Richard Hart

Something @ Somewhere
Kent, UK

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  • I can’t help but wonder if the constant chase of revenue growth for established and profitable companies is what results in stressed and overworked staff, constant firefighting, unhappy stakeholders, angry customers, and a never-ending backlog of tech debt. Shouldn’t businesses ask whether more is better? Or does a business reach a point where it is so big that it has no choice but to relentlessly strive for more?

    What if a company purposely focused on not getting bigger? Instead, focusing on keeping existing customers and employees happy, fixing all the obvious problems, and just creating better and better products. Would that shift in focus lead to overall better outcomes?

    There is the idea that our unhappiness stems from the gap between what we have and what we want. We feel that we can only achieve true happiness once we have that new piece of tech, that new car, that new house, or that fancy job. If we learn to appreciate what we have, we won’t feel such discontent, and will find the happiness we seek. If we substitute the concept of happiness for revenue, focusing on revenue growth will only lead to suffering, but perhaps focusing on internal factors may be the true path to sustainable long-term success.

  • At my first Improv class, we played a game called “That’s 8 Things!”. You’re given a subject, like countries or fruits, and you have to name eight as quickly as possible. No hesitating, no stalling, say anything at all. It doesn’t matter if you repeat the same thing multiple times or say something off-topic. I was told to name pieces of furniture, and I ended up saying the word “chair” four times and even saying “shoes” at one point. Being fast was more important than being correct. Taking time to think of an answer meant stopping.

    I enjoy thinking and spend a lot of my time caught up in my own thoughts. Thinking about life. Thinking about problems. Thinking about work. Taking time to think has served me well when it comes to big problems or decisions. Ensuring I was covering all my bases, exploring all the possibilities, and considering what choice would lead to the best outcome.

    The downside is that too much thinking can become a blocker to getting things done. It can cause me to go over my opinions and decisions endlessly. Even thinking about whether I have thought something through enough. This manifests as procrastinating getting started on things or hesitating when contributing to conversations or meetings.

    An aspect of needing to think is wanting to have the right answer. When the presence of an infinite number of variables controlling the outcome means there is no right answer. The amount of time spent thinking has diminishing returns. Going from being 50% certain about something to 60% may take double the effort it took to go from 0% to 50%. Going from 90% to 100% may take forever.

    Sometimes you just have to shout “shoes”.

  • Nearly everywhere I’ve worked, someone will make the point that everything we do is tactical and not strategic. We focus too much on work that produces short-term results rather than work that will serve us in the long run.

    Everything I would observe would suggest that “leaders” were thinking strategically. After all, isn’t that the core of their job? To be thinking about the long-term future of the organisation.

    The more I think about it, the more I see this as a symptom of the divide that develops between those thinking about the work and those doing the work. Leaders that sit in ivory towers, disconnected from the reality of how work is done. They don’t understand the implications of their strategy because they haven’t thought through their problems and haven’t taken the time to understand the context of how work takes place.

  • Decision-making in an organisation is like a train passing through stations on its way to a final destination. Picking up passengers along the way who want to be part of the process of reaching a final decision.

    But some trains pass through our station without ever stopping. We patiently wait to get on so we can have our say, but it flashes by, leaving us confused, frustrated, and wondering why it didn’t stop for us. Sometimes, we weren’t even at the station when it passed by. We wait for it to arrive, only to realise we missed our chance to get on completely. Causing us to ask ourselves how we ever ended up in this situation.

    We then make the mistake of expecting the train to come back and pick us up. Depending on your seniority, the size of the decision, and the size of the organisation, that might be possible. But many of us may have to scramble to catch up to it, hoping that once onboard, we can influence a train already in motion. Then, we find we have no say over where it’s going.

    In larger organisations, many decisions will be made without our input. Being uninvolved makes us feel deflated. We throw our hands up and wonder why we even bother. We start to question ourselves. How did we miss the train? Why they didn’t wait for us? or who was even driving it?

    There will always be decisions that are out of our control. If someone a lot more senior wants something and we don’t have the political capital to influence the output, it may be better to get on board and look for interesting opportunities along the way. There will be decisions that need questioning, and we should strive to challenge those we feel strongly about, especially if they cross our own moral or ethical values.

    Some trains are fast, some trains are slow, some will stop for us, some won’t stop at all, and many trains we’ll never see or even know about. Then there will be trains that will be our responsibility to drive.

