Managing Difficult Conversations: How to Plan the Best Outcome

The secret to managing difficult conversations is the way you prepare yourself

Managing difficult conversations is consistently cited as one of the most disliked aspects of being a line manager. No surprises there, because facing someone’s distress or anger can be extremely discomforting, and causes anxiety about saying something that aggravates the situation.

This is why we tend to avoid difficult conversations or end up having watered-down versions that fail to resolve the situation or worsen it.

However, managing difficult conversations is a skill and process that can be learned and fine-tuned. In many cases, skilful handling of difficult conversations can build stronger work relationships and improve success at the individual and organisational level.

Preparation is an essential component for successfully managing difficult conversations, so let’s look at what they are when to have them, and how you can ready yourself.

What is a Difficult Conversation?

Fundamentally, managing difficult conversations refers to any conflict situation. In the workplace, it tends to mean circumstances where an employer and employee are at odds, which is why many difficult conversations happen between managers and their team members. For example, conflicts might relate to workplace performance, pay issues, inappropriate behaviour or redundancy.

Difficult conversations can also happen between customers and suppliers, such as handling complaints, admitting mistakes, raising costs, or realising you are unable to fulfil a contractual agreement.

Employees may also need to have difficult conversations with their peers about conflicts such as workplace behaviour and hygiene.

When is the Right Time to Have a Difficult Conversation?

Naturally, leaving situations to fester can be disastrous. Not only does it allow conflicts to endure, but it can also cause emotions to escalate. If left too late, you risk emotions boiling over and causing extensive damage to relationships.

However, jumping on issues too early can also be problematic if you have not gathered enough information to manage the conversation effectively.

The best time to have a difficult conversation is the earliest possible moment after you become clear about the situation and have prepared your response.

For example, if you suspect workplace performance issues, or receive a complaint about an employee, you need time to assemble the facts. If you need to notify team members about redundancy, wait until the specifics have been confirmed. Obviously, don’t take too long, or the situation may escalate, causing a much wider set of problems.

In some cases, the only way to understand a situation is to have an initial conversation with those involved. In all but the simplest cases, limit this meeting to fact-finding only. Without adequate time to prepare, any early attempts to resolve the situation may do more harm than good.

What are the Objectives of Preparing?

Three key objectives will prepare you for managing difficult conversations:

Gather enough information to state the issue clearly and confidently
Plan a narrative for the conversation to help you steer it towards the best possible outcome
Think about the situation from other people’s perspectives to appreciate their reasoning and also anticipate their responses.

State Your Position

Assemble as much relevant information as possible, isolate the key points and phrase them in a professional way that minimises the emotion of the situation. Like a lawyer in a courtroom, stick to the facts and provide enough evidence to ensure your position is not in question.

A key tip is to consider very carefully whether you need to apologise. Naturally, an apology will be necessary if you or the organisation you represent is at fault. But many of us simply say sorry because we feel it will ease a confrontational situation.

When managing difficult conversations, bear in mind that apologising unnecessarily can undermine your position and assertiveness, and can also introduce an unhelpful emotional element. Also, if you are known to say ‘sorry’ a lot, then it can come across as insincere.

Plan a Narrative

In the same way that professional speakers prepare speech notes, think about how you want the conversation to play out.

Identify the ideal outcome, which gives you something to steer towards, particularly if the conversation is being drawn off track. However, remain flexible to valid points that the other person makes and, if appropriate, consider a compromise position.

Varying the way you ask questions is a useful tip for managing difficult conversations. Human beings naturally place greater value on their own subjective experience, but combining an open and closed question can encourage someone to think more objectively.

First, ask an open question to invite them to speak about their own experience, but follow it up with a closed question that forces them to consider another perspective.

For example

“How did the situation make you feel?”

followed by

“Do you think the other person felt the same?”

Consider the Other Person’s Perspective

Perspective is an essential ingredient for your preparation, and you should consider any viewpoints that are relevant to the situation. However, don’t fall into the trap of simply considering other people’s perspectives from your own.

Bear in mind that you are likely to have a completely different life experience to the person you are speaking to, which makes “walking in their shoes” almost impossible. You need to understand something of their history and personality in order to see the situation through their eyes.

This is why flexibility is so important when managing difficult conversations. A simple response or a subtle movement could cause you to see the situation in a different light.

Talking it Out

When it comes to the conversation itself, choose a suitable environment that is quiet and private. Begin by stating your position clearly and confidently, and then ask the other person for their response.

Be empathic to what they say, which means actively listening and genuinely trying to understand their position. Steer the conversation towards your objective unless a new insight changes your mind about the situation.

Essential for managing difficult conversations is to try to keep a handle on the level of emotion. Pausing to collect your thoughts can calm your own feelings while steering the conversation back to the facts can help calm the other person’s.

Finally, if the conversation uncovers something that changes your opinion, then don’t be afraid to schedule another time to continue. It is far better to take a break to assess new parameters than to continue unprepared.