The why and how of difficult conversations in the workplace

The why and how of difficult conversations in the workplace

We’ve all had to participate in difficult conversations at work – as either the initiator or recipient. Whether it’s addressing performance issues, delivering bad news about a delayed project, or addressing ethical issues, these conversations can be uncomfortable and stressful. However, as a leader or a team member, avoiding difficult conversations can lead to unresolved conflicts, decreased morale, and sometimes, a toxic work culture. In this article, we explore the importance of having difficult conversations and provide some practical steps for handling them effectively.

10-second summary:

  • prepare for the conversation ahead of time, being clear on what your message is but leaving space for things raised by others in the discussion
  • consider the time and place
  • nip things in the bud
  • approach the conversation with empathy, respect, and a willingness to listen and find solutions

Difficult conversations are the ones that can make us feel uncomfortable, either a little or a lot. Even if the thought of having a difficult conversation at work can make you anxious, in the back of your mind you know they are important to have.

Isn’t it better just to keep quiet?

This is a question you may have asked yourself or heard other people say. But while it can seem easier to keep quiet and avoid difficult conversations at work, this approach can sometimes lead to misunderstandings, unaddressed problems, and damaged relationships. By keeping quiet you may feel it is an option to stay safe and avoid fear. But in some cases, avoiding difficult conversations can even lead to a toxic work environment where issues are swept under the rug rather than being resolved. 

By having difficult conversations, you can nip things in the bud and address issues before they become bigger problems. It can even lead to building stronger relationships with your colleagues and develop a foundation of trust.

Even though it may not feel like it at the time, difficult conversations can provide an opportunity for growth and learning, as you gain a better understanding of your colleagues’ perspectives and how to work together more effectively.

How do you go about having difficult conversations at work

The process of having a difficult conversation doesn’t mean just blurting out what’s on your mind, as and when you feel it. It’s important to approach difficult conversations in a thoughtful, respectful and empathetic way. The primary rule in having a difficult conversation is to make sure that taking time to prepare yourself for the conversation.

Here are some steps you can take to approach difficult conversations at work:

1. Learn how to handle fear and step into courage
Speaking the truth doesn’t mean doing it without fear. The people that have difficult conversations do so not because they find them easy, but because the conversation needs to happen.

2. Nip things in the bud
Regular communication can often help contain a small issue and stop it becoming something larger and more difficult to discuss. For example, regular discussions about performance with staff are preferable to withholding issues until an annual performance review which may be at some point in the future and include a range of different topics.

3. Have a clear message and know your goal
Take the time to prepare for the conversation, but don’t stick to a prepared script when you are talking. You want to focus on talking with the person and not talking at them. During your planning for the conversation remember that the most impactful courageous conversation is straightforward and simple.

In his book ‘Think Again’, Adam Grant suggests that as well as being clear on your message, don’t be too rigid and have a series of “dance steps” that you have considered before hand so that depending on what the other person raises, you can take an alternate path if needed.

4. Consider the time and place
A difficult conversation needs the time and the place for both you and the other person to be present, not distracted, and have the time to go into as much detail as is required. Allow a time buffer either side of the meeting so you can prepare and allow extra time for the conversation, if needed.

5. Share thoughtful and honest truths
Sometimes when having a difficult conversation you need to share an uncomfortable truth. When stating your points, consider 3 questions when preparing the conversation.

  • Do you mean it?
  • Can you defend it?
  • Did you say it with empathy?

6. Communicate in a way that elevates not denigrates
If you are delivering difficult feedback be specific and factual about the behaviour and provide examples, remain calm and avoid an accusatory approach.

7. Listen without judgement
Once you have shared your message it’s time for you listen to the other person. Don’t just listen to what’s being said but also what’s not being said. Give them time to share their thoughts, and feelings, about the conversation. They may not be able to clearly articulate their thoughts in the moment, so give them time to process things and arrange another time to discuss things further if required.

What are the benefits of having a difficult conversation

Having a difficult conversation can be challenging, but there are many benefits to facing the issue head-on and having the conversation:

Improved understanding

Difficult conversations can help both parties gain a deeper understanding of the issue at hand and each other’s perspectives. This understanding can help to reduce misunderstandings, build empathy, and increase cooperation.

Strengthened relationships

Addressing difficult issues directly and respectfully can help to build trust and strengthen relationships. When both parties feel heard and understood, they are more likely to work collaboratively and productively in the future.


Difficult conversations can help to identify the root cause of a problem and find effective solutions. By working together to find solutions, both parties can move forward with a clearer understanding of how to avoid similar issues in the future.

Personal growth

Engaging in difficult conversations can be challenging, but it can also help you develop your communication skills, elevate your emotional intelligence, and improve conflict resolution skills. These are all transferrable skills that are highly sought after in all roles and organisations.

