System Changer Interview: Abadesi Osunsade
“It’s a hard time to be in the tech industry. We’re in the first ever downturn since I started Hustle Crew and there are very vocal, well respected leaders in tech who are devaluing the work that I do. Elon Musk takes over Twitter and fires the entire ethics department. The Founder of Basecamp says he no longer wants to be guilt-tripped into doing diversity work and he’s grateful for it. You have to take a step back a little bit and work out how to react to that. And the way I’ve done that is to focus on the leaders who are rightfully thinking about this long-term and not divesting. It’s a different world to two years ago but doing any type of entrepreneurial work, you’re going to have to constantly adapt.”
Abadesi builds products for ambitious and inclusive leaders. She is Founder and CEO of Hustle Crew, a diversity-in-tech community that turns insight into inclusion education for employers. She has professional experience in growth and product roles at leading tech companies like Product Hunt, HotelTonight (acquired by Airbnb), Amazon and Groupon. Most recently she served as Brandwatch's first ever Global Vice President of Community & Belonging from 2020-2022.
Abadesi is the co-host of Apple Podcasts' Top 20 tech podcast, Techish, part of the HubSpot podcast network. In her free time she loves to write. Her careers guide 'Dream Big. Hustle Hard: The Millennial Woman's Guide to Success in Tech' is available on Amazon.com with 5-star reviews. You can also read her articles in publications like Bloomberg and The Financial Times. Her work has been recognised with many awards, such as The Financial Times Top 100 Influential Leaders in Tech and Forbes 25 Black Business Leaders To Follow.
So tell us about your journey, Aba!
My upbringing plays a huge part in being drawn to diversity and inclusion because, well, first of all, I grew up in a multicultural family and that meant that my life was diverse by default so that was my norm growing up. Frankly, growing up as an international school kid spoiled me because I was used to going to school with people from all corners of the world, every religion or no religion, different languages. It wasn’t unusual for my friends to be incredibly culturally sensitive and aware. I think back to my 12th birthday party in Kenya and there were people from every continent there, we were playing games from every kid’s country! 20 years on from that I realise how special and exciting that was, to have my curiosity constantly piqued, and my assumptions constantly challenged, by the people around me. I think as I got older in my career I really missed that. My first startup experience was anomalous in that it was diverse. It was Groupon, a year before the IPO, it was growing so quickly that I guess there wasn’t time to let affinity bias win, which is what usually happens when you’re building a startup. Leaders were probably thinking “crap, we need everybody!” Spending three years there and taking that for granted meant that no team I’ve worked with subsequently has compared.
That’s why I started working on Hustle Crew. I had a deeply personal reason for starting my business. I was working in a startup where I faced microaggressions and I felt excluded. There was also a bigger theme which was knowing how fun it is to be in a diverse environment, and I wanted everyone to have that fun at work! I was the only black person on my team at Amazon and Hotel Tonight, and they were not fun experiences. Being ‘the only’ or ‘one of the few’ is never as fun as being one of many diverse, interesting people.
When you’re in an environment which is all about “innovation” and “getting out of your comfort zone”, it doesn’t really work if everyone’s from the home counties… It felt so performative because we were in an echo chamber of people who were largely the same. I was very mindful of the limitations of homogeneity and when I challenged the culture and the lack of representation, I saw the limits of their comfort zone and their willingness to experiment and innovate, so I guess I was right!
Can you explain the work you do?
If I was to summarise the work that I do, I’d say that I’m in the business of re-distributing power. I’m very aware of the systems of oppression that exist, whether it’s capitalism, the patriarchy, white supremacy, and I’m very interested in how I can re-distribute power in these systems and one of the ways to do this is through education. At Hustle Crew we’re trying to give power to employees to get the changes they want from leadership. We’re trying to give power to women to get the changes they want from their male leaders, to people of colour to get the changes they want from their white allies alongside them. When I think about Techish, my podcast, I think about all of us interacting with technology and how important it is for us to have a voice in how we interact with it and recognise that we can have a voice in that. Whether that’s going directly to the makers of the product or whether it’s going directly to our elected politicians and campaigning for change around how our data is used, how our privacy is protected, how corporations are taxed.
