5 Lessons Learned from Managing a Crew

in Life at Sea / Sailing the World / Spain / Travel
5 lessons in managing a crew sailing blog

When Cheeky Monkey reached the Canary Islands after five days at sea, it was clear the crew needed a stiff drink and some space.

This was our “shakedown,” our test run for the Atlantic crossing with our full crew of six: Meg and Kristi, our friends from the ’13-14 Clipper Round the World Race, Morgan, a French solo sailor we met sailing in the Bahamas, and Xavier, a close friend of Morgan’s who briefly sailed with him in the Caribbean. Our crew didn’t all know each other, as Ryan and I were the only common denominators, but we were excited for them all to get to know each other during our passage to the Canary Islands.

When we hit the fuel dock in Las Palmas de Gran Canaria on Kristi’s 29th birthday, we popped open a bottle of champagne not just to celebrate, but to let off some of the steam that had been building over the last five days at sea. For better or for worse, alcohol tends to act as a release valve for pressurized circumstances on a boat; it lubricates the tongue so that all the blocked-up grievances of the last few days and weeks come gushing out, filling the awkward spaces between crew. Which is exactly what happened on our first night out in Las Palmas.

If I ever thought introducing friends from different parts of my life was tricky on land, inviting virtual strangers to live together on a boat for a month as we crossed the Atlantic Ocean had the dramatic weight of launching a reality TV show.

sailing blog 5 lessons in managing a crew
In the Canary Islands: Ryan, Xavier, Tasha, Meg, Kristi (holding camera), Morgan

I watched as the drinking progressed and crew started to let loose some of the complaints they had about how the last five days at sea went, making it clear we would need to amend some of the rules and schedules Ryan and I had established at the start of this trip.

In our former lives, before we sold everything in 2015, Ryan and I were the bosses of a series of successful schools that we built from a seed of $800 and grew into a multi-million-dollar enterprise that succeeded in large part because of the talented people we’d hired and motivated to turn our educational and entrepreneurial visions into a reality.

And now it suddenly dawned on me that running a boat is very similar to running a company – in essence, someone needs to act as the head to establish the vision, the direction and the short-term goals that lead to the fruition of the big picture, the dream. In the case of a company, that dream might be to expand its operations across the country. Or, in sailing, it might be to cross an ocean, win a race, or circumnavigate the world.

But what if you found yourself in charge of a group of close friends? How do you manage people who aren’t your employees? How do you act as the head of a vision without acting as a “boss” to your friends? These were questions we asked ourselves when we finally got to the Canary Islands because, clearly, there were a few things we screwed up on that passage from Morocco.

It took some experimentation and a little hindsight to work out our successes and our mistakes managing a crew of friends for the first time, but here’s a little insight into what we learned on that first passage…

sailing around the world 5 lessons in managing a crew
Top-of-mast view of Cheeky Monkey in the Canary Islands

1. Crew happiness hinges on crew expectations…

…And it’s your job as Captain to manage those expectations. If you tell your crew they’ll have a private cabin to themselves and you stick them with a roommate when they arrive, they’ll be upset no matter how luxurious the room is you give them. If you tell your crew they may have to sleep in the cockpit and, when they turn up, they have a queen-sized bed to snuggle up in, they’ll naturally be thrilled.

That’s how expectations work – if you are transparent about the cons, people are often pleasantly surprised by the pros.

A few of our crew, having only experienced sailing in the Clipper Race on board 70-foot ocean racing yachts with no comforts to speak of, were thrilled to find themselves on board Cheeky Monkey with queen-sized beds, en suite heads and an espresso machine. They were used to long, 4 to 6-week passages while crammed into a smelly boat full of 20 crew whose personal hygiene depended solely on the regular use of baby wipes.

Being a solo sailor, however, makes it tougher to adjust to a boat full of people. It’s nothing like having an entire boat to yourself, enjoying long watches in solitude and setting your own schedules. Coming on board Cheeky Monkey to find watch schedules were drawn randomly out of a hat and that we banned alcohol consumption during passages was a surprise to some of the crew — this was not the carefree cruise with friends they were expecting. And though Ryan and I like our drink, we have always done dry passages because we don’t feel comfortable drinking at sea in unknown territories, so we never considered this rule would cause issues on board.