Improved workplace culture

When issues are addressed directly and respectfully, it can help to create a more positive and productive work environment. By fostering a culture of open communication and trust, difficult conversations can build a culture where employees trust that issues are addressed and they can feel safe to speak up. 

Difficult conversations are almost never about getting the facts right. They are about conflicting perceptions, interpretations, and values.

Douglas Stone

Difficult conversations can have some downsides

While there are many benefits to having a difficult conversation at work, there can be some downsides as well. Here are a few potential risks to keep in mind:

Damage to relationships

Difficult conversations can be emotionally charged and may lead to strained or damaged relationships between colleagues. It’s important to approach these conversations with sensitivity and respect, and to prioritise maintaining a positive working relationship whenever possible.

Increased stress and anxiety

Having a difficult conversation can be stressful and anxiety-inducing for both parties involved. It’s important to approach these conversations with care, to take breaks as needed, and to seek support from colleagues, mentors, or a counsellor if necessary.

Unintended consequences

Difficult conversations can sometimes have unintended consequences, such as misunderstandings, hurt feelings, or unintended outcomes. It’s important to approach these conversations with clear goals, a plan for follow-up, and a willingness to course-correct if necessary.

Reduced productivity

Difficult conversations can take time and energy away from other important tasks and projects, potentially leading to reduced productivity or missed deadlines. It’s important to plan for these conversations and to communicate with colleagues and managers as needed to ensure that workloads are manageable.


Difficult conversations can sometimes lead to miscommunication or misunderstandings, particularly if there are language or cultural barriers involved. Make sure you approach these conversations with clear communication, active listening, and a willingness to clarify and check for understanding as needed.

While downsides are important to keep in mind, it’s also important to remember that difficult conversations are a valuable tool for growth and positive change. When you approach a difficult conversation with care and intention, you can minimise any potential risks.

So what does a difficult conversation look like?

Difficult workplace conversations can arise in a wide variety of situations. Here are some of the more common examples:

Performance issues

Addressing an employee’s poor performance or behaviour can be a difficult conversation to have. It’s important to approach this conversation with empathy and respect while being clear about expectations and offering constructive feedback.


Giving and receiving feedback can be difficult for many people. Regardless of whether you are giving feedback to a colleague, a person on your team, or management, it’s essential to approach feedback conversations with a growth mindset. Focus on specific behaviours rather than personality traits, and offer constructive suggestions for improvement.


Sometimes, it can be difficult to set and enforce boundaries in the workplace. For example, if a colleague is consistently interrupting or overstepping personal boundaries, it may be necessary to have a difficult conversation to establish clear expectations and boundaries.

Conflict resolution

When two colleagues have a disagreement or conflict, it can be challenging to navigate the conversation. It’s essential to approach the conversation calmly, listen actively to both parties, and work together to find a resolution. You will generally find that conflict can fall into 3 different categories:

  • task-based conflict
  • status-based conflict
  • relationship conflict

Cultural or diversity issues

In today’s diverse workplaces, it’s not uncommon to encounter cultural or diversity issues that require difficult conversations. For example, if a colleague makes a derogatory comment about someone’s race or religion, it’s important to address the issue directly, calmly, and respectfully, while reinforcing the importance of respect and inclusivity in the workplace.

Ethical issues

When ethical issues arise it can be challenging to navigate the conversation. It’s important to approach ethical conversations with honesty, transparency, and respect for all parties involved, while upholding the organisation’s values and policies.

Salary negotiations

Discussing salary, bonuses, or promotions can be uncomfortable regardless of whether your role is as the employee or employer/manager. It’s important to approach these conversations with transparency, research, and a clear understanding of expectations and company policies.

Changes or restructures

Major changes or restructures in the workplace can be unsettling and create anxiety and uncertainty for employees. Having a clear, honest conversation about changes or restructures can help to set expectations and reassure employees that the company is committed to their wellbeing.

Layoffs or terminations

Delivering bad news about layoffs or terminations can be one of the most challenging conversations to have. It’s important to approach these conversations with sensitivity, empathy, and clarity, while providing support and resources to help the affected employees.

Raising hurt feelings

Not everyone processes information in the same way, and what may be “just facts” to one person may cause an emotional response in another. If you have processed a situation in a way where your feelings were hurt or it caused you to be upset, the difficult conversation maybe to speak up about these feelings. By having this conversations you get to clarify your perspective, which the other(s) may have been oblivious to or give them an alternate way of viewing the situation through your eyes.


Remember, difficult conversations are an opportunity to learn, strengthen relationships, and ultimately lead to improved understanding, better problem-solving, and an improved workplace culture. By approaching them with empathy, respect, and a willingness to find solutions, you can turn a potentially challenging situation into a positive experience.

For the past 25+ years Leah's professional roles have been at the axis of business operations, people development and technology. She possesses a wealth of experience in areas of people, process, communication, coaching and counselling.