Always Be Unblocking

April 2025

The most impactful engineers I know do not just write code. They remove obstacles for others.

Your impact is not measured by the code you write. It is measured by how much faster your entire team moves because of you. At Cherrypick, we call this “always be unblocking” and it has become one of our core values.

Always be unblocking

Take your team from unfocused to unstoppable.

Sign up for regular emails on how to help your team deliver fast, gain real clarity, get the right things built, be a place people love to work, and more.

    We won't send you spam. Unsubscribe at any time.

    From Adder to Multiplier

    Most engineers start their careers focused on individual contribution. They measure success by features shipped and code committed. This makes sense: technical excellence matters. However, the best engineers evolve beyond this. They transform from adders into multipliers.

    An adder contributes their own velocity. A multiplier amplifies the velocity of others.

    This shift in mindset changes everything. You begin to see opportunities everywhere to remove friction from the system. Your code is a liability, but your ability to enable others is an asset. Small investments in tooling and knowledge sharing compound over time, creating exponential returns as your organisation grows.

    What Does This Look Like?

    Here are some examples from our experience at Cherrypick:

    • Building small tools that let customer support handle password resets without engineering involvement
    • Ensuring multiple people know how to manage license keys and other critical systems
    • Spotting patterns where teams get stuck and fixing them before they become bottlenecks
    • Creating clear documentation that prevents the same questions being asked repeatedly
    • Sharing context about decisions to help others move faster independently

    The best part? This approach compounds. Each obstacle you remove does not just help today. It keeps paying dividends every time someone does not hit that same blocker.

    Speed Through Enablement

    In my recent article about how to avoid bad startup culture, I wrote about how speed of execution is crucial for startups. However, speed is not just about moving fast yourself. It is about enabling everyone around you to move faster too.

    This is particularly important as your organisation grows. The more people you have, the more valuable it becomes to remove obstacles that slow multiple people down. A day spent building a tool that saves ten people an hour each week is a phenomenal return on investment.

    The Highest Leverage Work

    As a CTO, I have learned not to ask “what can I build?” Instead, I now ask “what is slowing my team down?” The CTO’s role is not to build - it is about enabling solutions and setting the example for others to follow. The highest leverage work often is not the code you ship. It is the barriers you remove for others.

    This mindset shift requires humility. You have to be willing to spend time on work that might not be technically challenging or visible. You have to care more about team outcomes than individual recognition.

    Teams that embrace “always be unblocking” will outperform those focused purely on individual contribution. They move faster, learn faster, and ultimately deliver more value to customers.

    Making it Part of Your Culture

    For this approach to work, it needs to be valued by the organisation. At Cherrypick, we explicitly recognise and reward unblocking work. We look for this mindset in hiring. We celebrate when people remove obstacles for others.

    Some practical ways to encourage this:

    • Make it safe to spend time on tooling and enablement
    • Recognise and reward those who help others move faster
    • Share stories of successful unblocking work - we use a #celebrations channel on Slack
    • Include it in performance reviews and career progression ladders
    • Lead by example: be willing to do the unglamorous work of removing obstacles

    The Compounding Effect

    The beautiful thing about focusing on unblocking is that it compounds over time. Each obstacle removed creates space for new possibilities. Each tool built frees up energy for the next improvement.

    This creates a virtuous cycle: as your team gets better at removing obstacles, they move faster, which gives them more time to remove obstacles, which helps them move even faster.

    The relationships you build through this work will outlast your job and even your code. When you help others succeed, you create lasting impact that extend far beyond the current project or company.


    The next time you are deciding what to work on, consider this: the highest impact work you could do today might not be writing new code. It might be removing the barriers that are slowing others down.

    Because in the end, your real impact is not measured by the code you wrote. Your impact is measured by how much faster your team moved because you were there.


    More articles

    Why Time Units Beat Story Points Every Time

    Story points, t-shirt sizes, and fibonacci numbers. We have created an entire vocabulary to avoid saying what we actually mean. The truth is simpler: we should just use time units.

    This realisation emerged from years of watching teams struggle with abstract estimation systems. The solution was right in front of us all along.

    Why time units beat story points

    Read more

    How To Get Clarity With a New Tech Team

    You have just taken over a new tech team. There is pressure to deliver, not much signal, and everything feels urgent. Perhaps the roadmap is packed. Perhaps the team seems busy. But is anything really working?

    This is your field manual. If you are overwhelmed and trying to get clarity, start here.

    Read more

    How To Avoid Bad Startup Culture

    If you are not paying attention to your startup culture, I have news for you: you are already building a culture into your company. Chances are that is not the culture you want.

    Every company has a culture. It is a summation of all the habits and practices that make up the work. It is every choice, good or bad, made by every person involved. Every action sets a precedent, a “how we do things here.”

    This is how we are wired. We are naturally social beings and are strongly predisposed to fit in to the group we find ourselves in, and to emulate their behaviour. This reinforces culture further, and compounds when more people are involved.

    A culture grows like plants in a garden. You cannot stop the life from growing, but you can decide how and where it grows. Left unattended, weeds will grow alongside the flowers. The key is recognising this and putting in the work to shape it.

    Here is a quick primer on how to do the minimum to avoid bad culture, and how to get good culture going with a little attention every so often.

    Read more

    Founder mode is emergency surgery

    “Founder mode” is emergency surgery. It is not the right way to run a healthy business.

    If your company is sick, you need to fix it. That means courageous decisions only you can make. You will need to dive in and operate sometimes. That doesn’t mean you create bottlenecks by deciding everything for years to come.

    Read more

    How to Build a Robust LLM Application

    Meal Generator

    Last month at Cherrypick we launched a brand new meal generator that uses LLMs to create personalized meal plans.

    It has been a great success and we are pleased with the results. Customers are changing their plans 30% less and using their plans in their baskets 14% more.

    However, getting to this point was not straightforward, and we learned many things that can go wrong when building these types of systems.

    Here is what we learned about building an LLM-based product that actually works, and ends up in production rather than languishing in an investor deck as a cool tech demo.

    Read more