Tyson Ballard kicks off his new podcast series with Alistair Maiden, CEO & Founder of SYKE. They discuss how Alistair ended up leaving ASDA to found SYKE, his decision-making process and morning rituals. Detours include evangelising about golf, discussion of Andy Murray’s work ethic and how Alistair juggles being a CEO with being a dad of 3…


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Please note this transcript was automatically generated and has been edited for length and/or clarity.

Tyson: Welcome Alastair to my first podcast for SYKE, very excited. I think we’re going to spend about 20 minutes together. Can you explain who you are, what you do, and how did you end up where you are today?

Alistair: I’m Alistair Maiden, I’m the founder and CEO of SYKE. I was a legal director for ASDA and I was responsible for the contracts team. Like most in-house lawyers I did lots of other stuff as well so I dabbled with IP, I was the protection officer, but fundamentally I got deeply frustrated by the fact that I could see that we could do law better. I think what I now call analogue law was very reactive. Most corporate legal teams were run as mini law firms and there was just such obvious opportunity for operational improvement and digitization that eventually I kind of tipped my hat off and threw it down and said look – I’ve got to do something about this.

Tyson: So, what was the moment in time where you had that internal conversation – you’re going to jump ship, give up your day job, become an entrepreneur and start a company? What was the internal dialogue and conversation you had in your head or with your wife on that day?

Alistair: I think there’s a kind of build-up to it happening which I think is really important. I’d almost compare it to a volcanic build-up really. This is as good an opportunity as any to apologize to anyone who had to deal with me before I made that decision, because I was a deeply frustrated and disruptive senior lawyer in the organization. I would sit in legal leadership meetings and, regardless of whether or not we were discussing an area or a subject matter that was relevant to what I was going to be doing and what I was responsible for, I would just sit there and kind of shake my head and mutter under my breath “but this is not as it should be”. And within my own control while I was at ASDA, I did a lot to rectify that. So first of all, understanding the problems and then data mining to really get into the detail of that, and then redesigning the analogue processes. Engagement with external funds and then digitizing that and creating something new, different, and effective.

Then at that point there was actually a real seminal moment for me where I went down to the law society in London’s Chancery Lane and gave a presentation to in-house counsel on what we’d done at ASDA and first of all I was quite shocked because I thought there’d be about 20 people there and the room was absolutely ram packed – standing room only. There was obviously a real appetite from corporate legal teams to actually change and a group recognition that they could be better.

And then the second thing was I was slated to speak for 20 minutes and there was actually an hour of questions afterwards and there was a real kind of frisson in the air and I remember having a great night out afterwards with some of the guys I went to law school with and there was a real excitement. I got the train back the next day and I just told Natalie, my wife, and she was incredibly supportive of the idea and I just did it. I think it’s really important that I didn’t really make the decision to become an entrepreneur and set up this big business that I’m now part of, it’s just the decision I made was to do something about it.

Tyson: So, you talk about the analogue versus digital which I think is a cool analogy, but what was the problem that you were trying to solve when you started SYKE? And we talked a bit before about how important it is to have a North Star – what do you think the north star is for SYKE?

Alistair: I came to the realization that dealing with things in a reactive way was not sustainable. When I arrived at ASDA, we had a two-week SLA to respond to an email, which is totally ridiculous. I always tell this story but when I used to go into the building at ASDA, I had to use the service entrance because if I went through the main atrium and upstairs and through the trading floor it would take me up to half an hour to get to my desk in the morning. It was people coming to me saying what’s happening with this contract, where is this? I just couldn’t cope with it and nor could any of my team and people were unhappy.

So, my objective but I guess my North Star at ASDA, and it’s still my North Star for SYKE, is the idea that a lot of these smaller requests and routine bureaucracy of chasing stuff down and getting stuff approved, along with basic negotiations should be empowered to the business user. Really the objective is to self-serve these things and that was what was so effective at ASDA was we empowered let’s say the procurement to go into a meeting with a supplier to use let’s call it an interview wizard – a digital checklist – all the things that they will need to agree in relation to a deal. We could guide them on what was an acceptable happy path and what they should avoid and what would require approval. So, for example it was notoriously difficult to get payment terms approved which were variations to ASDA agreed payment terms so we told them that in the questionnaire and hey presto they stopped trying to vary the payment terms and negotiated a bit harder.

