Tips and Guidance on How to Approach Tough Conversations at Work

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— By Jean O’Neill

Conflict with others is one of the major contributors to stress in the workplace. People leave jobs to get away from people.


Facing difficult or uncomfortable conversations bring a sense of fear and anxiety due to preloaded build-up of perceived judgement or bias and/or existing tensions ahead of the conversation rather than the conversation itself.

I would urge you to reality-check your thinking; fear and worry have a habit of clouding judgement and distorting the facts, especially if there is a surge of emotional charge in play.

If the situation you are putting up with is causing you emotional or mental distress, it is always best to try and seek solutions. What is it costing you if you don’t have the conversation? Focus on the benefits attached to being brave and speaking up, list the potential positive benefits of having the conversation.

The irony of avoiding tough and uncomfortable conversations runs the risk of increasing the strain in peer employee relationships, creating a disconnected and negative energy in your work environment or escalating the problem to bigger proportions.

I encourage people to have the tough conversations and not to shy away from them. Preparing for an uncomfortable conversation can affect the choices
you make during the difficult talk and put you at ease. When we learn to let go of our pride and ego in exchange for constructive and purposeful dialogue, the discussion translates into a conversation as opposed to a debate or conflict.

Prepare for tough conversations the same as you would for an important interview or presentation. Preparation is key, and it opens up the opportunity to create an intentional co-active space for an open, honest and transparent conversation. Part of which is to be mindful of being present, actively listening, sharing ideas, using discovery questions, and seeking to solve problems together.

Understand your ‘Why’

What is the desired ‘outcome’ you wish to achieve from the conversation?

Explore your ‘Why’

Is it something important you are looking for? Do you want to mend a situation? Is it some type of support or help you need? Do you need to negotiate flexibility to help you adjust and adapt to new working arrangements?

Clear Mindset

Having a very clear perspective on what your desired outcome is, will help navigate your approach, positive traits and behaviours

Clarity on Objectives

Clarity on what points you wish to raise backed up with evidence and facts ‘to the ready’ to support what you are saying to give you ‘buy-in’ and credibility

Feedback From Others

If you have feedback from others that adds credibility or facts to your discussion, then use it

Set Your Intentions

Express that you would appreciate being ‘listened to’ and your concerns taken into consideration

Solution and Options

Where there are problems or challenges – have solutions and options you can recommend and outline the benefits

Invite Input

Equally, be open and invite input and suggestions from the other person (s)

Create Curiosity

Demonstrate flexibility in your approach, use discovery questions to open the conversation up further

Actively Listening

Listen tentatively to what the other person has to say – this will intuitively enable you to intrinsically ask the right questions

Be Comfortable with Silence

If you are greeted with something unexpected in the conversation – don’t be afraid to pause – don’t be afraid of silence – politely say you need thinking time for a moment

Have a Pen and Notepaper with You

If there is something you can’t answer in the conversation, note it down and say you will revert (you may have to gather information or reflect on options put forward)

Remain Grounded and Calm

If you have specific strategies or breathing techniques for handling stress – use them ahead of the conversation – and remember to breathe throughout the meeting

Manage Your Emotions

Understand that emotional triggers have the power to throw you off track. Reality check your thinking, see the problem or situation for what it is with a helicopter view creates spaciousness for objectivity. Label the event/conversation as opposed to how you are feeling about it. Having the ability not to take the situation personally reduces emotional stress and enables clearer, rational thinking

Bring Water to the Meeting

Often, we can become emotionally vulnerable when we find ourselves in uncomfortable conversations.
This can lead us to lose our voice (biologically, we stop producing saliva when we end up in our freeze neural network pathways). Drinking water will buy you time to recover and reset in the moment

Summarise Key Points

Ensure you leave time to close the discussion properly at the end of the conversation. Summarise at the
end of the meeting. Walk away with clarity on verbal agreements and double click on anything you are unsure of. Establish if a further discussion is required and agree on a follow-up date


Have clarity on actions items agreed by either party and due completion dates and or status update


Request agreed on items and action items in writing where applicable. Thank the person for their time, understanding and listening.


Author: Jean O’Neill

I hope you enjoyed my article. You are welcome to get in touch to offer feedback or enquire about one-to-one or group coaching in Conversation Intelligence, Emotional Intelligence or Neuro Wellness (Stress Management and Performance) Masterclasses.

Jean O’Neill Coaching
Master Coach with Neuroscience

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