A skipper’s hardest job? Managing crew expectations – Nikki Henderson
Being a good skipper goes beyond keeping the crew and boat safe—it means delivering the right experience
Most people agree: skippers are responsible for the safety of the crew and the boat. But the job far exceeds keeping everyone alive and afloat. A good skipper also has to deliver an experience. One that aligns, at least partly, with the expectations of the crew.
In my view, that’s the most overlooked and arguably the hardest part of skippering.
For commercial skippers ‘experience provider’ is literally on the job description. Crew sign up to a defined trip, often with a detailed itinerary, and they pay for their place on board.
The task is to keep a group of strangers safe, meet their expectations and finish on time. Sounds tough? It is.
But it isn’t just a commercial skipper’s problem. Every crew, even friends and family, come aboard with expectations. In fact, I sometimes think delivering an experience to strangers is easier than doing it for loved ones. At least if I disappoint paying customers, I don’t have to hear about it for the rest of my life.
I recently had one of these crews join me for a cruise from Alaska, USA to Victoria, Canada. They wanted wildlife encounters, a taste of Pacific Northwest sailing, and some kind of ‘offshore’ experience.
In seven days I needed to deliver overnight sailing, coastal cruising, a remote wilderness anchorage, and a 600-mile passage.
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The timing was tight. The weather wasn’t playing ball. A slim downwind weather window was followed by four days of forecasted no wind – the worst thing ever when you have eight crew members keen to sail.
So, we rallied. I adapted the safety brief to run underway, anchored on the US border, left again at 0500, motored eight hours in the rain, and made it to Prince Rupert – our Canadian port of entry – just before customs closed.
By 8pm, we were cleared into Canada, and I faced a dilemma. The weather window was fast diminishing. And, so were my energy levels. Do we go? Or do we stay?
The forecast was clear: the only wind for the next four days would come that night. No matter how many times I refreshed the GRIBs and compared models, the message was the same – we had to leave that night to catch the wind. But the thought of slipping lines, hoisting sails and heading into the darkness filled me with dread.
The truth was, the only obstacle was me. The boat was ready, the crew were briefed, the conditions perfect: 15 knots on a broad reach all night.
But I was running on fumes. I gathered the crew and explained that while we had everything lined up for an amazing first night at sea, I was calling it: we’d stay on the dock and leave in the morning. They supported the decision, but I still felt I’d failed them.
The next day, the sun shone, and so did I!
With my fresh energy, I embraced whatever nature threw our way. We slowed down to watch whales, chased an afternoon sea breeze, and practiced upwind helming as we zigzagged through forested fjords.
The week ended as a total success. And it was a valuable reminder: one of the greatest influences on a good trip is the skipper’s mood.
Most crews will choose no wind and an enthusiastic skipper over perfect wind and a miserable one.
A happy crew is a very important thing. But sometimes a skipper needs to be ‘the bad guy’
Making the tough calls
For skippers, making unpopular calls comes with the territory. Whether it’s delaying departure, dropping the spinnaker, waking someone early for a sail change, or pulling someone up on bad behaviour – at some point, you’ll make a call that not everyone on the crew agrees with. Sometimes, they may downright hate it. And yes, this part of skippering always sucks.
It’s uncomfortable. It’s lonely. And, like my night in Prince Rupert, it can feel like you’re failing people. But there are ways to cope.
Ideally you’ll win respect for your decision, even if no one likes it. Share as much of your thinking as you can.
The more involved the crew feel, the more likely they’ll empathise.
The harder calls are the ones when you have to weigh fatigue, gut feeling, or that intangible sense that ‘something isn’t right’. My advice is to listen to those feelings. I’ve had to learn and relearn so many times to treat them with the same weight as the hard data.
Just as you wouldn’t push sails, equipment or crew past their limits, don’t push your own nerves either. Even if it’s just a touch of anxiety or feeling a bit ‘off’, remember: your job isn’t just to drive a boat or keep people alive – you’re providing an experience. And that matters just as much as the wind and the weather.
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