How Does That Feel?

November 7, 2016


“We cannot direct the wind, but we can adjust the sails.”
-Bertha Calloway

I was out racing for the first time in a long time this weekend. I was rusty and sailing on a boat that I was unfamiliar with. Furthermore, I didn’t know anyone on the crew. So I started doing what I like to see others do when racing: I just started talking about what I was seeing happening around me.

“Do you see that boat over there?”

“Hey, look, there’s a puff of wind over there.”

“It looks like the breeze might be filling in from over there.”

I kept that little monologue up, not constantly, but on a fairly regular basis. Just letting others know what I think I’m seeing. At some point during the race, one of the guys looks at me and says, “Tom, I hear you talking about pressure over here, and puffs over there, and I’m not really sure what you are talking about. How do you know there’s really wind over there?”

That’s a great question. And there are a couple of answers. The first answer is that I simply don’t know. I’m really just guessing. It’s the wind that we are talking about after all, and I have no more special insight than the next guy when it comes to divining the nature of the winds. However, I do have a few years of experience, and it turns out that more often than not I tend to get it right. That’s because I’m looking for certain signs on the water that indicate what might be the presence of wind. Something like a telltale pattern of ripples on the surface can indicate a small downdraft…or it could indicate a small school of fish ruffling the water. Now I usually know the difference, but I could be wrong. Trust me, it happens all the time. But I don’t worry about that when I’m racing. I think there is value in sharing all observations about the race course that help to give my team a tactical advantage.

People tend to assume that the person driving the boat, usually a very experienced and capable individual, knows what is best and has a good grip on the situation on the water. Nothing could be further from the truth. It turns out that when you are the skipper, you often have your head stuck in the boat. It’s not the skipper’s fault – it comes with the job. You are trying to steer to the telltales on the sails. You are reacting to pressure on the tiller. You are worried about the next mark rounding. But you can’t look at everything at once. That’s where a crew that can be feeding you that information is very valuable. It also helps if they can be sharing the information with each other. After all, they are no more likely to get it right than anyone else. That’s OK if there are more than one set of eyes looking at the issue. So if I think I see a puff and I call it out, another team member may disagree and point out the school of fish just beneath the surface of the water that I missed. The dialog is self correcting. It’s a constant patter of conversation where we share our impressions, some false, some true, that help us to confirm or deny our race strategy.

The other thing that I frequently do is ask questions like, “how does that feel?” Again, I have lots of experience sailing, but I’ve never sailed on this boat before. So I make changes to the sail trim and then I ask, “Did that help?” Maybe it does, or maybe not.

So not only am I talking about the physical nature of the race course, but I’m also checking in with my crew mates. Now I don’t do this out of any overabundance of concern about their well being. It’s much more practical than that. My actions are impacting their performance. Now maybe they will tell me how they are impacted or maybe they won’t. In fact, it’s often the case that people won’t tell you unless you ask. So I ask a lot. I change the sail trim and I check back with the skipper, “How’s does that feel now? Better? Worse?” I check with the guy trimming the main, “How about you?” Sometimes the answer is just a shrug. That’s fine, that’s good feedback too.

I’ve noticed a curious thing that seems to happen. As you model this behavior, others start to pick it up and do it too. At the start of the race, maybe I’m the only guy who’s talking. Two hours later as we cross the finish line, people are calling out puffs and asking for feedback from each other. People seem to pick up on it pretty quick if it’s useful. And if not, well, then maybe you don’t get invited back. Like I said, I don’t always get it right.

I wonder if the same sort of communication is useful for our development teams? What sort of things should we be talking about? What kind of observations are useful? Where are the ripples on the water for a software development team? I know they are racing – that much is for sure. Is the boss’s door closed? Is Joe late getting into the office? Does that meeting have an agenda? I don’t know, I’m guessing that some of that is water cooler conversation that probably isn’t worth a whole lot. On the other hand, what if I come into the office and mention that one of our biggest competitors just made a key acquisition. That’s going to send a few ripples through the water. What if there is an issue in production? More ripples. Maybe even some waves.

