How is Project Leadership Like a Road Trip?
Lessons Learned from the Redesign of Next Big Sound’s Profile Page
I recently led a four-month-long project to redesign Next Big Sound’s Profile page, the core of our product’s offering. I’d like to share some lessons I learned as the project’s leader, and I thought I’d use a rather useful, if somewhat corny, simile to structure this post.
First — a little bit about project leadership at Next Big Sound. At NBS, we work agile, in two-week-long iterations that sometimes serve a longer goal that we call a project. Members of every project select a team lead who is responsible, primarily, for communication: within the team, with the rest of the company, and with clients. Everyone’s welcome to lead; every lead is welcome to lead however he or she pleases, so long as the work is done, on time and with excellence.
As I mentioned, I lead the redesign of our Profile page for the past four months. I was directly responsible for the user research, architecture, and wireframing for the project. As project lead, I was then responsible for coordinating with and supporting the rest of the team — from visual design to back-end engineering.
Here’s what I learned along the way.
Plan your trip.
Let’s start at the beginning. You’re not just going to hop in your car and drive, are you? Where are you going to go? What are you going to need? You’ll face these same questions as a project leader. Do your research. Reflect on previous projects and what did and didn’t work. I spent three days exploring documents like client emails and user interviews, which saved myself and my team weeks of exploration. Try to understand the problem that you’re solving as best as you can before solving it.
Pick a good crew.
Though a long drive by yourself does have its virtues, the best road trips include some of your dearest friends. You’ll want to make sure you’ve got the right crew, for your team or for your drive — fun, dependable, and maybe with some unique skills. You’ll do best with a lean team with complementary skills to address the problem at hand, from designers to engineers. Don’t forget that space is limited — too many team members make for decreasing returns on productivity as communication overhead increases.
Know where you’re going…
Driving without a destination? That’s some hippie nonsense. A road trip needs an objective, just like projects. When you start with the end in mind, the path towards your goal becomes much more apparent. If you work backwards from your objectives, the necessary tasks become clear while the nice-to-haves fall by the wayside. Furthermore, as project lead, it’s on you to have the long-term vision and to bring that vision to every decision along the way. A great technique we used was a “premortem” — we imagined that the project had failed, imagined why, then planned to avoid those risks.
… and ask for directions if you’re lost.
Even if you have a smartphone, you can still end up taking a wrong turn. It happens, and it’s perfectly okay. We live in an ambiguous world where things are constantly changing — especially client requirements. You’ll need to periodically reassess your goals and make sure you’re still on the right path. If you’re not, if you’re confused, you should absolutely ask for some feedback or input. For our team, frequent client check-ins, as well as periodic references to the premortem, helped keep us on track.
Make sure everyone’s buckled up and comfortable.
Safety first, guys. While this calls for passive restraints in a car, in a project you should make sure that your team members have what they need to be successful and stay out of trouble — information, answers, resources, what-have-you. Although everyone should watch out for his or her own safety, as a project leader, it helps if you’re double-checking.
If you can help raise questions, clarify communication, and understand how people like to interact with one another, you’ll find that your team will be immeasurably happier and more productive for it.
Try to make good time…
I am always trying to beat my best time. Always. Time-to-destination is, for me, the one true measure of success on a long drive. It means you were diligent throughout the drive — you knew your way, you were focused, you maintained your rhythm and you made it to your destination — you were also probably a little lucky. It’s the same with projects — you’re going to get tired and you’ve probably got people waiting on you, so get to it! Make your deadlines ambitious, but realistic, and hold yourself and your team to them.
… but stop for a break if someone needs it.
There’s no need to be punishing in your pace, however. If your team needs to stretch and get some fresh air, let ‘em. It won’t take too much time and it will pay dividends in mood, which pays dividends in productivity. Three months into the Profile project, we decided to take a two-day break which increased our productivity for weeks. We all can use a day or two to switch things up, even if you’re working on something different, rather than simply relaxing.
Make decisions — even wrong ones.
Can I pass this truck safely? Should I stop at this exit for gas or hold out for one with better food options? Do your users really need this new feature or can we ship without it? Prepare to make split-second decisions with limited information. Someone has to make ‘em — it might as well be you! In the driver’s seat, you have the best perspective, and indecision has its own dangerous consequences. While designing the Profile page, I believed in showing users as much data as possible, but a lot was just too much for many users. You’ll make bad decisions, and that’s okay — own up to them, learn from them, and move along.
Look out for landmarks.
Landmarks along the way are critical for orienting yourself during your journey. Your project will likely have its own landmarks, whether it’s the first code to ship, the first beta tester introduced to the project, or the final delivery of a new feature. These are important landmarks to aim for, work towards, and, once achieved, it’s really important to pause and celebrate before moving on to the next phase.
Don’t get sidetracked.
