Interview: Dale Clareburt, CEO of Weirdly

I have to admit, I have a bit of a girl-crush on the person featured in today’s Leader’s Digest interview. Dale Clareburt, founder and CEO of high-growth kiwi tech company Weirdly has attitude and spunk and makes the Energiser Bunny look like a lazy sod. I first noticed Dale’s X factor when I placed her in a senior executive role a few years back. It’s no surprise to me that she’s at the helm of a company that’s turning heads and going places. (Weirdly won the Emerging New Zealand Innovator Award at the New Zealand Innovation Awards in 2015). Here she is to tell us a little about what it’s like to lead Weirdly through its start-up and growth phase and what she has learned about the ups and downs of the tech space.

Dale Clareburt, Weirdly CEO

Suzi: If you could go back in time and give your former self (the one that was just starting up Weirdly in 2014), some sage advice, what would it be?

Dale: Look after yourself more. It’s definitely not going to be a sprint. It’s going to be like running a marathon. No scrap that. You’re running the Marathon des Sables (five marathons across the desert). Don’t use the “overnight unicorns” as your inspiration. The pressure that tech start-ups put on themselves and that is put on them by the industry itself is ridiculous. Overnight sensations are not the reality for nearly every single start-up. The reality is you’re going to be living as if failure is never far from you door. And you have to get used to living like this for a long time.

The best thing is to realise that you don’t actually have to move as fast as you’re trying to make it move. Get comfortable with a slower pace. This is realistically a 10-year journey at least. So take care of yourself, be kind, and make sleeping and eating well your priority.

Suzi: “We learn more from our failures than we do from our successes.” This is the saying people come out with when you’ve just had a monumental f-up (often accompanied by a sympathetic “glad it’s you and not me” look on their face). So with that phrase in mind, minus the look, what’s been the biggest failure you’ve experienced during your Weirdly journey and what did it teach you?

Dale: We haven’t actually had an epic failure as yet. I tried to raise $1 million in NZ last year. I went down some traditional paths and didn’t get the amount I was after. If felt like a failure at the time, but this year I am so grateful that it didn’t work out because we ended up getting money from two amazing investors. It’s not as much as we wanted originally, but we have a new plan for this year and we didn’t end up diluting ourselves. This is the benefit of failures – sometimes failures are actually opportunities in disguise.

Suzi: Unfortunately, as a woman who is a CEO in the tech space, you’re a bit of rarity. I’m going to give you a soapbox for a minute. What’s your soap box message about diversity? You can be just marginally ranty…

Dale: It’s not just about diversity, it’s about inclusion too. There are obvious diversity issues. It’s taken me a while to come to terms with the fact that the most immediate solution is actually tokenism and quotas. We have to get used to seeing more diversity on boards, in C-suites and technology companies. We have to get used to seeing women, and a variety of ethnicities and age groups.

We can’t have diversity without inclusion. When we start opening the doors for more diverse workforces we need to ease the transition. How does it feel to be a minority, what measures are we putting in place to make everyone at ease? How can we make people feel more at ease, welcomed, and valued? If these things aren’t addressed at the same time, then we are prolonging the problem.

Suzi: Having been a recruiter for more than 15 years in a former life, nothing annoys me more than really bad interview questions. One of the worst interview questions IMHO is, “tell us your strengths?” Bleuch. It’s SO wrong on SO many levels. What’s the worst interview question you see trotted out regularly?

Dale: The opposite question is also annoying “what are your weaknesses?” or “what are your long-term goals?”. I think the biggest problem with these questions is the formality of the language. I want to know what people think about these things but no one uses this language any more do they?

I want to know about the things that people deeply care about. What challenges keep you awake at night? When was the last time you volunteered to do something that wasn’t part of your job, or took up your personal time? What’s your favourite activity that you do at work when you need a break? What do you want to be when you grow up? Those questions are so much better than “what are your long-term goals?”.

Suzi: The best leaders I know, work to their strengths and have well developed self-awareness. When are you at your best? And, what feeds that state of flow or that ‘Dale on fire-ness’? Conversely, what are your amber lights, or red flags that tell you it’s time to pause, take stock (maybe have a gin and tonic) and recalibrate?

Dale: I am at my best when I’m sitting with team of people and where I am reacting most of the time. I love to be interrupted and asked questions all day. Making decisions quickly and under pressure is one of my best and favourite skills. I am best when I am talking. I’m an extrovert who needs to get things out and talk things through to get to a good solution.

