CTO in Training : Intentional Balance

Back to the future

In some ways, my previous role as a Director of Engineering at a large comparison business couldn’t be more opposite to what I am doing now when considering scale, org size, and availability of funding; yet as a small team at DeadHappy, we have managed to achieve an astonishing amount in the last 2 years (with a pandemic thrown in the middle).

On reflection, there are many reasons for those achievements, most notably the capability of our team enabled by our self-managing culture and values. For this blog, I’ve decided to focus on the importance of Intentional Balance. By this I mean, being cognisant of where your company is in its growth stage and carefully balancing the decisions you take in the areas of people, process, and technology. This is so important when you realise the impact of your decisions on sensitivities of cash runways, getting features live to customers and, securing the next round of funding. All of that while keeping in mind team members’ well-being.

Below, I discuss 7 areas that I have found as worthy of applying intentional balance to (disclaimer: we are not balancing all of these perfectly) 

Intentional Balance #1:

Fixed versus Flex

“That which yields is not always weak.” – Jacqueline Carey, Kushiel’s Dart

I really value and enjoy working with a core of permanent team members who are fully invested in DeadHappy’s vision of changing attitudes to death. The reality of a startup is that you want to ensure you have enough flexibility in your tech team to allow you to grow and shrink in line with the ebb and flow of cash and importantly ensure that your permanent team members can feel stability in their jobs. I have found it very useful to utilise a blend of permanent and contract team members through partnering with a supportive Near Shorer who helped us to rapidly grow the team and deliver some big projects and then conversely shrink their team when we needed it to happen quickly. Additionally, it is a fantastic way to bring in instant expertise in an area that might not have yet matured in your team.

Intentional Balance #2:

Perfection versus Pragmatism

“Pure pragmatism can’t imagine a bold future. Pure idealism can’t get anything done. It is the delicate blend of both that drives innovation” – Simon Sinek

We have been careful to prioritise shipping new features to customers over achieving absolute perfection, and very early on we even tolerated a certain level of bugs slipping through. For example, is it really important that we have the most polished, pixel-perfect UX? Will the customer care or even notice? Instead, asking ourselves: what value will this add? This approach has the cumulative benefit of delivering a lot of value to our customers over time and means we can be agile and productive. This is greatly helped by being brutal on prioritising and not being afraid to say “no” or “not now”. Remember there are still red lines, e.g. don’t compromise on security if you can avoid it.

Intentional Balance #3:

Build versus Buy

Early on in our evolution our team agreed on a principle of build core and buy commodity. This means that we focus our engineers on those areas of the platform which can be constituted as our core product or delivering our IP / USP and we integrate best of breed third-party tools for functions where others have done it better than we ever could (e.g. Payments, Content Management and Cloud Infrastructure ). Certain functions might eventually be brought in house (at the right time). This principle has proved really useful given that we have a small team but you do need to ensure you account for assigning some of your team’s time to support the integration of these tools.

Intentional Balance #4:

Manual versus Automated

“You’re either the one that creates the automation or you’re getting automated”  – Tom Preston-Werner

We built a collaborative DevOps culture into our team’s fabric from the start and our DevOps engineers’ mission is to automate themselves out of a job. They focus on continually finding things to automate and assisting other team members if they are repeating manual processes more than a handful of times. This has genuinely helped us to keep the team lean and yet still achieve a lot.

In our very early stages, we spent a chunk of time automating our pipelines and building our Infrastructure as code. Since then we have continued to automate where we can including things like backups, automated testing, and some system anomaly detection and alerting. We are by no means near done and will never be. 

In all of this, I agree with Bill Gates’ observation that “automation applied to an inefficient operation will magnify the inefficiency”, so you need to be mindful about what you choose to automate.

Intentional Balance #5:

Hands-On versus Hands-Off

“Leaders help people to see themselves as better than they are.” – Jim Rohn

In my last role, I spent little time with my sleeves rolled up, and most of my time in meetings. In our current stage at DeadHappy,, we all have to muck in to get the job done and I have found myself involved in a level of detail that I haven’t done for years. It has been equally invigorating and challenging to get more technical again. However, I have been careful to create the space for the tech team to have the autonomy they need to do their job and to grow. My approach with them has been to provide context and offer direction and then get out of their way. Our value, “you’re not a child” embeds this approach in the business. With this, I need to be prepared to jump in as needed to help the team remove blockers or fill a gap if someone is not available. It is a tricky balance but both sides of the equation are important to ensure things like employee growth. An ex-colleague of mine used to say that part of our job was to remove every excuse from our teams to be able to do their job and I think I agree with that.

Intentional Balance #6:

“Too little” versus “Too much”

“Simplicity is the ultimate sophistication” – Steve Jobs

Whether it is architecture, software, an org structure, or a process; it is very easy to find yourself over-engineering things, and in the early stages of a start-up this can be fatal. This applies to the way you organise the team, in our case we started with what was an over-engineered team structure and full scrum processes for what was really a simple product and small team, and we found that it quite quickly got in the way of agility. So we scaled it back,  removing a few roles to be reinstated later as well as cutting back the agile process to be as lean as possible. Always keeping one eye on future scaling, we use regular team retrospectives to highlight if and when we need the next specialist role (e.g. test engineers) or a process improvement and we bring them in with intentionality.  In many ways, this is about applying an agile philosophy to growing the organisation, starting with a Minimum Viable Team and then growing based on real data and experience.

Intentional Balance #7:

My needs versus business needs

“You can’t pour from an empty cup. Take care of yourself first.” – Unknown Author

Our value, “people over business” was introduced to encourage people to prioritise their mental and physical health sufficiently so that they have the spare capacity to be “on it” when they are undertaking work activities and the same when engaging in personal activities. We have no rules on working hours or leave, and we trust our team to balance their time and activities accordingly and, unsurprisingly, they do. 

When we asked employees what they thought this value meant, one person provided this elegant example: “if you need a haircut, go and get the haircut”. This principle has served us all well, particularly through the Covid lockdowns, and it is the first organisation where I have worked where I don’t often feel guilty for not working horrific hours to prove that I am adding value. With one google search, you can find hundreds of articles in which 5% and 10% of failed start-ups cited employee burnout as their reason for failure.

No compromise on values and culture

“A nation’s culture resides in the hearts and in the soul of its people.” – Mahatma Gandhi

This is one area in which we don’t balance or compromise. In the very early days of DeadHappy a small group of us spent many days painstakingly debating and articulating what culture we desired in DeadHappy and what our values would be to seed and grow this culture. We don’t compromise on these and we aim never to. We have created an environment of high autonomy, low hierarchy, supporting self-managing employees to do their best job.  We are proud of this and we will keep working to improve it, ironing out the creases and ensuring that we can make it scale as we grow. Each new employee adds to our culture and changes it for the better but our values still remain a common thread as we grow.

Go forward and keep growing

Whilst I have focussed on these 7 areas, every business will have their own unique challenges and priorities. Nevertheless, the idea of intentional balance can be useful to help you and the teams surf the unending cycle of chaos and reorganisation (we think the word “Chaorder” best describes this) in a business that is in its development stages.  Working in a start-up has already been an incredible learning opportunity for me, and an unlearning opportunity. There are  many things that one would automatically assume to be a ‘must-have’ in a big organisation that aren’t right for an early stage start-up and this requires some careful balancing and knowing when the right time is to introduce those best practices around people, process or technology. I also have a strong sense that I may well challenge myself to resist fully shifting the balance to the far end of the scale in certain areas.