They would go through this process with the supplier they’d agree the deal, they’d get their contract immediately if they’d gone down a happy path, the contract would be pre-approved and they could get the supplier to sign the contract in the meeting. There was also a really interesting positioning piece because most suppliers just signed it, they didn’t actually send it to their lawyers to review it which is interesting because we’re looking to that level of empowerment not just to the procurement team but to the supplier as well.

From where we had been it was magical – I wouldn’t use that term lightly but when I first sat in a meeting and saw it happen, I was just amazed that it could be so different to what we’d been struggling against for so long.

Tyson: Let’s talk about something a little bit more personal. You’re very successful, SYKE is doing great. One of the key things that I think are important are rituals, so what are your morning rituals?

Alistair: I’m actually really unstructured in the morning, I have a busy house, I have three kids, one of which is Livia who’s 10 weeks old. The morning tends to be really focused on them and just getting everyone set up and ready in the morning. So, this morning for example my first duty was to wake everyone up and my second duty was to go and get some seriously strong coffee to wake me up! I’m not one of these guys who get up at five in the morning, I don’t do an hour of yoga before work, I’m not like that. I guess it’s just that I quite like to make sure that everyone in the family is set off on the right path and then that allows me mentally to switch on to work. I start work quite early and I work long hours so I need that peace of mind that everyone is okay from a family perspective first.

Tyson: We spend a lot of time advising GCs and in-house counsel to make sure they have the right balance of doing and thinking in terms of the strategy – obviously, the running of a company requires that as well. Do you set aside time for you to do that thinking? It’s not always at your desk or anything like that but where do you do your best thinking?

Alistair: Two things: Swimming and golf.

Swimming is great for thinking and I think it’s because you’re immersed and when you’re underwater or semi-underwater then it blocks out stuff and you can just get on. It’s also very programmatic and routine, so you forget that you’re swimming and I do some of my best thinking when I’m swimming.

But my number one thinking spot is undoubtedly on the golf course. When I really am stressed about something, I’m really lucky that I live right next to the golf course so I just go on my own and work it out over nine holes. I usually come back refreshed and energized. It’s quite interesting because if you’re playing well, you only have to focus for four or five seconds in each hole, the rest of the time you can just think about other stuff. It’s very relaxing and therapeutic but likewise I don’t think it has to be either of those things it could be anything that switches your brain off – for me it’s just those things are convenient for me.

Tyson: And do you find you do your best thinking by yourself or do you tend to bounce your ideas off other people?

Alistair: I have a fairly close group of trusted people that I’ll talk to very regularly but I also think it’s fair to say I do have quite strong opinions on things. Once my mind is set on something I go for it. I think I’m quite good with directional thinking but I’m not very good at detailed thinking so I’ll be like “go and do this please” but I trust the people close to me to actually make it happen. I’m so lucky to be able to rely on the absolutely fabulous people at SYKE who are great at implementing my crazy ideas and that works pretty well for me!

Tyson: What about coming back to your North Star vision of the Legal Tech process, how far do you think the technology providers are away from achieving what is needed and where do you see the gaps in the marketplace at the moment?

Alistair: Well, we’re five years into SYKE and I still think we’re in the foothills of doing this. And why are we in the foothills? I think you’re still seeing quite a lot of consolidation in the market and I still think the technology is generally rather difficult to implement. I think, bizarrely, some corporates still like to implement the technology themselves which never works – that might account for, I don’t need know, 30% of them failing.

I also think and the providers, or all the best providers, are aware of this that it’s still often the case that you buy a shell product and then you need to write the content into the product. Whereas I think most of the best providers are actually aware of that and they are producing products with configurable content and that’s really exciting. SYKE are working on some really interesting stuff with World Commerce and Contracting on that subject – watch this space. I think those things will make it so much easier for this technology to become widespread and adopted.

Most of the configurations that we work on or have worked on so far relate to one part of what’s quite a holistic grounded process. For example, if you break the contract process down, I will say it’s triage, creation, negotiation, approval, signature, storage, management. Most of the projects we’ve worked on so far focus on one, two of those aspects, rather than the end to end. And we have worked on projects that do focus on the end to end and those are so much more impactful, I think.