I play lots of different roles! I’m a trustee at Art Fund and I was really excited to be involved in the arts because I believe that education comes in many forms, obvious ways and less obvious ways through art and the media. The stories we consume are the stories that we believe and that shape our decisions and our actions, and I’m fascinated by the storytelling that happens in the arts and the capacity it has to make us better humans. To make us kinder and more loving humans! So getting involved in what work gets commissioned, and what work takes up space on walls is really powerful. I’m also an Angel Investor because I think it’s important for me to put my money where my mouth is. I remember how sad I was when I was first starting Hustle Crew, going to meeting after meeting with investors, hearing people tell me my idea was never going to work. So I said to myself, if I’m ever able to, I want to be in a position where I can tell women and other underrepresented founders with good ideas to keep going. I don’t ever want to be the person who crushes a dream, especially for an under-served market, who am I to decide?
Re-distributing power is about getting people to change and getting them to act differently. I think we can influence people and I’m really creative with all the different ways that I do that!
What’s it like for you, wearing all those different hats?
It’s really interesting! I’m the kind of person who, since childhood, starts something then gets bored and struggles to finish things! I remember all my school reports saying “she’s really talented, really bright, but she doesn’t finish things.” When I started working I really wanted to keep doing things on the side so I was blogging, going to London Fashion Week. Recruiters would always mock me and tell me to pick one thing and I was like, “why?!” Who says I have to pick one thing? It’s exciting for me to do many different things and now that I’ve had some success I enjoy proving those people wrong. We’ve got Emma Gannon out there writing ‘The Multi-Hyphen Method’, putting a name on this way of working. I find it an amazing way to stay curious and motivated, and I never get bored.
One of the things I became increasingly concerned about as I continued the Hustle Crew entrepreneurial journey was becoming the problem. A big part of my work is pushing leaders out of their comfort zone and their echo chamber and saying “hey, this is the status quo but it’s not good enough. You need to swim against the tide and expand your mindset.” And started to question “am I becoming that person?” I run an inclusion company, I spend all my time speaking to DE&I practitioners, all the content I consume is Brené Brown and incredible people working in social change. Am I cushioning myself a bit here? I’m excluding certain groups and voices! The irony wasn’t lost on me. I wanted to take on additional responsibilities so that I had greater diversity in my environments, so that I could do the work too.
Tell us about Hustle Crew!
Hustle Crew came from a really dark place if I’m honest. I’d just quit my job at a tech startup where I’d tried and failed to show everyone that what I was experiencing was really problematic. By virtue of being the only black employee, I was the first person to have to bring up why it wasn’t ok to touch someone’s hair without their permission. As the first vocal feminist I was the first person to bring up why it wasn’t ok to Instagram-stalk candidates. One of the most profound conversations I had was with the founders, when I was appealing for their help, and they summarised it as “you’re the only person dealing with this and so you’ve got to fix it.” That’s very reflective of attitudes towards inclusion at the time. It was 2015 and MeToo hadn’t happened. We lacked the language and the awareness to identify the problem collectively. So being able to turn that dark moment into a community was incredible. The first Hustle Crew meetup was full of women in tech talking about what we wanted the industry to look like, how much better it could be. “Imagine if we got regular training on how to fight bias, imagine if we had gender pay gap reporting! Imagine if we had mentors, sponsorship!” We turned that negative into a positive, into a community and then into actual workshops for employers. It’s been such a lovely journey to be on and I’m so proud of the fact that we’ve been able to take our training into organisations like the NHS and help the whole of NHS England to create shared language and shared meaning to promote inclusion together, to be better allies to each other. All of the Bloom & Wild team, all of the AllPlants team. Being able to transform an entire organisation is something I’m really proud of.