So there may indeed be some utility in sharing your observations about the business, the technology, the current state of the production system. It’s all wind on the water. It’s tactical information that may or may not be useful. But you are definitely better off talking about it.

So What about asking questions? You know like, “How does that feel?” Boy, there’s a question that software guys just absolutely love to get asked. How often are we checking in to get feedback on how our actions have affected those around us. Once a sprint? Of course I can’t wait that long in sailing, because the race is long over by then. The feedback would hardly even be relevant if I waited that long. In order for us to fine tune our performance and work together as a team, we need to be constantly engaging in a dialog that tests our assumptions about the value of the changes we are making. Did that help? How does that feel? It’s a fuzzy sort of qualitative conversation that I’m sure makes some folks uncomfortable. But maybe that’s because we’re using it wrong.

You see, when I ask the helmsman how a change feels, he knows what I’m asking about. He knows I don’t give a damn about his emotional state. I want to know if the boat just got easier to steer. Did the boat speed up? Did it slow down? Perhaps the same should apply to software teams. We need to make sure that we understand how the conversation is intended. When I ask how things feel, it’s not necessarily the touchy feely question you might think. Rather, I might really be interested in how fast you think you are going.

So, how does that feel?

Push v. Pull: A Leadership Story

November 10, 2014


It hadn’t been a very good race. In fact, it wasn’t an understatement to say it had been a disaster. To Peter Smith it was embarrassing just to show his face in the clubhouse afterward. He was at a complete loss to explain how it had happened. He felt like had just managed to snatch defeat from the jaws of victory.

He’d put together a decent crew. There were no rookies on the boat. Everyone knew their jobs and some had even sailed together before on other boats. Some even had more experience sailing than Peter did. It should have been a pretty decent team.

The boat was brand new. It was the latest club racer with all the bells and whistles. It was blazing fast on the water upwind and downwind. They had all the right equipment, the right sails, and every reason to win.

That’s why their performance was all the more frustrating for Peter. They’d sucked. There was no getting around it. He felt like he’d made all the right moves and still managed to fail. He’d reviewed it backwards and forwards and still had no idea what to do. It was definitely time for a beer.

Still licking his wounds Peter took a seat at the bar. Things were hopping and the whole place was abuzz with sailors recounting the day’s action. It happened that Pete had picked a spot next to one of the club’s old timers, Rex. Pete knew him only by reputation, but he was supposed to be one of the best racers in the club.

Rex was the gregarious type and soon introduced himself to Peter and asked how his race had gone. Beer now in hand, Peter proceeded to tell the story of the day’s humiliation.

“We went out on the water early and did some practicing before the race. We needed to get used to working with each other and get the kinks straightened out. We had no problem there. A few short tacks, a few gybes and we were ready to go.

So race time comes around and we get to the start and begin working for a good spot on the starting line. You know how it is, it’s a tough fleet, so there are lots of boats and they are all pretty intense. If you leave those guys an opening, they are going to take it and you can kiss a good start goodbye.

This is where we had the first hint that there might be an issue. As the maneuvers on the start line became more intense, the crew execution started to weaken. A boat would cut us off and we would have to spin to avoid them. As we would execute the spin, one of the trimmers would make a mistake and we would get stuck, stalled out behind the line.

Of course we would recover and try again, but is was the same story all over again. I’d have to execute another rapid maneuver and the trimmers would blow it again! It was intolerable. I began to yell, because we were never going to win a race performing like this. I don’t think the yelling helped much (in fact they seemed kind of annoyed), but what else was I supposed to do? I couldn’t exactly trim the sheets for them, could I?”

Peter saw Rex frown as he described this last bit, but he was starting to get some momentum in the story, so he powered on, “Anyway, when the starting gun when off, we weren’t in a good position and ended up starting in the second rank, sucking wind behind all the good guys who had managed to get off the line with good starts.

From there, things went tolerably well on the first beat to the windward mark. We did the best that we could with a bad start, but we still ended up toward the back of the fleet as we prepared to round the windward mark. Strategically, there wasn’t much we could do until we reached the mark, and we managed to execute well, with no major screw ups.

