How to Have Hard Conversations at Work (and Beyond)

How you navigate difficult and challenging conversations is a key skill. And not just for leaders — for everyone.

By building your confidence to have hard conversations at work, you foster an environment of transparency, openness and candor. This underpins trust, respect and psychological safety in the workplace.

So, how can you go about building the skills you need to be able to handle hard conversations with aplomb? Let’s explore the ins and outs of hard conversations.

What are hard conversations?

Hard conversations are those that cause stress, uncertainty or discomfort for one or both participants.

You may start to feel the uncertainty, discomfort or stress in advance of the conversation, like a sense of dread or a stone in your belly. At other times, the discomfort can arrive unexpectedly during the conversation.

Hard conversations (n.): interpersonal exchanges that cause stress, uncertainty or discomfort for one or both participants.

Don’t wait until you feel comfortable to have a hard conversation. That moment may never come. Instead, you need to acknowledge the discomfort you are feeling and have the conversation anyway.

What makes some conversations hard?

Hard conversations often make us feel afraid. They can trigger a deep, psychological need we have to be accepted and make us fear rejection.

Hard conversations make us feel uncertain. How will the person respond: will they get angry or go on the attack? Will they become defensive or shut down? Will they have a strong emotional response that you’re not equipped to deal with? What will the outcome be?

Hard conversations can make us feel sad or guilty, if we’re sharing difficult information with someone that may be hard for them to hear.

We may fear not being liked by the other person. Especially for people pleasers, this fear can be difficult to overcome.

Few of us are tooled with the healthy communication skills we need to navigate difficult topics from a young age. We become afraid of differing opinions and conflict and learn to avoid it, rather than embrace it as a natural part of human existence.

Common examples of hard conversations at work include:

• Providing negative feedback

• Owning up to a mistake

• Providing feedback to a direct report

• Discussing redundancies and terminations

• Reporting a colleague’s misconduct

• Investigating inappropriate behavior

• Mediating disputes and conflict resolution

• Establishing boundaries with a colleague

• Asking for a raise or promotion

• Turning down an idea

• Turning down a request for a raise or promotion

Why hard conversations are important

Some of the reasons why hard conversations are essential to a healthy workplace include:

• So people (including you) can learn and grow

• To avoid assumptions

• To clarify situations and provide context

• To ensure a safe and inclusive work environment

• To create insight and shared understanding

• To build the experience of navigating discomfort

• To retain focus on goals and adhere to strategy

• To bring transparency and build trust and respect

• To foster a culture of candor and creativity

What do we often get wrong about hard conversations?

• In order to avoid the discomfort of having a difficult conversation, you delay it or procrastinate. You may avoid the conversation completely, hoping the issue will magically disappear of its own volition (spoiler: it almost definitely won’t).

• You rush through the conversation it in order to ‘get it over and done with’.

• You fail to form a genuine connection with the other person. You stay stuck in your own emotional state, avoid eye contact and remain disconnected.

• You over prepare in order to attempt to exert control and mitigate your own discomfort. Perhaps you end up writing and delivering a speech rather than allowing a two-way dialogue.

The consequences of avoiding hard conversations

There are many consequences of failing to handle a hard conversation well or avoiding them altogether. Primary examples include:

Miscommunication / non-communication

The wrong message is communicated, or the information is not conveyed (or gathered) at all.

People make assumptions

Rushing through conversations leaves room for assumptions, which can damage relationships and give rise to rumor and misinformation. In some situations, unverified assumptions can lead to devastating consequences in the workplace.

The elephant in the room

Usually, when you avoid or procrastinate the hard conversation, the issue remains. This unaddressed truth can cause damage, as you are lying by omission. Eventually this can lead to feelings of betrayal.

Distrust and disrespect

People often pick up on signs when there’s something unsaid between you. Eventually, avoiding hard conversations can lead to disconnection and distrust. It can leave people feeling disrespected and undermines their sense of dignity. Handling a hard conversation poorly can have similar consequences, diminishing your leadership.