So what did we learn from our mistake? We need to be explicit about what the crew can expect in terms of accommodation, jobs and rules on board Cheeky Monkey before they get anywhere near the boat. If our crew have time to mentally prepare for what to expect on board, they’re more likely to be happy with their circumstances when they arrive.

5 lessons in managing a crew sailing around the world
The girls on Cheeky Monkey are happiest when there’s good WiFi 🙂

2. The skipper is the boss of the boat…

…Which is harder to establish on a boat full of friends rather than paid crew.

On Cheeky Monkey, the boss is Ryan and that’s because it’s our boat, our responsibility and, between me and Ryan, Ryan has the most experience as skipper. Ultimately, everyone should feel responsible for the safety of the boat, the crew and its equipment, but no one feels the weight of responsibility as heavily as the person who owns the boat.

When we set strict parameters for when to reef or drop a sail, it’s because Ryan and I know how much it costs if we damage the sails, the boat or any of our equipment. The Parasailor, for instance, is a $13,000.00 spinnaker. To rip the spinnaker because we didn’t drop it early enough would be a mistake that would tear a hole in our pockets alone, not the pockets of the crew on board.

Even if crew feel they have more than enough sailing experience to do maneuvers on their own, Ryan often insists that he be woken up for any change in direction, sails, etc. It may seem excessive or unnecessary, or even a bit too bossy for our sailing friends on board, but ultimately we are the ones who are responsible for the boat, the equipment and the safety of the crew.

So, in this case, being bossy is an unfortunate necessity.

 5 lessons in managing a crew sailingRyan has the tough job of being a manager to his friends

3. Being too relaxed causes stress.

That sounds like a contradiction, but when it comes to rules and schedules on board a boat, it’s true. When we set out from the Canary Islands, everyone drew their watch schedules out of a hat. If you got the crappy 2 am – 4 am watch, that was life. Drawing out of a hat was the only fair way to distribute the good and bad watches.

When we established the meal schedule on board, however, we weren’t strict at all about who did what and when. We stated that everyone was on their own for breakfast, but lunch would be served between 12 – 1 pm and dinner would be served between 6 – 7 pm. And the rule for clean-up was if you made a meal, you didn’t have to clean up from the meal. And we figured people would just rotate the responsibility of cooking lunch and dinner as they felt appropriate.

It seemed like an easy enough thing to do with six people on board — to share out the cooking — leaving plenty of time for me to read, write and sunbathe.

But what actually happened was that meal times had a kind of halo of stress hovering over them, as I never knew for sure whether I was off the hook or on the hook to cook a meal on any given day. So, as lunch or dinner would approach, I would find myself unable to focus on whatever I was doing because I’d be preoccupied with a kind of internal monologue. “Who’s cooking today? Is it my turn? No, wait, I cooked lunch yesterday, so it’s someone else’s turn. But it’s noon…has anyone decided what to cook? If I made lunch now, then I’m definitely off the hook for dinner. Should I just make lunch now?”

And then, after an hour of having this mental conversation with myself, usually Meg or Kristi would step up to the plate and save us all from having to think about making a meal. Which would make me feel guilty because it seemed like Meg and Kristi were cooking the majority of the meals.

So it wasn’t the cooking that was cutting into my guilt-free alone-time, it was the process of thinking about cooking that was interfering with all the things I’d rather be doing. Not to mention, it didn’t seem like the meal rotation wasn’t being shared out fairly and equally.

We fixed that problem in the last few days of the passage by simply assigning lunch and dinner duties to crew according to a schedule and implementing the rule that whoever was assigned to cook the next meal would do the washing up for the meal before it. It was simple, it worked, and it stopped the pointless conversations in my head for hours each day about whether I should or shouldn’t get up and make a meal for everyone.

