As both a keen sailor and product manager, I have come to realise that there are some interesting lessons to be learnt from sailing that could also be usefully applied to product management. Both disciplines are a blend of art and science, both have built-in constraints, and both require continuous learning because their environments are very dynamic. They require both physical and mental stamina for success.
It’s Destination “Towards”
When sailing, prior to setting off on a longer journey, the skipper and others will sit down with their tools of the trade to plan the voyage. They take into consideration the ship and its condition, the crew and their experience, the provisions needed to keep the crew fed, the weather expected en route, alternative destinations in case of wind or weather changes, and so on. Waypoints will be plotted to enable them to track progress. Above all, those planning know that the direction is approximate. My logbook header has the space to record the port where you started, but then asks to state your destination as “towards…”. Many times I’ve made a plan to reach a specific port, only to change it en route. For product managers, being agile doesn’t mean no planning. It does mean being able to replan on the journey and make course corrections as you go, when conditions force a change.
Make Sure You Have the Right Resources
When you plan a sailing journey you’re always conscious of the weather, both the immediate and the likely conditions for the time of year and place that you plan to go to. Crossing the English Channel in winter is possible, but gales, poor visibility, and a lack of sun makes it much less pleasant and a longer journey than the same trip in spring or summer. You want to be sure your crew are strong enough to cope and that they understand what they are getting into.
As a product manager I have tripped up a couple of times by planning to start a project with the wrong type or amount of resources available to execute. I have found this to have knock-on effects well down the project. You can get there, but it takes longer, the trajectory is rougher, and the impact on the team is higher. There is tremendous satisfaction in battling the elements and bringing the team together, but it can destroy cohesion as well.
Be Ready to Change Tack
We can compare establishing market fit to trying to sail to windward. Sailing boats cannot go directly into the wind. They must sail at a narrow angle to the wind in one direction, then tack and do the same in the other direction. As you speak to users and try to understand their needs, they quite often may not directly tell you what the issue is or may jump to a solution before really establishing the pain point. So, getting to grips with the right fit may require you to “tack” multiple times before you really get to where you want to be. You think you know where you want to go, but there may be surprises.
Moreover, as this sailing diagram shows, there are several different options that can get you to the same destination. The one you take in sailing depends on other factors including weather conditions, other ships, tides, and shallow water. Product managers must deal with practical limits on budgets, availability of users and hippos!
Take the Helm
If you think sailing upwind is hard, then most sailors will tell you the most dangerous conditions are when you are sailing directly downwind. You can go fast with a decent amount of wind behind you, but the slightest inattention at the wrong moment can cause the sailboat to broach uncontrollably. This is where the boat swerves violently off its course and heads in completely the wrong direction. The other possible alternative is that the mainsail moves violently from one side of the boat to the other, possibly hitting crew members and even knocking them into the water. This is what sailors call a gybe. A good helm on a sailing yacht makes this less likely, making small moves at just the right time to keep the boat moving fast and safely. A bad helm will end up exhausting and possibly hurting the crew and damaging the boat. As a product manager, ideally you anticipate business shifts and steer gently along your planned trajectory, but if you don’t there could be a lot of damage to crew and project.
Make Last-Minute Adjustments
On longer journeys, you may well be out of sight of land for a time. The weather can easily change, and poor visibility may limit your sight of the destination. At sea, it is quite difficult to make out the details of a distant shoreline, and it is easy enough to end up having to make last-minute adjustments to your course to get to port. At this point you often must navigate with ferries, commercial ships, fishing vessels and others getting in your way and forcing you to make a detour. How often as a product manager have you had to add significant scope to your delivery to satisfy a stakeholder or an unanticipated need?
When There’s Little Visibility
The two pictures above show Table Mountain in Cape Town, South Africa, before and after the fog rolls in. Stuff in the distance disappears. Experienced sailors know that fog descends in minutes and blocks your visibility. There is nothing scarier at sea than being in fog with large ships all around you. Yet product managers are often expected to operate with less than ideal visibility of the market and the competition.
Teamwork is key
Arriving at your port ought to be the easy part, but experienced sailors will tell you that arriving at your berth in port can be the tensest time. There is other traffic to watch for, you need to make sure that the crew know their role as you approach the marina berth, and you need to think about tides, wind and how your boat will behave in the prevailing conditions as you navigate into a narrow berth. Get it wrong and you cause a lot of expensive damage. Good teamwork at this stage, when people are tired, ready for a drink and some food, perhaps standing out in the rain makes all the difference. The best sailing boats approach the finish with a few quiet words, and very little drama. Others have lots of yelling, screaming and contradictory orders. After all, as a product manager, you want your crew to be happy with the success, and willing to come back for the next project.
There is tremendous satisfaction to sailing and something for everyone. Some prefer single-handed sailing, preferring to rely on their own resources. But most people have a crew, with different abilities. The bigger the boat, normally the larger the crew. The longer the voyage, the more need to have people assigned to watches, so that there is always a fresh pair of eyes and hands available. Mixing less and more experienced people together allows those with less experience to learn from others. Team roles also become better defined as the team size grows. Establishing a watch routine, and then handing over to the next people at watch end becomes very practised over time. Product managers also need to find out where they get best fit. Some enjoy the chaos of new businesses, some prefer a bit more structure and more of a team.
For a while, a short-handed crew can manage the ship. But morale and capability decline over time if there is no prospect of respite. Good product managers are sensitive to the atmosphere, the needs and the capabilities of their teams and know when to push for more and when to do what they can to provide respite for their overworked teams.
A Blend of art and Science
Sailing, like product management, is a blend of science and art. To keep a boat sailing fast under the prevailing conditions requires a blend of knowledge and intuition. The physics of sailing impose constraints on what you can do, how fast you can go, and how long it will take to get to your destination. But as conditions change, you can optimise your route and react to make distance in the right direction. VMG or velocity made good is applicable both to sailing and product development. You make course corrections to optimise speed and direction, using changes in the wind to help you get there faster. Done well it looks effortless. But good sailors and good product managers know that there is a lot of craft to be learned before it becomes natural and effortless. I wish you fair winds, a successful voyage, and a well-earned drink at your destination, whether you are a sailor or a product manager!