Career Shaping Conversations: Deepa Shekar

Who are you and what do you do?

I’m Deepa and I’m the Chief Operating Officer at Maisha Meds, a donor-backed health tech start-up working to strengthen the private healthcare system in East and West Africa.

My role allows to be to wear lots of different hats. I’m responsible for customer acquisition, engagement and retention, rolling out our programmes, and internal ops.

I love it, and it’s a real privilege to learn about different problems and mindsets, different cultures, and the healthcare systems in different countries.

I studied Law but always knew that wasn’t the direction I wanted to go, so I started my career with Teach First, teaching Citizenship to kids in South London, before moving into consulting at Accenture.

My passion for Africa and start-ups came a bit later alongside a massive life change when I left London and moved to Uganda in 2017.

A conversation that changed things

I met the founders of SafeBoda (an Ugandan ride-sharing app) for a coffee in London as I was really excited about what they were doing, I was really interested in working in the development field, and in moving to Kampala.

I’d emailed them saying that I didn’t have the right experience but I felt I had transferable expertise and skills that could be useful to them. And they agreed!

I went into the conversation with clarity, and knew I wasn’t making a decision out of fear or guilt. I’d always applied for the ‘next’ job, the one I knew I could do, and made sense career-wise. This was the first time I pushed myself out of that comfort zone.

I knew what I wanted to get out of it. I wanted the adventure, I wanted to learn, I wanted to build something. My eyes were open and I was prepared for all eventualities. And it changed my life.

Ultimately, it was a lesson that people don’t always hire you for what you’ve done, but for who you are. If you can articulate your values and what you’ve learned from an experience, then anything is possible.

A wake up call conversation

I was lucky enough to have a coach while I was at SafeBoda and it was during one of our conversations that I had a bit of a wake up call. As much as I loved my job and life in Uganda, I realised that after four years I was ready for a change but wasn't sure where to begin.

Until this point, I really thought that moving on from a job meant getting a more senior job somewhere else. What my coach taught me was that it’s ok to consider other factors in career growth. Your health, where you live, who’s in your life.

Career growth does not have to mean just climbing up the career ladder, it is also about exploring what works for you based on what you need or value in that moment. And that it doesn’t need to be a fixed plan forever, you can change things as often as you like.

What I knew was that I didn’t want to do something that didn’t mean as much as my current job, but I did want to do it somewhere where I could be nearer to the people that mattered, and in that moment, I wanted to do something at a different pace.

Through that conversation I was able to articulate what was most important to me right then, and to accept that it wasn’t ‘unambitious’ to focus on different things in my life.

A conversation that changed my mindset

I’ve always prided myself on being a people person, on leading with empathy and being the ‘friendly’ one but in one leadership role I found I was struggling to make an impact, and these traits - which I’d relied on so often in the past - were not helping me succeed. In fact, I was failing.

While talking this through with a friend, I was pointed to an HBR article about the ‘authenticity paradox’ and it made so much sense. I’d also thought it was important to be my authentic self at work, but realised that by doing that I was inadvertently limiting my own growth by fixing my mindset.

We tell ourselves narratives about who we are, and what we’re like, but the reality is this is often a way to mask our need to change the way we do things. It can stop us evolving and cause us friction and pain at work.

I realised I needed to let go of some of my pre-conceptions about always being the ‘nice’ leader, and adopt different, tougher behaviours which might not feel as natural to me.

So by adapting my style, watching others, and combining elements of myself with the person I needed to be, I was better able to operate as the leader the organisation needed. And I was happier as a result.

Someone I’d like to have a career conversation with...

I would love to sit down for a chat with Erin Meyer - a professor at INSEAD. She’s written an incredible book called The Culture Map which looks at the way working culture varies across different countries.

She defined eight indicators of how cultural differences influence collaboration in global business. For example, how building trust in the US is completely different to how it is in, say, Kenya.

I found her work - which is really rigorous and data-backed - so helpful in figuring out how to navigate the different approaches to work in the countries we operate in. In many African countries, there’s a huge focus on building relationships and getting to know people well socially, whereas in the Global North building trust is more focused on task delivery.

She also co-wrote a book with Reed Hastings, the CEO of Netflix, about the culture there, and it is wild..! So yes, I’d love to pick her brain!

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