My free time returned to its blissful, guilt-free state because I knew exactly when I was on the hook.

sailing 5 lessons in managing a crew sailing blog
As you can see, it’s a big job to feed 6 people on board Cheeky Monkey

4. Even experienced crew need training.

The first few days of our passage with crew, we pulled Ryan out of the watch rotation and had him be a “roamer.” The idea was that he should be woken up any time there was a question about whether wind speeds were picking up, whether we should reef or change a sail or whether we should be worried about a boat on the horizon.

It also meant Ryan could wake up periodically to check on crew at the helm during night watch to make sure they were following safety procedures (like having a personal AIS clipped onto them) and not falling asleep on their watch. This was as much to instill confidence in the skipper that the crew could handle their responsibilities as it was to make sure the crew got to learn all the maneuvers on board, like sail changes, reefing, tacking, jibing, etc.

Having the skipper be well-rested so he can spend ample time training crew is a crucial process that we go through with any new crew on board and it’s worked well for us so far. As in, we haven’t sunk the boat or lost any crew overboard as of yet. Success!

 parasailor 5 lessons in managing a crew
The Parasailor is an amazing sail, but it’s not cheap — it requires TLC and crew training

5. Put as many procedures / rules in writing as possible.

There are things we’ve gotten used to on board Cheeky Monkey that we don’t even think about and, therefore, we find it hard to remember what to tell new crew members when they come on board for the first time.

We have a written “departure checklist” in the front cover of our logbook so anyone on board can run through the list and make sure we’ve done all the engine checks and various items needed before we leave port.

We’ve also now written out our safety protocols, in addition to talking our crew through them, and posted them in the galley so crew can refresh their memory on where the EPIRB and fire extinguishers are located and what to do in the event of a man overboard.

One item we consult daily is the reefing chart for our sails, which came with our boat. Having absorbed all the disaster stories about catamarans being dismasted in high winds, I take our reefing chart very seriously and talk it through with the crew so they know how important it is to reef early. Having a written list of apparent wind thresholds just makes it easy to know when to reef without having to think about it too much.

sailing blog 5 lessons in managing a crew
The happy crew of Cheeky Monkey

All in all, our crew shakedown from Morocco to the Canary Islands went well. Despite a few arguments and tears in the bar when we arrived, everyone on board seemed to get along well and understand what their roles on board were.

Our French crew got over the alcohol ban and we allowed them to bring several bottles of Pastis on board for the Atlantic Crossing, and we stocked up on wine and rum, so long as the crew promised not to drink while on watch. Meal responsibilities were mapped out on a rigid schedule so everyone knew when to cook and when to clean, and we decided new watch schedules would be drawn out of a hat every week so that no one got stuck with a bad watch for too long.

The fact is, managing a crew of friends can be tricky because you want to please everyone and yet, as skipper and owner of the boat, your primary responsibility is to keep the boat and the crew safe.

Coming up with the boat rules can be a democratic process, but the final decisions should be based on what the skipper is comfortable allowing based on his/her experiences.

Those decisions may be disliked by paid crew but, ultimately, paid crew do what they’re told. When those decisions are disliked by friends on board, it can make things uncomfortable and more difficult to justify, as disagreements can have an emotional impact among friends.

There’s no easy solution to dealing with disputes on board a boat full of friends but, regardless, the skipper reserves the right to do whatever he/she feels is right. After all, it is his/her boat.

But I can say one thing I’ve learned in all this is, wherever possible, don’t try to take away a Frenchman’s Pastis.

Comments on this entry are closed.

  • Patricia April 28, 2016, 4:56 pm

    I only have one experience to draw upon but I have to say it went fairly smoothly. Last year I helped crew a 46′ Morgan center cockpit from the BVIs to Horta, Azores via Bermuda. There were the two owners, a husband and wife, and then two of us crew, one that had crossed the Atlantic several times and me, who has a 21′ day sailer that I have sailed for years along with being race crew and picking up a few certifications 🙂

    The wife made a great schedule for the four of us that ran across two days. Basically the sifts were broken down to two short overnight shifts, midnight to 3am and then 3am to 6am. On either side of those were two four hour shift, 8 to midnight and 6am to 10am and the day was two longer shifts, 10am to 3pm and 3pm to 8pm. This meant that most of the time we had between ten and fourteen hours between shifts and the captain had no problem if you wanted to have a drink after your shift was over.

