Mastering that tricky work conversation
- Jordan Bernard
- 3 days ago
- 5 min read
A difficult conversation is something that not many people tend to look forward to. And they can be just as uncomfortable for the person initiating the conversation as they can be for the person on the receiving end.
As many of us know, however, there's no avoiding the fact that in work, difficult conversations are often required. When there's turbulence in the economy or significant change within our organisations, they become even more commonplace and critical. If managed effectively though, these conversations address problems head-on, effectively securing as much of a win-win outcome as possible for all parties involved.

Difficult topics
So, what kind of things do we struggle to chat about? According to a poll conducted in 2015 with 2,000 adults in the UK, the top ten topics we dread speaking about in work are:
Pay packets – 33%
Inappropriate behaviour in the workplace – 31%
Feedback on poor performance – 30%
Promotions – 23%
Sex – 19%
Relationship break ups – 17%
Family relationships – 16%
Money – 16%
Health – 15%
Letting someone go from a job – 10%
Emotions can certainly run high if these conversations aren't conducted properly. The conversation may well be doomed even before it begins if consideration hasn't been given to timing, location and how to incorporate other person’s thoughts, feelings, and voice.
However, knowing how to tackle these conversations is an essential leadership skill. Avoiding them can have a negative effect on our relationships as well as our health and wellbeing. The avoidance of difficult conversations comes at a literal cost for organisations, too; while many reports, articles and surveys report sensationalistic losses per every conversation avoided, the reality is that organisations are bound to incur some degree of cost, especially if avoidance of conversations is a consistent and recurring issue.
By approaching these conversations properly, we can build trust, create progress, clear up misunderstandings, and build essential skills. Indeed, there is evidence to suggest that when leaders use the right strategies in difficult conversations with their team members, they are able to mitigate power imbalance, creating shared meaning, validating thoughts and feelings that emerge, and preserve positive working relationships. Demonstrably, effectively conducting these conversations sets up for much greater positive outcomes in the long-term, rather than avoiding them altogether.

Tips to navigate difficult conversations
Reflect on the purpose and prepare the conversation beforehand
One of the key things you should ask yourself is: "What am I aiming to accomplish by having this conversation?". Ensuring that there is a clear aim helps to confirm that the conversation is necessary and that there is a positive outcome for both yourself and the other person.
As a general rule, it's always good to let the person know in advance that a conversation is coming up, and what it's going to be about. Int his way, it's not just you who's prepared - they are, too.
Securing an appropriate place and time
There is never a 'perfect time' to approach a difficult conversation, but it is important to be mindful of the other person’s schedule and commitments. Approaching them just before they head into an important pitch wouldn't exactly be the ideal strategy, nor would trying to squeeze a difficult conversation into a five-minute slot. Try to have the conversation in person where possible and choose a location that is private, not to be overheard by others.
Balance task and relationship
One of the trademark internal tensions leaders and managers must grapple with is the balance between task- and people-orientation. Research shows that successful outcomes from these tricky conversations require a delicate and considered balance of the two. A disproportionate focus on tasks and objectives, and we risk appearing inhumane. A disproportionate focus on the welfare of others, and we may fail to deliver the gravity or essence of our message.
So, how do we get the balance right? Firstly, we shouldn't enter the conversation with the assumption that our prior knowledge or understanding of the subject is incorrigibly correct. That said, being clear on our objective, message, and envisaged outcomes before entering the conversation helps to ensure the conversation delivers on 'task'. In many cases, the reason for the conversation is to explicitly and clearly deliver an important message - this shouldn't be forgotten.
While in the conversation, empathy is key: this enables us to understand other perspectives and makes sure that we acknowledge those perspectives appropriately. Techniques like paraphrasing what someone has said back to them is useful not only to demonstrate we've heard what they've said, but that we have their message right. It's important to work together to reach a resolution and maintain the dialogue by asking questions and ensuring both parties have a fair chance to speak.
Managing escalated moments
Inevitably, things can heat up and conflict may arise in conversations like these. Here, it is important to actively avoid critical personal judgement of your conversation partner, and to do your best to understand their perspective and perhaps what triggered this conflict. Try stick to the facts and aim to focus more on listening to the other person than asserting your point of view.
Our feelings can be a barrier in effective communication if we are not aware of them and how they are being conveyed. However, when we acknowledge them, they can aid positive communication. One useful tip is to replace ‘you’ with ‘I’ at the beginning of sentences. This helps the other person to understand how you feel and also prevents the other person from feeling attacked.
In particularly tense moments, the best thing to might be to pause the conversation there (or at the soonest appropriate moment) and revisit at another point in a couple of days for a more productive conversation.
Following up after the conversation
After the conversation, take some time to reflect on it. Were your objectives and envisaged outcomes met? Did you convey your message effectively? Was your perspective broadened in a two-way dialogue? Reviewing how it went is useful not only to assess that conversation's impact, but for learning you can apply to your next conversation.
Sometimes people may be left with strong feelings of embarrassment, anger, or resentment after a difficult conversation, too. Checking in with them may be beneficial to preserve a positive relationship and keep things moving forward.
In summary, difficult conversations can be uncomfortable and challenging, but they are an essential leadership skill that helps to build trust and maintain positive working relationships. Avoiding these conversations doesn’t help anyone, but by seeking to understand the other person's perspective, working together to reach a resolution and acknowledging our own feelings, we can iron out misunderstandings and prevent conflict. This, ultimately, paves the way to much greater success.
Comments