From bustling behind the counter at her cousin’s photography shop at just 16, to early mornings processing sales tickets and durable stints at Marks & Spencer throughout university, Jayshree Jupp’s journey into the professional world was shaped by hands-on customer service and a deep understanding of people. These formative experiences not only taught her resilience and empathy but also planted the seeds for her future career as an executive coach. In this insightful Q & A, Jayshree shares how her early working life paved the way for her passion in coaching, revealing the personal values and moments that continue to influence her approach in helping others unlock their potential.
DECD: What was your very first job?
Jayshree:
My working life started early—at 16, I was behind the counter of my cousin’s photography shop, carefully handling people’s holiday snaps and family memories. It was my first taste of customer service, and I quickly learned the power of a smile and a well-timed “your photos are ready!”
On Sundays, while most teenagers were still asleep, I was up at 6am processing sales tickets at a shoe company—lured, quite frankly, by the magic words: double time.
By 17, I’d landed a job at Marks & Spencer as a summer sales assistant, and I kept this job all through university. Every term break, you’d find me back on the shop floor—earning just enough to avoid student debt and learning even more about how people tick.
Those early experiences taught me resilience, empathy, and the quiet strength of consistency—all of which now shape my coaching.
DECD: What inspired you to become a coach?
Jayshree:
It started with a feeling: I was bored. I was working as a medical sales rep for Pfizer—on paper, a great job. I was selling life-changing treatments to doctors and hospitals. But something was missing. I couldn’t shake the feeling that I wanted more… I just didn’t know what “more” looked like.
So I did what I always do when I feel restless—I asked for more responsibility. My manager gave me opportunities to run team sessions, support with selling skills and product knowledge. That was the lightbulb moment. I realised I loved helping people grow. It did something to my soul.
A Field Sales Trainer role came up and I went for it… but didn’t get it. What I did get was a 12-month development plan. It involved shadowing reps, coaching them in the field, and writing up transcripts of every session. It taught me a lot—about listening (properly!), holding back my own instincts, and recognising that great performance can come in many different styles, not just mine.
By the time I completed the plan, I was heading off on maternity leave. While I was off, the same trainer role came up again—and this time I got it.
That role changed everything. It gave me the space to deepen my craft, work with people in a tailored way, and discover that coaching isn’t just about skills—it’s about unlocking what someone already has inside them.
If my manager hadn’t thrown me extra projects all those years ago, I may never have realised what I was meant to do. Coaching makes my heart sing. Helping people see what’s possible—especially when they don’t yet see it—is what I’m here for.
DECD: As a coach what led you to specialise in the particular area that you concentrate on
Jayshree:
I’ve spent most of my career as one of very few ethnic minority women in senior leadership roles. In some organisations, I was the only one. And even when I led high-performing teams, the credit rarely came my way. Their success was visible—I wasn’t. That experience of being both present and invisible stayed with me.
Over the years, I co-founded an Ethnicity ERG, analysed organisational data on pay and performance by ethnicity, gender, and grade—and saw just how deep the inequities run. I also lived them. Being paid less than peers doing the same job wasn’t just frustrating—it shaped what was possible for me and my family. It limited my choices around where we lived, the schools my children could attend, and the future I could plan for.
These barriers—glass ceilings, class ceilings, and the class cliffs that come with them—fuelled something in me.
Now, I coach in both directions:
I support individuals—particularly from underrepresented backgrounds—to find their voice, accelerate their careers, and navigate systems that weren’t built with them in mind.
And I work with leaders inside organisations to become more conscious, more inclusive, and more accountable—so they can be the kind of leaders who don’t just notice talent, but champion it.
I didn’t fully recognise my own potential until my 50s. If I can help someone see theirs earlier— and help organisations become places where everyone gets seen, valued, and paid fairly — that’s the impact I want to leave behind.
DECD: What is the most interesting part of your work?
Jayshree:
It’s witnessing the shift. Watching someone’s perspective of themselves evolve between our first session and our last is something I never get tired of.
I see people arrive tangled—overwhelmed by the noise of work, life, and expectation—and leave lighter, clearer, and more grounded in who they are. They begin to see themselves more accurately, with greater self-awareness and compassion. That shift in energy, in presence… it’s powerful.
What fascinates me most is how, when given the right space—free from judgment, rich with curiosity—people uncover their own answers. As one client put it: “I learnt so much and yet you taught me nothing.” That’s the magic. I don’t give people the map—I help them realise they’ve had the compass all along.
The most interesting part? It’s that quiet transformation. The one where people reconnect with their power, their voice, their dreams—and often, their purpose. Especially when they’ve spent years being told (explicitly or subtly) to play small.
Whether I’m working with an executive preparing for their next big step, or supporting someone from a marginalised background navigating systems not built for them—I get to hold space where life and leadership meet. That’s a huge privilege. And the impact of that work doesn’t stop at the individual. It ripples out—to their teams, their organisations, their families, and their futures.
DECD: What is the one project/case that you’re most proud of in your career and why?
Jayshree:
In 2021, as Head of Talent & OD, I led a full redesign of the organisation’s performance management process—with fairness, trust, and human connection at its core.
Replaced outdated reviews with quality 1:1 conversations and introduced a new 6-point scale to reflect performance more accurately.
Rolled out Emotional Intelligence assessments for all people managers to build empathy and improve leadership relationships.
Co-created organisational principles through a bottom-up approach, engaging staff at all levels to shape how performance and culture were defined.
Investigated concerns from diverse employees (via the Ethnicity ERG) that they were being rated more harshly—then analysed anonymised data by ethnicity, gender, grade, tenure, and age.
Found disparities in ratings tied to ethnicity (not gender), and presented the impact to the executive team—showing the direct link to pay, bonuses, and long-term equity.