    We can’t be on every train, so we should be sure to pick the ones worthy of our time and effort.

  • For a long time, I thought the hardest thing about being a leader was the art of giving constructive and timely feedback. I found it difficult to measure and constructively articulate someone’s performance. So it would usually come out as simply, “You’re doing great, keep it up”, even if that’s not what I truly felt deep down inside.

    Over time though, I now believe that being able to effect change is the hardest thing about being in a leadership position. It’s too easy to be passive. To turn up, tend to our admin tasks, and keep things ticking over. But doing so does a huge disservice to the role of a leader.  Creating change, especially when the odds are stacked against you, is the hallmark of a great leader.

    Change is difficult because people do not like it. We want to maintain the status quo. Asking a team to change their ways can be an almost impossible task. Asking can be especially difficult when joining an already established team with an endless supply of “we’ve tried that before, and it didn’t work” responses.

    Long-lasting change naturally takes a long time. Adding something to someone’s already full plate means they may not get to it as quickly as hoped, then maybe it’s forgotten, intentionally or not, so it never gets done. We repeat our ask, and it feels like we can never get it through no matter how hard we try. It’s disheartening. We eventually ask if the change is worth it, whether it needs to be done, and if we should just let it go. It’s a slippery slope of negative thinking. Then we become distracted and chase something else, leaving behind a trail of half-forgotten dreams. 

    Ultimately it’s our role as leaders to effect change. To actively improve the situation we find ourselves in. If we don’t persist, if we don’t push through the discouragement, then we miss the opportunity to do right by our teams, do right by the organisation we work for, and ultimately achieve great things.

  • When knowledge walks out the door, so does the reasoning for many decisions that led to the current architecture along with it.

    We all know that rewriting something from scratch is rarely a good idea. The most common time for people to fall into the “big rewrite” trap is when the original authors are no longer around to explain and defend it. Writing code itself is far easier than reading it, so given the chance, often developers will opt to start from scratch. As systems grow, evolve and become increasingly complex, the ability to understand it as a whole goes down. So we take what we know of the system and believe that we can create a more straightforward representation of it by starting again. But in the same vein as Gall’s Law, any complex system has evolved from one simpler that worked, and over time, any rewrite is destined for the same fate if taken over by a new set of developers. It’s too much work to understand the existing system because it’s complex. We don’t understand the system, so we take nothing but assumptions into our rewrite.

    So how can you protect yourself from this endless cycle of rewrites? The most straightforward but most challenging solution is to ensure that you don’t have any employee churn. All the authors of the system stay on the team and never leave. Simple in theory, difficult in practice. Another simple but complex solution is to try and architect your software into discrete modules, which are individually easy to understand and refactor, but that can then be composed together to form a more complex system; Think microservices. The trouble is that there is a lot we don’t know about a system when we start, so unless you’re staying on top of your tech debt and refactoring your code to match your evolving understanding of the problem, then you will end up with a “big ball of mud”. Clear and up-to-date documentation can help. Especially documentation that explicitly calls out designs (Design Docs) and individual decisions (ADRs). But who reads documentation anyways?

    This isn’t to say that there aren’t times when a rewrite is a good idea. Not all systems built for the challenges of their time will necessarily address the challenges of today, so starting from scratch may be the optimal solution. And when the original authors of the system are present to acknowledge the shortcomings of a system and how a new architecture could address them, that can be a strong signal that it may not be a rewrite for rewrite’s sake. 

  • This post first appeared on the Which? LinkedIn Page.

    We can never step into the same river twice.

    During my five and a half years at Which? I’ve worn a few different hats. I initially joined as a Ruby contractor to build a new publishing service. The project lasted a year and was a fantastic mix of successes, failures and learnings for the whole team. As the project came to an end, I pitched to my manager that I should come on board full time to lead the Backend team and help set the architecture’s future direction. That pitch led me to come on as a Tech Lead.

    Previous to working at Which? I had spent a few years running a couple of startups with two friends. Even though we ultimately closed shop, we accomplished many great things, and I learnt a lot along the way. It was refreshing stepping back into a developer role where I could enjoy the feeling of satisfaction from writing code. Fast forward back to becoming Tech Lead, I found myself gradually coding less and being more involved in long term planning and decision making. That change started to reawaken the passion and excitement I previously had during my time running a startup for building a vision and using technology to get there.

