Toby Heppell gets advice on skippering with friends and family from Pete Goss, Dee Caffari and Conrad Humphreys

Good leadership sounds like something required of the Navy, or a perhaps a committed race team and not something necessarily required for a day’s sail with friends and family.

In reality, although we might not all think about our skippering skills in leadership terms, good leadership is often the difference between a skipper people like sailing with and a bad one, or an enjoyable day on the water with a happy crew or a long sail with arguments.

Accept mistakes will happen

In a perfect world no one would ever make any mistakes and we could all go about our lives in a blissful and error free – if rather dull – utopia.

Expecting an error-free sail is, in itself, a relatively large mistake.

A good skipper should look to minimise the possibility of significant errors, but also be able to allow those they are sailing with to make mistakes and so learn and improve their own sailing skills.

A crew sailing on the Solent

As skipper, watch what’s going on, but don’t step in too early. Mistakes create the opportunity to learn. Credit: Andrew Sydenham/TI-Media

‘In order for people to improve you do need to give them a level of responsibility,’ says Pete Goss, who has raced in the Vendée Globe, sailed to Australia in an open lugger and is now cruising around the world with his wife Tracey.

‘A big part of that is allowing them to do things wrong. If you see someone making a mistake, your role as skipper is to judge the potential consequences of that mistake, and if you know they are likely to be fairly minimal, sit back and allow it to happen. Then you can gently coach them afterwards.

‘Shouting at someone, even through urgency not anger, when they don’t know what they are doing wrong or perhaps have not even had a chance to do something wrong, drastically reduces their confidence and only has the effect of making them less likely to give things a try in the long run.’

There are few of us that would disagree with this in principle, but it can be much harder in practice when you are on board and someone is about to make a mistake that you have spotted.

Pete and Tracey Goss

Remember the aim is to have a good time. Credit: Pete Goss

Typically the natural instinct is to call out to them to prevent the error.

So how do you counter this natural urge and allow errors to happen?

‘It would be wonderful if none of us ever made any mistakes and we went out on the water every day and everything ran like clockwork. Unfortunately that’s never going to happen,’ says Dee Caffari, who skippered Turn the Tide on Plastic in the most recent Volvo Ocean Race.

‘Something will always go wrong that you have not planned for. The wind will change, the helm will do something, the wave-state will shift. Whatever it is, the important thing is not to have a blame culture. You need to be able to get out of those situations and the only way you can do that is through good teamwork and collaboration, not pointing the finger. It is the flexibility to adapt that allows you to get out of these situations.’

‘Much of what makes a skipper a good skipper is thorough forward planning and delegation’ agrees Goss.

Dee Caffari helming during a leg of the Volvo Ocean Race

Dee Caffari brought together a young team of sailors as skipper during the Volvo Ocean Race. Credit: James Blake/Volvo Ocean Race

‘Having a clear idea about what each person’s responsibility is when you are on the water means you can identify areas where mistakes that are not major problems are likely to happen and so be more prepared to let them go if and when they come up on a passage. Defining roles like this also means you are able to allow people to develop their skills and increase their responsibility over time.’

‘Of course there are always going to be moments when the error or potential error could be dangerous and this will need preventing. In these circumstances, dealing with the fallout in the most effective and empathetic way possible is very important.

‘In the military, the saying was always “never give someone a bollocking in public”,’ comments Goss.

‘If a crew member has made a dangerous error, then choose an appropriate moment to say gently, ‘Comeup to the mast and give me a hand tidying these halyards’, or whatever, and then you can calmly explain the problem and what you would like to see done differently away from the other crew.’

Managing tiredness

A key issue when out on the water for any extended period of time is fatigue.

Even in crews made up of many bodies, tiredness is bound to cause tension – or make people more sensitive than they might usually be.

This is something that needs to be considered if you want to get to the end of a long sail with the crew all still talking.

‘In my experience, it is always eating and sleeping that are two key points that result in tension,’ says Caffari.

‘I’m sure we have all been in that ‘hangry’ state where we are sleepy and hungry and it is just the worst thing ever.

A man asleep down below on a yacht

Sleep should be regarded as part of the ‘job description’ and taken seriously. Credit: Alamy

‘A key problem here, is that sometimes people want to be seen to be enthusiastic and super-keen, so they’ll try to work through their off watch. But that does not help anyone. It’s really important to try and instill in your crew that they are of no value once they are too tired.

‘Any boat I am in charge of, I always operate with the rule that if you’re sleeping, then your job is to sleep and it is the job of those on watch to wake you up when it is time for you to go on watch. That way you should be able to sleep properly without having that feeling of waiting for an alarm in the back of your mind and waking every few minutes to check your watch – it also helps with building trust throughout the crew.’

