Skiller Whale

‘I was really impressed with the overall quality of the experience and the session itself. If I were running a team now, I would contact Skiller Whale to discuss how they could help support my team’s development.’

Joel Chippindale, CTO Coach and Adviser

In CTO Craft’s world of technology startups and scale-ups, training in technical skills is generally looked at through squinted side-eyes by management. It is often relegated to an activity that team members are expected to pick up on their own time, even if the budget is made available. 

The standard for building skills is typically self-paced, with traditional live training seen as overly expensive and not impactful enough. “Live” learning and learning as a group has fallen by the wayside while being a great way to build and embed knowledge, and Skiller Whale have thoughtfully stepped into that void with a new approach. 

We wanted to see what all the fuss was about, so Joel Chippindale, CTO Coach and Adviser, and I experienced the product ourselves and spoke to people in our networks who had used it to ascertain how far the approach could accelerate the kind of ‘organic’ learning we’ve learned to wait years for in our tech teams.

In this review, I’ll discuss with Joel how he sees the future of technical skills training and how Skiller Whale can continue contributing to the successful development of engineers’ skills.

Who are Skiller Whale?

Founded in 2018, Skiller Whale has bridged a gap in the market to personalise technical skill learning by teaching through live team coaching. They work with companies like Pleo, Wagestream and JustEat For Business as an adjunct to their tech strategy.

The Skiller Whale live team coaching is personalised to meet individual needs; it gets to the heart of learning and focuses on existing skills gaps rather than wasting time covering areas that individuals already know. It could shape the future of technical skills learning and help CTOs solve team development issues.

My interaction with Skiller Whale

I met Skiller Whale CEO Hywel Carver long before Skiller Whale was born. When I was a freelance CTO, Hywel approached me to discuss the freelance world, and since then, we have worked together on a few different projects. 

Now, Skiller Whale is a CTO Craft sponsor, something I’m pleased about as our content aligns in many areas. 

Skiller Whale supports us by speaking at our CTO Craft conferences, cobranding dinners, sharing knowledge with our audience through our Bytes training sessions, and writing insightful blog posts for us. We’ve also worked together on their podcast. We have a close relationship, and I’m happy about that.

While I felt confident that I could write a completely objective product review, I fully appreciate that there could be a perception of a conflict of interest. For that reason, I brought Joel Chippindale in as an impartial third party. 

Meet Joel Chippindale

‘I could see this being particularly useful for newer starters switching tech stack and increasing the depth of knowledge across the wider team.’

Joel Chippindale

Education has permeated Joel’s career as he was once a maths teacher and was CTO at education learning company FutureLearn. Today he focuses on CTO coaching and mentoring.

He said he has always been interested in developing his teams, ‘A key part of the role as a CTO is to build a team who can deliver and ensure that the team is more capable next year than it is this year. Developing skills across the team is essential to this.’

Joel and I met years ago when Joel was thinking about his next CTO job, and he said, ‘Andy was a really good person to speak to because he seemed to know everyone in the CTO world in London. More recently, I’ve been very privileged to join the roster of CTO coaches for CTO Craft.’

The current technology landscape

While there’s no question that ongoing learning and development is required for engineers, the current tech landscape has impacted development options and delivery. 

The market at present for funding in startups is very tough, so many companies have either let people go or are freezing their hiring process or both. So there must be other solutions to fill the skills gaps you’d typically fill by hiring people within companies because there isn’t necessarily the free budget floating around.

Educating tech leaders on skill development

Joel said CTOs might need help with budget constraints and understanding their people’s development needs. ‘When improving your team’s skills, it’s too easy to think about the cost rather than the benefits because it feels easier to quantify. This prevents CTOs from making a good business case.

‘Often too much of that conversation is focused on the monetary cost and not nearly enough on the much more expensive resource, which is the time cost.’ Joel added, ‘So accelerating the learning of your team can be valuable even if it costs money.’

