Managing Difficult Conversations At Work

As an introvert, there are unfortunately a range of situations that fill my heart with dread. Big crowds, public speaking and having to make small talk are among them, and I’m not a big fan of difficult conversations either. Whether these conversations happen with family members, friends or colleagues, it takes a lot out of me – and at times, can be quite unpleasant. But being a manager has meant I have had to learn how to deal with difficult conversations more effectively – whether it’s highlighting a mistake to a team member, explaining to a director how tight capacity is, or going through team grievances with other managers. Beyond reading useful guides for introverts – I strongly recommend Psych 2 Go’sAn Introvert’s Survival Guide‘ – I’ve been on assertiveness training with our lovely Operations Manager, Cicely, and recently attended a great session on  ”Managing Difficult Conversations” – run by Catherine Brown – professional coach and barrister trainer. Who better than someone who helps those debate, defend and argue in court? I found the session very useful, and therefore, thought this blog may be helpful for others who struggle with this too. Fellow introverts unite – this one is for you. 

How To Have Difficult Conversations At Work

In the session, 10 of us were watching through our laptop screens, as Catherine detailed how to go about these challenging conversations. ‘’To start with…’’ she said, ‘’…have a purpose.’’ It’s hard to tell if you’ll get what you want out of a conversation, if you don’t actually know what you want in the first place. As she explained, ‘’Work out what’s going on, why that is, potential feedback you may get, and then have a clear plan.’’ For example, say a team member accidentally put the wrong client name in a strategy document:

  • What is going on: The team member has made a mistake that the client is not impressed with.
  • Why that is: They didn’t check their work.
  • Any feedback you may get: This will depend on how you go about the conversation. Explaining the mistake they made, and how they must rectify the mistake, is far more useful than yelling at them, or making them feel bad. The team member may take the feedback well, apologise and promise to do better next time. They may shift blame in all directions, and you may need to be more stern. I’ve had to deal with both types of situations, and sometimes, the only way to deal with the latter – is by extending probation, to make them realise how serious the issue they’ve caused actually is.


How about a more positive example? One Catherine gave was a promotion:


When given 2) or 3) as an answer, you need to tell them (ie your manager) what you want and why they should give it to you. You don’t need to go into great detail about how fantastic and amazing you are, you just need to keep it simple, factual and provide supporting evidence. Show client feedback. Support colleague feedback. Keep a record of your hours. Show results where you can. Like a solicitor in court, it’s hard to argue against facts, no matter how slick you may be. But it’s all about timing too. Asking for a promotion when a company isn’t doing so well isn’t likely to go down so well either.


Difficult Conversations Are All About Preparation

Another part of managing difficult conversations is knowing your audience, and tailoring your speech and content accordingly. You can’t assume that everyone knows what you’re talking about – believe me, I’m still not 100% convinced my parents fully understand what I do. When explaining your side in a debate, ensure you use layman’s terms. It’s hard for others to see your side if they can’t comprehend it.

Now, for the tough part. You have to be prepared for a grilling. Anticipate objections so that you can deal with them if they arise. Questions to consider include:

  • What questions are you likely to face in this situation?
  • If you were on the other side of the conversation, what would you want to know, what would you be interested in, and what questions would you ask?
  • How can you show that you recognise their opinions, while still remaining true to yourself, and your own?

By preparing answers to these questions, and practicing them, you’ll find yourself feeling more confident about the task at hand. In the assertiveness training, I learnt that using phrases such as, ‘‘I understand your point…’’ or ‘’I can see where you’re coming from…’’ can help, and it genuinely does. By being reasonable, while still getting your point across, the other side has to listen.

Other helpful tips for managing difficult conversations include:

  • Being the person who knows the most about the topic.
  • Not being repetitive – Points should be strong enough that they shouldn’t need repeating. However, you can show understanding by repeating what the other person has said, to show appreciation for their side.
  • Work on your listening skills – Communication is a two-way process. You may have brilliant points, but so too may the other side.
  • Be brave. 


The last point Catherine touched on was how to deal with negative responses. If the person gets angry or upset – let them get it out, but ensure your safety first. Asking them to take a break and go cool off can help, so that you both have a chance to formulate your thoughts. Being supportive can also go a long way. 

The ideal situation is one where feedback is taken on board, considered and discussed fairly. You may not always get your way with a promotion, but when it comes to giving constructive feedback, mature individuals will learn from their mistakes and try to improve. There’s no shame in being wrong, but as a manager, having these discussions are important for professional development, and team growth.


To find out more about the session, and Catherine’s guidance, click here.

To learn more about Embryo and our range of services, which include content marketing, SEO, Digital PR and social media, I encourage you to get in touch with us today on 0161 327 2635.


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