Relational harm

When you fail to handle a hard conversation well, it can cause serious relational damage with the other person.

It is entirely understandable that we fall into these kinds of behaviors in the face of a difficult conversation. However, there are simple tactics you can use to improve your ability to create healthy, candid conversations. Let’s take a look at these now.

How to have hard conversations

Let’s break down the process into chronological sequence: here are the before, during and after of hard conversations.

BEFORE

• Get clear on your goal for the conversation. This does not mean predetermining what the outcomes of the conversation are, but giving direction to the discussion. The ultimate goal may not be seeing eye-to-eye or finding a definitive solution. Often it’s about finding a sense of shared understanding, and a plan for change

• Be clear on, and ready to articulate, the facts of the situation (as opposed to opinion, assumptions, inferences or judgment about those facts)

• Ask yourself — what am I assuming about this situation? Do I have a desired outcome from this conversation? If so, am I genuinely open to changing it?

• Reflect on your own feelings going into the conversation: are you nervous, scared, worried, filled with dread? What can you do to soothe your feelings and build your confidence both in advance of the conversation and during it?

• Consider the situation from the perspective of the other person. How might they be seeing things? What might be important for them to know?

• Anticipate how the other person might react during the conversation (defensive, angry, shut down, passive aggressive) and role play these reactions with a trusted person in advance so you’re clear on how you will respond if that situation arises.

• Choose the right timing and setting. Should other people be present for this conversation? If so, make sure that person knows what their role is for the purposes of this conversation and what you expect of them.

• When informing the other person about the conversation, give context to manage expectations. Frame it in a non-confrontational yet clear way. Instead of saying: “we need to talk about what happened in the team meeting,” try saying: “I’m curious to hear your thoughts on the different opinions that came up in last week’s team meeting. Can we chat about it at your next one-on-one?”

DURING

• Be present. Give the other person your full attention. You may want to take a few deep breaths or place your feet on the ground, or any other ritual that helps you feel relaxed and ‘in the moment’, rather than flighty or distracted.

• Be calm, but not impersonal, cold or flippant.

• Create an open dialogue. Use your active listening skills, including open questions where useful.

• Where appropriate, support statements with data without ambushing the other person with an excessive amount of evidence.

• Stay focused on the topic at hand and keep the conversation on track, even (especially) when it gets uncomfortable.

• Clarify what the other person says without minimizing their views.

• Don’t make it about you: avoid statements like “this is hard for me too”.

• Actively work to keep an open mind, seeking to create a shared understanding, throughout the conversation. This can be harder when you are uncomfortable as you are often tense, and want to get things over and done with.

• Aim to understand, not be right. Don’t try to win the conversation.

• There might not be complete agreement — prepare for this eventuality.

• Be clear on confidentiality. Do not disclose information that you’re not meant to.

• Commit to ‘what next’: Articulate what will happen after the conversation.

In some situations, for example, if things are really heated or you’re coming to an impasse again and again, it may be better to pause a conversation and continue it at another time, perhaps later that afternoon or the next day. This approach should not be used as a means of avoiding discomfort but to enable emotional regulation and perspective, which is next to impossible when you are in a heightened emotional state.

AFTER

• Follow up: do what you committed to doing as part of the ‘what next’ and communicate this to the appropriate person.

• Reflect: what went well? Were there moments when I was particularly uncomfortable or triggered? Which emotions came up during the conversation? Did I miss any opportunity to communicate better? What could I have done better? Jot down any learnings from the experience so that you can use these in preparing for your next hard conversation.

It says it on the label: hard conversations are not easy. However, by building the skills to have difficult conversations, you foster a healthy, open culture of transparency and inclusion. Start preparing for your next hard conversation right now.

If you'd like to book my Handling Hard Conversations training session for your team or organisation, reach out now.