How to ace difficult conversations

Leadership expert, Chris Pearse, explains how to check your prejudices at the door to achieve the most optimal outcome

Let’s start by being completely honest; most of us would rather avoid difficult conversations if possible. They stir up emotions, upset relationships and it can take time for the dust to settle and for normality to be restored.

Of course, there are exceptions – someone oversteps the mark, triggers you and despite your generally unflappable nature, in a flash of justifiable irritation, you decide to let them know exactly what you think. And then there are those (not you or me, of course) that seem to relish combative exchanges and find any reason to challenge and provoke others.

According to the received wisdom, difficult conversations are… difficult! So, like anything else, they should be avoided unless necessary. Then, when there is no alternative, they need to be carefully managed, every possible outcome considered, and potential damage minimised.

If all that sounds familiar, it should. It’s how most so-called difficult conversations are avoided. It should also feel rather disheartening. As soon as we apply the adjective difficult to a conversation, we immediately become defensive and employ strategies and tactics based on fear.

So let’s get one thing straight from the onset: there is no such thing as a difficult conversation.

Self-fulfilling prophecy

There are conversations and then there are those conversations that we predetermine as difficult. Difficulty is a self-fulfilling prophecy that we superimpose on situations; sometimes with good reason – no one would find climbing Everest easy. But conversations are as easy or as difficult as we make them. Let’s start from the premise that whatever conversation needs to be had, it need only be difficult if we choose to make it.

How do we lose the mindset of difficulty? What I have found over the years of working with business owners, entrepreneurs, and senior managers, helping them improve relationships with others, is that the fear associated with some conversations often arises from a misplaced sense of responsibility. They will fixate on how they think the other person will feel when the “difficult” subject is broached. Sometimes this arises from a warped sense of responsibility to the other; sometimes it is down to just wanting to be liked. Both are pernicious.

Getting your priorities straight

When you prioritise how someone else feels over your own feelings you serve no one and undermine your integrity in the process. How can this be? Firstly, you can never know exactly how someone else feels, even less how they will feel when you talk to them. If your strategy is based on this fantasy, it can only succeed by luck, never judgement.

Secondly, how you feel is the only true guidance that you have access to and it needs full disclosure to yourself. That means acknowledging not just the fear that may be holding you back, but also perhaps the much quieter voice that’s been telling you for some time that a conversation needs to be had.

When you give all your feelings the attention they deserve and stop ignoring or suppressing those you may not like, the next step will inevitably become much clearer.

What’s next?

You are not accountable or responsible for the way another feels, provided you have acted with integrity and good intent, which is the basis of compassion. Why? Because every functioning adult is responsible for how they feel whether they have yet realised it.

The other step to take prior to having a conversation that you may be inclined to label “difficult”, is to banish any thought of wanting to be liked. Wanting to be liked or even respected is an ego-based strategy to compensate for the lack of love or respect that you have for yourself. And it never works very well. Have you ever liked someone that is desperate to be liked or respected, someone that clearly lacks respect?

Of course, that is not to say that we should be disliked, just that hankering to be liked leads to counterproductive behaviour.

Ego activity

Once you have put these psychological drivers into perspective, do not try to change them. It is quite enough to identify and acknowledge them. Any self-criticism and judgement are just more ego activity. Seeing them in action will give you the choice that you need to change your behaviour very naturally and in the moment.

If you are brutally honest with yourself, you may well be able to spot a whole barrow-full of assumptions that you could easily bring with you into the conversation. You may think you know exactly why the person is behaving in such a way that needs to be challenged in a conversation. You may think you know how they are going to react when you speak to them. You may believe that the person is fundamentally difficult, contrary, recalcitrant, pig-headed, weak, undisciplined, and lacking “gumption”. Whatever you think about them, bringing these prejudgements – or prejudices – into the conversation will always work against the optimal outcome.

Optimal outcome

The best way of temporarily neutralising these opinions, as far as one can, is to employ non-judgemental curiosity – which is simply to start from an attitude of “I don’t know” and to begin the conversation by asking questions based on genuine curiosity, without judging the responses.

As with any real-world scenario, there are exceptions. If you have reason to believe that the person is emotionally vulnerable, the best starting point will be to ask a trained third party to have a preliminary conversation, establishing the best next step.

In broaching any difficult subject, be open with your observations or your feelings. These can’t be challenged. However, if you start to share your opinion or your thoughts on the matter, these are judgements that can and may well be refuted.

“Your work has been below par for months now, Sam – what’s going on?”, is not a good opener. It passes judgement that is open to dispute, it is far from specific, and it drags the past into the present. If it’s gone on for so long, why did you not mention it before?

“I notice you didn’t meet the deadline on your last report, Sam – what got in the way?” This is specific, can’t be disputed and addresses the present or recent past.

The biggest obstacle to having difficult conversations is the fear of what may happen and very rarely does. In my experience, with the above approach, outcomes are always much better than anticipated and both parties leave feeling so much better than before, whether or not the issue gets resolved there and then.

10 tips for handling difficult conversations

1. Don’t label it difficult – it doesn’t need to be
2. Leave your assumptions at the door
3. Be specific – don’t generalise
4. Be curious – ask questions
5. Don’t judge – until you have listened
6. Stick to the facts
7. Keep to your observations
8. Stay with the immediate past
9. Be compassionate – don’t pity
10. Don’t take responsibility for their feelings

Put it to the test…

Andy has a problem that everyone in the office knows about. To put it bluntly, he smells. He has an off-putting body odour. The rest of the office has no issue talking about it with their colleagues but, of course, never with Andy himself.

Andy has been at the company for many years. He’s always had a strong odour, but it’s gotten worse in recent months, certainly since you all started going back to the office after the lockdown. As the boss, you’re hearing more and more about Andy and his problem. You know that leaving deodorant on his desk is not the best tactic but talking to him directly about such a personal matter would take more courage than you have.

You hope the whole issue will just go away. But of course, it doesn’t, it just gets worse. What do you do?

Your plan of action

Firstly, you are determined to have the conversation at the next opportunity – today or tomorrow.

Secondly, you consider the opening gambit – one that is non-judgemental (as far as it can be) and makes no assumptions. It needs to be a bald statement of fact made compassionately. For example, “Andy, I notice you have a very strong smell about you.”

Next, we need a question to start the conversation, “Is everything OK with you?” You may spot an assumption that there could be something wrong in Andy’s life, but you’re asking a question, not stating a fact, and it gives Andy a way forward.

Also, note that there’s no mention of an ongoing problem. There’s no dragging the past into the present and burdening Andy with more than you need to.

No other rehearsal is required – in fact, it is unhelpful as it detracts from the need to focus on the conversation as it unfolds spontaneously. So don’t rehearse, instead:

• Be specific
• Be curious
• Don’t judge
• Stick to the present

It’s also important that you own what you say. Don’t relay what others have said, stick to your own observations and keep them recent. Go into the conversation having no idea or desire for a particular outcome other than a little more clarity. The way to get that is to ask simple questions, free of judgment. If Andy deliberately blocks the flow of conversation with one-word answers, you can reinforce the need for change, ask him to reflect on the issue and come back to you with his thoughts tomorrow.

The author

Chris Pearse has started and led businesses in the UK and overseas. Today he helps leaders accelerate their evolution through insights into their inner dynamics of thought, feeling and perception.