1. What have you found most challenging as a leader of a small or medium enterprise?

I believe the key to success in today's software driven world is to lead, organise and grow business in a radically different way from our industrial based ancestors.

The challenge for me is changing the mindset of others to essentially ignore traditional management processes and techniques. To compete and be successful in the modern VUCA world we need a more flexible outcome rather than output-based business model and ROI metrics.

Although many organizations are working in more ‘agile’ ways, there is still a long way to go before we can fully capitalise on the benefits of a more dynamic and abstract way of working.

2. How did you become a leader of an SME? Can you please briefly tell the story?

I started as a developer in 1991 with a background in computer science and designed and wrote software for various industries from operating system software to globally distributed real-time application suites.

I continued this for 18 years and remained in hands-on development while also team leading for several years. I moved into more formal project management for 5 years where I coordinated teams to prioritise and schedule portfolios of software product releases.

This led to my current role in senior leadership for the last 7 years where I coordinate across the entire business. My primary function is to create technical strategies and lead technical departments to align business vision with product development and customer experience.

3. How do you structure your work days from waking up to going to sleep?

I am usually up by 05:30 or 06:00 with an espresso and biscuit. After waking up I get washed and dressed and go to a local coffee shop around 07:30. I work from home regularly, even before Covid, and this simulates the daily commute. When based in the office I go to a coffee shop nearby.

I get settled with a light breakfast and double espresso then begin reading online news and blogs, many will overlap with work topics due to personal interest, but some are completely unrelated.

I read 2-3 books on different topics at one time, dipping into each every few days. It can take several weeks, but I like to keep a range of ideas in focus at one time. I find different or opposing topics can highlight surprising or similar patterns that would otherwise be missed.

Depending on priorities and urgency I may start checking work email/slack but usually wait until heading home (or the actual office) around 08:30 or 09:00.

A typical day begins with a general disaster check for things like critical system issues, staff sickness, angry customers. Then it is an ad-hoc chat related to current tasks then observing or steering some type of stand-up with the tech teams; at this point I know where we are from a technical perspective.

Next is ad-hoc chat with the CEO, department heads, customers/partners, etc. I now know where we are from a business perspective as well and can adjust existing plans and tasks or make new plans if needed.

Most of my time is spent communicating, either to learn or confirm where we are, to direct current efforts, to guide or coach teams and to communicate strategy and decisions. In a typical week there will be formal and informal meetings for me to make final technical decisions, to represent the technical face of the company, briefing stakeholders, collaborating on product management, etc.

The CTO role is broad and deep, it cuts across every area of the business to collaborate and find consensus to realise the overall business strategy, as well as extremely detailed discussions within the technical department to brainstorm and guide architecture, designs, best practice, etc.

I usually finish around 17:30/18:00; if commuting from the office I continue reading – or sometimes fall asleep!

It can be extremely busy and challenging but also extremely rewarding when staff, teams, products, and business grow and continuously improve.

After that I (usually) cook for myself and my wife and settle down to enjoy dinner and once or twice a week I wash it down with a few beers or red wine - for the polyphenols of course!

4. What's the most recent significant leadership lesson you've learned?

I have high standards and can be impatient. Combined with some OCD and perfectionism once I make a decision, I want immediate and high-quality results, which is obviously not possible.

As a leader it is important to recognise my own strengths and more importantly my weaknesses to ensure I do not negatively impact colleagues and staff I am responsible for.

This was a problem in my early management days, and this did cause problems initially. Fortunately, it was short-lived, I realised what was happening and I learnt (and continue learning) how to communicate and reassure more effectively.

I set unreachable targets with high expectations to force continuous improvement, however I am explicit and avoid ambiguity to create an environment where everyone is challenged in a positive way.

By communicating extensively, I encourage improvement but create an environment where we accept reality and where staff are supported to fail safely as part of learning without punishment.

5. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

One of the most interesting and thought-provoking books I have read recently is “The Wicked Company” by Marcus Kirsch; I believe every leader can benefit in some way from this book.

It describes the industrial revolution origins of most management and organisational structure that is still practised today, and more importantly how it fails to address the issues in the modern (primarily technology experience based) VUCA world.

In many ways, I found it reassuring because it aligns with many of my own observations and radical ideas of business and leadership, ideas which have proven difficult to gain acceptance of.

The book is enjoyable, educational, and actionable, however, to truly take advantage of the ideas requires a radical change in the mindset of leaders, stakeholders, and investors.

If a leap of faith can be made from traditional concrete based thinking to more abstract, reality-based adaptability, I believe we could change the world of business, employees, and the lives of everyday people in more positive ways.

6. How do you build leadership capacity in an SME?

The most important aspect is to lead by example, this means promoting (primarily) humble leadership and integrity.

There are natural leaders in teams (or already leading teams), and they will bubble to the surface, however there may be others who could be great leaders who are not so easy to identify.

It is our responsibility as senior leaders to monitor and develop everyone we are responsible for. Those who have leadership qualities without the (current) confidence and gravitas to stand out need the opportunity to explore leadership.

Once identified (and confirmed leadership is something they want to try) I slowly expand their knowledge and understanding of general leadership practices, and more importantly I steer them away from thinking “how do I perform this task” to “why are we doing this”.

Once their mind opens to higher level constructive questioning, they can think more abstractly to find patterns, reasons, and alternatives to reach a particular objective in more innovative ways.

7. What is one meaningful story that comes to mind from your time as a leader of an SME so far?

For me it is a repeating story about seeing teams and individuals reach their potential.

It begins with recruiting or inheriting one or more teams. I explain, somewhat oversimplified, that my job is to make their job as easy as possible and that I encourage feedback and honesty.

I gain trust quite early and as their confidence grows, they are keen to revolt and push back on various things, a certain practice, a prioritisation of tasks, etc.

I encourage this but having also gained respect my decision is accepted, if not always agreed with.

At some point in the future something always happens that validates that decision. The teams have a light bulb moment and understand the bigger picture and eventually agree with the decision they rebelled against.

The pattern repeats several times, and the teams continue learning by example, not only technically but also commercially by understanding more about the business as a whole and how their contribution (though vital) is one part of the overall strategy.

The greatest reward is when individuals thank me for ultimately protecting them and allowing them to grow and improve.