How to initiate tough conversations at work

Benjamin Kluwgant · 02 Dec

Whether it be with a colleague, manager or subordinate, there will eventually come a time in every work environment that difficult conversations need to be had. While these tough exchanges are never particularly comfortable, knowing how and when to initiate them can help take the edge off and make them far more productive.

In an ideal world, work-related conversations would always be positive. People would be sharing their praise and appreciation for each other, they would be brainstorming and strategizing together, and general correspondence would be positive and for the betterment of the organisation.  

But the reality is quite different. Given the high pressure environment of many workplaces, there will always be instances where difficult conversations need to be had – and sometimes, you’ll have no choice but to initiate a tough chat with a colleague, a direct report, or even someone who is more superior than you are.

The difficult conversations that need to be had at work from time to time are normally about things like criticism of behaviour, uncomfortable situations, attitude or quality of work. Here are three examples of tough conversations that can happen through all levels of an organisation:

  1. Your colleague might be doing something that is disrupting your ability to work properly – so you need to initiate a conversation to let them know.
  2. You need to head away on leave during a busy period – so you need you need to figure out how to bring it up with your manager.
  3. Your direct report might be underperforming – so you have no choice but to flag it with them.

In all of those instances, there is a very important message that really should be relayed but confronting the relevant person can be quite tough. So, the person is faced with the conundrum of whether they should avoid conflict and let the conversation slip past or face it head on.

Ultimately, if the workplace is to develop and thrive, it’s important that those types of conversation take place – so if you’re facing this internal dilemma of deciding whether or not to go ahead with one, here are three tips to help make those conversations easier and increase your chances of them achieving the best result.

Make sure you’re the right person to have this conversation

Before you even begin thinking about how you’re going to approach the conversation or what you’re going to say, you need to critically analyse the situation and decide whether it’s you who should be initiating the conversation.

When it comes to tough conversations at work, there are many instances where someone might be involved in a situation and feel like it’s their responsibility to deal with it, when in reality, the discussion should be initiated by someone else.

Read: Keeping the whistle-blowers of the workplace protected

However, if you’ve explored all the other options and ended up at the conclusion that it’s your conversation to have, then it’s time to start preparing yourself to step up to the plate.

If you fail to plan, you’re planning to fail

As cliché as it might sound, mapping out the conversation and thinking it through before going ahead with it can have a really positive impact on how the chat goes. If a tough conversation is initiated on a whim, it is basically set up to fail before it even starts.

Planning such a conversation is about much more than sitting down with a pen and paper and jotting down the things that you should and shouldn’t mention. Thought needs to go into the tone you intend to use, responses need to be anticipated and emotions need to be pre-empted and managed.

Most importantly, remember to embed a sense of empathy within your approach.

Read: Helping employees improve with the right type of criticism

They say words that come from the heart penetrate the heart – so if you don’t want the difficult conversation to fall on deaf ears, make sure that you initiate the conversation empathetically and that you’re open to the other person’s side as well.

Focus on the solution

As crucial as planning is when it comes to initiating difficult conversations with people at work, it’s impossible to know exactly how things will pan out during the exchange and there’s always a chance that you’ll need to do a bit of freestyling.

The danger of being unprepared and entering into the freestyle zone is that it becomes much easier to lose sight of what you’re trying to achieve during the chat, and that’s when things head south and unnecessary conflict surfaces.

Read: Dealing with bullying in the workplace

A great way to steer clear of conflict is putting your solution to the issue at hand on the table as early on in the conversation as possible, instead of emphasising the issue itself.

Spending too much time focusing on the problem is normally a sign that your emotions have gotten the better of you, and when that happens, you end up losing focus and the everything goes haywire. 

Tough conversation ≠ bad conversations

These three tips are all cut from the cloth of treating people with respect and fostering a work environment which looks at all people equally when it comes to empathy and fairness.

Initiating a tough conversation at work is never going to be easy – there’s no way of avoiding that. But regardless of your paygrade or position within the organisation, approaching those conversations with the attention and respect that they deserve is the key to ensuring they turn out to be worthwhile.

Ultimately, tough conversations don’t have to be bad conversations. Twists and turns are inevitable when travelling along the road to success, and when you find that there’s a spanner in the works and a difficult conversation needs to be had, it needs to be looked at as an opportunity for learning and development – instead of something that to shy away from.