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Having a “difficult” conversation with your boss

If you have just read my blog on “How to Manage my Boss” you may be saying, “ok, great Susan.  I understand what you are saying, but how do I actually DO it?”.

You see, my blog ended with the suggestion that to change and improve the relationship you have with your boss you need to take charge and do something different and that a great starting point is to help him or her see your view of the world.

My short coaching corner video will give you some tips to help you have that “difficult” conversation with your boss and gain a more positive outcome.

(If you don’t have access to the video, you can read the transcript below).



So, let me now answer your next question – “how do I actually DO that?”.

It is simple:

  1. Make the time to do it
  2. Plan and prepare what you will say
  3. Anticipate a positive outcome
  4. Then JFDI!  Just Do It!

Firstly, if you wait for the “right time” to have this conversation, you will be old and grey before it happens so, you need to make the time to do it.  In your working week, you may find the beginning of the week is busier and more time precious than the end or you may find morning’s are more challenging to find any spare time.  In which case you may opt for Thursday afternoon.  You may, of course, work in an unpredictable environment where you have to be reactive to what happens at any given moment.  In either situation, you will need to be flexible BUT that does not mean, when it gets near to the time you have allocated that you find something else to distract you!

Commit to a date and time and stick to it.  If your best friend said they needed to talk to you and asked you to meet them for a drink on a certain day and at a certain time, would you stick to your arrangement?  If your children were running in their last ever sports day at school and you committed to going, would you stick to your arrangement?

Ok, so you can do it, if it is important enough to you.  So, place the same level of importance on having this conversation.

Secondly, unless you want to stumble over your words, say something you might later regret or find your boss does all the talking…..you will need to prepare.  It is far easier to be clear about what you want to say when you are not in the heat of the moment.  Writing it down also helps as it forces you to be clear and concise and makes it more difficult to waffle.

Ask yourself, “what is the real issue here?” and be very specific about what your boss actually does or does not do and what you would prefer instead.  Stay away from making judgemental comments about why he does or doesn’t do these things, that will only end up in an argument.  Be objective and factual and explain the impact this behaviour has on you.

Thirdly, and potentially most importantly, anticipate a positive outcome.  If you imagine your boss getting angry, turning the situation around so that you feel like the problem or nodding but then doing nothing to change, guess what…..that is exactly what will happen!

You don’t think that Usain Bolt anticipated losing the 100m final in the 2012 Olympics or that Andy Murray anticipated losing the USA Open Tennis in 2012 do you?  No!  To get the outcome you want, you need to imagine it happening.  So, create a picture in your mind of how this conversation will go.  Hear it, see it, feel it.  The more vivid you can make this picture the more success you will have in creating the reality.

Finally, get out there and do it!  We can all be great at procrastinating when we want to and sometimes we even enjoy having that difficult situation to moan about, so we put off making a change.  So, to really motivate yourself you need to focus on why you are going to push yourself into taking decisive action and confronting the situation.

Remember, there is a mutual benefit…..you will improve your situation and regain that lost motivation and energy for work and your boss will thank you (maybe not immediately, but they will), when they realise how valuable your feedback has been and how you have opened their eyes to a new way of leading which will enable them to get the best out of you and ultimately make them a more effective manager.





  1. Thank you Susan – this is sound, practical advice for tackling the frustration with your boss. I’ve also found this approach is very helpful with any difficult relationship.

    As you say in your blog, it’s all about being proactive and taking responsibility for what is going on instead of remaining passive expecting the other person to fix everything.

    • Thanks Trevor. You are absolutely right that this approach can apply to many different relationships, not just with the one you have with your boss. Taking responsibility is key.

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