The Elephant in the room, the hard chat, the “I will deal with that later”. Having that difficult conversation can be the one thing many of us dread at work. In fact, a survey of 2,000 workers found, 57% of respondents said they would do almost anything to avoid a difficult conversation; and 52% said that they would rather put up with a negative situation at work than having to talk about it (Chartered Management Institute, July 2015).

Throughout my career, I have had to have difficult conversations regarding poor performance, inappropriate and negative behaviour and redundancies. These discussions have the potential to become emotional and unpredictable and may leave you vulnerable and open to criticism.

Due to this, many people fear them and ultimately avoid conducting them, which can mean the situation continues to worsen. Moreover, as a leader, it is often expected that you know how to have these confronting conversations. So what if you have never done this before? Where do you begin and how do you make sure it is done in a respectful and timely manner?

Here are my top six tips for getting through difficult conversations, keeping your relationships intact and achieving positive outcomes from them.


As Benjamin Franklin famously said, “honesty is the best policy”. Let the person in question know from the outset the purpose of the meeting. Don’t invite them for “a coffee and a chat”, leaving them blindsided once the session has commenced. In my corporate life, I was once asked by my manager to have a coffee catch up. I turned up, and my manager and HR also turned up and went on to explain that due to a restructure my role would be changing, and my team size and accountabilities were increasing.

A far more appropriate approach would have been to explain the meeting purpose upfront, give me time to prepare myself mentally and then have a far more constructive discussion around the change in the situation.


Depending on what you need to communicate, you want to ensure the environment and timings are right. For example, sitting in your office, behind your desk, or in the open-plan kitchen, may not be conducive to open and honest rapport. Conversely, taking someone to public, noisy café to “have the conversation away from work” probably won’t work. Plus the free cappuccino may not make up for the difficult chat.

Instead, opt for a private meeting room which is booked in advance. Also book the meeting room for longer than required, so that the person receiving the news has time to digest things in private. If you think the meeting may become emotional, be prepared with tissues and water.


Timing is critical. If you notice something is not going well then be upfront and call it early. For example, “I saw you missed the last two deadlines. Let’s get together tomorrow and work through this. ” This will be far more effective than sharing this thought nine months later at the end of year performance review. By acting quickly, you are giving your team member the best chance at correcting performance and getting back on track.

Also have the conversation as soon as possible. Don’t schedule the meeting for later in the week and let people stress about the conversation. Ideally, have these conversations first thing in the morning and then if required give your team member time to reflect and digest what has been discussed. Your role as a leader is to leverage timely feedback to drive improved performance, not punish people.


Before you meet with your team member, establish exactly why the meeting is occurring and what you expect the meeting outcome to be. Depending on the complexity of the conversation, discuss the approach with your manager and an HR rep. Do your research beforehand and ensure your facts are correct. Don’t assume anything and never let yours (or other’s) opinions cloud the situation.

By not assuming, this will enable you to answer your team members questions rather than “I will get back to you on that one” or “we need to continue this at a later date”. These are not an ideal response if your team member is upset or anxious. If it is a fact-finding meeting, be impartial and open to all manner of information your staff member gives you.


Save the small talk for your backyard BBQ and don’t evade a difficult conversation by spending the first 10 minutes making small talk. Lay it bare and remain sensitive and compassionate, acknowledging that they are probably feeling anxious.

Once you have provided context on the issue, it is important not to rush your team member’s response or their understanding. Give them time to digest the matter. Remember you have had more time to deliberate on this issue and now it is their turn. Let them ask questions. Let them have their say. Work through their problems and concerns with them. Try and make it as constructive an exchange as possible. You want to preserve the relationship.


Give yourself a check-up from the neck up. That is, make sure you go into the conversation with a clear mindset and with your emotions in check. Some meetings may become emotional which can be challenging. Acknowledge emotions such as sarcasm, defensiveness, anger. Allow your team member to work through this, however, never respond in the same way. Always allow them their dignity and due respect, but keep the meeting on track.


Don’t have the meeting and then pretend it never happened. If there needs to be a follow-up conversation, make sure it occurs. If you need to check in on your team members welfare, make sure you do. If they need to provide anything to you, make sure they do so. It is about achieving the predetermined outcomes and rectifying the issue that existed.

Never intentionally avoid that person. A friend once worked for a CEO who had to make several senior staff redundant. Once it happened, they then avoided them for the remaining four weeks they were in the company. They felt humiliated, isolated, and took it very personally.

These are just a few insights into how to manage difficult conversations and to achieve positive outcomes from them. If you have any more tips, please leave a comment below.

About the Author – Rajiv Jayarajah is the Founder of Bare Inc, a consulting and professional coaching firm specialising in creating clarity for business owners and leaders so that they can achieve their goals faster. It’s easy to connect, find me on LinkedIn, Instagram @bare_coach or

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