The Brief

TrustedHousesitters is the world’s largest pet-sitting and travel community, connecting pet owners with verified sitters to create a trusted, mutually beneficial exchange of care and adventure. 

With a rapidly growing global team and a strong people-first culture, TrustedHousesitters wanted to further equip their Team Managers with the tools and confidence to to approach challenging conversations with openness and candour, ensuring they can bring out the best in themselves and their teams.

As a remote-first business, they needed an interactive, reflective and safe learning space for the team to reflect on the barriers that hold them back from the tough conversations.

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Our Solution 

Recognising that meaningful behaviour change doesn’t come from a “once-and-done” workshop, we designed a two-part Masterclass series to help TrustedHousesitters’ managers build the confidence and skill to navigate difficult conversations effectively.

Across the two 2.5-hour sessions, delivered virtually a few weeks apart, managers explored:

• Their own mindset blockers and triggers around giving feedback
• The company’s feedback culture — where it was thriving and where it needed a reset
• The neuroscience behind defensive reactions and how to manage them
• How to facilitate feedback conversations with curiosity, empathy, and coaching techniques

Spacing the sessions gave managers time to practise and embed their new skills between workshops, bringing real examples back for reflection and refinement.

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The Impact

The result was a noticeable shift in both confidence and behaviour. Managers began initiating more feedback conversations, approaching them with openness and composure rather than hesitation.

Every participant reported feeling more confident to give and receive feedback, with outstanding engagement and satisfaction scores:

• Average session rating: 9.26 / 10
• Facilitator rating: 10 / 10 (yes, we have cracking coaches!)
• 100% said the workshops were both interesting and enjoyable

Most importantly, managers left with practical tools and the belief to have the conversations that strengthen trust, accountability and performance across the business.

Participant Testimonials

“Everything covered was relevant to our existing company culture and prompted open, transparent discussions.”

“It was comforting to hear other people's similar experiences around giving and receiving feedback. Reminder to myself to focus on open and honest communication”

“I think it was good to have some self-reflection on what I need, as I don't often take time to do this. I am able to focus on external problems to fix than actually thinking about what I might need too”

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