Challenging Conversations at Work
A 6-step team training programme to help your people speak clearly and confidently when conflict is a risk.
This is for teams who…
- need to give and receive feedback more clearly
- find conflict, challenge or dominant voices hard to navigate
- want a shared language for difficult conversations at work
Your team will leave with…
- clearer preparation tools for pressured conversations
- more grounded, direct and empathy-led communication
- greater confidence in saying what needs to be said
It’s not just about staying calm. It’s about helping your team handle difficult conversations with clarity, empathy and authority.
Most teams do not struggle because they do not care. They struggle because difficult conversations are loaded: emotion rises, pressure kicks in, people get defensive, dominant voices take over and what really needs to be said gets lost.
This programme helps your team build a shared approach to handling those moments. We work on preparation, language, presence and clear expression so people can stay grounded and communicate directly without becoming combative.
The result is not forced confidence. It is better judgement, stronger communication and a more useful way of navigating difficult conversations at work.
This is especially powerful for teams who need to give feedback, stand their ground with ideas, challenge well and make sure quieter voices are not drowned out.
The aim is a common language and skillset your team can actually use when tension is present, not just when things are easy.
Want to explore whether this is right for your team?
Book a short meeting and we’ll look at where conversations are getting stuck and what would be most useful.
The 6 steps we’ll work through together.
The programme gives your team a practical framework for preparing, navigating and reflecting on difficult conversations, so they can stay clearer and more effective when it matters.
Identify the different categories of challenging conversations in your role and sort them into clearer preparation styles.
Develop an empathy-led way of preparing so people can go into difficult conversations with more awareness, clarity and intention.
Learn language that helps your team give and receive feedback directly without escalating, softening too much or losing the point.
Build strategies for coping in real time, maintaining presence and communicating clearly when pressure rises.
Work with concepts such as observations vs evaluations, feelings vs thoughts, needs vs strategies, requests vs demands, SMART language and non-violent communication.
Rehearse in a safe space, then use materials, workbooks and follow-up coaching to help the learning embed into day-to-day work.
Fact finding, immersive workshop, then follow-up integration calls.
- Fact finding. We start by understanding the kinds of challenging conversations your team is dealing with and where the biggest blocks are.
- 1-day immersive workshop. The main training is usually delivered as an immersive day (or split over two 1/2 days), giving your team time to learn, practise and build shared language together.
- Safe rehearsal. During the work, people get to practise and troubleshoot in a non-judgemental space rather than trying to learn live under pressure.
- Follow-up accountability coaching. After the workshop, we support integration so the work does not stay theoretical and actually shows up in real conversations.
What’s included
- Fact finding and programme tailoring
- 1-day immersive workshop
- All materials and workbooks
- Follow-up accountability and action coaching
- Tools for feedback, conflict and pressured dialogue
- Online or on-site delivery
This programme is designed for teams who need a practical way to handle pressure, feedback and challenge without losing empathy or clarity.
Curious what this could look like for your team?
Let’s talk through the difficult conversations your people are facing and whether this is the right fit.
Clear pricing, immersive delivery, practical follow-through.
We’ll always start with a conversation. From there, I’ll shape the delivery around your team, the kinds of conversations they’re navigating and what you want to shift culturally as well as practically.
This work is often funded through leadership, culture or professional development budgets. I’m happy to provide what you need internally for that conversation.
This is designed to help your team handle feedback, friction and challenge more clearly, not just talk about communication in theory.
We rehearse the hard bits before people have to do them live.
One reason difficult conversations go badly is that people are trying to figure out language, tone, regulation and timing all at once in the moment.
This programme gives your team a safer place to practise, reflect and sharpen their approach first, so they are better prepared when the real conversation comes.
Book a short call about your team.
If Challenging Conversations at Work sounds like it could be a fit, the easiest next step is a relaxed meeting to talk through your team, the conversations they are facing and what you’d love to be different afterwards.
We’ll explore what’s needed, what format would work best and whether this programme is the right container for that work.
Choose a time on the calendar and you’ll get an automatic Zoom link and confirmation email.
Prefer messaging? WhatsApp me here to start the conversation.
What clients say.
“Matt’s session was transformational, not just for myself but for other attendees too.”
Meg Fen – BrightonSEO Speaker“Matthew’s 6-Point Speaker Programme is a game-changer. His structured approach helped me refine my communication style, build confidence, and deliver with impact and credibility.”
Tom McMahon – Lead, EMEA Communications, MongoDB“I had the privilege of attending Matt’s coaching and it was nothing short of transformative. I walked away not just with new skills, but with a completely different relationship to speaking.”
Verity Stainsby – Director, Chrysalis Talent Development LtdLet’s help your team handle difficult conversations with more clarity, steadiness and skill.
If you’re curious about Challenging Conversations at Work, the best place to start is a straightforward conversation about what your team is dealing with and what would be most useful.
Or send me a quick WhatsApp with what your team is navigating.