How to Start ‘Awkward’ Conversations

I was recently asked for some advice on the thorny topic of starting awkward conversations. (I wasn’t asked about finishing them – that’ll be another post!)

An awkward conversation might be one where you need to be critical of the other person, as in they are continually late for work and expecting you to cover for them. Or maybe you need to raise a topic that is potentially embarrassing, for example, working alongside someone with unpleasant body odour, or who is behaving in an inapproriate manner to you.

Non Direct Route

You may have tried out all the subtle and not so subtle methods.

‘Phew, what IS that smell?‘ said to no one in particular being one of the not so subtle variety, or raving loudly in the office about this amazing new shower gell you have found!

Similarly, someone who is perhaps invading your personal space, standing too close, or making very slightly suggestive comments that leave you feeling uncomfortable, may not respond to your continually moving away, standing behind chairs, and resolutely not laughing at their innundoes!

When the non direct route fails it’s time to have an assertive conversation!

Be Assertive

Now is the time for honesty while still being very respectful of the other person. Being assertive is not about winning or scoring points: it’s about having self respect and respect for the other person. It is very respectful to treat them as adults and actually discuss with them what is bothering you, adult to adult. They might not like what you say, but done properly it need not be disrespectful and may lead to an enhanced relationship all round!

Start Here

First, you need to let them know you want to have a chat with them and this usually needs to be in private. Find somewhere where you can both be comfortable if at all possible so not a busy corridor but preferably an empty office. (NB But not when you’re being assertive with the person who is behaving innapropriately! Then you need to be able to speak without being overheard but still be visible to colleagues and friends. You don’t want to give a mixed message and add to any potential embarrassment).

When I’m working with groups on assertiveness I don’t usually give out any form of words because everyone is different; you have to be able to say it in your own words, or you’ll feel silly and sound insincere! But as this post is about starting those awkward conversations, I have included some phrases which may work for that awkward beginning:

Use their name when possible, make appropriate eye contact and remember your body language is saying far more than your words; if you look shifty and uncomfortable they will receive what you say in that mode. Aim for ‘concerned and professional’, not ’embarrassed and tortured adolescent’.

Beginning with pleasantries about the weather may be helpful but more likely they will be a liitle anxious about what you have to say so don’t irritate them by going round the houses. Be pleasant and direct.

‘Could we have a word in private, there’s something I’d like to discuss with you’.

‘I have noticed that you’ve been late a lot recently. Is there a problem I can help with?’ (Bearing in mind that your help is not going to be continually covering up their lateness!)

The body odour one is difficult and you have to be prepared for them to take umbrage initially, but you could try:

Forgive me for being so personal, but it’s so out of character for you that I wanted to have a quiet word. Are you aware that you have been giving off a very strong odour of late? Are you unwell/on tablets/particularly worried by anything?‘ (Even as I write this I am cringing but I have actually done this! Spoken to someone I mean, not given off an odour- at least no one has told me…)

‘I appreciate that you have a friendly nature and other people are comfortable with your style but I feel uncomfortable when you (insert) and would prefer it if you (insert what you do want them to do).

Try not to let anxiety about what you have to say give you a bad case of the blurt, or sound angry or aggressive. Take a few deep calming breaths and mentally rehearse what you are going to say.

These are just a few tips to get you thinking. It’s also useful sometimes to consider why we find some things so difficult to say. This may be linked to our own feelings of confidence in ourselves and fear of the consequences. Remember, you have a right to respectfully express your views to another person- and they have the right to do the same!

More on this is available in the free download that comes when you subscribe to my newsletter.

Professional Relationship


Posted on March 4th, 2010 by

4 Responses to “How to Start ‘Awkward’ Conversations”

  1. This year I’ve found that I’ve been given many opportunities to choose to have ‘awkward’ conversations in order to be able to be true to myself. I’m getting the hang of it now and it’s very liberating!!

    In the past I would often have let things go unmarked however that’s a bit like playing ostrich. My situations have been about giving feedback on team members’ performance and managing expectations in a separate team situation.

    As you suggest, a few deep breaths to centre myself and using a tone of voice and speed which kept my nerves at bay were so useful.

    I believe all conversations and communication should empower the other person no matter the context and that’s the premise I start with. I use questions to help oil the wheels and find out more from them so that there’s a greater understanding and I’m not mindreading or making assumptions.

    The proof is in the pudding when you both end with a smile and a handshake (or hug).

    • Jane says:

      Thanks Jackie, I particularly agree with your point about testing out your assumptions. Always to be recommended! Jane

  2. David Winter says:

    Good advice. Working as a career coach it is often my duty to raise uncomfortable issues with clients. I tend to think about the acronym BEAR

    Behaviour – describe what they have been doing but don’t make judgemental assumptions about their attitudes or intentions

    Effect – explain how it impacts on you. Claim responsibility for your own feelings rather than blaming the other person for them.

    Action – explain exactly what you would like them to do instead of the difficult behaviour because they may not be able to think of an alternative themselves

    Result – make it clear how thing will be better for both of you if they follow your suggestions

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