It’s also a hard time to be in the tech industry. We’re in the first ever downturn since I started Hustle Crew and there are very vocal, well respected leaders in tech who are devaluing the work that I do. Elon Musk takes over Twitter and fires the entire ethics department. The Founder of Basecamp says he no longer wants to be guilt-tripped into doing diversity work and he’s grateful for it. You have to take a step back a little bit and work out how to react to that. And the way I’ve done that is to focus on the leaders who are rightfully thinking about this long-term and are not divesting. It’s a different world to two years ago but doing any type of entrepreneurial work you’re going to have to constantly adapt.
In 2020 there was an incredibly strong sense of collective power created by lockdown and all of our attention being in the same place, Twitter, Instagram, whatever it was. We as individuals had power collectively, and what we’ve seen shift since then is the fragmentation coming back, which just reminds me of the importance of continuing to re-distribute power.
What are your superpowers?
One of my superpowers is my ability to learn. I’m a very fast learner, I have a brain that can interrogate complex things to the point where I can simplify and explain it to someone else. I’ve not always appreciated my ability to do that, but it’s something that’s come up a lot and it’s something that lots of people in my life are very grateful for.
I’m good at remembering things, things about their lives. I’m curious and nosy so I hold onto little facts about people. I think it’s a really great way to build connection and intimacy. It’s one thing to remember their name and where they work but it’s another thing to remember that their dog’s called Rothko!
What enables you to do work that is really brave?
It’s something really personal. I lost my sister when we were both really young. She died in a scuba diving accident. It’s really sad when someone dies in an accident like that because it’s something they’ve done loads before, something that they love. She was a doctor living in New Zealand, the place she and her husband had chosen to relocate to, where they planned to spend the rest of their lives together until it was cut short. That was an incredibly destabilising life event for me because she was my role model, she was older than me, she looked out for me when I had to start boarding school. A lot of my teenage years, she was my closest family member. When she died I didn’t really know how to keep living for a while.
I think a lot about what I’d say to her now and what she’d think of me now. When people challenge me or my work, the fearlessness and the courage to live my truth, to do what I believe in, comes from losing her. It comes from the idea that I’m getting the chance she never got, I’m already older now than she was when she died and I think about how I don’t want to waste this chance for her.
What does your support system look like?
My husband, of course. We always joke that he’s the silent partner in Hustle Crew. Silent because he’s this cis-het white guy in the background and that’s not super on-brand haha, but it’s cool, he’s flying the flag for us. It’s so funny, in the 90s the saying was “behind every great man there’s a great woman” but now we know that behind every great woman in a heterosexual relationship is a great man! We have dinner together nearly every night and dissect our day.
I rely a lot on a close circle of great women friends and I’ve known them since school. The people I speak to the most are the people who’ve known me the longest. It’s nice to have a group of people I can call upon when a crisis strikes who are not in my industry! We have an iMessage group and we’re often in totally different parts of the world but we speak there daily, whether it’s “send me affirmations I’ve got this talk” or “listen to me vent, don’t give me advice, I just need someone to tell me I’m right for being angry here.”
Other founder friends like Michael who I do the podcast with, he’s also bootstrapped and a solo entrepreneur.
I definitely feel that I’ve lost the shame and stigma that comes from asking for help, the older that I am. When I was young I was too worried about what people thought about me to do that. Now that I’m more internally validated, albeit with some way to go still, it’s a lot easier for me to say “help!” and not feel ashamed about that.
I’ve become very selfish over the last few years. Being in lockdown helped me to focus on my own needs more. I make sure my day includes the things that ground me. Meditation, journaling if I can, reading fiction is very important for me. I have to read or play the piano, something that’s fun. I also love to exercise and look after my body. I have acupuncture. I did a gong bath meditation the other night. The weighted blanket, eye mask, drums, breathing! It was an hour but went so fast. It was amazing to be so connected to my body, when they hit the gongs the vibrations travel through you. I try to do something for my mind, body and soul every day and that’s something I’ve tried really hard to keep up. I’m very conscious that my work is very cerebral and I don’t want to leave my body behind!
What successes have you had in this work?
