Holding the tough conversation - a life skill of real import

Learn how to hold tough conversations and you'll have a life skill that will support you at work, at home and with friends.

Go to the profile of Judith Leary Joyce
Jun 12, 2018
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Life requires that we face up to tough conversations on a regular basis. It may be at home with the family , with friends or at work with direct reports / colleagues. Getting through it with respect and dignity intact on both sides is a skill to be cultivated. It will stand you in good stead, improve your ability to manage people and gain you a reputation for being sincere and honest. 

 How to hold a courageous conversation

 There are numerous reasons for holding a courageous conversation. If a friend is in difficulty and needs some tough love; if your partner or child behaves in a way that’s unacceptable to you; or if something is harming the business and you can see how to help, then speaking out is positive. If you’re a manager, courageous conversation is a skill you must develop, otherwise you’ll have no chance of developing talent and delivering strong results through your team. All the Inspirational Managers I know are really good at this and it is part of their positive reputation. 

 So how do you go about it? 

 In preparation:

 Consider the person on the receiving end- Reflectors will need time to process, so outline the situation and catch up again the next day.. Others may need to keep talking and put their side of the story there and then, so make sure you leave enough time.

Decide what you’re looking for- think through the outcome you’re looking for, the messages you want to give, the questions that may come up, what to do if the outcome isn’t as you hope. Be as fully prepared as possible. 

 Be ready with examples- if the conversation is about behaviour, give examples that will help the person understand their impact. Work out how you can do this without humiliating the other person. 

 Find a private place - this can be difficult in a modern office with glass walls. If you have no other option, arrange the seating so the person you’re talking to has their back to the glass. This provides a modicum of privacy. Going out to a coffee shop can also be a possibility. Make your decision in the light of the subject of conversation and how the person is likely to react. One way to decide is to think about what you would like if you were on the receiving end. 

Get into the right frame of mind - give yourself a moment beforehand to settle and adjust your mindset. These conversations are not about punishment or battle. To be successful, they need good intention towards the other person and a desire to help. When people have all the information they have more freedom to act, so this is about honesty and support to change and improve. 

Guidelines for holding a tough conversation

Give advance notice- let the other person know that you need to speak and give them warning of the content. The day before will be enough – you don’t want to worry the person unduly. 

Set the scene– outline the core of your message clearly and succinctly. If you have examples, provide them but without masses of preamble. The purpose of this stage is to inform about the issues, not to go into great detail. 

Stop and listen – give the other person time to speak. They’ll want to justify, explain or defend (depending on the content). If you skip this stage, they won’t hear anything else you have to say. You’ll understand more of what they need if you’ve put yourself in their position as part of your preparation. It will enable you to be empathic, even if you don’t agree. 

Use active listening – ask open questions to explore the issue, reflect back to check you’ve understood what is being said and summarise what you’ve heard. It’s rare for people to have a ‘good listening to’ and it will make a big difference to how the other person feels about this experience.

 Respond to what you’ve heard– once you’ve fully understood the other point of view, respond honestly. If there is anything you can agree with, let them know and step back. Tell them where you understand, what help you will give, what questions you still have. 

 Keep going until you are both clear– go through this process as often as you both need ie: putting your point of view, then listening fully to the response. This isn’t about just repeating yourself, it’s about building understanding and, eventually, agreement on the way forward. You may need to return to the discussion if the other person needs time to think or gather themselves. 

 Make a statement about the outcome – summarise the outcome eg: this is where we have got to; we will continue the discussion on ….; I will need this from you in the future; I agree to help in this specific way.  

 Tough conversations can easily leave people feeling badly about themselves or something they have done. If they can come out of it feeling heard, understood and with a way forward, then you’ll have an advocate for a long time to come. Being respectful of the other doesn’t require you to step down (unless appropriate). It is quite possible to come out with the tough decision andpositive feelings about the event. 


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Go to the profile of Judith Leary Joyce

Judith Leary Joyce

Great Companies Consulting

In 1996 I made the shift into business, taking my knowledge of Gestalt Psychology into the realm of Executive Coaching, Facilitation and Leadership/ Management Development. In 2001 I worked on the 100 Best Companies to Work For list, then went on to write my first book Becoming an Employer of Choice which was followed by Inspirational Manager and The Psychology of Success. Since then I have worked with organisations across the sectors from large corporates through to young start ups, public sector and charities. Now it’s time to help you have a love affair with your work and get exactly what you want from your career. To find out more about my work and coaching go to www.judithlearyjoyce.com

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