Executive check-ins: experience what good looks like

1:1 check-ins for executives to lead, feel, and role model what good looks like.

Executive check-ins are where wellbeing, leadership, and culture meet.

Led by an organisational psychologist, these 1:1 sessions give executives space to reflect, receive support, and experience what good looks like. It's practical, private, and powerful. The insights are captured directly into the HeyPenny platform, building visibility from the top down and boosting adoption across the organisation.

“Surveys are great for rating your uber ride home but rather inhuman when it comes to understanding wellbeing”

Set the tone from the top

Executive check-ins give senior leaders the opportunity to lead by example, experiencing the HeyPenny approach firsthand and setting the standard for care, reflection, and psychological safety. When leaders go first, it signals that wellbeing isn’t a “nice to have” it’s a shared responsibility that starts at the top and ripples through the culture.

Real conversations, real insights

These aren’t coaching sessions disguised as tick-box chats. They’re confidential, 1:1 conversations designed to explore the pressures, challenges, and psychosocial factors unique to executive life. The insights gathered feed into the HeyPenny platform, building clarity at the highest level and helping organisations move from assumption to action.

Led by an organisational psychologist

Each check-in is led by a trusted organisational psychologist, bringing evidence-based expertise, neutrality, and psychological depth. This ensures leaders feel supported (not judged) and enables conversations that are grounded, safe, and meaningful. It’s not just about asking the right questions, it’s about knowing how to hold the space for honest answers.

Why have executive check-ins?

  • Executives get to walk through the same supportive approach their teams will experience, building buy-in and modelling behaviour from the top.

  • Check-ins provide a space for executives to reflect, reset, and receive the support they often give but rarely get.

  • Conversations reveal the hidden stressors, pressures, and dynamics affecting senior leadership which are often overlooked but critical to address.

  • When leaders engage with the platform firsthand, they’re more likely to champion it across the organisation, driving faster uptake and deeper impact.

  • Having leaders participate in wellbeing conversations sends a clear signal: care isn’t just encouraged, it’s embedded and woven in at every level.

  • All insights from executive check-ins are fed into the HeyPenny platform, contributing to a clearer picture of organisational health from the very top down.

Strong communication is one of the most powerful predictors of leadership success.

The research is catching up to what most of us already know. Strong communication is one of the most powerful predictors of leadership success. And yet, it’s still one of the most underdeveloped skills at the executive level. 1:1 check-ins create a rare space for leaders to actually practice in real conversations, real time and with a real expert. It’s not theory. It’s experiential learning that sharpens how leaders listen, respond, and connect. The payoff? More capable leaders, more cohesive teams, and a culture that actually communicates.

Want to see how it all fits together?

Executive Check-ins are just one part of the bigger HeyPenny picture. Explore how we support organisations at every level: building capability, culture, and care from the ground up.

HeyPenny Approach
A leader-led approach for creating lasting cultural change.

Leadership Training
Practical, psychologist-led upskilling for confident, capable leaders.

HeyPenny Platform
Your central hub for conversations, insights, and action