Ten top tips for courageous conversations at work

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That difficult conversation might be about a performance issue or something more personal. It can be with a peer, a subordinate or indeed a boss. Understandably, people are often highly anxious about having this conversation. So, they either avoid or rush at it like a bull in a china shop just to get it over with. Here are some top tips to help produce a good result. Think about these before embarking on a difficult conversation and reduce your own anxiety and help to generate a positive and productive outcome for all parties involved.

1. 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. Is it an apology, an agreement about something, a change in behaviour in the future, some sort of restorative action or maybe a resubmission of a piece of work? Be clear what the successful outcome is and listen for it.

2. Be clear what you are listening fo

Being highly anxious can make us deaf. You need to 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. Otherwise you run the risk of producing a new source of conflict as your conversational partner feels unfairly berated when they’ve made a concession. This can sabotage the chances of recovery.

3. Be clear what gives you the right to initiate this conversation

It really helps us reduce our anxiety if we can understand how the conversational intent aligns with our values. For instance, you may have to tell someone that they didn’t get the promotion they were after, and give some hard feedback as to why. The clearer you are that giving this feedback is, for example, helpful behaviour (and it is important to you to help and develop others) then the easier it will be to say what needs to be said about the current shortfall in their experience, manner, etc. if they are to succeed in the future. Fobbing them off softly is easier but less helpful to them in the long run.

4. 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 there may well be a drop in productivity as they become distracted wondering what it is about. There is also 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 in some way. It’s a judgment call and depends on the situation and circumstances.

5. 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? Many mistakes start out as good ideas or intentions. 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.

6. Listen first

It is often a good idea, once you have outlined the area, topic or incident that you want to discuss, to give the person a chance to give their view on the situation. 

Many a manager taking this approach has found the other person only too aware that there is a problem and they have been making themselves miserable over it. Of course you’ll also have people who take the opportunity to ‘get their defence in first’ but at least you have the lie of the land before you say your piece - and indeed you may not need to say much at all.

7. 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.’ Or ‘my sincere hope is that we come out of this conversation with a shared understanding of what happened and how we can make things better’.

8. Be honest about the effect on you 

The more able you are to be honest about your motivation for having the conversation, the more likely you are to be acting and talking with integrity. Authenticity and integrity tend 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; it’s about being honest about your investment in this as well as the favour you are hoping to do them.

9. 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. Steer away from evaluators like ‘aggressive’ and say instead something like ‘you were speaking in a louder than a normal speaking voice, leaning in very close to B. Your face was going red and your forehead bulged. I also noticed B leant backwards and raised her hands. She didn’t speak for the rest of the meeting. 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. I need both your inputs. Let’s see if we can find a way where you both feel able to make your points’.

10. Look forward to solutions, not backwards to blame

The aim of the discussion 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. 


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