We’ve got one customer who’ve had more than 20,000 contracts self-serve this year already – that’s such a game changer for that business, it’s a seismic difference and the reason that they’ve done so well is that they’ve tried to address the holistic process rather than part thereof.

Tyson: Switching it up a little bit – what about if you were asked to give a TED talk on something that isn’t your main area of expertise what would the TED talk be about and why?

Alistair: I think it would probably be – and it’s appropriate that I’m being interviewed by an Aussie – I think it would be about why Australia beat England at cricket. That’s like a specialist subject for me…

Tyson: And in an elevator pitch, what would be the takeaway on that?

Alistair: It actually touches back to some of the things that we’ve talked about earlier – I just think essentially, it’s because Australians are relentlessly focused on beating the pomps, whereas we get involved in all kinds of nonsense which is not related to that. If I were running English cricket – which would be great if I could do that one day – I’d just be like stuff everything else we just need to beat the Aussies… I mentioned earlier that directional clarity is so important in any organization, well I know you’re going to go on to interview some of the leading figures in legal technology and I think you’ll probably find from all of them that clarity of direction and I think that’s just absolutely critical

Tyson: Well, we’ll have to try and line up that TED slot for you! What about if you hear if you think of the word success – who’s the first person that comes to your mind and why?

Alistair: Do you know what actually the first person that came to my mind was Andy Murray which is quite weird because he’s not being very successful at the moment but I know Andy Murray is quite a divisive character and a bit of a grumpy Scott. I just always thought whenever I was watching it, this is not the most talented guy, but I was just so impressed through, at times, grim determination, dedication, physical transformation, he was able to compete with the greatest tennis players ever and win! And also, the astonishing pressure when he first won Wimbledon, I mean I just found that incredible.

Tyson: A couple more questions and then we’ll wrap up so the next one is, what advice would you give to your younger self whether it’s prior to university or leaving uni – now that you’re older and wiser?

Alistair: That’s quite easy actually because I was giving some advice to one of our customers the other day who was rather frustrated with his inability to influence organizational change. And for me that was quite easy to give that advice because I was totally in that position when I was younger and I was very deeply affected by that at the time. I think it’s fair to say it influenced my work behaviour, and probably my private behaviour, people who knew me around that time knew me as a very edgy character, very edgy character.

And it’s because really, I was just impatient, I was frustrated, I was the kind of guy who’d get up at the weekend and I’d be like “what are we doing, we have to win and conquer.” And the truth is I wasn’t at that point in a position to make too much of a difference and what I really needed to do, what I would tell myself now is, bide your time, make the right decisions, wait for the opportunity, and then go for it. Go for it with everything you’ve got, don’t hold anything back. Go for it.

And I think realizing to a certain extent that it was outside of my control and therefore not worrying about it too much. I look back and wish I’d done that.

Tyson: And are you the type of person that, to make decisions do you follow your heart or do you use data? Do you consult people? How do you make decisions?

Alistair: Well, you’ve been on the receiving end of this a few times but I think I have an instinct for things – a Spidey sense – but I am also really data driven so I will say “Okay, but what do the numbers say? So, this is what I think but what do the numbers say?”

Tyson: So, instinct drives a hypothesis for you – do you want to prove the hypothesis essentially?

Alistair: Yeah, that is something that’s come to me, the data part of it, that’s come to me latterly actually. So, when I was first into this I was very in-stream, instinct-driven, but I actually over time recognized that that was probably a bit irritating to my colleagues, because I would jump around a lot and I would send them on goose chases. And so over time I’ve learned to say okay let’s take a little bit more time to work out that this is actually the right decision before jumping to it, and it’s a respect thing too.

Tyson: Yeah, all right I think final question just to kind of wrap it up… If you were to think of one song that, what would be your theme song? It could be to life, to SYKE, to you, what would be that song and why?

Alistair: It’s got to be Always Look on the Bright Side of Life. I think that’s really important because most of the people listening to this podcast, whether they’re students or they’re starting out as trainees or down a legal tech path or they’re busy corporate lawyers or whatever, we’re so busy and stressful and pressured… I think it’s really difficult to get to everything but there is a better way, there is a better way and things can get better, and it does require strategy, patience, and persistence but yeah things are always brighter…

Tyson: Excellent all right well that’s it thank you very much, thanks for your time and yeah obviously I’ll be speaking to you soon!