I know it’s time to take a break when I’m not sleeping well or when I start saying things that sound a bit mad. A skill I had to learn early on was that when I have an idea or a solution I need to take people on the journey with me. I start to sound mad when I just spit out the idea or solution but nobody knows how I got there or why I’m even talking about it. If I’m busy or stressed it can start to hinder my ability to take people on the journey.

I find colouring, going for a walk or having a chat with someone who I don’t normally talk to are the best ways to get my mind to stop racing and calm myself down.

Suzi: Unfortunately the ‘Bad Boss’ stories are plentiful. I’m more curious about the ‘Best Boss’ stories. Who’s the best boss you’ve ever had and how have they influenced you as a leader?

Dale: Easy. Marisa Fong and Wynnis Armour who were the owners of Madison Recruitment. They were my managers for nearly 10 years. I can’t believe how much I grew and what I achieved while I was there. They gave me all the rope I needed, and kept me constantly challenged. It was so much fun too. There were just so many successes.

I think of the time with them as my formative years in management. They both had different styles that allowed me to pick and choose what would work best for me. They taught me how important feedback is when developing people and to make fast decisions under pressure. They taught me to learn fast by sometimes making mistakes. It was a hard way to learn but definitely the fastest.

Suzi: As this is a leadership blog, there might be something we can learn vicariously from your response to this next question. What’s your current ‘work on’ from a leadership perspective? What are you trying to improve as a leader and what specifically are you doing to tackle that?

Dale: I always thought that I led by example and that my example was a good one. But I realised that last year I pushed the pedal a little too hard and was super tired at the end of the year. And that was the second year in a row when I kind of hit a brick wall. I didn’t have the same expectations of anyone else in our team, it was just my MO. This year I’ve realised that it’s about showing the team and myself how to succeed in a way that is sustainable and fun. This is more of an attitude change really. I think about Weirdly all the time. I even dream about it. It’s not that I necessarily need to work less but more that I need to find ways to switch my brain off from time to time. Don’t get me wrong, these levels of intensity can be really beneficial at times. But it’s just not sustainable for long periods.

Suzi: I got my first tattoo this year and I’m totally in love with it. I catch myself lovingly caressing it on my wrist (scary, but true). I think tattoos show us something about the person they are on (hey, maybe something to include in your Weirdly questionnaire?) I noticed yours on your arm the other day when we were talking via Skype and I love it. Tell me something about it; how you chose it, what it means, something about the story of getting it done….anything.

Dale: Tattoos are a fairly personal topic. What I can say is that I wanted a tattoo that was beautiful so I chose flowers. And I chose flowers that had meaning for me. I have a lot of dahlias because my grandfather was famous for growing them, I have kowhai because they make me think of my sister who has lived on the other side of the world for 20 years and whom I hardly see, and I have lilies as they make me think of my mum who I don’t see often enough either. I have other tattoos too. I guess I’m someone who likes tattoos. It’s kind of cool that you can choose something personal and individual.

Suzi: And finally, what’s next for Weirdly? World domination?

Dale: Of course world domination! Ha! Our ulitmate goal is to create a platform that qualifies people on their key characteristics, attributes and aptitudes. And this platform will match people and businesses and opportunities together. Because we believe that the future of recruitment can’t be just about skills and experience. In a world where completely new jobs and new ways of performing jobs are being created every day, and current and old jobs are dying just as quickly, recruitment based on skills and experience just isn’t sustainable. The value placed on attributes such as curiosity, creativity, adaptability and critical thinking is growing every day. This is the future.

Weirdly’s got a way to go on its journey yet, but our overall focus is on evolving our product further down the AI/ML route. We’re only taking the very early baby steps down this path, but the early signs are very promising.

1 Comment

  1. Emma Dean on April 15, 2017 at 11:18 am

    So much of this is so relevant to me right now as my team grows and I strive to be the best leader I can be to the girls in my team. I want to inspire them and gelp them everyday… We definitely learn by our mistakes AND I sooo want a tattoo (also first) for my upcoming birthday!! Want to see yours too btw! Xx

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Suzi McAlpine

Suzi McAlpine is a Leadership Development Specialist and author of the award-winning leadership blog, The Leader’s Digest. She writes and teaches about accomplished leadership, what magic emerges when it’s present, and how to ignite better leadership in individuals, teams and organisations. Suzi has been a leader and senior executive herself, working alongside CEOs and executive teams in a variety of roles. Her experience has included being a head-hunter, an executive coach, and a practice leader for a division at the world’s largest HR consulting firm. Suzi provides a range of services as a Leadership Development Specialist, including executive coaching, leadership workshops and development programmes for CEOs, leadership teams and organisations throughout New Zealand.

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