5 Ways To Deal with Difficult Conversations – Assertiveness Training

At various points in your career, you’ll find yourself having to have a difficult conversation with somebody. Sometimes at the receiving end, but as you progress to management it’s more likely that you will be the one instigating a difficult conversation.

There will be any number of reasons that a difficult conversation might be required from poor employee performance to conflict resolution.

As a line manager, it is your job to learn to be assertive and deal with these kinds of conversations upfront and with confidence. It is important for you to maintain a positive work environment and ensure that these types of issues are dealt with as soon as possible.

Looking for a comprehsive covering to become assertive? View our assertiveness training courses, we offer a flexible package tailored to your needs!

If it is not something you are used to doing, you may need to learn the art of assertive communication so you can drive yourself and the business forward.

People having a difficult conversation


How to Deal with a Difficult Conversation – 3 Top Tips

It is one thing to know the effects of having/not having a difficult conversation with an employee, but it is another to know how to handle one.

An assertive management style is essential to deal with these sorts of conversations.

Here we explore some tips on how to prepare for and have a difficult conversation in relation to poor performance or badly executed tasks.


  1. Plan the conversation

Be careful not to ambush somebody with negative information on the spot.

They probably will not receive it well and won’t be prepared for their own response which is likely to be very emotional.


  1. Be direct

People actually appreciate direct feedback without dancing around the actual subject matter.

Assertively explaining the problem and allowing them to address it with an agreed action plan often leads to a very positive outcome.


  1. Offer clear examples

You can’t tell somebody they aren’t performing to a good standard without explaining why and also providing concrete examples so that they don’t view this as your opinion.

If you can’t back up your assertion, it can come across as a personal attack or aggressive communication.


  1. Manage your emotions

The line between passive communication and aggressive communication means balancing your feelings.

Stand firm on your reasons for the conversation but keep it fact-based without allowing personal feelings to get involved.

Managing your emotions is also a key skill for interviews! View our 50 Tips For A Great Interview here!


  1. Be empathetic

You want whoever you are having the conversation with to understand where you’re coming from while also allowing them time to process the information.

Listen to their explanation and ask questions where you’re not clear. This is especially important. If the conversation is difficult the natural tendency is to want to get it over as soon as possible. A recipe for misunderstandings and making things worse!

Try to stay calm and take the time to really understand them by using active listening. It might take a bit longer, but its nothing compared to the time that a broken relationship can take to fix! Also, it makes sure that the other person feels heard.

It is important that they feel heard in this conversation as well if you are to maintain your relationship.

Woman having hard conversation on phone


Negative Effects of Avoiding Difficult Conversations

  1. Causes lack of trust

When things are left unsaid in situations of conflict, your team may start to lose their confidence in you.

It is vital that they view you as someone who they can trust and who will deal with the difficult aspects of management head-on and not avoid them.


  1. The conflict can escalate

What may have started as a simple disagreement can expand and blow out of proportion if it is not nipped in the bud.

Obviously, if things get worse then this will lead to the need for a more difficult conversation further down the road so it is always worth dealing with these things promptly.


  1. Increased personal stress

With everything else you may have on your plate, the last thing you will need is the stress of dealing with a difficult conversation.

Anxious thoughts about an outcome that hasn’t even happened yet can form when things are left to build up, and this leads to more stress. Dealing with the conversation promptly is the best way to get a good result and keep your stress levels low.


  1. Leads to further misunderstandings and assumptions

I things are left unsaid then staff will assume that they are progressing as they should and doing a good job.

This can lead to you redoing their tasks and putting more work on your own plate.

As a manager, your job is to have these conversations to benefit your team and individuals, but also to maintain a stress-free environment.


Couple having difficult conversation on bench


Positive Effects of Having a Difficult Conversation

  1. It becomes results-focused

Assertive management means turning negative conversations into positive ones.

By taking a look at it from both sides you are able to see where it can benefit both parties with an end result in mind.


  1. It gives accountability

It could be you apologising for a certain failure or allowing an employee to see where they made a mistake.

An assertive conversation is not about placing blame but reviewing shortfalls, recognising your own faults and being accountable if you haven’t communicated your initial intentions well.

It also places accountability on others that are responsible and puts the ball back in their court to show drive and improvement.


  1. It stops unnecessary time loss

Delaying difficult conversations means that time is wasted as the issue isn’t being dealt with.

In the instance of a conflict between colleagues, it is better to be assertive and mediate the resolution so everyone can get back to doing the work they are tasked with and stop spending time and energy thinking about the conflict.


  1. It improves working relationships

There will always be some form of conflict in the workplace, but it can obviously become detrimental if it builds up too much.

Many people leave companies because they felt they weren’t being listened to and heard. Conflict resolution is about listening to both sides but being assertive enough to step in when it gets tough.

Once a difficult conversation has taken place, the stresses involved are lifted and the majority of the time, relationships actually improve.

People learn how to communicate with each other through having difficult conversations and taking this learning forward with them in future interactions.

Coworkers having difficult conversation


Difficult conversations are not easy to have in all instances, but as a manager and as you get more practice being assertive and dealing with difficult people and your ability to communicate assertively expands, these conversations can start to feel less difficult and more rewarding.

Looking for more Assertiveness Tips? View our 5 Assertiveness Tips For Managers here!


About Ben Richardson

Ben is a director of Acuity Training which he has been running for over 10 years.

He is a Natural Sciences graduate from the University of Cambridge and a qualified accountant with the ICAEW.

He previously worked as a venture capitalist and banker and so had extensive experience with Excel from building financial models before moving to learn SQL, Microsoft Power BI and other technologies more recently.