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Tips For Having Difficult Conversations

In the workplace, there are often times when we are required to have difficult conversations with our teams, people, employers, leaders, and even stakeholders.

These conversations could surround lay-offs, feedback, conflict resolution, and performance. But they can also include more personal conversations, such as those that address health issues, such as menopause, mental health, well-being, challenges women face in the workplace, and diversity and inclusion.

Although these conversations are essential for many reasons, research shows that approximately 57% of leaders prefer to avoid conversations that could result in conflict. But why?

As leaders, we want to ensure that our people are always happy. We also want to avoid causing additional distress or risk losing our top talent. For some of us, having conversations surrounding some topics, take menopause for example, can feel difficult if we aren’t well-informed or if we don’t have any experience – be it personal or professional.

If you can resonate with the above, we share some tips for having difficult conversations to support you in this blog.

Why Do We Fear Having Difficult Conversations?

At The Leadership Coaches, we hear a lot of leaders saying that they worry about having difficult conversations with their people. However, the reasons behind this significantly differ from person to person.

Sometimes, leaders worry about having challenging conversations due to not knowing how. They may not know how to approach the conversation, and some may feel unsure of what terminology to use. This is especially true if they need more training or experience.

In addition, many of us worry about upsetting our people. After all, we want to create a workplace culture where everyone feels happy and works in harmony. In this instance, having difficult conversations can be stressful and anxiety-inducing.

Furthermore, for some of us, our lived experience of difficult conversations might be associated with past trauma and situations with which we don’t feel able to cope.

Other reasons that we fear having difficult conversations in the workplace include the following:

  • Worrying that we won’t be liked by others within the organisation.

  • Being afraid of the consequences that come hand-in-hand with saying it how it is.

  • Not knowing how to give feedback.

  • Being unsure of how to follow conversations up with support to evolve the challenging area.

  • Concern surrounding our reputations as leaders and managers.

  • Worrying about conflict and how to navigate it.

  • Not knowing what’s right or wrong to say but being afraid to ask.

Tips For Having Difficult Conversations At Work

While it can be concerning to engage in challenging conversations, it is crucial to address them rather than avoiding the problem and hoping it will disappear.

Failure to have these conversations can result in losing valuable employees and creating a hostile work environment. Yet, by engaging in open dialogues – no matter how difficult – we can effectively resolve conflicts, tackle problems, foster personal and professional growth, and build stronger trust with our team members.

Man sharing tips for having difficult conversations at work

If you’ve found yourself requiring additional support in having difficult conversations at work, we share some tips below in no particular order.

Seek Feedback From Peers and Employees

For leaders who aren’t yet experienced in having difficult conversations, seeking feedback from peers and employees can be a fantastic starting point. Often, we’re our own worst critics, and we analyse whether we’ve said the right or wrong thing.

When we ask our peers – such as our managers and leaders – for feedback, they can offer different perspectives and provide constructive criticism that we can learn from and take on board.

Likewise, asking our people – our employees – for feedback through anonymous surveys enables us to understand how they’ve benefitted from the support we’ve offered and what they’d like to see us do differently in the future.

Expand Your Knowledge

Think about the last time you had a difficult conversation with a team member. Now think about what made that particular conversation difficult.

Was it a lack of knowledge and being unsure of what solutions to offer? Or was it something else?

As leaders, we aren’t expected to know everything. But when an employee approaches us, or we need to approach an employee regarding a specific topic, expanding our knowledge can make the conversation much easier.

Let’s take supporting neurodiversity in the workplace as an example.

As a leader, you may not have previously been required to support a neurodiverse individual in the workplace. For this reason, you may find conversations with them about their performance or any adjustments you need to make in the workplace to accommodate them challenging. You may worry about using the wrong terminology when speaking with them. Likewise, you might worry that you’ll upset them or seem confrontational when talking to them about their personal needs.

But by expanding your knowledge on neurodiversity and familiarising yourself with autism, ADHD, dyslexia, Tourette’s, and mental health, for example, having difficult conversations might not seem as challenging as you thought.

When it comes to expanding your knowledge, there are various things you could do. We share some ideas below:

  • Complete continued professional development.

  • Enrol in short courses.

  • Ask your peers for guidance.

  • Read books that explore neurodiversity in the workplace.

  • Attend seminars or lectures for additional insight.

Develop Your Emotional Intelligence

Emotional intelligence is an important leadership skill for several reasons. It supports us in understanding our own emotions and how they impact our behaviour. But more importantly, emotional intelligence enables us to develop better interpersonal relationships, display empathy, and solve problems.

Emotional intelligence helps us navigate sensitive topics and conflicts respectfully when having difficult conversations. It also allows us to remain calm, think more clearly, make rational decisions, and better understand other people’s perspectives.

Emotional intelligence can help us create trust and openness in the workplace. When we develop trust and openness at work, we can solve problems with the vision in mind and limit negative self-talk that may lead to worrying that we won’t be liked by others within the organisation.

Actively Listen

Difficult conversations are often a two-way street. Conversations can be challenging for leaders, but they can be equally tough for our people. For some individuals, having conversations surrounding their personal needs can be just as anxiety-inducing as it can be for leaders.

Man actively listening in difficult conversation

Most of the time, when we’re conversing, we listen to respond. But really, we need to listen to understand. After all, by understanding, we can alter our approach to difficult conversations in the future and learn from them.

When engaging in difficult conversations, we must actively listen and try to understand how the other person is feeling. Doing so enables us to learn how to follow conversations up with support to evolve the challenging area.

Likewise, actively listening allows us to consider each individual's thoughts, concerns, and worries. This is especially true when it comes to navigating workplace conflict.

Consider Whether Difficulty in Having Conversations Is Internally or Externally Driven

Do you always feel anxious about what the conversation might be like? Do you start ruminating a while before the conversation is going to happen? Are you fraught with fear about how the conversation will go?

Take a breath, and ask yourself, what is driving this? Is it my thinking? Is it because I know the other person will likely react and behave a certain way?

Knowing what’s driving the fear is key to managing your response. In neuroscience, our brains are triggered to fear the unknown, and the stories you tell yourself are unknown. Yet, the brain also has this wonderful system of neurons that connect to create neural pathways. Our neural pathways develop through use and imagination, so a visualisation activity with a coach can be very helpful.

Try this: consider the resistance you are anticipating from the other person. How can you handle this? What thinking, behaviour, body language and tone of voice are required in such a situation? Practice this out loud. Knowing that you can handle a difficult situation calms the nerves and makes the situation less daunting.

Consider Leadership Coaching

Finally, in our tips for having difficult conversations are considering leadership coaching. Many leaders find leadership coaching beneficial, particularly one–to–one and executive coaching.

Not only can working with a leadership coach offer a fresh perspective on some of the challenges workplaces and leaders face but they’re often equipped with their own lived experience in leadership roles and can share their expertise with you.

Executive leadership coaching conversation

Furthermore, leadership coaching can support you in developing skills like emotional intelligence, empathy, and active listening. Coaches can also help you gain self-awareness of your strengths and weaknesses regarding your communication style.

More importantly, working with a leadership coach can help you identify and manage any emotions or personal biases that may influence your approach to difficult conversations.

To Conclude

Having difficult conversations at work can be challenging. But by developing your skills and expanding your knowledge, topics, including those discussed throughout this blog, can seem more manageable.

If you want to take advantage of leadership coaching to support your leadership skills, we’re here to support you. At The Leadership Coaches, our team of experienced coaches have a wealth of experience working within organisations and with people.

To find out more about our team, our coaching services, and how we can assist you, contact us today.


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