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How to Have Difficult Conversations at Work

Work conversations are always difficult and complex, specially when they are intense, or overlap with personal life, or with personality related attributes. There are situations where unpleasant things need to be said, or tough feedback needs to be shared. There are also situations when someone is grieving and while we want to support them, we do not want work to suffer. So how does one navigate such situations and communicate with people?

We researched a bit, spoke to leaders in their respective domains and shortlisted some valuable insights that help people navigate difficult conversations.

The first thing to do is to accept that every conversation is an opportunity for transformation. No matter how seemingly difficult a conversation is, there always is something new that opens up. A firing conversation is an opportunity for feedback and starting afresh in a new organization. A conversation with someone who lost their temper in a meeting, has an opportunity for them to not just apologize, but also share what is actually at the root of their anger. A conversation about a lie, even if inadvertent is an opportunity for coaching in integrity. If dealt with compassion and in line with the policies, these conversations can be quite empowering as against the common belief.

The next thing is to understand that no conversation in life is difficult. ‘Difficult’ is an adjective. That’s all. An adjective that we attach to a conversation that we are afraid of. Conversations have impact on people, no doubt. For instance, if you’re firing someone there is an impact of them losing their salary, their immediate livelihood, the money that pays their bills and their kids’ school fee. However, there’s a reason why they are being fired.

Now you might say that this logic doesn’t may a conversation easy. No, it doesn’t, but giving someone a promotion and taking a stand for their salary hike isn’t easy either. At work, we do what we need to do without attaching a personal meaning to it.

That said, there are ways to reduce the negative impact of a conversation. One of the best ways to do it is to do a full root cause analysis of the reason why this conversation is needed in the first place. That way, it no longer remains personal to you. The second way is to come up with solutions that you can offer to the person with whom you’re having this conversation.

For instance, if you want to tell someone that they were caught lying, albeit inadvertently, you can give them options to restore the truth with whoever they lied to, or to resign, or to move to a role which may be mundane but doesn’t need them to lie. Unless the severity of the offense and the company policy demands immediate termination, this doesn’t have to be confrontational.

However, what this also means is that you have to own your conversations. You have to be very responsible about what you say in a conversation and what you accept from the other person. If there is something you or they have agreed to do, as a follow-up of the conversation, none of you can get away with not doing it. Holding yourself and the other person accountable, not just for what they said or did in past, but also for the promise they are making for future is the key to all the insights above.

Most importantly, even when there is no hope for redemption, or fixing things, compassion and empathy is the least you can offer. You can be firm and still non-confrontational. You can refuse to negotiate in so many words, but that doesn’t mean you have to make them feel belittled. You can carry out whatever charges you may have to carry out against someone who embezzled funds, but you do not have to publicly humiliate them while they are in the process of leaving.

What other insights do you use to deal with tough conversations at work? Do share in comments or email us at

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