This lack of understanding or confidence by CTOs about how to tackle training (especially for first-time leaders) is common. Often, people will have a budget per person for learning and development-related stuff, but they need to figure out how to get the biggest bang for their buck.

Training courses and self-paced development are the most obvious choices because that’s the traditional way of building skills in a person, but can be a considerable investment of time or cost. And from my experience, the return on investment isn’t always there from doing it that way. I think there’s also a spectrum of risk in that there are things that you can just expect an engineer to go off and find out how to do on their own.

As Joel and I investigated the Skiller Whale approach to understand how it differed from the status quo, we were intrigued by how advanced and nuanced much of the offering is – it’s not the kind of thing you’d necessarily want someone just to go off and find on Stack Overflow or Google because it requires deeply understanding it.

The challenges of self-paced learning

There’s also the issue of learning alone or knowing where to begin with development research, which may not reap optional motivation or knowledge retention. For example, if developers search for answers online, it only caters for what they know to search for. If they are unaware of an approach that is more elegant and creates less tech debt, they are unlikely to find it in this method of learning.

Joel agreed, ‘With self-paced courses and books, you tend to be on your own, and that can be tough in a learning environment; it can take far longer than the more conversational, practical approaches that you might get in a more traditional training course.’

He added, ‘There is a challenge for companies about how training fits in with what their teams are doing. The great thing about developers searching for answers on the internet is that it ties in exactly with the challenge that they face right now. It also means they retain what they learn because they can use their new knowledge immediately. However, there’s very little structure, which can leave developers feeling lost.’

‘At the other end of the spectrum, you’ve got structured instructor-led training courses taught across multiple days. However, many of these courses are organised to be the same for everyone; In this case, often, the course will overlap with much of their previous knowledge and so waste some of their time. And again, it’s not interleaved into their work and so makes it harder for people to practise and retain.’

Live team coaching blow-by-blow

With all this said, how did the Skiller Whale live team coaching fare in practice?

Joel experienced Skiller Whale’s coaching first-hand by doing a one-hour 1-1 session (NB: it is normally delivered in small groups) to complete the first half of a module, Advanced Locks’ from their Postgres programme, a subject he knew little about.

He was impressed with the pre-session setup, and Joel said the coach’s introduction made him feel comfortable with the environment and asking questions. The content was delivered by the coach (with the written content being more to refer back to), and Joel noted the content was well judged in terms of how much new content to share before switching to a practical and the level of detail to go into. When he asked follow-up questions, the answers were clear and relevant.

The exercises worked well for trying out the concepts that Joel was learning. The Skiller Whale set-up means that you can work on the exercises in your editor on your machine, but the instructor can see the work that you have done through Git commits, and help you debug issues if you get stuck.

Joel’s final thoughts were, ‘I came away from the session with a much clearer sense of the variety of locks which Postgres uses, how they relate to one another and the situations where these locks may cause problems. The interactive nature of the session, in conversation with the coach and having practical examples, made it feel much more engaging. I will retain the information far better than if I had just read a tutorial.’

Catering to individual learning styles

In addition, no matter what industry you’re in, individuals have different learning styles, and it’s difficult to appeal to these through a traditional ‘one size fits all’ online learning. 

Everybody has a different approach to building the knowledge that works for them. And so you have to be able to personalise the learning experience, and this is made possible in a live setting like Skiller Whale’s.

When I did the Skiller Whale demo, the biggest standout for me was that it was being tweaked, and the approach and the language used were being adjusted continuously by the coach all the way through, which made the difference for me.

What do others think of the coaching?

Joel and I had a taster of the Skiller Whale experience, so we’re able to comment on the methodology and immediate results, but in terms of longer term team-level outcomes, we turn to the CTO community who have used Skiller Whale to get input: 

Nick Rogers, VP of Engineering at Wagestream, says, ‘Through Skiller Whale’s focused coaching, we’ve seen our engineering team’s command of Python and PostgreSQL grow remarkably. Not only has this led to a more robust, efficient product, enhancing user experience and satisfaction, but it has also boosted our team’s confidence. Empowered with new skills and knowledge, our engineers now tackle technical challenges with increased assurance and efficiency, reinforcing the stability and reliability of our product.’

