The Dirty Secrets of Fast Moving Projects

The rules work when you want to iterate, but when it's time to disrupt you need new tricks.

Writing code that works is not always easy, but it is a solved problem. As is deploying infrastructure, interviewing customers, or doing a user study. Building a disruptive project which launches on time is a much darker art than any of these things. Even the best teams and companies have fallen victim to slow velocity, to a great idea being diluted to a so-so implementation which misses it’s own mark, or to the cowardice of the masses which turns a disruption into an iteration. Even at successful companies, every project is by-default behind schedule and failing to meet its own goals, and overcoming that handicap requires every trick in the book.

Shrink The Room

An amateur does things alone, they don’t get enough buy in or exposure to get the resources they need to launch. An intermediate brings everyone into the room, spending their time politicking and soothing. Each interested party is invited to a meeting which fills the calendar and their ego. A professional, however, mercilessly controls who is kept up to date about their project. Meetings with ancillary parties are ruthlessly denied until the right moment in the project. Great operators say no.

You will find that any large organization is stocked with people who will happily collect information to satisfy their curiosity or provide political ammunition. As the project appears more successful these requests will pile on, all with apparent good intentioned legitimacy. Before adding another meeting to your calendar, ask the question: does this person need to be informed, or simply want to be informed?

Other departments may operate at a different cadence than fast-moving disruptive product building. If you allow it, they will accidentally drag your project down to their speed. Each meeting will have follow-ups which require follow-ups, which delay a project. Amazingly though, if they aren’t informed, these delays will never occur! The same legal team which might consume six months reviewing something will suddenly be capable of doing the same in a week when a week is all they have. They might not be thrilled, and they might bring up pseudo-legitimate reasons why more time was necessary, but they will also not understand a simple fact of this type of work: It’s all a risky compromise. If we were able to eliminate every risk it wouldn’t have the tremendous upside associated with building something new. You can’t explain this to everyone, sometimes you just have to control who is in the room.

Never Have Enough Time

Deadlines and urgency have long been used as a technique to force more work out of well-intentioned employees than a company has any right to demand. This is not ethical or wise. There should be a balance of urgent work with breaks and time away for any person and any team. That said, it is critical that a fast moving project must have an aggressive deadline. This is necessary for the simple reason that doing more always is safer than doing less. It’s always safer to add a feature, to add a setting, to wait to hear from an important stakeholder, to let one more legal wrangling occur, than to launch. The only solution to this is to force the project to launch (or even to just be publicly announced, or brought into beta, or brought into alpha) very, very soon. This pressure gives you the weapon you need to make tough decisions, and to the get resources you need to accomplish things quickly throughout the company.

Take solace in the simple truth that you always learn more per-unit-time after launch than before. Consequently any work done before launch is less meaningful and efficient than after your work sees the customer. Get through that phase as absolutely quickly as you can. If it seems impossible, challenge the company’s assumptions about how software has to be built or deployed.

You Will Not Be Universally Liked

Not everyone dreams of fast-moving disruptive work. Many very intelligent and well-intentioned people see it as reckless, or misaligned with the core needs of the company. They aren’t wrong, iterative work will always make the company grow more in the immediate term. Similarly though, you aren’t wrong for believing a company which only ever iterates will eventually sink in the wake of one who disrupts.

The job of getting things done quickly in an environment used to more planning will often be fraught. You will be throwing a wrench in precious schedules, ruining the fantastic attempts of excellent planners to plan excellence. You may be a party to telling hard truths, like that a team shouldn’t be involved in a project or isn’t doing work of a high enough quality to build what’s necessary. This can be softened, but at the end of the day it is a simple fact that some situations require a choice between keeping everyone happy and building great things. You should make that decision consciously, communicate well, and be prepared to live with the consequences of what you decide.

Remember that being the nicest person in the room won’t always get you the furthest in your career. You must balance tact with a commitment to building something great.

