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Webinar report: Mastering difficult conversations

‘If you don’t take action, don’t expect change’ Jacqueline Heron

The job that doesn’t involve having difficult conversations hasn’t been invented yet. If it ever is, the chances of finding it on the in-house lawyer’s career ladder are slim.

So it was a great subject to tackle in The RPC Female Insurance Group (FIG) December 2021 webinar.   Presenting the webinar, Mastering difficult conversations, was Jacqueline Heron, who regular delegates will remember from the FIG webinar, Imposter Syndrome, in December 2020.

Jacqueline is a highly experienced executive career and resilience coach. A European Mentoring and Coaching Council accredited practitioner, Jacqueline specialises in coaching executives through stress, people management, change management performance management, succession planning and other challenging aspects of senior roles.

What’s the problem?

Anyone who has ever woken up at 3.00am to rehearse their handling of a tricky confrontation – only for their eloquence to abandon them when the moment arrives – will know how uphill confrontation can be.

The prospect of an awkward conversation can induce feelings of fear, apprehension and anxiety. All of which are quite normal – we’re human, after all. For many of us, the default response is to delay the conversation for as long as possible in the hope that the need for it will go away.

It rarely happens. Sooner or later that chat must take place. Because if you don’t take action, you can’t expect change to happen.
The good news is, you can take action, starting with thorough preparation. 

Preparing for a difficult conversation

Preparing will take time, but it’s worth it. The more thought you put into planning your conversation, the less difficult it will be. Ask yourself:

  • Why must I have this conversation? Perhaps you need to change something, maybe something has happened that shouldn’t have. Or maybe something that should have happened, hasn’t and you need to find out why. Whatever your reason for holding the conversation, it’s also a good idea at this point to be clear about the role – if any – you played in it coming about;
  • What’s my ideal outcome? Once you’ve defined the goal of the conversation, you can begin to plan your approach accordingly. This will also help you evaluate how well it went afterwards;
  • What assumptions am I making? You may feel that someone is out to press your buttons or wind you up. Test those assumptions by putting yourself in the other person’s shoes for a moment. If you think you may have jumped to a conclusion, bear that in mind when you have the conversation. Similarly, recognise that judgments and suspicions are unlikely to be helpful and that it’s safer to deal with facts only; and
  • What mindset am I going into the conversation with? If you’re telling yourself it’ll go badly, it probably will. A positive mindset, on the other hand, can have the opposite effect. Get into the right mindset by labelling your emotions, taking some deep breaths and reminding yourself that calm is your superpower.

Tip: a great way to find calm before a difficult conversation is to play it out with a friend, family member or uninvolved colleague beforehand. 

Making a difficult conversation easier: the 5 stages

Like many daunting prospects, a difficult conversation can be broken down into manageable portions. As you plan yours, work through these five stages:

One: keep it simple and focused. Get straight to the point without skirting the issue. Avoid digging up irrelevant history and, as mentioned about, stick to the facts. That way, you’ll minimise the chances of triggering a defensive reaction in the other person. Keep your choice of words, tone of voice and body language positive.

Two: be curious. Remember, you’ve had the luxury of preparing for the conversation, whereas the other person is hearing what you have to say for the first time. Be patient and give them time to respond. They may come out with a knee jerk reaction, but don’t take this personally. Instead, use your listening skills to work out where they’re coming from.

Three: acknowledge what you’ve heard. Even if you disagree with the other person, make a point of letting them know that you’ve taken in what they’ve said. One of the keys to getting what you want from a difficult conversation is to show empathy, not steamroller your agenda through.

Four: have your say. Having listened and shown respect in the previous stages of the conversation, give your response clearly and calmly. Take your time. Speaking slowly will give you two advantages here. Firstly, it’ll convey the impression of calm and self-control while, secondly, buying you more time to think. Take this opportunity to clarify your perspective and communicate your position.

Five: agree next steps. Summarise the conversation and agree between you what is deliverable by both (or more) parties. Clear up any misunderstandings and look for win-win opportunities. Aim to end the conversation with a sense that together, you’ve covered all you need to discuss, agreed a way forward and are ready to move on.

About FIG

RPC's Female Insurance Group works to promote gender equality in the workplace. The network, which has over 1,000 members, aims to put women from across the insurance industry in touch with one another for support and professional development. FIG provides opportunities for members to learn, develop and hone their skills on a wide range of topics, including stress in the workplace, keeping career fit and mentoring skills.

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