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Best Work

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Careers Technology

#66 Kimeshan Naidoo - The philosophies of work

In this conversation, Ben speaks to Kimeshan Naidoo, the CTO at BX, and former co-founder and CTO at UniBuddy. They explore stress, health, meditation, stoic beliefs, and the philosophies that guide Kimeshan’s working life.

#65 Mike Fisher - An accountability community

In this conversation, Ben speaks to Mike Fisher, the (outgoing) CTO at Etsy. Mike and Ben discuss why he sees high-performing teams as “accountability communities”. Why grounding our identity firmly in our job title is misguided. How he’s found the courage to ask critical questions of himself and his peers. Why his career has been defined more by running towards things he loves than away from things. And why scrutiny is important to his work. Mike has built multiple consequential companies - and through his insights - it is clear why he is so well regarded.

#64 David Heinemeier Hansson - The purpose of humans

In this conversation, Ben speaks to David Heinemeier Hansson, the creator of Ruby on Rails - and Co-owner & CTO of 37signals - the company behind Basecamp and Hey.com. They explore David’s past and it’s influence on his work. Why he finds meaning by pushing himself harder. Stoicism and its continuing influence on David’s life. How to externalise factors beyond our control. How to work through adversity. The differences between loyalty and obligation. The meaning of legacy, and much more. It makes for the type of conversation Ben wishes he'd had years ago, and one he won’t forget.

#63 Andy Skipper - Coaching and empathy

In this conversation Ben speaks to the Founder and Chief CTO Coach at CTO Craft, Andy Skipper. Andy was previously the CTO at MADE.com, Lumitrix and Comic Relief before founding CTO Craft. After finding himself in a CTO role at a pre-product startup almost by accident, Andy had his first experience of burnout. Experiences like this early on in his career seem to have fuelled Andy to look for opportunities that save people from similar circumstances, highlighting red flags to people early so they don’t have to learn through experience. They discuss self-awareness, Andy’s early influences and the value of professional coaching, as well as Andy’s own experience with chronic illness and how that’s affected how he uses his energy effectively. Andy has a deep care for individuals, learning from environments where he wasn’t able to access the support he needed to grow. He now places a lot of focus on helping to improve the individuals within a team, not the entire unit, putting more emphasis on a coaching style of leadership, driven by empathy. Their conversation is highly personal - and by going so deep - they uncover truths all of us experience - but don’t articulate. Multiple people recommended Ben speak to Andy - and after listening - he thinks you’ll see why

#62 Sara Stephens - Build yourself as a new person

In this conversation, Ben speaks to Sara Stephens, CTO & Co-founder at Rest Less. Her own story is a distinctive one, which has seen her uproot herself geographically throughout her life. Sara speaks in detail about the process of self re-invention that accompanies each of these shifts. And she shares how she realised that other needs besides her financial ones could be satisfied through work. Rest Less is a digital community for people in their 50s and 60s, with support on a range of topics including work and careers. As such, it is unsurprising that the impact, and irrationality, of ageism at work is one area on which Sara shares her insight during their discussion - one that many of us over look.

#61 Min Ong - Growth and fulfilment

In this conversation, Ben speaks to Min Ong. Min is the ex CTO at nate and now an Engineering Manager at WeTransfer. They discuss how Min transitioned from an IC role to a managerial one - a move that was not straight forward. They talk through the challenges associated with changing your place of work, and the importance of creating environments where people can safely reflect. At every step, Min accepts the challenge of being true to her intrinsic long-term motivators - and their conversation is a deep dive into the mind of someone not willing to sacrifice what matters to them.

#60 Kate Pljaskovova - Boxes and clouds

In this conversation, Ben speaks to Kate Pljaskovova, Founder and CEO of Fair HQ. Ben and Kate discuss how work and a career take shape - and use her own experience as the backdrop. In an interesting turn of events, having begun as a nanny, she stumbled into working for the start-up the child’s father was building … and then didn't look back from there. They reflect on the importance of patterns, in our cultures and our memories, and reflect on the influence of our parents. Kate talks about why she feels able to step “outside of the box” in a way that others can’t - and she reflects on becoming a mother. Kate’s expectations of work, are defined above all by freedom, learning, autonomy and this sense of adventure. She makes big career decisions based on learning and excitement, not opportunity cost - and it makes for one of the most free-flowing conversations to date.

#59 Irina Bednova - Output and ourselves

In this conversation, Ben speaks to the Founder and CTO at Cordless, Irina Bednova. Irina is an experienced Software Engineer, having led payments and operations at Monzo before leaving to join EF and found Cordless. Irina is beautifully, and brutally, honest. She approaches taboo subjects like being money-motivated with a refreshing honesty that make the counterintuitive feelings we associate with them wash away with clear logic. They talk though independence and how we can understand and respect our own limits when applying ourselves to work, and the safety nets we can build into our professional lives so that we engage with it in the long run. They also talk the psychological battle of fundraising and more. Irina communicates with such truth and honesty - that her prolonged self-reflection makes it easier for us to frame how we view our own work..

#58 Charlene Hunter - Creating a community

In this conversation, Ben speaks to Charlene Hunter, CEO & Founder of Coding Black Females. Coding Black Females is a nonprofit organisation who support Black female developers by providing networking events and learning opportunities. Charlene talks Ben through the incredible story of how she founded CBF. She talks about the fact that opportunities that seem to just “fall into our lap” are often the result of years of dreaming and painstaking planning; and that big, “risky” decisions can be made in a risk-averse way. Charlene talks about the barriers to entry for black women into technology, both in terms of how lots of companies sometimes think about recruiting, and how would-be engineers pigeon-hole themselves. And fascinatingly, Charlene describes herself, and perceives her work at CBF, as an exact mix of the careers of both her parents. They talk about the influence that parents, and grandparents, have on us as individuals, as well as the way in which inspiring figures are often people who stood for something bigger than themselves.

#057 Olov Eriksson - Facing fear head-on

In this conversation, Ben speaks to Olov Eriksson, Chief Product Officer at Pleo. Their conversation focuses on the intersection between relationships and decision-making. They discuss how Olov prioritises inputs over outputs. He explains how to use and understand your emotions to make big professional decisions. And they discuss the topic of fear; how it can drive us, hinder us, and help us navigate our working journey.

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