How to win at difficult conversations - 35 Thousand

How to win at difficult conversations

Posted by Susannah Taylor on

For many people, (especially those who are non-confrontational and introverted), the idea of having a difficult conversation with a boss, employee or a colleague is positively terrifying. Yet the tsunami of the Corona-crisis will undoubtedly leave many companies in chaos over the coming year and there are going to be many difficult conversations to be had.

You may be an employee and wish to change the way you work for example, you may feel you aren’t getting paid enough (are you doing the work of two people whilst they are furloughed?), or you may have a new desire to work partly from home having done so successfully for the past three months. On the other hand you might be a boss and have to make the very stressful decision of restructuring your team.

Whichever situation you find yourself in, at some point over the coming months you may have sleepless nights about a necessary but awkward discussion that you can’t avoid. We spoke to the founder of 35 Thousand and top executive business coach Misty Reich to find out how to tackle these conversations with confidence.

SHIFT YOUR MINDSET – How to move your mind from a state of fear to a state of calm confidence

Know that everyone finds these conversations difficult

When we have something stressful to discuss, we can often berate ourselves over the fact that we are finding it difficult and can even question how capable we are. But according to Misty, nobody finds these situations easy. “Unless you are one of the miniscule percentage of people who don’t have any empathy, you should know that these conversations are difficult for almost everyone. They just show that you have a heart and you have empathy which is a good thing because it means you connect with people.”

Once you recognise that you are not alone in this, you may stop layering fear on top of the important conversation you need to have.

Preparation is key

It’s probably true to say that most of us spend more time getting ready for a Zoom party than we do preparing for an important work conversation. However, it’s just as important to prepare for these chats as it is an important interview. “It’s a real skill and it takes proper preparation,” says Misty. (See the below ‘toolkit’ for ways to prepare)

Question that tape playing in your head

Misty explains that we can all have ingrained tapes in our head that replay over and over because of past experiences. “Some people for example, may have grown up believing that it’s not right to highlight issues,” she says, “Whilst others fear that the person they are speaking to won’t like them, or perhaps they are scared at the thought of upsetting others.” Many people she coaches feel they are not qualified to be having the conversation they need to have for example.

Misty explains that it’s a good idea to question these negative beliefs, and to ask if they are in fact valid. She suggests pausing also to ask yourself why this conversation is important to you and what is triggering your beliefs over it. Through this process you can then reframe your thinking to something much more positive.

Shift your mind from a place of negativity

If you have to deliver bad news to a colleague then it’s important that you shift your thinking away from the negative. “You have to instead speak from a place of love and positive intention,” says Misty. She suggests that instead of telling yourself that you are doing this ‘to them’, to remind yourself that you are doing it for a bigger purpose/ for your integrity/ to improve a working relationship.

This also works if you have requested a conversation with your boss – ask yourself the reasons why you want this conversation and let that good reason drive your attitude in your meeting.

YOUR TOOLKIT – Practical tips for conversation confidence

Get a coach or counsellor

Firstly Misty says if the conversation is really important, then not to think twice about asking a coach or a counsellor for advice. Often two heads are better than one and a fresh perspective can really help to shape your own.

If in doubt, write it out

Many of us assume that most people are good at having difficult conversations. That’s not the case, but the people who are best at it have often prepared in advance. Misty suggests journaling out the conversation and writing down what you want to say. ‘If you are really worried about how it’s going to unfold,” she says, “Play through the conversation. If the conversation took one direction, how would you respond, and if it took another, how you might respond to that?” This can help you to feel prepared for anything that is thrown at you, plus “The act of doing this takes some of the hot air out of the balloon in your head” says Misty.

Roleplay the conversation

If it helps, then find someone that you can trust and go through the conversation with them.


Misty’s tips on diplomatic phrases to use
For when you will be having a two-way dialogue…

If Misty is going into a difficult discussion and it’s going to be a two-way dialogue, she will start with “I want to share something with you that’s happening for me. I want to then hear what’s happening for you and discuss a good way to move forward.” By saying this, you are implying that somehow you can move forward together, and that you want to hear their side of the story. This will also prevent the other party from feeling immediately defensive.

If you have to make someone redundant…

‘There are some discussions,” says Misty, “That are not a two-way conversation, such as a job elimination.” If this is the case, then Misty starts off as follows: “I want to share something with you that’s happening and a decision I’ve had to make as a result. I then want to talk through what that means for you.”

By saying ‘I want to share something that’s happening’ you are taking the conversation away from being their fault, but by saying that it’s a ‘decision’, this implies that there will be no back and forth.

For diplomatic negotiation…

If you are in a situation where you think that your colleague or your team can improve on something then Misty uses the following equation: Appreciate/ More effective

This means that you can frame up your wording so that you tell your team that you appreciate what they are doing but then go on to say how we could be more effective.

This also works if you are negotiating something with someone more senior. For example:

“I just want to say that I hugely appreciate how supportive you’ve been to me, but I feel like going forward, my roll could be even more very effective if…”

Specific conversation advice

When you are negotiating money…

It’s not the best idea to bulldoze into a meeting telling your boss that you deserve more money with no justification of why. Misty says the best way of looking at this conversation is to put yourself in the company’s shoes and ask yourself how they might see you. Ask yourself how valuable are you to them? Then you will be in a position to say “Here’s why I think this makes sense for the company, you and me…”

Misty also thinks it’s a great idea to think creatively about whether there’s anything else you can take on and can you offer as part of the discussion. For example, “I’m seeing that my pay isn’t what I want it to be and I have brainstormed some options and thought of some things I can do in exchange for that.”

If you fear not being able to get your point across

If you are terrified of an important conversation because you are worried about getting tongue-tied or not getting your point across properly, then you may be an introverted thinker. Misty says that for these people, the preparation is absolutely non-negotiable. “Give yourself the chance to practise,” she says. This means making notes, going through the conversations as above and really mapping out the key points you want to say.

If you are scared of your boss

We’ve all been there with an intimidating boss who makes you feel you don’t know what you’re talking about. Here Misty suggests doing some journaling about that boss and what makes them feel comfortable and confident. It’s important to remember that despite their important role, they are only human – just like you – and in that respect you are perfectly equal.

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