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Lessons Learned – Sailing and Project Management


By Thom Kay


toujours 112 small.jpgIt is funny how often life can teach us lessons about a topic through completely unrelated activities. Most of my friends know that among other things, I get great enjoyment out of two areas of my life: 1) sailing, and 2) helping clients with their projects.  Every once in awhile I stumble across good life lessons while sailing that helps put perspective in my business life. 


Every time I set out on a sailing journey (albeit just an afternoon sometimes), I make a habit of checking all of the key components of the sailboat. Since my first priority is focused on safely returning with all of the crew, it is imperative to check that the engine, rigging, and electronics are in good working order. I even use a checklist to insure that I don’t overlook something (particularly when I am easy to distract as I look forward to getting out on the water). Just as important, it is vital to insure that the crew understands their role and basic safety guidelines before getting out on the water and putting up canvas. When the boat is under sail and the wind gets up over 25 knots, there is precious little time to review boating basics.


Preparing and planning for a client’s project can be often as important as the execution work itself. For any project of reasonable size, success or failure can often be determined by making sure that roles are defined, sponsorship is engaged, and clear communication channels are established.  Even simple projects can benefit from using structured project schedules (much like a checklist) to keep tasks and owners on track. When major problems occur due to poor planning and preparation, it sends a loud message regarding weak leadership to the project team and the management.


Even with the best planning and preparation, things can go wrong very quickly while sailing. It has happened too many times that in spite of carefully planning my approach when bringing a boat into a guest berth, a strong gust of wind can easily put me on a collision course for another boat or a dock. I have learned through experience that even with cautious planning, I always assume that things can go haywire very quickly. The most important lesson is to stay very alert and ALWAYS remain calm in order to give clear unemotional direction to the crew.


Although I would like to be able to say that client projects never get in trouble, that would be dishonest. As long as projects are staffed by people, and people have dual roles and conflicting priorities, things are bound to go off the track on occasion. Much like when things get intense while sailing, a project team needs to quickly be assured that the project management and sponsors are engaged and clear on how to put a project back on its course.  It is perfectly normal and acceptable for a project to hit unexpected gusts… It is “how” those unexpected issues are dealt with and “how quickly” that really matters. Whether leading a project as a consultant or an internal employee, the objective is the same: calmly insure that the entire team understands the steps needed to recover. The cost of a drifting project (resource waste) can be enormous.


Sometimes when sailing, it just comes down to a “gut check” on what is the best thing to do in a difficult situation. On a recent sailing trip up to the delta, my wife and I were awoken at about 2AM as the winds picked up to 35 knots and our anchor started to drag. We were heading straight towards a muddy island and had to make some tough decisions. As my wife took the helm and started the engine, I pulled up the anchor to find it completely covered in an invasive water plant that prevents the anchor from getting a solid hold in the mud below. I cleared off as much of the weeds as possible until I could stow the anchor while my wife patiently circled the boat for over a half hour in the moonless pitch black. Once the anchor was secured, we had a tough decision… try to reset the anchor in a fierce wind and poor holding conditions or head back towards San Francisco Bay in the total darkness. It didn’t take me long to decide that we should motor back and cautiously use our GPS to stay away from any fixed objects (like land). It took us nearly 3 hours before we could adequately see our course in front of us, but it was a great feeling to get out of the predicament while also getting a jump on our return trip home.


Most complex projects include unscheduled surprises. In fact, sometimes the only thing predictable is that they are unpredictable. Worse yet, it is even more common that obstacles can be rooted in hard to identify internal politics or resource constraints. More often than not, it requires the project management to perform the “gut check” to determine the best course to take. This can be anything from removing resources from the team, to an escalation, and all the way to petitioning for the project to be cancelled or postponed.  Much like sailing, experience and listening to your own intuition can both play very useful roles in putting your project back on the right course.

Thom Kay is a principal and founder of Pinnacle Intertech. He can be reached @