Meri Williams, CTO at Pleo adds, ‘We really gelled with the Skiller Whale mentality that learning shouldn’t be a bolt on, or a perk. It’s a key part of our long-term technology strategy and will help us continue pushing our innovation and strengthening our overall product offering. It’s a bit of a no-brainer really – we want to help our engineering teams build their careers with Pleo and this is a fantastic way to personalise and super-charge that learning and development.’

Jerome Basdevant, CTO & Co-founder, Datamaran believes, ‘Since we started with Skiller Whale, I can really default to trusting the team to write the code the right way. To the point that I hardly check PRs and code base, and the autonomy has significantly increased.’

‘As a team, we have become more mature in our approach. We are now including more advanced coding patterns, actively engaging in discussions around standardisation and advanced coding practices, and our efficiency has improved.’

Hok-Him Poon, Founder & CTO of Pirical, adds, ‘For the past two years, we have been using Skiller Whale for Python and SQL upskilling for engineers at all levels. The platform’s assessments are a useful part of our onboarding process, as they provide me with a more granular understanding of new team members’ technical skills.’ 

‘A recent feedback survey indicated that most team members have been applying their newfound knowledge directly to their work. Team members believe Skiller Whale to be an effective learning method and feel it aids in their career advancement. Some team members have reported that the sessions have helped them reshape their problem-solving approach. Some have also expressed interest in having sessions on topics that they feel were relevant but were not on their coaching plan.’

‘Overall, I believe Skiller Whale has improved productivity by enhancing relevant skills and has assisted me in fostering a culture of continuous learning.’

The future of engineer skill training

‘Skiller Whale is bespoke, personalised, human facing, and I think that makes the biggest difference.’

Andy Skipper

So, looking to the future of skills training for engineers, where do Skiller Whale’s learning offerings fit in?

Retention is a massive issue even though the market is very subdued. If you’re not providing growth opportunities (not just going off and buying a book or doing some training on your own), then you will stand a much worse chance of retaining key people.

Skiller Whale is bespoke, personalised, human facing, and that makes the biggest difference. Plus, what sets it apart from different training is the conversational approach. 

Yes, you have pre-prepared material, and you know that there is a “right do this, then that will happen” kind of thing, but you’re in a coaching environment, you’re in a video call and with an expert, and so what that gives is the ability to personalise in real-time. 

I think personalisation is absolutely vital to this kind of learning.

Can Skiller Whale replicate the real-life work environment?

When we think about inter-team learning and teaching, it most often happens through pairing, mob programming, or brown bag sessions. So being in a coaching environment with Skiller Whale is either like any other pair programming where you’re the only other person in the session or a mob programming where you’re learning with everyone else, and everybody’s dipping in, asking questions and giving ideas. 

This is spot on in emulating a real-life work environment for learning.

Skiller Whale’s coaching is very focused on skills building through improving the technical knowledge of your existing people rather than necessarily hiring people. They fill an important and under-represented space.

And Joel made a valid point about another valuable takeaway from Skiller Whale learning for leaders, ‘There’s an additional benefit potentially for people going along because what Skiller Whale is doing is modelling good coaching behaviours for how you teach things in your teams. It will provide a model people can look back on when explaining things to their coworkers.’

My final thoughts

One thing is for sure, the way you develop yourself and your team will continue to evolve, so you must consider the most time and cost-effective ways to do this. As we’ve seen in Joel’s review, team coaching can personalise and adapt the learning experience to tackle the skills issues and get straight into the heart of technical learning.

To find out more about how Skiller Whale’s live coaching sessions can develop your team or to set up a free trial, get in touch now. 

Andy wrote this case study which includes interviews with a CTO coach who trialled the Skiller Whale product offering by attending a live coaching session. All feedback and opinions are honest and in no way influenced by any member of Skiller Whale.


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