Let’s talk about difficult conversations at work webinar highlights

As part of Mental Health Awareness Week 2026, we hosted a webinar exploring one of the issues that comes up time and time again across the legal sector: difficult conversations at work.

The discussion highlighted just how common these challenges are, whether that’s raising concerns about workload, giving feedback, managing client expectations, addressing behaviour, or speaking up when something doesn’t feel right.

The webinar, chaired by LawCare Champion Lloyd Rees, brought together panellists Andrew Croft, Rupa Mooker and Justine Thompson to share practical advice, personal experiences and simple approaches that can help make these conversations feel more manageable.

A clear message ran throughout the session: avoiding difficult conversations usually makes things harder. While these conversations can feel uncomfortable, dealing with issues early often prevents them becoming bigger problems later on.

Managing expectations and workload pressure

At the start of the webinar, attendees were asked which workplace conversations they found most difficult. The highest response was around managing unreasonable demands and expectations.

The panel reflected that this is deeply connected to the culture of the legal sector, where responsiveness, availability and client service are often heavily rewarded. Many people feel pressure to say yes to everything, even when workloads are already unmanageable.

One of the strongest practical tips shared was to avoid simply agreeing to unrealistic requests in the hope things will somehow work themselves out later.

Instead:

• clarify what is actually needed
• ask whether deadlines are fixed or flexible
• explain capacity concerns early
• discuss priorities openly

This keeps the conversation focused on practical solutions rather than conflict.

The panel also stressed the importance of recognising the difference between genuine emergencies and “manufactured urgency”, where poor planning elsewhere creates avoidable pressure for others.

Don’t avoid the conversation

One of the biggest mistakes discussed throughout the webinar was avoidance.

People often put off difficult conversations because they are worried about conflict, damaging relationships or getting the response wrong. But several panellists reflected that issues almost always become harder to manage when they are ignored.

Communication is one of the most important tools for preventing problems escalating.

Top tips included:

• speak up early if something feels wrong
• keep talking regularly and openly
• address issues before they grow into bigger problems
• make time for informal chats and check-ins

The panel also suggested changing the environment when conversations feel difficult. Going for a walk or grabbing a coffee can sometimes help people speak more openly than sitting across a meeting room table.

Pause before reacting

Another strong theme throughout the discussion was the importance of slowing down before responding emotionally.

Several panellists warned against immediately replying to difficult emails or reacting in the heat of the moment.

“Don’t say the first thing that comes into your head.”

Instead:

• pause
• take a breath
• think about the outcome you want
• focus on facts rather than emotion

This can help conversations stay constructive rather than becoming defensive or confrontational.

Focus on the issue, not the person

When challenging someone’s approach or behaviour, the panel stressed the importance of separating the person from the issue.

Rather than criticising someone personally, it can help to focus on the shared goal or practical concern.

For example:

• “I’m worried this could create a risk for the client”
  rather than:
• “You’ve handled this badly”

This small shift can reduce defensiveness and make conversations feel less personal.

Another important tip was to avoid challenging people publicly wherever possible. Difficult conversations usually go better when people feel respected and not put on the spot in front of others.

Listen more than you speak

Listening was one of the biggest themes running through the webinar.

Several panellists reflected that people often go into difficult conversations focused entirely on what they want to say, rather than genuinely listening to the other person’s perspective.

One attendee commented in the chat that “listening is a rare skill”, something that clearly resonated with many people joining the discussion.

The panel also encouraged people to stay open to the possibility that they may not always be right. Humility and self-awareness can go a long way in difficult situations.

Create psychological safety

The webinar explored what psychological safety actually looks like in practice.

The panel described psychologically safe workplaces as environments where people feel able to:

• admit mistakes
• ask questions
• say they are struggling
• challenge behaviour respectfully
• raise concerns without fear

A major point raised was that leaders help shape this culture through their own behaviour. Top tips for managers and leaders included:

• be open and honest
• admit when you’ve got something wrong
• say sorry when needed
• check in with people regularly
• focus on fixing problems rather than blaming people
• follow up after difficult conversations to see how someone is doing

The panel noted that when senior people are open and honest about struggles or mistakes, it helps others feel safer to do the same.

Giving feedback well

Constructive feedback was another important topic.

The panel discussed how feedback often becomes more stressful when it is only delivered formally or saved up for annual reviews.

Instead, feedback works better when it is:

• regular
• specific
• supportive
• linked to development
• part of normal day-to-day conversations

One practical suggestion was to work through feedback collaboratively rather than simply sending someone corrected work with tracked changes and criticism.

The webinar also highlighted that many people are promoted into management roles without training on how to manage people or give feedback effectively.

Learn from mistakes rather than hiding them

One of the most memorable parts of the webinar came when Rupa shared a story about making a significant mistake early in her legal career.

Expecting anger from a senior partner, she instead received a calm response focused on fixing the issue and learning from it.

The story prompted a wider discussion about how fear-based cultures can discourage people from speaking up when something has gone wrong.

One key message was that it’s better to deal with mistakes early and openly. Supportive responses help people learn and improve, while blame often makes people more anxious and less likely to speak up.

Practical tools for difficult situations

Justine Thompson also shared a practical framework called the “four Ds” for handling difficult situations:

1. Direct – Address the issue in the moment if it feels safe to do so.
2. Delay – Have the conversation later in a calmer one-to-one setting.
3. Delegate – Ask someone else to step in if they are better placed to handle the situation.
4. Distract – Interrupt or redirect a difficult interaction to create space or support someone.

A fifth D was also discussed: Document – Keep factual notes where appropriate, particularly if patterns of behaviour are developing.

Final reflections

Difficult conversations are part of working life, especially in the legal sector. But they do not have to damage relationships or make things worse.

Small actions can make a big difference:

• communicating earlier
• listening better
• showing empathy
• staying calm
• apologising when needed
• focusing on solutions rather than blame

The webinar highlighted that difficult conversations are not about saying everything perfectly. They are about being honest, clear, respectful and treating people like people.