Of course that all changed when we reached the mark. That’s where everything fell apart. As we rounded the mark, the bowman wasn’t ready and we launched the spinnaker late as I was trying to gybe set and cover the competition. Nobody was ready! We ended up with the spinnaker wrapped around the forestay and the bowman was screaming at the trimmers to ease up on the sheets. There he was on the foredeck, flailing away trying to untangle the mess, as boats went by us on either side. Jesus was he slow! I hollered at him to hurry up, but I don’t think he was listening, because nothing changed. It was costing us the race.

Finally we got the spinnaker sorted out and we got ourselves back in the race. Only now we were at the very back of the fleet. That’s right, we were dead last. As if that weren’t bad enough, when we eventually got to the leeward mark, it was an even bigger disaster!”

Peter paused for a sip of his beer and continued, “I told the crew that we had to move faster to keep in the race, but it didn’t help. They just couldn’t execute. By the time we crossed the finish line, there was complete silence on the boat. No cheers from the crew. We all felt like we never wanted to do that again. I’m completely baffled. How could this have happened? Where can I get a good crew? I need a crew that can execute, not a bunch of whiners who shout at each other when things go wrong.

Look, I can’t change that it’s a race. We’re not in this to have a good time. We’re here to win a race. Why can’t anybody understand this? I need a little positive attitude here. I need people with a will to win! Where can I get some of that? We sucked!”

There was a long moment of silence. Rex was shaking his head and chuckling quietly to himself. He paused and looked at Peter with an assessing sort of gaze and said. “That’s a helluva story. I’ve seen it before. You want my advice?”

Peter looked down and swirled the beer at the bottom of his pint thoughtfully for a moment. Then he looked up and replied, “At this point, yes. I’ll do anything.”

“Buddy, what you are doing is pushing these guys, and what you really should be doing is pulling with them. You don’t succeed by pushing a team, you succeed by pulling along with them.” He said.

Peter frowned, “What the hell are you talking about?”

Rex paused to take another sip of his beer and continued. ”It’s like this, You can push the problems on the team. You can make it all their problem. In that situation, at the best, you are simply not helping, and at the worst, you are actually creating additional problems for the team.”

“Problems? What do you mean? I don’t give problems.” objected Peter.

“Hold on, let me explain: Let’s take your race today as an example. When you were maneuvering on the start line, what did you do to your trimmers?” Rex asked.

“I didn’t do anything to them. I spun the boat about and it was their job to trim the sails properly to execute the spin.”

“And did you tell them you were going to spin, or did you just slam the tiller over and wait for them to figure it out?” Rex tilted his head as he asked this last question.

“Well…I had to spin. I didn’t have any choice. Otherwise we would have hit another boat.” Peter said rather defensively.

“OK, so you had to spin, but you didn’t tell anyone what you were going to do, right?”

“OK, alright, yeah.”

“So, here’s the question: When you do that, turning without telling anyone, are you suddenly creating a problem for the trimmers or are you helping them?”

“Well OK, it’s not helping I guess.”

“That’s right. You’re creating a challenge or impediment for the trimmers to overcome – you’re pushing the problem on them. Not only do they have to trim the sails as fast as they can, but they also have to be mind readers – guessing at when you may spontaneously change direction without telling them.

Let’s look at this another way. What could you do to help them?”

Peter looked a bit sheepish and said, “I could call out the maneuver before it happens?”

“Right, if you did that you would be helping to make their jobs easier. You would be setting them up to succeed rather than setting them up to fail. You would be contributing to the successful execution of their work.”

“Yeah, I guess.” Peter said a little petulantly. “But I’m still not really sure what you mean by this ’pushing vs. pulling’ thing.”

“OK, well let’s talk about that mark rounding you did. What do you have to do to round a mark?”

“Hundreds of things!” Peter exclaimed. “Everyone has dozens of tasks that they each have to perform in a choreographed fashion in order for a mark rounding to be successful.”

“And what did you do to help them round the mark?”

“I did the steering, their jobs are their problem.”

“So again, how could you help?”