On the recruiting side of things, I’ve worked with a company who’s leadership had decided that time to hire was the most important factor in their hiring efforts, so hiring quickly is what mattered. And then hiring managers in engineering and product, teams that were very male dominated, who said “well no, because if we just hire quickly we’re going to keep hiring more men so can we hire for diversity?” Being able to make those changes and say just for two quarters lets change the metric, we were able to dramatically increase the representation of women and people of colour in the candidate pool, and I mean 6, 7, 8x what they were seeing before. That for me is incredible because we got leadership to experiment and reap the rewards of that.
Organisations and employees who’ve been through our training now have the language to talk about their experiences at work, to challenge leadership and do things differently. People have said “I genuinely feel the workplace is so much more inclusive now, I see people asking me if I’m ok, checking in. My levels of psychological safety are so much higher than they were before.” By providing a space for people to have these conversations we give them a chance to practise so that it’s not such an alien thing when they’re on their own.
Have you had any experiences of winning over people who are real skeptics?
That’s probably the most satisfying thing I can ever think of! I can think of someone who was in the c-suite in his company and he couldn’t have been more different to me. He was white, middle aged, he voted for Trump. He’d say things point-blank to me like, “I’m offended that you’re calling me privileged.” And I’d be like “ok, let’s unpack that a bit!” I remember we had a conversation about microaggressions and his response to a list of microaggression examples was “I think people are too sensitive these days,” and I found that so interesting. So I asked “ok so if I have a problem with someone touching my hair, that’s me being too sensitive?” Anyway, fast forward two years later, his team had really seen the impact of my training, they were really happy with the quality of candidates they were getting from all sorts of backgrounds, and we were all on a call and he came off mute to say “oh if I may, I just want to say how transformative working with Abadesi has been. I’ve learned so much and I’ve changed as a person and if anyone thinks that carving out time for inclusion work isn’t important I can’t tell you how wrong you are. I was that person and I was completely wrong.” And I was completely blown away! I hadn’t paid him to say that, asked him to say that… he’s just said that of his own accord. I remember messaging my best friends and my husband immediately after and just being like “I don’t know what just happened!” It happened two years after we first started working together, so I guess we slowly chipped away at it over time.
I’m always really excited when people who don’t seem like they’re going to be the most engaged Hustle Crew community members suddenly stand up and endorse us!
What’s in your toolkit?
A pen and a notebook! I still like to write things down a lot. Listening skills. A lot of the time I’ve listened but not always understood and there’s a big difference so I’m always trying to be a better listener. Curiosity is in my toolkit. It’s the key to everything, it makes everything better. It’s a conduit to love, and other positive things. The word “no” is in my toolkit. I’m not great at this, I’m a bit of a people pleaser, but I’m getting better at saying no and being more selective about the people I please!
I’m really into scents and smells, so I’ve definitely got lavender oil and eucalyptus oil in the toolkit. If I’m really upset, a good scent can calm me down a bit!
And then there’s also going to be a snack. It’s important to not be hungry, we can’t think properly when we’re hungry and also a drink of water!
And then the final thing is something that’s really nice to touch, I have shells by my bedside table, maybe a dried flower, stones. I have a pretty good rock collection, some stones that I picked up on the beach in Patagonia, I got some from when I did the fisherman’s trail in Portugal last autumn. Rocks that look cool and remind me of how irrelevant I am to the universe.
What are the three hardest things about the work that you do?
The first is that I’m trying to answer unanswerable questions. This isn’t something I tell my clients all the time because I’m being paid for expertise haha, BUT I’m literally trying to answer questions that Plato asked 2000 years ago. Like “what makes a great leader?” I’m in the business of people and people are complex. The first thing I’d say is that I’m dealing with complex human beings and that makes the work hard.
The second thing is the emotional labour involved. It’s a lot. Sometimes I joke that I wish I just sold zippers! Everyone needs a zip! But instead, I’m in the business of helping people to fix really traumatic things. When clients come to work with Hustle Crew, it’s often because something really bad has happened. There’s lots of pain and emotional scars, and we’re trying to navigate our way through that and create a strategy or new policy. It often stems from a deep emotional experience, and then becomes something quite abstract.
