Having difficult conversations with leaders at work
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Seven tips for having difficult conversations at work

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Having difficult conversations at work with leaders can be uncomfortable. The earlier we talk about issues, the easier it is to come to a place of understanding if done properly. Neuroscientist and C-suite mentor Dr Lynda Shaw shares seven practical tips for having challenging conversations.

11th Jul 2023

With only 46% of employees agreeing that their organisation has effective procedures in place for resolving interpersonal conflict, it can be largely up to individuals to find ways to overcome problems at work. 

Individuals who feel there is a lack of psychological safety at work are unlikely to feel comfortable speaking up or expressing their opinions. 

It can also be tricky to raise concerns about leaders to HR who also might fear for their own positions meaning they struggle to find a consensus and activate change.  

Here are seven tips on how to have difficult conversations with leaders.

1. Check if the conversation is needed

Ask yourself if you need to have this conversation, what appropriate outcome you want and why you are avoiding it.

Evaluate your reasons and accept that how they see the situation may be different to how you do.  

Be cognisant that the brain doesn’t do gaps so it tries to find information to fill the holes by choosing information that suits, according to your biases and perception.  

Have a goal in mind. Be clear and specific in what you want to accomplish going into the conversation to keep you on track.  

Plan a little, take a deep breath and present yourself in a calm manner.

When you have an anticipated good outcome then dopamine will be fired, your brain chemicals will work for you, not against you and you are likely to perform better and have a better demeanour

2. Assume it is going to be a positive meeting where you can work together to fix a problem

Go prepared and describe the changes you would like to suggest, rather than simply complaining about the problem. Leaders love to hear of solutions. 

Aim to have reached an amicable conclusion by the end of the meeting. 

When you have an anticipated good outcome then dopamine will be fired, your brain chemicals will work for you, not against you and you are likely to perform better and have a better demeanour.   

3. Go into a difficult conversation feeling in control of your emotions

Maintaining a calm and composed demeanour can help maintain a productive dialogue and keep things professional. 

Try to park any emotionally charged feelings. If you feel uncertain or anxious, start by acknowledging you may need to understand better. 

Communicate clearly and use concrete examples so there is less room for miscommunication or misinterpretation. Explain how the situation makes you feel

4. Communicate and listen

Communicate clearly and use concrete examples so there is less room for miscommunication or misinterpretation. Explain how the situation makes you feel. 

Allow space so you can check with the other party that you have all the information and be open to their perspective and show empathy and compassion. 

Listening is the key to solving issues and enabling a healthy, productive conversation. 

Take some time out from making your points to hear the response and understand it instead of thinking what you want to say next. 

Ask questions to further your understanding of each other’s issues. Aim for non-blame communication.

5. Accept responsibility when appropriate

Equally, accept criticism and acknowledge your own mistakes, as interpersonal problems have interactional causes. 

Good leaders will know that ultimately an inability to effectively manage conflict or talk about issues will have repercussions on growth, communication, productivity, creativity, talent turnover and work culture

6. Don’t set up win / lose stakes

Each of you will have your own sense of personal reality. It may be helpful to view the leader as a colleague who has similar goals as opposed to an opponent. 

Work together strategically to pool information to get a better picture and opt not to choose conflict or the need for victory.

7. Know that it is possible to have difficult conversations that are supportive, productive, and meaningful

After all, effective leadership involves establishing the necessary conditions for others to bring about transformation. 

Good leaders will know that ultimately an inability to effectively manage conflict or talk about issues will have repercussions on growth, communication, productivity, creativity, talent turnover and work culture. 

Fixing it takes courage and perseverance to do the right thing so creating the right conditions to allow people to speak up and be heard is vital.

 

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