Difficult conversations quest

Practice tough conversations in a safe, playful setting and build a more honest, trusting team.

Let’s be honest.

Your team probably says they value open communication.

But… how’s that going in practice?

  • Feedback isn’t landing

  • Tension builds and festers

  • People talk around problems, not through them

  • And everyone’s just a bit too “nice” to say what needs to be said

The Difficult Conversations Quest is a 2-hour, game-based session that helps teams practise courageous conversations in a low-stakes, high-trust setting.

outcomes

  • A shared team approach to feedback and difficult conversations

  • Greater trust, honesty, and psychological safety

  • Clarity on each team member’s conflict style

  • Tools to handle tension instead of avoiding it

What you’ll gain from your adventure

  • A shared team approach to hard conversations

  • Practical strategies to hold tension, not avoid it

  • Clarity on your own conflict style — and how it shows up

  • Greater trust, honesty, and safety within the team

  • A map for feedback, boundaries, and course-correcting culture

Who should embark on this quest?

  • Teams avoiding conflict or stuck in politeness mode

  • Leaders who want to speak up but don’t know how to land it

  • Companies trying to build feedback culture without the drama

  • Founders and execs who want to hold more tension with more grace

A person's hand holding several booklet-style cards with images and text related to social issues, with a blurry background of colorful lights or objects.

why play?

When the stakes are imaginary, the learning gets real.

This isn’t a role-play exercise where you pretend to be Susan from sales.
This is a fictional leadership challenge where you’ll:

  • Navigate tricky power dynamics

  • Deliver difficult feedback

  • Handle emotional reactions

  • Decide when to push and when to pause

In the process, you’ll surface your real instincts — and learn how to handle tough conversations with more skill and less stress.

how it works

  • 2-hour facilitated session

  • Up to 8 participants

  • Online or in-person

  • Zero improv pressure — all game-based and easy to step into

  • Facilitated by Tamara Buckland, leadership strategist and game designer

Optional add-ons:

  • Custom team feedback playbook

  • 1:1 debriefs for individual development

  • Follow-up workshop to build team feedback principles

What leaders are saying

  • “This is the most unique, wild, engaging and fun workshop I have ever been to. The experience and the learning will stay with me for a long time.”

    Cordula Plassmann | Coach & Facilitator

  • "I think this is an awesome way to bring leadership teams together. Role playing removes the natural inhibitions from the participants and lets you learn new aspects and perspectives, ultimately bringing you a better understanding of the team you work with as well as yourself. "

    Ed Letifov | TechTime

  • “The game creates a safe and engaging environment to explore leadership strengths and areas for growth. The debrief sessions were especially powerful, offering insights that conventional leadership courses often overlook.”

    Annelies Griemink | Thankyou Payroll

  • "Most people have done at least some of the stock-standard professional development that's out there, so why not try something new? The worst case is *just* having a whole lot of fun, and the best case is that fun sparking deep insights and reflections that help you to be a better leader. It's a win win, I reckon."

    Nicole Skews-Poole | Anchordown

  • “I was super sceptical, having never done anything like this before and it being VERY out of my comfort zone! BUT by the end of session one, I had one of those "ah ha" moments, and I then understood what it was all about! I learned so much about myself that I never knew or realised before.”

    Beckie Coe | Thankyou Payroll

  • "A Quest Within" was incredibly fun and engaging. I gained valuable insights into myself and the leadership skills I want to develop. It also inspired me to take action!

    Wenjing Xie | Snapper

  • "It was very enjoyable to partake in a Quest Within and immensely beneficial to learn and reflect on applying leadership skills in an adventure with my co-workers."

    Participant | Snapper

  • "This is the kind of workshop to attend whether or not you have been to other leadership trainings. It will bring up new ideas and experiences that you wouldn't have been able to tap into before. I thoroughly enjoyed this new take on a leadership workshop that I know I will be referencing to others for months and years to come."

    Victoria Young | Zealandia

  • "I haven't been able to stop thinking about my day on the Leadership Side Quest, I discovered unexpected things about myself, learnt a lot from my fellow adventurers, and it has sparked an interest in and joy for incorporating gameplay into my leadership, but also my day to day life - including parenting!"

    Kelly Hudson | Five and Dime

  • "The journey showed me parts of myself that I'd like to focus on, as well as some comparitive strengths through the reflection process. I highly recommend!"

    Angela Wei | Wētā FX

  • "Seeing how your team members react in a situation free of judgement teaches you a lot about them. It's worth doing for any team."

    Patrick Peters | TechTime

  • "It's refreshed my love of giving specific feedback. Receiving feedback on my gameplay was really helpful for reflection."

    Julie Reddish | Catapult NZ

  • "It's a practical, on the court, safe way to enhance leadership skills"

    Rachel Collingridge | Totara

Ready to help your team stop tiptoeing?

This is the safest way to practise the hardest part of leadership.

A person holding colorful game pieces over a game board with rivers, forests, and a small house depicted on it.
Person signing a colorful Exploreer's Log Book for an event on May 9th, 2025, at a table with photos, cards, and game pieces.
A person sitting at a table with a board game, writing and drawing supplies, and a name card reading 'Kelly' on it.
Three women standing outdoors in front of a large tree during daytime, engaged in a discussion; one woman holds a notebook, another a black folder, and the third a log book, dressed in casual outdoor clothing.
A table with various items including a magazine titled 'Explorer's Guidebook', a pink sticky note, several multi-colored dice, a card with the word 'Insight' and an image of a person, two black cups filled with colorful markers, and some sheets of pa
Young man with glasses sitting and writing in a notepad while leaning against a large tree outdoors.
Hand holding five small booklets with titles related to leadership skills, including "COURAGE," "CURIOUS," "TENSION," "INSIGHT," with blurred background.