    I had grown a genuine love and respect for the craft of leadership and the possibilities that it could bring. So when the position of Head of Engineering became available, I jumped at the chance to apply. After pouring my heart and soul into my presentation and interview, I was offered the position. 

    Throughout my career, the one thing I have come to expect more than anything is change. We are creatures of habit. Those habits form a significant part of what we do every day, from our morning routine, to what we eat for lunch, to how we do our work. So we avoid anything that threatens that and actively resist change. But what if on the other side of change is something better? What if, instead of running away from change, we embraced it? What if we became aware that what got us to where we are now won’t be what gets us to where we want to be in the future. And as a first step, if we recognise that change is happening around us all the time, we start to be comfortable with it and begin to use it to our advantage.

    Changes in my role are not the only thing that has changed over the years.


    Working in technology, the most significant change that we’ll experience is that of technology itself. In the space of a few decades, we have gone from using punch-cards to run Fortran and Cobol on large mainframes to now using ephemeral “Function as a Service” platforms such as AWS Lambda to run anything from Javascript to Go. 

    Through the lens of Javascript frameworks alone, for a long time, the running joke was that it wasn’t worth learning any as a new one would be out soon to replace it. When the jQuery library came out in 2006, it transformed frontend development. Yet, only a few short years later, a whole raft of new frameworks came out, such as Knockout, Backbone, Ember, Angular, React and Vue all coming out within a couple of years of each other.

    While changes in technology can often be dizzying and challenging to keep up with, the boosts in productivity they create can often be significant. Work that was once highly complex and required weeks or even months of development time is now available as drop-in modules that can be configured and running within minutes. The months of time that would have taken to build and maintain your own on-prem infrastructure can now be spun up all around the globe with just a few scripts. 

    Making continual choices about technology is a key part of ensuring we are building products and platforms that will see us into the future, as well as sunsetting ones that are holding us back.


    The work of an engineer has changed significantly over the years as well. For most, gone are the days of Waterfall, and it’s rare now to find an organisation that doesn’t approach software development with an agile mindset. Yet the Agile Manifesto, which popularised many of the values and principles used by organisations today, is only 20 years old, having been published in 2001.

    For a long time, engineers were seen purely as a delivery vehicle for what the business wanted. There was no say in what got built. Requests would make their way to a Project Manager, scheduled, built, and released as part of a yearly, or maybe even twice yearly, release cycle. 

    When I first joined Which? in 2015, engineers worked in delivery teams. Features and tickets would be decided outside of the team but passed down to them to be implemented. Today, engineers work as part of cross-functional teams in collaboration with Product, UX, and other parts of the business to figure out what would be valuable for users and to decide what to build. Engineers are expected to understand their product’s users and to have a voice when it comes to the features that are delivered.

    Not only has there been a change in how engineers interact with the organisation and people around them, but there have also been changes on a day-to-day engineering basis. Pair Programming, Trunk Based Development, Peer Reviews, Continuous Integration, and Deploy on Demand are some of the practices that have come into their own, as engineers have honed and sharpened the software delivery process. 


    In an organisation that has been around since the 50s, change is not only important, it is necessary. But ways of working can be difficult to change when they have been the modus operandi for many years, and yet long term success is based on the ability to adapt to new and different ways of doing things. Squads and OKRs (Objectives & Key Results) are two examples of how Which? has started to make that change.

    The introduction of OKRs means that there is a continual focus on ensuring that what is being done aligns with the organisation’s objectives. If it doesn’t help the organisation meet its objectives, it doesn’t get done. Simple. This, combined with the introduction of Squads, means we can make better decisions on what we build to ensure we are constantly delivering value.

    At the technology level too, with new competitors not encumbered by the challenges of maintaining systems that have been around for many years, we have to ensure that we strike the right balance between delivering new features, stability, and addressing tech debt. This is like trying to change the engine and the tyres on an already moving car—no mean feat.

    Productivity and Success

    How we measure productivity and success has also changed. Crude measurements such as lines of code written, the number of tickets completed, or team velocity, have been replaced with much more meaningful ones. Cycle time measures how quickly value is being delivered to users, driving you to look for ways to reduce bottlenecks. Deployment frequency measures how often you are getting new code in front of users, driving you to break work into small batches. Change Fail Rate measures how often your changes result in a system failure, driving you to improve and automate your quality checks before each release.

