Career Coaching Services
Building Working Relationships – Part 1: How to Have Difficult Conversations
Careers in Depth
Career Coaching Services
Building Working Relationships – Part 1: How to Have Difficult Conversations
Careers in Depth

As much as we might try to avoid it, there are times when a difficult or uncomfortable conversation at work is necessary. It could be anything from telling your boss that you disagree with an important decision, to navigating a way forward with a co-worker when you have differing ideas on how to approach a shared project.

Often, we feel that avoiding conflict and ignoring difficult situations is the best way to maintain good working relationships but in reality, this can lead to a toxic working environment of quiet resentment and worse outcomes for all involved.

Procrastinating over difficult conversations won’t make them go away but, perhaps somewhat surprisingly, having these awkward conversations as soon as issues arise can actually substantially improve our work relationships and even our home lives.

Ultimately, many people don’t engage with difficult conversations because they simply don't know how to have them and fear saying the wrong thing and making the situation worse. Here we explore some useful tips on how to approach difficult conversations for a more positive experience.



It is advisable to try not to build up the idea of a difficult conversation as ‘difficult’ in your mind as this can lead to anxiety. It is often better to ‘rip of the band-aid’ and just get it over with while also approaching it with curiosity rooted in seeking to understand the viewpoint of the other person, whilst remaining connected in yourself with what you want to accomplish from the conversation.

Perhaps write down a rough plan for what you want to achieve to help you stay on track during the discussion and aim for your ideal outcome but equally don’t enter into it with a fixed result in mind. It is vital to be flexible to allow for understanding, exchanging of views and compromise.  


Be Clear & Confident

It is likely that the other person in the conversation will pick up on your mannerisms and behaviour. Being polite but direct will convey that you are comfortable with the topic being discussed which, in turn, can help the other person to feel more at ease and less like the conversation is awkward for either party.



Empathy is key to making difficult conversations successful. 74%of employees believe that empathy drives motivation and 84% of CEO’s believe that empathy drives better business outcomes so it’s clear that seeing something from another person’s perspective is very important to making people feel valued even if you disagree with their point of view.

Consider how it may make you feel to be on the receiving end of the discussion and bear that in mind when expressing your responses and delivering negative comments about their efforts or ideas. Reassuring the person you are speaking with that you are raising the issue for a purpose and that you understand it could be difficult to take in the information can make the situation seem less confrontational.

Give your counterpart time to absorb the information if they need it, allowing them the opportunity to formulate a response. Also, try to avoid playing the victim yourself with phrases such as ‘I hate to have to say this but...’ or ‘this is so hard for me to do…



While we may have a clear idea in our minds of what we want to say, it is extremely important to listen to the other person’s opinions and views. Active listening, (i.e. listening with the intent to understand rather than with the intent to respond), lets the other party in the conversation know that you acknowledge and respect their ideas and feelings. Active listening involves being visibly attentive and not just being in the room while looking at your phone when your counterpart is speaking, or waiting for your turn to speak without really taking in what they are saying.  It will allow you to relay to the other person that you understand what they have said and enable you to respond with empathy to their words. This can not only help with resolving the issue being discussed but will also assist with maintaining or repairing your long-term relationship after the discussion is finished.

Listening is also important as it could be that something is said which you hadn’t considered which could change your own perspective of the situation and create a different solution which you hadn’t thought of.


Calm & Considered

It is easy for tough conversations to get emotionally intense which is unlikely to lead to a constructive outcome. If you feel a conversation is getting a little heated, it can be useful to slow down. One way to achieve this is to literally, slow your talking speed. Taking a pause before   responding can diffuse tension and help your counterpart to relax too.

It is also important to recognise when you might need to take a break. Not every discussion can lead to a direct resolution and it maybe that you need to step away to gather your thoughts for a short time or even agree to disagree on a contentious issue on the understanding that you will revisit it another day.


Be constructive

Where possible, acknowledge and build on anything of worth which the other individual has put forward, offer options, alternatives or add value to the conversation rather than focussing on the negatives. In the event of having to convey some difficult information this approach may help show the other person that, while you may not be able to change the nature of the issue, you respect them enough to have tried to come up with something to help them find a solution.



Difficult conversations can be emotionally draining so it is important to take some time afterwards to be calm, perhaps by going for a walk or taking a coffee break. You may or may not have got the exact outcome you were hoping for but either way you will hopefully feel proud of yourself for addressing the issue head on and helping create a work environment which encourages healthy communication.

You can reflect on the conversation itself too and analyse what went well and what could have gone better which will help for the next time you need to have a tricky discussion with a co-worker.

Finally, it is important to check in with the person you spoke with. Not immediately, but once the dust settles a few hours or even a couple of days later. This can help to smooth things over and rebuild relationships as the other person will be aware that you recognise that there were elements of the conversation that may have been hard for them to hear and that you care about how it made them feel.

Click here for further reading on the subject from Harvard Business Review.


For more information about career development and coaching contact Careers in Depth today.


Leave your email and number in the box below and we'll be in touch to arrange a free consultation with an experienced career consultant.