The Brief

Planday, a workforce-management platform and part of the Xero group, helps shift-based businesses simplify scheduling, communication, and engagement to empower managers and teams to work smarter and more humanly.

The CEO and VP of People wanted to elevate their Executive and Extended Leadership teams, focusing on trust, psychological safety, innovation and accountability. They’d observed a pattern where leaders were seeking permission before acting, slowing execution and limiting ownership. The goal was to build a culture of empowered decision-making, egoless collaboration and bold, feedback-driven leadership.

Given the seniority and size of the cohort, with almost 20 leaders, credibility and facilitation of the coaches and provider were critical.

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Our Solution

To meet the needs of a time-poor, distributed leadership team, we co-designed a blended learning experience combining virtual and in-person sessions. Two online Masterclasses were followed by a high-impact, in-person session at their London offsite, co-facilitated by two senior facilitators to ensure deep engagement across the larger group.

The three Masterclasses were designed around Planday’s key leadership priorities:

• Fostering a feedback culture
• Building a high-performance culture
• Developing coaching skills as a senior leader

As part of the experience, the team completed Coachable’s Psychological Safety Audit, which is a diagnostic that revealed how the team was currently operating and where trust and safety could be strengthened. These insights were used to spark honest, transformative dialogue about how the team leads, collaborates and challenges one another.

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The Impact

Working with a senior, high-performing team meant expectations were high, but the outcomes exceeded them. Through the sessions, leaders reported feeling more connected, more courageous in their decision-making and more consistent in how they role-modelled feedback and trust.

• Average session rating: 9.78 / 10
• 100% of participants felt more confident as leaders (avg. 9.56 / 10)
• Enjoyment score: 9.78 / 10

The programme strengthened cross-functional trust, accelerated ownership and laid the groundwork for a leadership culture built on empowerment and accountability,  positioning Planday’s senior team to lead with greater clarity and collective impact.

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What are the exec doing differently?

Following the series of Masterclasses, the shift in mindset across the Executive and Extended Leadership teams was immediate and visible. Leaders began translating the learning into tangible actions that strengthened trust, transparency and ownership across Planday.

• One of the ELT said he would be running a dedicated team day on psychological safety, using the tools and frameworks from the programme to spark open, transparent discussions about performance and future direction.
• Leaders committed to “bringing the elephants to the ELT” to address difficult topics directly rather than avoiding them.
• Executives began holding more space for active listening, resisting the instinct to jump into advice and focusing instead on curiosity and coaching-led dialogue.

As one participant noted, “The 5:1 feedback ratio was a new statistic to me, and the content was delivered in an easy-to-remember, super professional way.” Another added, “It was great. I always love the brain science behind it.”

Planday’s CEO, Dave Lee, described all three sessions as “excellent.”

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