    And on a personal level, at each step of my journey at Which? I have had to re-evaluate how I measure my own productivity and success. As an individual contributor, the feeling of accomplishment is felt with every line of elegant code, every successful commit, every successful build, and every successful deployment to production. Moving into a management role has meant the loss of that feeling of continual success. There are fewer feedback loops, and sometimes it can take months, if not years, to see the fruits of your labour. This is often a difficult transition that managers go through, so finding a way to measure your success is essential to staying motivated, learning and growing as a manager.


    Change is as much about what you start doing as it is about what you stop doing. To move forward, we have to be prepared to give up something in return. Whether that’s technologies, ways of working, roles, responsibilities, or simply the metrics by which we measure performance.

    Heraclitus, the Greek philosopher, said, “No man ever steps in the same river twice, for it is not the same river and he is not the same man”. The world that we work in is forever changing. More importantly, we as individuals are constantly changing as we evolve and learn to adapt to that world. Change can either take us by surprise, but if we take the time to look around and prepare for what is on the horizon, we can make the most of each opportunity as they arrive.

    This post was originally published on LinkedIn.

  • A situation that often comes up in meetings is that someone will raise an issue, using a recent situation as an example of what’s going on, but the discussion switches into being about the recent situation rather than the original issue itself. For example:

    Person A: We really need to think about re-architecting Project X. Just last week, the team’s changes had a significant performance impact on the production site. What could we do differently to make the system more scalable?

    Person B: Marketing were the ones asking for the changes because {insert long back story} …

    Person C: Marketing are always putting pressure on us to deliver features that make little sense. Can’t we push back on them?

    Person A: Well, the problem with Marketing is…

    The discussion went from trying to address issues with the system to being about Marketing. It’s easy to get sucked into carrying on the thread because it feels productive, but the original point is forgotten, and then the meeting runs out of time.

    When a discussion veers off course, I try to remind people what the original challenge was to get things back on track. But often, precious time has already been lost. It can be difficult to rein a discussion back in if strong characters are involved or from not wanting to be rude and interrupt the flow of the conversation.

    For everyone taking part, listening to understand, rather than listening to respond, is an essential skill to ensuring discussions stay on point. One question I learned during my coach training is, “What is the real challenge here?”. I often say that to myself while listening to ensure that I’m paying attention to what’s being discussed when a problem is being described, resisting the urge to latch onto something related but isn’t the real challenge.

  • When I was a Senior Engineer, I thought if I moved into a Tech Lead role, I’d have more say and control over what the team did. When I was a Tech Lead, I thought if I moved into a Head of Engineering role, I’d have more say and control over what the department did. I’ve found myself to be wrong both times, and both times, it’s felt like I’ve had less say and less control than I thought I’d have.

    As a Senior Engineer, I wanted things to be built and created a certain way, so moving into a Tech Lead position seemed like the logical way to do that. But once in that role, my problems became so much wider that I didn’t have the time to get into the details of how one thing was coded and created. Over time, as Tech Lead, I wanted things to be architectured and built a certain way, so moving into the Head of Engineering position seemed like the logical way to do that. But once in that role, my problems became so much wider that I didn’t have the time to get into the details of how architectures were built or created.

    The point is that you can influence and solve the problems you have, right now, in the role you’ve already got. Maybe you’ll need permission, but you can get that if you need it. Getting promoted into a role doesn’t give you any power to fix the problems you had before because those are now someone else’s problems. When you’re promoted, you’ll be solving the problems of that role, not the role you’re in. You’ll be playing a different ballgame, in a whole other arena, that’ll make the problems of your previous role pale in comparison.

  • The majority of my time so far as Head of Engineering has been spent looking at the team’s health. Team health is a broad term, as it encompasses more than “is the team doing okay?”. At a minimum, it means, are people on the team engaged and happy, right through to, are there processes and documentation in place to support them in the day-to-day process of delivering software.

    Managers tend to spend a lot of their time looking at just the output of their team. Are we delivering? How can we deliver faster? How can we write better code? etc. But unless you have your underlying team health in order, this is the wrong thing to be thinking about.

