What to do when...you need to have a tough conversation at work

They're not something anybody looks forward to - but unfortunately at some time or other - there are some tough conversations that need to be had at work.

They might be necessary because a conflict has arisen, as a manager you need to deliver some negative feedback, or you might have to raise something tricky with your boss.

Whatever the reason, they are not fun. But the consequences of avoiding them may be even worse. Putting them off is not the answer. If you don't have the difficult discussions - the risk is that the problem/situation will get even worse.

It can take courage to initiate a tough conversation, but if you make sure you have the facts and approach it in a business-like and respectful manner, the potential benefits of a resolution can outweigh the initial discomfort.

To make it easier:

Set up the conversation in advance

Send a short email requesting some time to discuss the business issue. The less time you ask for the more likely you are to get,

 or even better,

Take a deep breath, pick up the phone and ask for the time. Practise what you are going to say beforehand if you are really nervous.

Often time - just being prepared to have the conversation will win you kudos from the other person.

Pick the most appropriate venue

Different locations are appropriate depending on your relationship with the person and the nature of the conversation you need to have.

If it is someone senior, and very busy, his or her office is likely to be the best place. If it's a peer or a staff member, find a meeting room where you can have the discussion in private. If it's someone you have an existing relationship with, offering to buy them a coffee and stepping out of the office might take the heat out of the situation and provide a relaxed 'neutral' environment.

Once you're talking,

Approach the conversation from the other person's point of view.

Ask questions to understand their perspective and understanding of the situation. In these circumstances, Steven Covey's "Seek first to understand, then to be understood" habit from the 7 Habits of Highly Effective People is a good approach to adopt!

Once you are talking you're on the pathway to resolve an issue. It might not be the whole answer as many situations are genuinely difficult. But it's a start.

Do you have any other ideas you've tried? Let's chat...

- Karen


  1. Hi Karen,

    Some very good points raised here - I am sure that (at times) we have all been guilty of picking the wrong time/place/tact for raising concerns or issues with colleagues.

    I often find that despite my willingness to discuss things anywhere and any time, others require an alternative environment and also some time to prepare for these types of conversations - Having utilised a number of the tips you have mentioned in the past, I have managed to avoid more than a few uncomfortable and unpleasant discussions!

    It may seem obvious, but I tend to find that if it was myself that instigated the "meeting/chat", I will request my colleagues point of view on the particular matter before putting my point across. Whatever the subject in question, this will make them feel that it is more of an open forum and will be appreciative at being given the opportunity to air their views, before you have.

    Additionally, the colleague in question will view the conversation as more of a one-on-one chat as opposed to an ambush, and be more receptive to the feedback that you will then have to (delicately) provide!

    Keep up the good work!

    James Lochrie
    On The Ball Personnel Australasia

  2. Good points.
    Others can be when come out from dicussion do not take it personal and treat the other person with equal respect. The worst thing is when people stop communicating afterwards.

  3. I had a tough conversation with my boss about inappropriate behavior and how uncomfortable it made me feel and interfered with my job. I got laid off--My position was conveniently eliminated shortly after that. I disagree that you always have to have tough conversations at least as an employee. Next time I'll keep my mouth shut and at least be able to pay my bills.

  4. very good advises you have there Karen, especially the last one. Where people fail to realize we have 2 ears and one mouth to listen more than we speak


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