Practical training for navigating difficult colleagues, interpersonal tension and workplace communication styles.
Working with Difficult Personalities Workshop: What you need to know:
Most workplaces have someone who “feels difficult” to work with. Sometimes it’s a colleague whose communication style clashes with yours. Sometimes it’s a stakeholder whose behaviour patterns leave you drained. Or sometimes it’s a team dynamic where two personalities just don’t click — consequently, everyone else absorbs the tension.
“Difficult personalities” show up in every workplace — and they’re one of the most common reasons HR teams book workshop support.
Our Working with Difficult Personalities Workshop equips teams with practical frameworks for navigating interpersonal tension, without labelling colleagues as inherently difficult. In practice, the workshop reframes “difficult” as a set of behaviours, communication styles and dynamics rather than personality flaws. Participants leave with skills for having difficult conversations, setting boundaries, understanding style differences, and recognising their own triggers. As a result, teams don’t just cope with difficult colleagues — they build better relationships with them.
What the Working with Difficult Personalities Workshop covers:
- What actually makes someone “feel” difficult: Communication style mismatches, unmet needs, behaviour patterns, personal triggers. Participants realise the issue is rarely as simple as “they’re difficult.”
- Personality style frameworks: We use evidence-based frameworks like DISC and the Big Five to help participants understand style differences.
- Recognising your own triggers: Notably, “difficult” is often subjective. Above all, someone difficult for you might be easy for a colleague. In a personal reflection audit notice what triggers your “difficult” response, and what does that reveal about your own style?
- The difficult conversations framework: We teach a practical framework for having the conversation you’ve been avoiding — drawing on the Harvard Negotiation Project’s work on difficult conversations.
- Boundary-setting without escalation: Sometimes the answer isn’t more empathy — it’s clearer boundaries. Learn how to set boundaries that reduce tension rather than provoke it, including specific language for common workplace situations.
- When it’s dynamics vs. genuine difficulty: Not every “difficult” situation is about interpersonal style. Sometimes there’s a genuine performance issue, bullying pattern, or discrimination concern that needs HR intervention. This workshop helps participants recognise the difference — and know when to escalate.
Working with Difficult Personalities Workshop outcomes
After the session, participants typically leave with:
- A clearer understanding of what actually makes interactions “feel” difficult — and what’s within their control
- Frameworks for reading personality styles and adjusting their own approach
- Greater awareness of their own triggers and reactions
- A practical framework for having the difficult conversation they’ve been avoiding
- Skills for setting boundaries without escalating tension
- Confidence to name behaviours without labelling people
- Clarity on when a situation needs HR intervention rather than personal skills
A note on our language:
We call this workshop “Working with Difficult Personalities” because that’s how the challenge gets named in real workplaces — it’s the language HR and People teams use when scoping this training. In practice, though, the reality is usually more nuanced. Notably, someone “feels” difficult when there’s a communication style mismatch, an unmet need, a specific behaviour pattern — or sometimes a genuine personality clash. Consequently, this workshop is built around understanding behaviours and dynamics rather than labelling colleagues. As a result, participants leave better equipped to work with different personality styles — not to categorise which of their colleagues are “the difficult ones.”
When the Working with Difficult Personalities Workshop is the right fit:
This workshop works hardest when one of these describes your team:
- A team where interpersonal tension is affecting how people show up. Furthermore, no crisis but persistent friction — colleagues avoiding each other, meetings getting tense, small comments landing wrong. Consequently, this workshop opens up the shared conversation the team hasn’t been able to have.
- Managers scoping better tools for team dynamics. Notably, most managers weren’t trained in navigating personality differences. In practice, this workshop gives them a shared framework they can use with their teams and in one-to-ones.
- Post-restructure teams with shifted dynamics. Above all, restructure often changes who works with whom — furthermore, some pairings work well and some don’t. Consequently, this workshop helps newly-formed teams navigate their differences constructively.
- Cross-functional teams with different working styles. Notably, cross-functional collaboration often surfaces style differences (engineering vs. marketing, finance vs. sales, product vs. legal). In practice, this workshop reframes those differences as complementary rather than conflicting.
- Teams building psychological safety. Furthermore, teams working on psychological safety benefit from having a shared vocabulary for difficult dynamics. Consequently, this workshop provides that vocabulary.
Particularly valuable for: cross-functional teams, leadership teams navigating personality dynamics, teams recovering from a difficult period, and managers scoping better tools for people leadership.
How this workshop pairs with others
Resilience at Work
Build the capacity to recover from setbacks and thrive under sustained pressure. Pairs powerfully with change and difficulty workshops.
Above all, Working with Difficult Personalities pairs beautifully with our other resilience and change workshops:
- Pair with the Building Resilient Teams Workshop — furthermore, this pairing is our strongest recommendation for teams navigating interpersonal tension. In practice, Building Resilient Teams gives the wider team framework; consequently, Working with Difficult Personalities gives the specific interpersonal skills. As a result, teams get both the collective and individual tools.