To perform at your best you need to sleep.

It is the same for everyone and the person in charge is often most guilty of not prioritising sleep as they are aware they’re ultimately responsible for what happens onboard.

That is where empowering your crew to take ownership and responsibility allows them to develop confidence in their capabilities.

So a key job as skipper is instilling the attitude that sleeping when onboard is just as important to being safe and efficient as any other aspect of life on board.

‘I did a lot of work with sports psychologists before doing a lot of the big races I have been involved in,’ says Caffari, ‘and this means I got to understand myself a lot more, understanding when I am tired and when I am hungry. There are moments now when I realise I just need to eat, take 10 minutes to rest and I am a different person.

A couple on a yacht

If possible always sail with potential crew before taking on any significant passage

‘Obviously not everybody gets the opportunity to work with a psychologist but often it is easier to see it in others than yourself. People tend to start getting emotional and they don’t know why. If as a crew you understand there are going to be moments like that, and it is discussed early, then it makes it much easier to say, “I think you might need a drink, food or sleep”.’

The compulsion people have to keep pushing themselves beyond the point of over-tiredness is almost certainly one most skippers can relate to and most likely something that many of us will have experienced previously, not realising how exhausted we are until we start to make the kind of mistakes we would not normally expect of ourselves.

‘Sometimes people even tend to elevate suffering into a sort of ends in its own right,’ says Goss.

‘For me that is totally the wrong approach. I want to enjoy my sailing and usually that means not doing too much, not getting over-tired or hungry and making sure we are able to stop when it stops being fun. A key to that is to be flexible. We do not make plans, we have aspirations so that gives us total flexibility.

‘Also, with long-term cruising you can get a compulsion to rapidly progress from one place to the next, without really enjoying each destination. You might, for example, get down to the boat and feel a bit tired yet push on through a long passage, which is almost guaranteed to result in seasickness.

Whereas if you’d acknowledged your tiredness and decided to take a short trip round the corner and anchored up for 24 hours, taking time to read, relax and sleep, then it would be a completely different story.

Proper briefing

Having a good briefing before you leave the dock is something most of us know to do in theory but how often do we actually sit down and talk through the plans for the day if it is a relatively short sail?

A good briefing is essential to enjoyable sailing and making sure everyone on board knows what your aims are for the day.

Without proper forward planning tensions can arise that often could have been avoided simply by planning.

‘It’s important to remember, it is really easy for people to go through life without having to experience a situation where teamwork is an absolute necessity,’ says Goss.

A crew sitting in a cockpit while sailing the Solent

A proper briefing keeps everyone on the same page. Credit: Andrew Sydenham/TI-Media

‘Many people have a job where if someone drops the ball, the consequences are not that big or it can be sorted elsewhere, but on a boat you do not have that luxury. So it’s essential to instill a teamwork mentality from the off.

‘On an initial briefing, when people join the boat, the first thing I ask is if everyone can swim and then I’ll say, “Look these are the lifejackets here, let me show you how they work, we wear them in these circumstances without negotiation but you can wear them all the time if you wish.” etc.

‘Another tip is to use positive language. Rather than saying what you don’t want to happen, you need to be able to say what you do want to happen, to articulate what you want to achieve. It’s easy to be in a negative language mode, but it’s hard to turn that around. A good management tool is to be positive, prioritise, and focus on things you can action.’

Not only does sitting together and going through your plans provide every member of the crew with a good overview of what will be happening, it also creates a moment for discussions about the best way to approach situations that may come up during your sail.

This is also a great moment to take on suggestions about doing things differently and learning from your crews’ experience.

Be able to back out

‘We always have a red card system in place,’ says Goss. ‘Tracey [Goss’ wife] and I always say if one of us has any doubts we just don’t go. Sometimes that is an intuitive thing, it just doesn’t feel right. If you allow everyone onboard the option to play their red card we all know that each of us has one and that it will be absolutely respected.

‘Sometimes it might be that someone has a bit of a bug and that can just be enough to say, “Look, I don’t feel right. Let’s not go”. Usually I find the next day we realise as a group that it was the right decision to make even if some are hesitant about staying.’

However, Goss adds that, though this card concept does need to be respected there does need to be the flexibility to have a discussion about why not, and not just make it a blanket ban.

This is a difficult thing to get right.

A Rustler yacht being sailed off Falmouth

Having options to cut your sail short is a good idea

Again, much of how you approach the situation comes from all the crew knowing how you approach the situation ahead of time.

It is important to strike the balance between understanding the core reasons behind someone not going and addressing any issues and falling into the trap of pressuring crew to go when their concerns are genuine.

‘Often people worry about things that are outcomes and not causes,’ explains Goss.