The third thing is that it’s deeply personal. If I could go back in time I’d probably say to a younger version of myself “do you really want to spend every day solving a problem that affects you and your loved ones on a really deep personal level, that you don’t have much power over?” Every rejection of our work feels like a rejection of myself. Every time I say “hey, here’s a better version of the world that would serve me and other people like me better” and someone says “I don’t agree with that”, it’s a little stab in the heart. It’s so personal, it’s inextricably personal and that’s hard. Sometimes I’m really tempted to become extremely compartmentalised, but I don’t want there to be a big gap between work Aba and home Aba, but it’s hard sometimes. Something I can do to make it more sustainable is to have clear lines around when the workday starts and ends, and hold myself accountable to that. It’s also about who’s voice matters. There was a time when work voices were louder than personal voices, and the other thing I’ve been trying to work on is “who deserves my energy?” If I’m using all of my kindness and gratitude in work mode, I’ve got none left! Now, in a really rudimentary way, I try to make it so that when it gets to 6/7pm when I’m shutting my laptop, I’ve still got 50% across the board, not running myself down to empty. And that’s really hard. I’m still learning how to do that.
Tell us about some work in your field that excites you
I’m really excited by the work of AI ethicists. There’s all this assumption around AI that it’s so advanced, the computers are just doing it all themselves now, they’re even designing their own algorithms, but it’s so overstated. Behind every complex automation is a group of human beings who designed a process, chose variables, selected datasets to train these things. We see Teslas all over the place now. What we don’t see is that they don’t recognise dark skin as effectively as white skin. There’s this pioneering group of individuals taking the minefield that is ethics and trying to apply it to one of the most ruthlessly capitalist industries the world’s ever seen… It's such a commendable act. It makes my work look easy! It’s fascinating and incredible for us to be humbled by how difficult it is to answer these hard questions. How do we keep ourselves safe, how do we make this fair?
The founder of the Algorithmic Justice League is amazing, Joy Buolamwini. She has a great TED talk.
What’s the biggest lesson you’ve learned working on this mission?
There is more that makes us the same than makes us different. I’m in the business of helping people to see and celebrate differences, but the more I do this work, the more I see that there is more that makes us the same. Truth be told, if I were to wake up tomorrow a cis-gendered, heterosexual, white man from a privileged background in a really well paid job in the c-suite of an organisation, reporting to a board that looked like me, and an email from Abadesi Osunsade landed in my inbox that said “hey! Invest 50k in training your whole team on how to be more inclusive”, would I be excited? Would I invest in that? Probably not. I try to put myself in the shoes of the people who have the most potential to make us succeed and help us change, because I get it. I don’t endorse it, but I get it! We all like the path of least resistance, right? As I get deeper into this journey, I realise that we are more the same than we are different and the more we use that to understand problems, the easier it’s going to be to solve them.
What have you learned about yourself doing this work?
That most of who I am was already formed in childhood. And a lot of adulthood has been trying to re-discover that person. I find journals from when I was eleven or twelve and I’ve written “I need to be a strong woman in a world where they don’t want me to be strong!” and “I need to be a role model for future girls so they can realise what they’re capable of!” I was a rockstar!
When you go deep on the questions like “what kind of leader do I want to be?”, “what kind of legacy do I want to leave?” and it’s always the same themes, they’ve always been there.
In what ways are you trying to grow as a person?
I want to stay broad-minded. I downloaded Trump’s social media app the other day. I was in America and everyone was talking about it so I thought ok let’s take a look, I don’t want to make assumptions, I want to see for myself. I need to take my own medicine, just like I ask people “how many black women do you follow?” Well, how many white men who vote republican do I follow?!
What does the world look like in ten years’ time if your work has been wildly successful?
If it’s been wildly successful, we’ll all be able to tolerate conversations about healthy work habits and environments without vilifying people. Even if you’re not a dominant voice, or you’re not part of the normative group, when you share your perspective, you’re not going to be attacked or othered for it. People will thank you for sharing.
If you could ask readers to do one thing to support your mission, what would it be?
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