    If you’re the coach of a football team, the aim of the team is to score goals and win matches. So you could spend all your time focusing on drills, improving core skills, and practising shots. But what if all the players on the team are sick or injured? All the will in the world won’t win you the championship if no one is in good shape. You need to let your players rest and recover before you focus on their skills and scoring. The health of the team underpins everything about the output of the team.

  • As Engineering leaders, it’s easy to get swept up by the day-to-day grind of delivering software. Code quality, broken builds, deployments that didn’t go according to plan, 1:1s, conflicts, stakeholders, and all the other things that fight for attention as we try to satisfy the organisation’s needs. This is us, working in our teams. We’re getting into the weeds of what’s going on and helping firefight issues as they come up. But to be effective in our role, we need to take a step back and think about how we can be working on our teams. To look for and cut through all the noise and waste. How can we improve our processes to build more robust software? How can we improve our ways of working to go faster? Where are we missing data that would allow us to make better decisions? If we’re not doing these things and just getting stuck in the details with the rest of the team, then what are we bringing to the table as leaders?

  • We often mistake the job we see managers doing with the job they are really doing. We’ve all asked, at one time or another, “What does my boss do?”. We see them go to countless meetings, ask questions, or send around documents. We then equate those activities with the actual job of being a manager. Until my promotion into the role of my departing boss, the perception I had of what they did was totally different to what I found myself doing. All this unseen work going on behind the scenes led to the countless meetings that led to the questions, and that led to all the shared documents. On top of that, the un-seen time and thought went into ensuring the right questions were being asked, and the right documents were being created and shared. This is no different to equating Engineers to writing code. There is so much unseen work involved in writing the right code. It is knowing what technologies to use, what techniques, data structures and algorithms to use, and how to put it all together into building a functioning product.

  • There are many mechanisms for understanding issues and creating fixes when there are bugs in your code. Your computer will tell you when you’ve made a mistake, give you feedback and await your next command. So as a developer, you learn to live in this constant cycle of feedback. Constantly making mistakes and constantly making changes. It becomes second nature. But it’s through these constant mistakes that we learn what does and doesn’t work. We learn to see patterns and spot errors sooner. These mistakes and what they teach us are what make us grow.

    Moving into a leadership role can often feel like the total opposite. There is no fast feedback for your decisions. Sometimes it may take months to know you’ve failed, and sometimes you may never know at all. So you can end up doing everything you can to avoid making mistakes. But just like the developer, you need to make mistakes to grow. It’s uncomfortable and painful, but you have to make calls when afraid or in doubt. You have to learn to live in the cycle of mostly absent feedback. Sometimes you’ll pick up on the effects of the choices you made, sometimes that feedback will be faint, but it’s only in that faint feedback that you’ll find growth as a leader.

  • As I have gotten older and my career has grown, many of my thoughts and opinions on software development, management and leadership have changed. Reading back through some of my posts from ten years ago, I see many of the same thoughts and ideas in discussions with more junior team members. And it’s not that they are wrong, but how the effects of experience and having a different vantage point can drastically change your view of things.

    Whereas I used to be for building a custom solution, now I would favour buying off the shelf more. I hated meetings, but now I value the high bandwidth communication and alignment they can give when run correctly.

    A big factor is the difference that being accountable can have on your opinions. Before my promotion, I would often rant about how “we have to immediately stop doing X” or that “we need to start doing Y before it’s too late”. But now that I’m in the role, all the second-order effects I had not previously considered start to raise their ugly heads. I had only seen things through the lens of my IC role. Now I see them through the lens of someone responsible for the team and how they can meet wider objectives.

    As my career grows, a lot of the thoughts and opinions I have now on software delivery, management and leadership will change. And all the things I’m critical of will look very different when I’m on the other side of the fence.

  • When you have sports coaching, whether, for martial arts or tennis, the coach will often look at your technique and say, “you’re doing it all wrong!”. And then you find that each coach has their theory on how it should be done, even claiming other coaches don’t know what they’re talking about. But when you look at all these different theories and techniques and put them into practice, at that moment where it counts, whether it’s contact with your opponent or with that tennis ball, they all generally put you in the same, correct position, ready to take your shot.

    Leadership is like this. Whether you’re quiet and gentle, or you’re loud and angry. When it matters, no matter your style, you have to be in the correct position in terms of vision and trust, ready to lead your team to success.