‘If someone is reluctant to go then you can work to address the cause of the concern which, in turn, solves the outcome issue.’

A good example of this might be if someone is concerned about the forecast, which does not look great several hours down the line.

Perhaps having a better plan for foul weather or several plans for backing out along the passage means you can still set off with everyone happy that they are not going to end up sailing three hours through some miserable weather, as the option to back out later is there and fully planned.

Friends and family

‘When we took the kids sailing we would switch to Swallows and Amazons mode and never sail anywhere that was further than two hours away,’ Goss explains.

‘Kids find long sea passages dull, so take time to choose short sails with destinations that have enough to keep them entertained.

A family aboard a yacht

Adapt your sailing plans for those onboard. Long passages for children can be dull

‘I think with partners, a big problem is that they will often have far more experience and sometimes come from a racing background. The number of husbands we come across that say, “My wife doesn’t like sailing” and you say, “Well how did you introduce her?” Quite often the response is, “We went out in a force six and beat the hell out of the boat for a day!” You can’t help but think, “What were you expecting?”’

Goss further makes the point that if you want to enjoy sailing with your partner and they have less experience than you, providing a list of potential options for the day, explaining how each varies in terms of difficulty and allowing them to choose the best option empowers them to understand what to expect and so helps their development and confidence.

Unknown crew

Mostly likely we will all spend the vast majority of our time sailing on boats with people we already know, but there are occasions when you might need an extra pair of hands for a particularly long passage or delivery.

It is usually difficult to tell just from talking to someone what skill level they possess and how they might behave sailing.

‘It is always a risk when you do not know someone you are sailing with,’ says Caffari. ‘You can make it as much of a calculated risk as possible, though.

Dee Caffari and her Turn the Tide on PLastic crew in the Volvo Ocean Race

Caffari (left) thinks finding crew that have the same views as the rest of your crew is the key to harmony. Credit: Jeremie Lecaudey/Volvo Ocean Race

‘Often if you are sailing with someone for a specific purpose, say a Transatlantic, then you usually do not have the luxury of sailing with them for 48 hours beforehand – which I consider a good stretch of time to really get to know how someone is at sea.

‘By the very nature of them putting themselves out there as crew, you usually have an idea of the sort of person they are. They’ll usually have some sailing knowledge in order to be available for a trip or to have put themselves up for it, for example.

‘What you really want is someone who is easy going and relaxed and who can blend in with the people you already have in your crew; ideally they will just seamlessly blend in with those around them.’

Caffari thinks a lot can be learned merely from sitting down together as a whole crew and seeing how everyone interacts, whether it feels like a relaxed environment or if there are any differences in aims.

‘It’s always worth going through any rules you have onboard too. With safety elements, such as lifejackets and when you wear them, if you see eye-to-eye on that subject, then it’s probably a good sign. Obviously if they disagree with some of those safety rules you are going to be set up for conflict from the off.’

In a perfect world, any unfamiliar crew you pick up will come with their own experience and knowledge that benefits everyone, but in many cases they may be less experienced than is ideal, in which case, you may need to do some on-the-go training.

‘You have to be patient, knowledgeable and enthusiastic enough to instruct beginner crew,’ says former RYA chief examiner James Stevens.

‘For instance, don’t say: “Could someone prepare the port jib winch for a tack?”. Say: “Charlie, prepare the port jib winch. We’re tacking soon”. If you don’t use names, nobody moves.’

Planning for success

The word success conjures images of competitive racing, but in truth, having an idea of what you consider a successful outcome to any sailing makes it much easier to end a sail with a happy crew.

‘When I look back at the British Steel Challenge, a big learning point for me was how we might measure success,’ says Goss.

‘Some said, as it was a race, success would be winning, but as a skipper the role is to look at the crew and consider whether this was the case.’

Goss recalls some boats were so focused on winning they only ever put the fastest sailors on the helm, meaning some never got a chance.

Pete Goss on his laptop

Try to plan what you will consider a successful sail. Credit: Pete Goss

‘I felt if we got to the end of the race and they were walking off with their family, I wanted them to look back and think ‘If that boat didn’t have me, then it would not have got round as well.

For me that was the success I wanted to deliver after discussions with the crew we had onboard. Really, for cruising, measuring success is all about defining the goals of a passage.

Often those goals will not be sailing – perhaps you want to go exploring – sometimes the sailing comes second and sometimes goals change over time. ‘I love the sailing,’ continues Goss, ‘but Tracey sees it as a means to an end. So we both have different ideas of what a good time is.

‘Cruising is really a patchwork quilt of experiences and we all have differing preferences. So you need to make sure that one does not monopolise their preference.