Peter gave it some thought and then said rather tentatively. ”Call out the maneuver?”

“Yes. What else could you do to help?” Said Rex.

“Well, I suppose I could slow down the turn in order to give them more time to make their adjustments?”

“Bingo!” exclaimed Rex. “That’s more like it. You have to be thinking of what you can do for the team to make their jobs easier. You need to think beyond your own role and be constantly asking yourself: How can I help the team? What can I do to help this team work like a well oiled machine? As long as you are thinking only of your job, you aren’t really part of the team. To be part of the team, you need to be pulling along with them to help them reach the goal.”

Peter nodded his head, “OK, I think I get that, but it’s kind of abstract don’t you think?”

“No, not really. I see it out on the race course all the time. You get these hyper competitive types rushing about without thinking about the team. They rush through mark roundings thinking only of themselves and winning the race and not about the crew. The poor crews are pulling as hard as they can, but they just aren’t in synch with the helmsman. They aren’t pulling together as a team.

It’s push vs. pull.” he finished.

Peter looked down pensively and was quiet for a minute. Then he called over the barkeep and bought Rex another beer. “Thanks. I appreciate the advice. I’m going to have to give that try.”

Failing Fast

August 6, 2014











“Forget your perfect offering. There is a crack, a crack in everything. That’s how the light gets in.”
-Leonard Cohen

How’s that for a weird quote? I heard it the other day on the radio and it stuck in my head. It has a resonance for me that I just can’t seem to shake. You see, like most folks, I’m intimately familiar with imperfection. I’m faced with it in many of the projects I’m most passionate about: My writing, my career, my boat…

Yeah, I’m building a boat. Technically, it’s my second boat. I think just admitting that qualifies one as insane. The first boat was a mere 9 foot skiff I made for my daughters. It took me almost 3 years to complete it. I should probably mention that I have absolutely no woodworking skills. So after I finished the first one, I decided to build another. This second boat is just for me. Well, me and my brother actually. We’re building it together in his garage. We’re about a year into it so far and it’s coming along pretty well.

OK, honestly it’s a little early to tell. We make a lot of mistakes.

I don’t know what it is about working with wood, but any mistakes you make tend to jump right out at you. Of course, the bigger the project the more room there seems to be for error. I’m discovering that a 17 foot boat leaves lots of room for error. Cutting parts to shape is hard. Getting screws to bite and not strip. Glue everywhere. One false move with a power tool and there are splinters galore. The whole project really is just a glorious catastrophe waiting to happen.

If ever there were a case study in failure, this boat is it for me. Now that might sound terribly defeatist, but it’s not meant to. You see, I’ll finish this boat too, one way or another. It’s just that I’ve got a whole lot of failing to do in between now and the day I finally launch her.

Of course, given all this failing, it’s still pretty astonishing how slowly I manage to learn. For instance, I’m noticing that I don’t seem to give up my standard ways of learning, even in the face of overwhelming evidence that they are not paying dividends. I’m fairly sure I’m not alone in this behavior.

First there is my innate impatience to see quick results. This whole measure twice, cut once thing just doesn’t seem to come naturally. For some reason I’m always in a rush. I find it extraordinarily difficult to slow down and just take my time. Maybe it’s some american thing where we are just impatient with anything that impedes progress…No, I don’t buy that either. I think slowing down is really hard work. It takes discipline to slow down and treat things in a very thoughtful and conscientious manner.

Savoring the moment and appreciating how things feel in the moment is not something that just happens to you. You have to make time for it. I can show you all of the places on the boat where I rushed the job. The places where I tried to drive the screws in with a power drill (I drove them right through the panels – genius!). The areas where the wood split because I didn’t take the time to test the bend first. The evidence of my own impatience is writ large in the construction of this boat.

Do you want to know the really amazing part? I still keep rushing!

Scary. Did I mention that slowing down is hard?