Other roadside attractions are distractions that can delay or even block you on your way to your destination. Scope creep, feature requests, design noodling, engineering obsession: these are the roadside attractions that can take your figurative road trip off course. At last count, we said “no” to over 60 feature ideas, and I couldn’t be more proud. As the project leader, you’ll have to ignore distractions and fight tirelessly against digressions.
Check your mirrors.
Tailgaters. Blindspots. Five-0. If you’re not checking your mirrors every few seconds, you’re bound to miss an opportunity to address some serious risks. Periodic check-ins are a great way to stay up-to-date on your project. Every morning, our team had a ten minute stand-up meeting where each team member shared yesterday’s progress, today’s plans, and any blockers he or she faced. Every Monday, we sat down as a team to regroup on progress and priorities for the week. These meetings were as invaluable as checking your mirrors before merging onto the highway.
Always have an out.
Keep worst-case scenarios in the back of your mind. What if the car ahead stops short? What if this third-party javascript library doesn’t work out? Will our users loudly demand the return of a feature we eliminated? It’s good practice to know where all the potential risks you face lie and to have an idea how you might address them. For example, we simplified some features from the old Profile, and downright eliminated others. To stay flexible, we introduced a module-based design framework that would support client requests and specialized features, should we need to introduce them.
Don’t fall asleep.
Long drives can be exhausting and the constant rhythm of the road can easily lull you to sleep. Projects are the same way, and as project leader, you’re not in a position to safely drift off to sleep for a few hours.
Stay focused and bring energy to your team, week after week. Enthusiasm is contagious; lethargy can sink the spirit and productivity of your team.
Have fun!
This last piece of advice is perhaps the most important — have fun! A major project, just like a road trip, is a big undertaking, a lot of responsibility, but it’s also an amazing opportunity to see and do new things, to get to know your team members better, and to learn. Even when the trip becomes stressful, keep having fun, or at least, stay relaxed. Every now and again, it’s good to take a moment to stop and reflect on the great work that you and your team are doing. You’ll be at your destination in no time at all — savor it while you can.
How is project leadership not like going on a road trip?
No similies are perfect. This one’s no exception. Here are a few other tips that don’t fit neatly in the above simile.
Stay organized — I recommend Trello.
Complexity goes hand in hand with size. The bigger the project, the harder it will be to keep track of tasks, feedback, due dates, and the rest, and responsibility for this organization lands squarely on the shoulders of the project leader. Here at Next Big Sound, we use Trello to track our work. Every project gets a board — to-do items are broken down by tasks, work in progress, blocked work, and completed work, then by the different features or tasks within the larger project.
As project leader, I held the reins and responsibility for the Trello board: helping team members select tasks, setting due dates, and holding everyone accountable for meeting those deadlines. I also kept our whole company, as well as some of our enterprise clients, up to date on our progress. Forgive me for sneaking in another simile: a Trello board is like a garden. It needs constant care to prune growth and root out weeds, but you’ll be rewarded for your hard work with… fresh vegetables?
Facilitate great meetings.
If you’re having meetings during your road trip, you’re probably not having a very good time. Similarly, if you’re not having meetings during your project, you’re probably not having a very good time. Meetings can be a bit of a chore — often times, only a fraction of the attendees are really engaged with the information being shared. Some meetings can go on and on, and others never go anywhere at all.
As project leader, however, you have the power to protect your team from unnecessary, boring meetings. Invite only those team members that need to be at the meeting. Make sure you have an agenda for yourself — know what outcomes you need from the meeting. Keep the pace up, ask to table conversations that don’t concern everyone, and explicitly recap next steps at the end of the meeting. I love to take notes on a big monitor during meetings — it keeps everyone focused, helps engage remote team members, and saves a lot of time (there’s no need to write a summary after the meeting). Finally, cap every meeting at 60 minutes, no more. If you have more content to cover, you can easily schedule another meeting, one that will be much more productive, and much less painful, after everyone’s had a break.
Communication
As a project leader, no responsibility ranks higher than that of consistent, complete, and clear communication. It is both your primary duty and your greatest power. You’re at the center of user needs, client requests, engineering challenges, design intentions, sales opportunities, and the long-term product vision.
In many cases, you’re the strongest connection between all these parties, and conflict and challenges usually stem from a breakdown in these connections.
Get to know your project from every angle and prepare to empathize with users, clients, designers, and engineers. It’s okay if you don’t have all the answers — so long as you’re constantly asking the right questions and documenting what you and your team learn. You don’t have to be the be-all and end-all of your project — if that were even possible! Your team should be empowered to think and decide for themselves. The buck may not always stop with you, but it will likely pass through you. You are the core, the keystone, the nexus, the linchpin, the hub of the wheel, the eye of the maelstrom, the…
(you knew this one was coming)
… driver of the car.