Enabled departments to access their own data and required leaders to take accountability during consistency meetings.
Result: Performance ratings became more consistent across all groups. Bias was surfaced, addressed, and no longer ignored.
Why I’m proud: This project was about more than processes. It was about equity, integrity, and doing right by people—especially when it’s uncomfortable.
DECD: What are your thoughts on diversity and inclusion in the workplace in today’s society?
Jayshree:
In today’s workplace, inclusion isn’t about policies or quotas, it’s about whether people feel they matter. Whether they’re truly seen, heard, and valued for who they are—not just what they deliver.
When people have to choose between being authentic and being successful, that’s not inclusion, that’s survival. And when leaders miss that, they don’t just lose people, they lose potential, trust, and innovation.
I’ve seen how bias—both conscious and unconscious quietly shapes who gets promoted, who’s heard in meetings, and who stays silent to stay safe. But I’ve also seen the shift when leaders lean in, act on data, and hold themselves accountable, not just once, but consistently. That’s when cultures change. That’s when performance grows.
This work is no longer just a moral imperative—it’s a business-critical strategy for the future of work. As we move into a more complex, human-centred world of work, leadership must evolve. We need cultures that honour life experience as much as job titles. Workplaces that recognise that life and work don’t exist in silos—and leadership that reflects that reality.
Real inclusion happens in everyday leadership—in how someone is managed, developed, and believed in. When we get that right, we don’t just drive engagement, we build the conditions where people and business grow stronger, together.
Yes, the language around this work can feel uncomfortable or politicised. But the need beneath it is universal: people want to be treated fairly. To contribute fully; to be safe enough to stretch. That’s not just good business—it’s the kind of leadership the future demands.
DECD: What about your heritage makes you feel proud?
Jayshree:
I’m a proud Indian Gujarati woman, born into a Hindu family here in the UK. One of four daughters, I carry the strength of both my culture and the women who came before me.
My parents came to the UK in the 1960s, my dad first, barely 24, leaving behind his pregnant wife. He had to find work, a place to live, and send money home. When my mum joined him with my sister, they had to build a life from scratch, working hard, supporting extended family, and figuring out how to make it in a country that didn’t always welcome them. I was born a year later, their quiet celebration of survival and progress.
What makes me proud is how my heritage has evolved. My family taught me about sacrifice, work ethic, and always putting others first. I saw how we pulled together, not just as a nuclear family, but as a wider community. My father stood up against unfair pay and conditions for Asian and Black workers at Imperial Typewriter in the 1970s. He even met with trade union leaders to fight for justice. That same fight for fairness lives on in me today.
My parents were strict. They believed in arranged marriages and didn’t think girls should go to university. But they also listened. My mum’s lived experience shaped her hope for us: that we’d be strong, independent women who could stand on our own two feet. And we did. My sisters and I were the first women in our family to go to university. That shift across one generation is something I carry with deep pride.
My heritage is my foundation. It’s where strength meets adaptability. Where tradition evolves, and where every step forward carries the legacy of those who paved the way.
DECD: What do you do outside of work?
Jayshree:
Outside of work, I try to live a full and balanced life, equal parts movement, connection, and joy. I go to the gym regularly and recently started lifting weights to feel stronger in both body and mind. I love to travel and explore new places, especially when it involves sun, good food, and books.
My husband and I have a little two-person book club. We read the same novel (usually on holiday) and then hold “official” meetings to discuss the plot twists and debate who we think really did it. It’s one of my favourite rituals.
I enjoy cooking and baking, especially when I’m experimenting or feeding people I love. Eating out is another passion, good food and good company is my ideal combination. I also enjoy going to the cinema and the theatre when I can.
Since losing my dad, I spend more time supporting my mum, and cherishing moments with my two sons (when they let me!). Life is busy and precious—and I try to be present for all of it.
DECD: What’s the most interesting thing you’ve read this week?
Jayshree:
I’ve been exploring the idea of paradoxes—those seemingly contradictory truths that actually coexist and shape our lives in powerful ways.
The one that’s stayed with me? That we grow stronger by being vulnerable, something Jenny Garrett was talking about recently. That leadership requires both clarity and humility. That people crave autonomy and belonging. That progress often begins with slowing down.
It’s reminded me that so much of coaching lives in that in-between space—the tension between who we are and who we’re becoming. And that’s where the transformation happens.
I’m especially drawn to the paradox at the heart of the future of work I’m helping to build: a future that’s more human and more high-performing. One where we honour life as much as leadership. Where we make space for complexity instead of trying to flatten it.
Paradoxes aren’t problems to fix—they’re truths to hold. And I find that endlessly fascinating.
DECD: What’s the best piece of advice you’ve ever been given?
Jayshree:
The best piece of advice I was given – to trust my instincts.
Someone once asked me: “How often have your instincts actually been wrong?” And I realised they never had. My spidey senses go off for a reason and they’ve always guided me, especially when something felt off but couldn’t yet be explained.
That advice has shaped not just how I live, but how I coach and lead. Because instincts, when tuned in, are often our most honest signal. They reveal what the data hasn’t caught yet. They tell us when a space is safe, when a decision aligns with our values, or when someone isn’t saying what they really mean.
In coaching, I help people reconnect with their own inner voice—the one they’ve sometimes learned to mute in favour of logic, approval, or expectation. Trusting your instincts doesn’t mean ignoring evidence; it means letting your whole self be in the room. And that’s where real clarity, alignment, and courage start to emerge.
DECD: What is your favourite movie, book, song, album or quote?
Jayshree:
A Suitable Boy by Vikram Seth.
Interested in working with Jayshree? Find out more about her professional coaching career here.
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