Another area where I struggle to learn: working as a team. Working as a team is hard too. First you have to keep those you are working with in mind all the time.  That doesn’t come naturally at all for me. I’ve never really been a good team player. I grew up participating in individual sports like running, wrestling and weightlifting. I operate very well solo. Working as a team has been an alien experience. For example, when my brother and I are working on the boat, I often struggle to figure out what he can do to help. I’ve seen this on software development teams too. Ask a developer what needs to be done, and you will get a detailed list of all of the work that remains. No problem. Ask that same developer how someone else can help them get that work done, and often you will get a blank look. When you are not accustomed to working on a team, it’s hard to picture what teamwork looks like.

To make matters worse, my brother and I have different skill levels when it comes to woodworking. This means that sometimes I need to take the time to show my brother how to do things (or vice versa). I find that hard to do when I’m rushing to get things done (see above). But without taking that time to show him how to do things, I lose the benefit of his help. I lose the teamwork. I’m finding that teamwork takes some serious patience. Ultimately I know I will go faster if both my brother and I can work at the same level, but that means initially I will have to slow down to achieve that goal. Slowing down to go faster.

I’m very lucky to have someone to like my brother to put up with all my mistakes. In a peculiar way, building a boat with him is teaching me a lot about software development. That’s probably good, because God knows if we’re ever going to finish that boat.

I’m Helping!

August 22, 2013


I used to race with a really experienced crew on a J120 (a flippin’ nice sailboat). We were all very hardcore about our racing. Many on the crew had been racing sailboats since their childhood. These guys were good – really good. We pushed each other hard and we expected a lot of ourselves and each other when we were out on the race course. So there was plenty of pressure.

I came to sailing relatively late in life compared to some, so I was very self-conscious. I didn’t want to make mistakes. In sailboat racing, there are a million little mistakes you can make that will slow the boat down. However, since it’s a team sport, you can cover for each other too. Not only are you trying to perform well yourself, ideally you are trying to help your teammates perform well too (at least on the successful teams). In sailboat racing you are always trying to anticipate what needs to happen next: clear the deck of loose sheets, make sure the spinnaker is prepped for the next rounding, re-run fouled lines, and Lord knows what other details. I always feel a bit like a bobble head doll when I’m racing – always trying to look in every direction at once.

I remember there was one guy on the boat who was really talented. He’d been sailing since he was in diapers. Things just seemed to come naturally for him. He was always where the help was needed most. He was easygoing and relaxed, learning was easy around him. But even he made mistakes from time to time – just like the rest of us. He’d pull the wrong string, blow the wrong halyard, grab the wrong winch. Whenever he screwed up he would yell,

“I’m helping!”

He would do it in an uncanny imitation of the Sesame Street muppet Grover. Super Grover to the rescue! We’d round a mark on the course and he would miss grabbing a sheet (in all the chaos and madness that we call making a left hand turn in sailing…).

“I’m helping!”

Usually everyone on the boat would bust up at this point. It broke up the tension we all felt when we failed a maneuver. It got us past the “Oh shit!” moment and allowed us to shrug it off and keep focused on our goal. I’ve been on other boats where someone made a mistake that cost the team on the race course without the help of ‘Grover’. Generally, on those boats we experienced something that felt like blame and recrimination. Perhaps we were less experienced, less able to forgive each other our mistakes, less able to cover for each other. Less able to allow for normal human nature to express itself. The problem was, we would struggle to recover our equilibrium for far too long after the event occurred.

A couple years later I was on another boat in a long distance race. It was early evening and the sun was setting over the Olympics on Puget Sound. As is often the case at that time of the evening, the wind died and we were left trying to race in the barest breath of wind. The water was flat and the sunlight was turning a deep shade of orange as it hit the mountains and reflected off the flat water around us. In fickle conditions like this, even the smallest mistake can cost you the race. As we all tacked into the shore to get relief from the current, I watched a nearby boat fail to release a sheet and blow the tack. They came to a stop and as we drifted past I heard,

“I’m helping!”

In the unmistakeable voice of Super Grover.

