” 


Example 4: Request for a pay rise


“I would like a pay rise. I believe I deserve a pay rise due to my hard work and contributions to [this company]. I have been here for [insert amount of time with the company]. During that time, I have achieved the following for this company: [insert list of accomplishments, big and small, that you have personally contributed to the company].


Other workers with the same job title, doing similar roles, in this area make [insert amount made by similar workers in your area if it is higher]. I do enjoy working with this company; I would just like my work to be appreciated appropriately.”


Example 5: Issues with management style 


“I have thought about how you are managing my work, and it is not a style that makes me comfortable because [insert reasons why it makes you uncomfortable, e.g.: I prefer to have more independence, I like to know exactly what is expected of me, I don’t like deadlines changing at the last minute…]. I realise that your style might work with others, but I feel that I am unable to perform at my best under this style. 


In managing how I work, can I suggest that maybe we try [insert suggested alternative, for example: give direction in writing, I check in with you at the beginning of each day, or once a week, or when I need guidance]. I feel that this will be more productive for us.”


 
Want to know more about how to communicate with impact?

Take a look at the guides we've made for you from the supervisor's communication toolbox.


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