‘Tracey used to say that nothing goes to windward like a 747, so originally she would fly to the destination and I would singlehand and meet her there, Recently she said, “Well I think I could do with a bit of ocean time”, so it’s interesting and it does change.’

It is well worth being flexible in your planning too. There is no point in having a goal of getting to Falmouth and seeing that single goal as the only marker of a successful trip. Try to have a range of options available. Here, a mix of crew can be a boon, as each might want to do some specific thing, then you can plan a range of successful goals, each of which is weather dependent and allow yourself to achieve goals even if your plans do change.

‘If it’s blowing hard, a fast passage along a weather shore could be a highlight of the trip – an exhilarating sail for the crew and good experience of strong winds in flat water,’ says Stevens.

‘However, don’t get trapped. If heavy weather is forecast, aim for somewhere sheltered so you can keep sailing. You’ll fare better in The Solent, Plymouth, Falmouth, The Clyde and Ipswich than Brighton, Salcombe, Aberdovey or Sunderland. A river trip is a good option if there is a gale outside.

Leadership in Mutiny

Mutiny

Stormy weather makes everyone more stressed. Credit: Channel 4

What happens when a group of strangers are thrown together into a 23-foot boat with limited sailing experience and cast adrift with only enough rations and drinking water for the first few days at sea?

Triple round-the-world yachtsman, Conrad Humphreys was the professional skipper for Channel 4’s Mutiny and gives his thoughts on leadership and how to avoid a mutiny whilst at sea.

‘When Lieutenant William Bligh was cast adrift in 1789 after the Mutiny on the Bounty, 18 loyal crew members joined him in the tiny 23ft open boat. All of which were highly disciplined and able sailors.

‘My situation was very different, I inherited a crew, many of whom had never even been to sea. The first time we would all be together would be in Tonga a few days before the voyage was due to start. This was deliberate, as Channel 4 wanted to explore how nine strangers would cope in a tiny open boat. In total, I was given just three days to prepare the crew for the 4,000 mile voyage.’

Get to know your team-mates fast

‘We needed to act quickly and to be able to establish a routine, meant understanding what roles we could play. Everyone brings something to the table, so focus on what people can do rather than what they can’t.

Quickly identify a leader and give people jobs. Banter can be great for morale, but keep a close eye on the quiet ones, often they will be the heroes when the going gets harder.

Agree how you are going to operate.

The sailors who took part in Mutiny

Creating the right culture is critical to success. Credit: Channel 4

Creating the right culture onboard is critical to success and time well spent getting people to agree on the way you’re going to operate will help prevent issues surfacing downstream.

Paint a clear picture of what success looks like and get everyone’s input.

Bligh led his crew to safety over 4,000 miles, that was his sole priority. He never let his crew feel in any doubt that they wouldn’t make it.’

Quickly build a routine and establish a leader

‘When you’re fighting for survival through a storm, it’s easier for people to come together and rise up to the challenge, but maintaining momentum through the doldrums will cause idle people to lose focus on the task ahead.

Building a routine will help people focus, gives structure to the day and ensures people rest when necessary.

Conrad Humphreys sitting in Bounty's End

Round the world yachtsman Conrad Humphreys was the professional skipper aboard Channel 4’s recreation of Blight’s open boat voyage, Mutiny. Credit: Channel 4

Establishing a leader who is able to look forward and keep up morale even in difficult times is critical for success.’

Prioritise – look after each other, shelter, food, sleep

‘With just 400 calories in our daily rations and only 28 gallons of water we had to prioritise food and water. We made landfall on the island of Tofua where Ant Middleton and two crew went off in search of food and water.

Onboard I tried to make the boat more seaworthy by making a canvas shelter to keep us from the worst of the waves and rain.

Mutiny - Channel 4

Try to get to know each other quickly. Credit: Channel 4

Frustratingly, Ant’s mission yielded only a few coconuts and the shelter didn’t really survive the first bout of bad weather.

The time delay on Tofua cost us dearly as we experienced headwinds and bad weather.

Our bodies suffered terribly in the constant wet and by the time we reached the islands of Fiji, half the crew were desperate to leave the boat.’

Storms are often temporary, but extended calms can sap morale

‘Often storms are preceded by calms which can give a false sense of security. Use the calm weather to rest, recover and make good any repairs, work hard to look after your boat.

Remember, stormy conditions may only last a few hours, rarely days, but calms can last a lot longer.

In the final few hundred miles before reaching our destination in Timor, we were becalmed in a huge area of high pressure.

Without shelter from the sun, dehydration quickly set in and we found ourselves in trouble.

Crew morale reached rock bottom and conflicts arose out of the frustration of our predicament, which needed to be nipped in the bud.