I remember feeling two things at the time:

  1. Damn, that’s funny
  2. We’re going to get our asses handed to us

Frankly I wish I saw more of Super Grover in the Agile software development community. All too often I see teams that are under tremendous pressure to deliver (is there any other kind?). When someone makes a mistake, it can all too easily turn into a situation where blame and recrimination slow the team down. There is no one there to help them shrug the mistake off. Someone with experience and the respect of the team. Someone who can look at his/her own mistakes and laugh,

“I’m helping!”

Sometimes I think that a team needs someone who can see that even though their efforts were well intended, even skilled – they were mistaken.  It is easier when someone you respect and admire can completely blow it and laugh about it. Suddenly the job doesn’t seem quite so serious. The task doesn’t seem quite so critical and we allow ourselves to get back to doing what we really enjoy.

Or perhaps I’ve got it wrong. Maybe this kind of thing doesn’t really apply to software teams. Maybe there is a better explanation for this kind of behavior. If so, that’s OK,

“I’m helping!”

Are You a Tweaker?

March 21, 2013


When I used to race sailboats in Puget Sound I got to sail with a lot of different kinds of people. Some people who like to sail are pretty laid back. The Jimmy Buffet types. You know, “The wind will come when the wind decides to come, and in the meantime, how about a margarita?” I really like sailing with folks like that. They are enjoyable and easygoing and that is important when you are trapped together on a cold, wet, boat for 8 hours or longer.

On the other hand, there was another class of folks that I might categorize as the “Tweakers”. Tweakers are the people who are compulsively changing the boat trim in an effort to get more speed out of the boat. They never stop. They are constantly pulling lines and adjusting the rig in an effort to squeeze every last ounce of performance out of the boat. Tweakers are awesome people to have on a boat when you are racing. A boat full of tweakers will almost guarantee you a win. That is if they aren’t fighting with each other over the things they are trying to tweak.

Personally, I preferred a mix of the two types. Tweakers are indispensable to winning a race, and winning is fun. On the other hand, there are times when frankly, the wind just isn’t going to show up. Tweakers tend to go a little bit crazy when this happens. They go into a veritable frenzy of tweaking. All to no avail. Sometimes what they need is one of the more relaxed folks to hand them a beer and point out that there isn’t any wind today.

Other times, the tweakers are the ones to point out that, with just a bit more effort, we could be in the hunt. Even if we are moving so slowly that our progress is imperceptible. Being in the hunt is fun. Sometimes the tweakers need to give the Buffet Heads a nudge in the ribs to put down the beer and get going.

So which type do you have on your team?


April 10, 2010

I’m reading Ellen MacArthur’s book, “Taking on the World”. She is arguably one of the greatest sailors around. It’s her story of her life leading up to and including her amazing race in the Vendee Globe.

Before she ever got to the Vendee, she spent years working on other people’s boats. She would prep them, repair them, and otherwise set them up for the big races. She had to know the systems of these amazing race machines inside and out.

These were largely solo racers that she was working with. Once they left the harbor and crossed the start line, they were on their own with no outside help for weeks, even months. Preparation for these racers was critical. Any undetected flaws would very likely come back to haunt them somewhere in the middle of the ocean. Not an attractive thought.
She would spend hours, days, weeks reviewing, inspecting these boats for weaknesses. She would be looking for the telltale warning signs of problems, like rust on the connecting terminals, minute cracks in the paint around areas of stress – anything that would indicate a possible problem.

She was engaging in a form of risk management. The inspections she was doing were designed to uncover the risks that might jeopardize not only the race, but perhaps even the sailor’s life. This sort of assessment goes on all the time in the sailing world. When you go to buy a boat, you get a survey. The point of the survey is to uncover risks to the buyer. Have you ever watched a surveyor in action? They use a lot of checklists.

I’ve watched some great sailors prepare for races too. You can see them wandering over a boat, running their hands over every inch, opening lockers and sticking their head in, tugging on lines – looking for risk. I imagine they have a mental checklist that they are using too.

When we are managing our projects, how do we inspect them? We can use checklists. We can ask others for advice (something that Ellen did very well). We can make things visible – the equivalent of sticking our heads into lockers and looking around. There are a variety of things we can to to look for risk. Being a good project manager, like being a good sailor, means being aware of and constantly on the watch for risk.