Do you dread having difficult conversations at work?

Having difficult conversations at work is a huge source of tension for many employees, regardless of how senior they are or if they are an experienced manager. Somehow, debating difficult topics – where friction is likely to occur – at work is much more confronting and daunting to many of us than in our personal lives.

Navigating a difficult conversation is a skill that needs to be practised like all other skills. The Covid-19 pandemic has highlighted just how important effective communication is in the workplace, with it now becoming one of the most sought-after skills. In August 2020, The Chartered Management Institute polled nearly 2,300 employees and found that effective communication had become one of the most valued qualities for managers in the UK and that 95% of those surveyed said communicating clearly is the most important trait right now.

A lack of training may be the reason behind our unsettling feelings towards difficult conversations at work. Natasha Chatur, Work Happiness Coach, says that employers and managers simply “don’t have coping strategies for having difficult conversations” and this results in high stress and anxiety levels. “In a 2015 research report, the Chartered Management Institute identified that 80% of managers said that they have never had any training to tackle difficult conversations.” This is surprising considering that most of us will have a difficult conversation at work once per month or more and that team leaders spend lots of their work time resolving conflict.

It goes beyond asking your boss for a pay rise. There are many examples of when these commonly dreaded situations can occur, such as:

  • Performance reviews (particularly poor performance / criticism)
  • Firing a team member or making them redundant
  • Dealing with a micro-managing boss
  • Colleagues going for the same promotion
  • Saying no to someone’s idea
  • Asking for more support/resources
  • Delivering bad news/results on a project
  • Talking with frustrated clients/customers

“The types of conversations can vary so it is worth spending time on learning how to be more effective at communication – then, you can apply those strategies in different contexts and have better outcomes,” says Natasha.

Emma Wainer is a Speaking Coach that works with executives, training them to become more confident speakers in situations aforementioned in the list above. She says that preparation before these interactions is absolutely key; “if you can take the time to work out your thoughts and organise them, and also get in control of your body and your breath, then you will start to build your own confidence towards tackling these pesky conversations.

Of course, this is great when you know that difficult conversation is coming, but what happens when you’re caught off guard by a manager or colleague?

Emma says you must do one very quick thing for your mind and one very quick thing for your body. Drawing on mindfulness practice, Emma encourages her clients to always ask “What state am I going to choose to be in for this conversation?” Select the state you want to be in and then channel that.

“Will you be confident? Will you be empathetic? Will you be inquisitive? Choose your state and then quickly focus on your body – take a deep breath in and subtly stretch. Open your chest and shoulders to open out your posture in order to be present and in control.”

How to overcome the difficult conversation fears

Leading from the above, the best things you can do are to make time for preparation (and practice) and seek out some professional training – whether that’s internally or externally. This is especially important in job roles where there is often mediation or conflict resolution required, but is arguably essential for anyone that wants to progress in their careers.

Avoidance is not the answer; although in the short-term you are saving yourself from a potentially painful experience, in the long-term you are creating a self-sabotaging (and team-sabotaging!) habit where you are unable to share negative feedback, stand up for your ideas and beliefs or ask for what you want or deserve.

Experts say that it’s best to take a step back and not take things personally in the workplace. Although personal vendettas do crop up from time to time, make sure your meetings and challenging conversations are objective and backed up with rationale – this is where, again, preparation is key.

Grace Ong, Women’s Leadership Coach, spoke about this recently in our Q&A session, when discussing how to increase confidence. If you have the facts and the evidence, you’re more likely to succeed in your ideal outcome, rather than simply using emotion.

Emma and Natasha run joint workshops on this exact topic, combining their expertise as coaches to equip employees with the toolbox they need to feel the fear and do it anyway. Their top tips are to:

  • Prepare your mind
  • Prepare your body
  • Visualise the scenario and how you will show up

They have both trained Yellow Eve members in the past with great feedback (as a member you can watch their training replays here). Join their next workshop on Thursday 25th February 1.30-2.30pm and please let them know that you found it through us so we can help them in future.

We would be interested in hearing whether this is a topic you struggle with, and whether a workshop for members would be valuable! Let us know at

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