CTO Priorities: The Last Mile for Projects

Over my years of working in the software industry, I’ve had the fortune to work in startups and Fortune 500 companies. Regardless of the size of the company, everyone complains about similar issues and there are several truisms that emerge. One prominent truism is that the most difficult part of every project can often be the last mile before it is released to production.

This last mile sometimes feels like a speed bump and other times it feels like Mount Everest where every step painfully matters. What’s interesting is that I’ve found everyone is always happy to provide their feedback and opine on what they think should get done from a high-level, or what’s going wrong. But when they are asked to provide detailed recommendations or contribute at a detailed level, the more vocal people often refuse to help or avoid the question.

To illustrate what this looks like, I’ve created a diagram called, The Last Mile for Projects. A key reason for the variance is due to the fact it takes very little effort to provide feedback, share ideas and talk about high-level concepts – this is why everyone does it. It’s much harder to start working on detailed concepts and even harder to get something to a working state, this is because the effort grows as you reason through the complexities and often, there is reputational risk that you might have something wrong or it may simply not succeed.

In the late stages, you often find that people you thought were working alongside you will start to resist forward movement and come up with features, changes or indecision that prevents releasing to production. Much of this is often unnecessary or simply can’t be understood until the project is released into the hands of customers – it may also be due to lack of planning, which also requires significant effort.

When this happens in software, it is often expressed as not having enough developers, enough time, enough capital, too many perceived risks and so on. It reminds me of the scene in the movie 300 where Daxos approaches Leonidas and suggests they retreat and give up – Daxos is questioning if there is enough human capital to match the perceived risks: https://youtu.be/R4dcQx32Dhc.

Fortunately, what defines people’s careers is not that they always have perfect products that everyone loves. Instead, it’s the quality of their work, their ability to follow through (in detail) and the stories along the way – a few determined, experienced people who are proud to call themselves engineers can do amazing things. Even now, I keep accumulating stories about people, customers, politics and circumstances that have turned a project into a great success or failure. All of those experiences create a personal brand that enables me to find work and add value in the right situations, even though I am far from perfect.

Maybe, if we all try a little harder to focus on how we can best use the people and tools we have and a little less on what we think we might need, we’ll all find the journey is worth the effort. Fortunately, most of us work on projects that don’t risk life or death, but our work does impact many people for a lifetime. This makes it worth the pursuit of completion even if there is uncomfortable resistance by naysayers or lack of preparation by those not willing to put in the effort – when we reach the end, the results make life more inspiring for all of us.