Have A Champion

Any type of aggressive action within a company will have a moment or two where someone has to be bold. It might require telling the billing team that it’s ok to ship even if the new product isn’t fully integrated into the accounting system. It might require telling the devops team that it’s not ok to require two months to spin up a new service. It might even require telling the company that this new product will cannibalize their existing revenue, and that’s ok. In any case, there will be a few moments when the company has to be bold, not conservative. In a traditional organization it will be hard to find the executive who is incentivized to make those choices. Most are well compensated by the traditional lines of business the company has. If you are unable to find an executive who will push back against some of those pressures, you should expect the heart-wrenching experience of seeing a lot of your work go to waste as something almost-great almost-succeeds before your very eyes.

The Two Silver Bullets

A former colleague of mine is famous for saying there are two magic powers in the world of product management: the summary email and the daily standup.

The summary email has an incredible ability to clear up the massive misunderstanding (and occasional spin) which besets any activity with more than two people. While 1-1 conversations have a tremendous power, it is so easy for messages to get confused. A summary email includes not just the people doing the work, but also levels of upper management, getting the decision making people in the same virtual room efficiently.

Frankly, it also allows the person writing it to control the conversation. If done tactfully it can be used to promote the great work of colleagues, and to gently scold attempts to delay and derail the project. As with all public communication the standard rules apply: push away credit, happily take blame, insist on ultimate success, provide options not arguments.

If you come from a background in engineering you might have rolled your eyes when you read ‘daily standup’. They are often used as a policing tool, a way to force people to do tedious work by shaming them for not making daily progress. What we are doing is distinguished by a simple idea: it’s not persistent. Instead we spin up a daily check-in meeting only in the few weeks leading up to a big launch. This daily check-in isn’t dedicated to forcing productivity, everyone in the meeting likely has plenty to be doing, instead it’s a solution to the communication mess that can lead to tight deadlines being missed. It allows everyone to know what is happening, and allows the product manager to know what is being done, without requiring constant disruptions. It should have a dramatic sense of urgency, as the deadline looms, with no one having enough time to waste anyone else’s. Start doing one when it feels like everything is running away from you.

If You Win, Everything Will Change

When you work on a baby project, you are often at-most amusing to other people in the company. It seems like what you’re doing is a silly experiment while they do ‘real work’. At some point though, a switch flips. The CEO stands on a table at the company retreat and tells everyone that the little project they weren’t paying attention to is having tremendous success and its the future of the company. From that moment, you will get a lot more interest and attention. People will schedule meetings with you, teams will want to integrate with you, and senior leadership will try to ‘help’ you left and right. You will also have a target on your back. People who build things 0-1 are often not expected to be very good at 1-100, and there will be pressure to bring in ‘experienced leadership’.

The startup industry has in some ways learned that this type of forced ‘maturation’ doesn’t work well for whole companies, and they’ve stopped trying to do it with founders. The same lesson hasn’t matriculated down through the ranks however. If you want to keep working on your growing project, you will have to mature your process, accepting some of the structure you rightfully eschewed early on. You will also have to build a relationship with the leadership who are now responsible for what you’re working on, and prove to them you can work for them just as you worked for change. In some organizations you may have to make a choice between remaining in the world of disruptive change - but on a new project - or staying with your project as it moves to a more traditional team. Make that choice with your eyes open, not by default.

Have Fun

In a world with fast coming deadlines, it can be tempting to always see peace over the next hill. You can easily believe that pushing yourself beyond your limit is acceptable because you just need to get one more thing done. Of course, if you are skilled, more projects will always appear and you will always remain as busy as the company can make you. In fact, the company will drive you as hard as you let it. Try to remember that you only get one life, you will never get this time back and if your personality is to drive hard, you will always keep driving hard. Learn to take the time you need, to maintain your boundaries, and to enjoy the process.

After all, it’s always harder to fight someone who is having fun; They don’t get tired and they don’t give up.