Having difficult conversations at work frequently comes up in my therapeutic work. These conversations are important, yet they can often feel challenging and uncomfortable. Here are some common scenarios that people face:

  • Raising a problem with your boss who repeatedly cancels your one-to-ones or allocates you too much work;
  • Speaking to your colleague about tension between you that is affecting your work together;
  • When in a leadership role, raising performance issues with a member of your team;
  • Informing a fellow manager that you disagree with how they spoke to someone in your team.

If these scenarios resonate with you, you may recall the range of tricky emotions and thoughts they come with. Feelings of anxiety, shame, frustration and fear of coming across badly are common. We may experience changes in our body, such as our heart beating faster, sweating, shallow breathing, holding our breath, our mind whirring, and tension in different muscle groups. All this can influence how we face the problem, and whether or not we become overwhelmed and/or freeze up.

Many people I speak to fear that these ‘negative’ experiences will cause them to lose their composure. Many also fear being seen in this state and worry that they will be judged as incompetent or unlikeable. Unfortunately, as a result, I see many people avoid difficult conversations altogether; they push themselves to keep going, whilst sacrificing their needs and suffering in silence.

It does not have to be this way, and this article aims to give you a glimpse of how developing a wiser and more open relationship with your emotions can enable you to have these important conversations rather than be held back by your fears.

1. Calling it out as it is

The thing is that difficult conversations are just that. Difficult. So, acknowledging that we are likely to feel vulnerable and that it may be messy can help us approach the situation without putting too much pressure on ourselves to feel overly positive and for it to go perfectly well. In practice, this means being honest with ourselves and calling it out as it is: ‘Of course this feels difficult; it’s because I am going into a stressful situation. It is hard for many people, I’m not alone with this’.

2. Connecting with your values

Conversations that are challenging may be some of the most important conversations to have. So, we need to be clear on why it matters to have them. Will keeping quiet serve us or cause further harm to ourselves, the team and organisation? What are the values that move us towards doing something hard? It may be a combination of values such as self-care, respect, compassion, honesty, assertiveness, challenge, growth, and connection. Our values still exist in uncomfortable moments and we can use them as fuel to drive us to do what is helpful, even though this may be a hard thing to do. Once you are clear on why having a difficult conversation is important, it’s about deciding whether you are willing to tolerate the discomfort in service of your values.

3. Allowing room for uncomfortable emotions

To be able to have tough conversations we need to get comfortable with the discomfort. This means accepting that uncomfortable emotions are likely to show up for us as well as for the other person, and we cannot control this. Many people have internalised beliefs that negative emotions are bad, overwhelming, or signs of weakness, and therefore invest a lot of energy in trying to prevent, get rid of or hide them.

What if we changed our attitude towards our emotions? Yes, they are uncomfortable, but they are not the problem. The problem is the situation at work which needs addressing. Our emotions are doing what they were designed to do; warning us of potential social threats and activating us to prevent them from happening.

Accepting that emotions will be triggered does not necessarily mean that we succumb to them without thinking. We can use our wisdom to remember that our alarm system may be over-sensitive to danger that may not never occur. We cannot control or predict the outcome of difficult conversations, though we can take an active stance in regulating our emotions so that we are not overly reactive in the moment.

Allowing room for negative emotions means learning to feel what we feel even if it is uncomfortable. It means learning to tolerate the uncertainty of not knowing how the conversation will go and trying anyway. Showing vulnerability is not bad or weak; it means that we are courageous enough to show up authentically in the moment.

4. Being with another person’s emotions

Another important angle to understand is how you feel and react when someone expresses their painful emotions or gives you feedback that is hard to hear. It may cause our alarm bells to go off, especially if we feel blamed, caught out, misunderstood, angry or ashamed. It may trigger underlying core beliefs we hold about ourselves and others, such as that we are not good enough, not liked or accepted, or that we are a burden. We may automatically jump into defending ourselves, offering solutions, being critical of ourselves or the other person, speaking over them, or doing the opposite and going quiet. This is where our self-awareness becomes a superpower in noticing that this is happening and purposely taking a breath to slow down our mind and body ever so slightly. This can help us tune back into what the other person is saying with openness and respect, whilst also remaining connected with our perspective and what we want to convey.

5. Draw on your resources

Doing all this is not easy in the moment, and therefore drawing on our resources can equip us to approach the situation and cope as best as we can. Taking some time to reflect ahead of the conversation can enable us to become aware of what comments may trigger painful emotions in us. We can anticipate our automatic reactions and styles of coping and think about how we would like to try to respond instead. It can also help to remember our values and strengths and to trust our ability to cope and problem solve if things get messy. Protecting some space afterwards to process what happened (on our own or with people we trust) can help us work through leftover emotions and thoughts.

6. Compassion

For those who have read my other articles, it is no surprise that compassion ties this article together too. Compassion towards others and ourselves is an invaluable foundation which can support us to express ourselves and to listen in difficult conversations. It enables us to approach something hard with a genuine intention to help and not cause harm. Wisdom is a core quality of compassion which reminds us to see the other person as a fellow human being who is trying and dealing with their own thoughts and emotions. A compassionate stance helps us to understand that even with the best intentions, we all become preoccupied with painful thoughts and emotions, and fall into old habits of reactivity. By courageously and gently turning towards our pain we have a chance to make sense of what is triggered in us, to attend to our needs, and identify learning points we can walk away with for that next conversation at work.


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