    As for food it was everyone for themselves at breakfast. The wife took most of the cooking duty but the other three of us including the captain stepped up to make meals. I love cooking so I often said I am doing lunch or dinner today. It all worked quite well.

    The only slight hiccup was originally I was only going to go as far as Bermuda and another crew was coming in to replace for the trip to Horta and then on to Portugal and the other crew that had experience was going the whole way but in Bermuda he suddenly decided he was leaving. We still haven’t ascertained as to why. Luckily I am a bit flexible with my work and so when I emailed my manager and asked if I could be away for another couple of weeks he was cool with that. The new crew member fit in great. When we arrived in Horta 18 days later we were still on speaking terms and had another couple of days to cavort around Horta before I had to go back home and they took off for Portugal.

    I would really love to do crewing again but I think I got really lucky with this one and it would be hard to find another great situation and experience like I had last year.

    Yes, it is very important to lay out expectations beforehand and to be firm with rules. The captain had a thick notebook and a list and the morning after out arrival in Nanny Cay we had a sit down meeting where he went over everything, ships systems, expectations, schedules, food, the whole nine yards. it sounds like it was strict but it wasn’t, it worked quite well.

    After they finish cruising in the Med for a couple of years they have already said the I and the second crew member (Bermuda to Portugal) would be their first choice, if we are available, for crew when they bring the boat back to the Caribbean. I would move mountains to ensure I am available when the time comes 🙂

    Anyway, loving your journey!

  • Bill April 29, 2016, 3:07 am

    Your spinnaker is much too tight in this pic light winds loosen it up.
    Skipper is boss only when they are too drunk are they not.

  • Kevin April 29, 2016, 10:47 am


    Excellent post. It is very difficult to run a boat (just like a business, everyone participates in the cause) when the crew doesn’t know the expectations in advance, or fail to “follow the rules”. Add into that mix the crew are friends and it makes it much harder to be in control. “Conflict arises out of differing expectations” is something I learned in my business years ago and always try to keep in the front of mind, even when I feel like my employee is a friend. Your experience is very instructive that you still have to “be the boss” for everyone’s safety AND enjoyment, and it will help eliminate the possibility of crew leaving or being asked to leave the boat at the next port. Happy to hear you survived the shakedown and I look forward to reading about your crossing. Love the videos but the written word can convey so much more. Fair winds… and open transparent communications with people who not only look like adults, but act like it too.

  • Russell April 29, 2016, 3:59 pm

    Thank you.

    This information was valuable for me.
    I’ll be assembling my crew soon – you have given me things to think about when selecting a crew.

    Again – thank you.

  • Greg April 30, 2016, 1:28 pm

    Your “lessons” are reasonable and valid. However, I have two problems here.

    First, there’s something missing here. Like you I have run a successful company and managed crew on my own boat. I have also sailed as crew on many boats. I know Morgan very well, and this does not sound like the Morgan I know. Obviously, you write from your own perspective, but there’s something missing from this story.

    Secondly, it seems discourteous and unprofessional to air your dirty laundry in public using the name of a sailor who volunteered as a friend to help you out. I would certainly avoid crewing on any boat that would write disparaging comments about former crew by name. I’m guessing you don’t really consider Morgan a friend any more. Still, that’s just shabby.

    SV Daystar

    • Tasha May 1, 2016, 3:15 am

      Hi Greg,
      My sincerest apologies to Morgan if he was offended by this post. I was simply trying to highlight how we’d let him down. I wasn’t trying to be malicious in my assertion. I consider him to be an incredibly valuable friend who I know we created a situation of conflict for.

      In consideration of this and Morgan’s comments, I will do my best to remove any offending statements. Morgan is an amazing sailor and has been an amazing friend…I was not intending to imply otherwise. I simply wanted to highlight what we learned from letting him down on that passage – I believe we alleviated those problems going forward on the Atlantic crossing. But perhaps I am wrong about that.

      All the best,