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Whether it’s a colleague, client, team member or boss, having difficult conversations in the workplace can be nerve-wrecking. Individuals may be well-versed with voicing their concerns or frustrations to family or friends, but workplace dynamics can be a bit trickier to structure a healthy conversation, especially when emotions are involved.

Typically, difficult conversations at work are prolonged, delayed or avoided altogether for a multitude of reasons. Issues arising in the workplace could be numerous, ranging from a promised promotion that never arrived or a due raise, based on all the hard work being put in. The issue could also be aggressive, discriminatory or disrespectful behavior from a colleague or manager, or even a team member not performing based on the set metrics. Whatever the situation may be, if frustration is involved and it is having an impact on performance, office culture or wellbeing at work, bring it up.

Here are tips and tools to prepare for the ‘big talk’.

Schedule time

Difficult conversations need to be scheduled. Imagine receiving negative feedback from a boss as they pass through the office, or facing a colleague over Whatsapp. Schedule an uninterrupted meeting that suits both parties, to give the topic sufficient time to find solutions or action plans.

Delivery options 

The point to be raised may be very sensitive, there may be a backlash or the other party may also have concerns to raise. With the more informal channels of communication at hand, one may be tempted to resort to texting or emailing. Assess the gravity of the conversation and accordingly decide on the best medium. If the matter has been escalating by email or words are being misinterpreted, pick up the phone or schedule a meeting. Reading people’s emotions and body language could give necessary cues on how to guide the conversation.


Every conversation needs to be prepared for… more so the difficult ones. Structure the conversation and jot down all the points that need to be raised. Typically, conversations should have one or two main messages, with supporting points to reaffirm the points. Also, expect potential questions or different types of responses, and prepare a strategy for each. Consult a friend or family member – is there a blind spot that has been missed? Role playing difficult conversations is also advisable. Choose someone that challenges opinions and viewpoints, and enhance the delivery of the messages based on their feedback.

Direct, open and honest

Depending on the context of the conversation, being direct and getting straight to the point is best. Raise the point of concern, frustration or issue directly, and then allow for time to converse and discuss solutions. By delivering the point in a clear and concise manner, there is no room left for confusion or matters getting lost in the details.

Keep emotions at bay

When it is finally conversation time, the delivery of the words and points needs to be clear and rational. Even body language needs to be factored in, showcasing openness and non-defensive facial expressions to ensure the message is well received. Emotions, especially in the workplace, should be kept at bay. Try opening the conversation with an ice-breaker or to showcase that both parties are on the same page with a common goal. This helps bring down the defenses or apprehension of the other party.

Come prepared with solutions

Having constructive conversations means coming with solutions or a proposed action plan to overcome the matter at hand. The person raising the frustration, challenge or issue needs to show that careful thought and consideration have been given, and accordingly suggestions can be provided. Always leave with clear next steps or decisions that need to be made.

Take a break

If the conversation is not going as planned, reconvene. Emotions can get the best of any individual, particularly in difficult situations. If the tension in the room is increasing or tempers are on the rise, calmly suggest taking a break and reconvene when both parties have reflected on the matter at hand.

Leave room for questions

Once the points have been raised, allow time for discussions and questions for both viewpoints to be clearly understood. Difficult conversations, if managed correctly, can lead to new and healthier dynamics. Use the conversation to your advantage, whilst ensuring empathy towards the other party.

Difficult conversations are never easy. With careful planning, scheduling time and remaining rational, they can be constructive, open and honest. Interpersonal communication and emotional intelligence are integral to understand the other party involved. Structure conversations with your audience in mind.

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