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Ten top tips for courageous conversations at work


Chartered psychologist, and author of ‘Positive Psychology at Work’, Sarah Lewis has 10 tips to help produce a good result when you have a difficult conversation to tackle.

Many people, at some point in their working lives, have to have a difficult conversation with someone. It might be about a performance issue or something more personal. It can be with a peer, a subordinate or indeed a boss.

Very often people are anxious about having this conversation. They either avoid it for so long that when they do tackle it it comes as a complete shock to the other party, or they rush at it like a bull in a china shop just to get it over with. Here are my 10 tips to help produce the result you're after.

Be clear what you are trying to achieve

You need to be clear in your own mind why you are putting yourself through the trauma of having this conversation, and what you hope to achieve.

Be clear what you are listening for

Being highly anxious can make us so focused on saying everything we have planned to say that we fail to hear the other person. So, stay alert to the first signs that you have made your point and be prepared to switch modes to ‘Ok what next’ even if you haven’t said everything you intended.

Be clear what gives you the right to initiate this conversation

Understand how the conversational intent aligns with your values. For instance, you may have to tell someone that they didn’t get the promotion, and give some hard feedback as to why. The clearer you are that giving this feedback is, for example, helpful to them then the easier it will be to say what needs to be said. Fobbing them off softly is easier but less helpful to them in the long run.

Give thought to how you set up the meeting

There are pros and cons to giving advance notice of wanting to have a difficult conversation with someone. The downside is a potential drop in productivity and the danger that their anxiety will drive them to push you to ‘just say it now, let’s get it over and done with’. On the other hand, springing it on them unexpectedly can lead them to feel ambushed or tricked. You’ll need to make a judgement depending on the situation and circumstances.

Look for the positive in the situation

Sometimes bad outcomes are the result of good intentions. Was the behaviour caused by a strength in overdrive? Was there an honourable intention behind the behaviour? Be alert to any good consequences that occurred in the situation you want to address, as well as the problematic outcome.

All of these give you a way to approach the behaviour that make it more likely the other person can own it, still feel good about themselves, and be open to making changes.

Listen first

Once you have outlined the area, topic or incident that you want to discuss, give the person a chance to give their view on the situation. Often you’ll find the other person is only too aware that there is a problem and they have been making themselves miserable over it.

Offer reassurance

There is an art to building and maintaining the relationship bridge while trying to convey information or a perspective that the other person might find hard to hear. Think about an opener such as ‘I feel this conversation may be difficult, but I am confident it will be to the benefit of both of us.’

Be honest about the effect on you

Authenticity and integrity tends to produce better responses in others. So say something like ‘to be honest I felt really embarrassed when...', and 'I like to feel proud of my team when...', 'that’s why I want to...’. This isn’t about trying to 'guilt-trip' anyone; its about being honest about your investment in this as well as the favour you are hoping to do them.

Use descriptive not evaluative language

Try to stick to an account that articulates what you saw and the consequences in a way that is factual and could be verified by any other observers. For example; 'you were speaking in a louder than a normal speaking voice, leaning in very close to B. Your face was going red. I also noticed B leant backwards and raised her hands. Later B came to me and said she felt intimidated by you in that meeting.' Here you can add your concern, 'My concern is that if B feels like that we will lose her input to the discussion. I know you are very passionate about this topic. Let's see if we can find a way where you both feel able to make your points.'

Look forward to solutions, not backwards to blame

The aim of the discussion, if possible, is to create a common agreement about the situation now without getting too lost in counter-arguments about blame in the past. It doesn't have to be complete consensus, just enough to allow the conversation to move productively to the next stage of finding ways forward that are acceptable to you both.

By considering these points before embarking on a difficult conversation you can reduce your own anxiety and help to generate a positive and productive outcome for all parties involved.

Sarah Lewis M.Sc. C.Psychol is an associated fellow of the British Psychological Society and a principal member of the Association of Business Psychologists. She is an acknowledged Appreciative Inquiry expert, a regular conference presenter and a published author, including ‘Positive Psychology at Work’ (Wiley) and ‘Appreciative Inquiry for Change Management’ (KoganPage). Sarah specialises in working with organisations to co-create organisational change using methodologies such as Appreciative Inquiry, and the practical application of positive psychology. Contact:

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