- Book alongside the Resilience at Work Workshop — notably, individual resilience helps participants stay grounded during difficult interactions. Consequently, this pair works well as a personal-capability programme.
- Add the Navigating Change Workshop — above all, change often surfaces interpersonal tension. Furthermore, pairing these two helps teams navigate both the change itself and the dynamics it creates.
Above all, many teams book this workshop as part of a broader resilience and change programme — furthermore, tell us your context on the discovery call and we’ll suggest the right sequence.
What our clients say
I can’t thank you enough for the Dealing with Difficult Personalities workshop today. It was simply fabulous and something that obviously resonated with so many people!
About your facilitator
Above all, delivered by an executive coach with 20+ years of corporate experience training teams across financial services, professional services, tech, healthcare and the public sector. Furthermore, our interpersonal dynamics facilitators combine evidence-based frameworks — DISC, Big Five, Harvard Negotiation Project’s difficult conversations research, Amy Edmondson’s psychological safety work — with the pragmatic, no-jargon delivery senior teams actually engage with.
Book a discovery call and we’ll match your team with the facilitator best suited to your context.
Book the Working with Difficult Personalities Workshop
If your team is navigating interpersonal tension, style differences or difficult workplace dynamics — furthermore, let’s talk. In practice, a 20-minute discovery call is enough for us to recommend the right format, facilitator, and whether this works best as a standalone session or paired with our other resilience workshops.
Schedule a call with us, or complete the form below.
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Working with Difficult Personalities Workshop: FAQs
About the workshop
What’s meant by “difficult personalities” in this workshop?
Above all, we use the term “difficult personalities” because it’s how the challenge gets named in real workplaces — furthermore, it’s the language HR and People teams use when scoping this training. In practice, though, the workshop reframes what “difficult” actually means. Notably, someone “feels” difficult when there’s a communication style mismatch, an unmet need, a specific behaviour pattern, or a personal trigger. Consequently, the workshop is built around understanding those behaviours and dynamics rather than labelling colleagues. As a result, participants leave with tools for navigating differences constructively rather than categorising who’s “the difficult one.”
Who should attend this workshop?
Above all, this workshop works for employees at all levels — furthermore, particularly managers, team leads, cross-functional teams and anyone whose work involves navigating multiple stakeholders. In practice, it’s especially valuable when a team is going through interpersonal friction, working across functional boundaries, or building psychological safety. Consequently, many teams book it for their whole team; others book it just for managers as part of leadership development. As a result, we can tailor the delivery to whichever audience you have in mind.
The workshop content and approach
Do you use personality frameworks like DISC or MBTI?
Notably, yes and no — furthermore, this is a nuanced question. Above all, we use DISC and Big Five personality frameworks as reference points to help participants understand style differences. Consequently, these are evidence-based frameworks with strong research foundations. In practice, though, we don’t run a full personality assessment as part of the workshop — that would be a separate booking. As a result, participants leave with a framework for understanding style differences without needing individual assessment reports.
How do you approach the “difficult person” without labelling colleagues?
Above all, this is the core of how we hold this workshop. Furthermore, the reframing is around behaviours and dynamics — not personalities. In practice, we ask participants to think about specific behaviours that trigger their “difficult” response, then explore what those behaviours reveal about style preferences, unmet needs or communication mismatches. Consequently, participants leave with sharper thinking about what’s actually happening rather than fuzzy labels. As a result, the workshop feels more useful and more respectful — furthermore, it’s genuinely more effective at improving working relationships.
Can this workshop help with specific interpersonal conflicts?
Above all, this workshop is designed for team-level skill-building — not to resolve specific ongoing conflicts. Furthermore, if there’s a live conflict between named individuals, that typically needs a different intervention (mediation, HR support, one-to-one coaching). In practice, we can talk about your context on the discovery call and help you scope the right approach — sometimes this workshop is the right fit; other times a coaching-led intervention is more appropriate. Consequently, we won’t push the workshop if a different intervention would serve you better.
Delivery and cost
Do you deliver this in-person and virtually?
Notably, both — furthermore, this workshop delivers well in either format. Above all, in-person lands more deeply for the interpersonal skill-building because participants can practice difficult conversation frameworks face-to-face. Consequently, we recommend in-person where budget and logistics allow. That said, our virtual format uses breakout rooms extensively for paired practice — as a result, distributed teams still get real skill-building rather than just theory.
How much does the Working with Difficult Personalities Workshop cost?
Notably, pricing depends on duration, format, team size and whether you’re booking standalone or as part of a programme. In practice, single workshops start from around £1,500 for a standard 60-90 minute virtual session. Furthermore, half-day bespoke programmes typically start from £3,500. As a result, the best way to get accurate pricing is a quick discovery call — consequently, we can give you a specific quote based on your team’s actual needs within 48 hours.
