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Unlocking leadership clarity and resilience with coaching: The Oddbox journey

When you are the co-founder of a purpose-driven business, the pressure to deliver on both impact and growth can be immense. For Deepak Ravindran, co-founder of Oddbox, the UK's sustainable food delivery company tackling farm-level food waste, the scaling journey was full of rewards but also real challenges.

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I was figuring out how to bring my wider senior leadership team along with my vision.

Deepak Ravindran | Co-Founder, Oddbox

As Oddbox moved from scrappy start-up to retail expansion, Deepak found himself grappling with questions that many leaders face but rarely say out loud:

  • How do I bring my senior leadership team with me as the company evolves?
  • Is my leadership style still serving the business or holding it back?
  • And perhaps hardest of all: am I still the right person to lead this next stage?

The weight of these questions left him feeling isolated, burnt out, and risk averse. It was an uncomfortable place for an entrepreneur whose mission relied on innovation and boldness. That is when he turned to More Happi coaching.

"Before I first considered booking a coaching call with More Happi, I was facing three main challenges. In the short term, I was trying to bring my senior leadership team on board with my vision – expanding our branded products and bringing them to life in retail. This shift required strong alignment, clarity, and belief in our future direction from the senior leaders. On a deeper level, I was also questioning whether the founder journey in a scale-up was still the right fit for me moving forward."

Rethinking Coaching

I just thought coaching was for the preserve of the elite and not for average people like me.

Deepak Ravindran | Co-Founder, Oddbox

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Like many founders, Deepak saw coaching as something reserved for corporate executives or people in crisis, and his early experiences with coaching had not helped much either. He found the open-ended questioning style frustrating, especially when what he really wanted were clear, actionable solutions.

"Before my experience with More Happi, I thought coaching was just for high-powered executives or people in the middle of a major crisis. It didn't seem particularly relevant to me, we were just trying to hold everything together. I'd tried coaching before but found the open-ended questioning frustrating; I was too impatient and wanted quick answers. Honestly, I believed coaching was reserved for the elite, not for everyday people like me."

And yet, something had to change. Oddbox was growing, and so were the demands on him as a leader. He realised that without support, the pressure might not just limit him, but also the culture and potential of the business he had built. That is where More Happi came in.

Why More Happi worked

No risk, no long contracts

He could trial different coaches until he found someone who fit his needs.

Easy to use

A simple booking system, clear coach bios, and scheduling that worked around a founder's busy life.

Confidential and safe

A space to express doubts and emotions that were not easy to share with colleagues, mentors, or peers.

Company backed

Because Oddbox covered the cost, there was no personal financial barrier to engaging fully with the process.

"The mentors I'd worked with in the past were great but expensive and time-consuming, often involving 90-minute sessions and six-month commitments. More Happi, on the other hand, felt approachable and flexible – it gave me a chance to explore coaching with low risk in a low-ego environment."

How coaching led to a mindset shift

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“After coaching, I started letting go of control more and focusing more on empowering the team.”

Deepak Ravindran | Co-Founder, Oddbox

Before coaching, Deepak's leadership style leaned heavily towards over-functioning. He was taking on too many problems himself and focusing on delivering answers quickly. It kept the business moving but left little room for his team to grow.

Through coaching, he learnt to:

  • Let go of control and give his team space to lead.
  • Stay curious about different perspectives rather than rushing to solutions.
  • Foster collaboration instead of relying on directive problem solving.

This shift not only lifted some of the weight from his shoulders but also transformed team dynamics. Decisions sometimes took longer, but they were stronger and more importantly, they were owned by the team. Along the way, Deepak also found greater self-awareness. He slowed down, aligned his actions more closely with his values, and learnt to lead with empathy and presence instead of intensity and urgency. By naming and exploring feelings in coaching sessions, he reduced his emotional burden and rediscovered the joy of leadership. Most importantly, coaching gave him the clarity to make one of the hardest decisions of his career. He recognised when it was time to step back from Oddbox and explore a new path more aligned with his personal values.

"People want to feel valued – not just told what to do. When you hire smart people, they want to contribute to solving problems, not simply execute orders. Shifting from a directive to a coaching style might take longer to reach an outcome, but it leads to better results for both the business and the team. People feel included, collaborative, and part of the solution – and that sense of value makes all the difference."

Beyond Oddbox

“If coaching has changed you and who you are as a person, that’s all the reason you need.”

Deepak Ravindran | Co-Founder, Oddbox

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The impact of coaching did not stop with his role at Oddbox. Deepak's new approach carried over into every part of his life. He found himself better equipped to handle difficult conversations, more patient in tricky situations, and more resilient under pressure.

The transformation was so profound that Deepak is now training to become a coach himself. He brings coaching principles into his mentoring of other founders, his advisory work, and even his parenting by choosing curiosity and open questioning over prescribing solutions.

"The personal and professional shifts I noticed during my experience of being coached with More Happi were kind of twofold. I'd become more self-aware and honest with myself as well about what I really wanted, not what I thought I should want or what other people wanted, like my parents, for instance. And coaching helped me slow down, tune into my values, understand what my values were in the first place, and lead more deliberately and intentionally."

Advice for other leaders:

Deepak now actively encourages other leaders, especially those in fast-growing businesses, to try coaching. His advice is simple:

Start small

Book one session and approach it with curiosity.

Test and learn

Trial different coaches until you find the right fit.

Pilot with a cohort

Give a selection of your leaders access and see the impact.

"Coaching helped me develop patience, with myself and with others, and learn to sit with tension instead of rushing to fix things. It also strengthened my ability to listen deeply and reframe challenging interactions, seeing them not as personal attacks but as opportunities to understand different perspectives."

The More Happi difference

Deepak's journey with Oddbox highlights exactly what More Happi is about. It makes coaching accessible, flexible, and genuinely useful for leaders at every stage. He describes More Happi as a turning point not just because of the coaching itself, but because of how accessible and flexible the platform made it.

For him, coaching provided something no book, course, or peer group could. It offered a personal mirror and sounding board, a safe space to explore challenges, and practical tools to grow as a leader and as a person.

Whether you are scaling a start-up, navigating leadership transitions, or simply seeking more balance, More Happi offers a practical way to unlock clarity, resilience, and authentic leadership.

For Deepak, it was nothing short of transformative. For other leaders, it could be the support that makes the difference between surviving and thriving.

Oddbox × More Happi in numbers

223
Coaching sessions completed
61
Active users accessing regular support
4.8/5
Excellent coach quality rating
84%
Would recommend More Happi coaching to a friend or colleague
26
Diverse coaching programmes utilised
2023
Joined More Happi

Team testimonials

"I had a great coaching session with Helen. She helped me look at my challenge from new perspectives and gave me the confidence to take a first step. She had a really calm and thoughtful approach, she listened intently and guided me using some great techniques to come up with possible steps forward."

Oddbox team member

"Completing this coaching programme with Jessica really helped me reflect on how I approach relationships at work – especially with cross-functional leaders. It clarified my thinking, sharpened my strategies, and helped me refine how I show up to have a greater impact and deliver more value to the business."

Oddbox team member

"Mel was absolutely fantastic during our coaching session today. She was incredibly patient as I worked through explaining the issue I wanted to solve. She didn't rush me at all, and her ability to ask exactly the right questions led me to a huge 'aha!' moment."

Oddbox team member

"Andrew was incredibly helpful in asking the right questions to help me untangle how I could improve my work/life balance. He guided the conversation in a way that helped me reflect more deeply and pinpoint exactly what needed to change."

Oddbox team member