Sailing Metaphor for Agile

When I was in high school, my friend Scott and I took his father’s sailboat out on the lake where our families spent summer vacation.  We had each been sailing numerous times; always as crew, never at the helm.  We both knew the lingo; “Come about” and “Pull that jib in tighter!”.  I had taken a boat safety course, so I knew all about life jackets and right-of-way.  There was even a page in the safety manual that talked about sailboats and gave a handy chart for the points of sail.  We were set for adventure!

We raised sail, looked hopefully out at the white-capped water in the middle of the mile-long hourglass-shaped lake, and pushed off from shore.  The wind was 12-15 knots out of the south, running straight up the middle of the lake between the two points that pinched in to form the hourglass.  The boat was a single-hull cat-rig, with a beautiful wooden daggerboard that you had to manually insert into a socket in the bottom of the boat.  By virtue of the superior experience imparted on me by my safety certificate, I was elected helmsman.

At first we had it easy starting in the southern end of the lake and running with the wind on a North/Northwest heading.  The main was swung out to starboard, jib fluttering uselessly in the lee of the main.  This was our first problem: a useless flapping sail seemed like a bad idea, so we cleated it in to keep it from luffing too much.  We sailed along just fine, until we’d gone three quarters of the way down the lake.  We were approaching the northern shoreline, and needed to turn around.

Turning.  How did that go again?

I knew one thing for certain.  I didn’t want to jibe.  Listening to all the other helmsmen on all those other boats had cemented two thoughts in my head: first, don’t do anything sudden, and second, jibing was bad.  So with the sail out over the starboard side, we had only one choice:  we had to turn to port.   I pushed the tiller to starboard beginning our gentle turn to port.  The boat started the turn, slowed down, then pulled back around to the north.  Two things:  we didn’t change the trim of the main so the wind was just spilling uselessly off the big sail, and we still had the jib cleated which presented a nice taught wall to push the boat back around every time we tried to turn.  Not that we realized that at the time.

As the northern shore loomed closer we started to worry.  Every time we tried to turn around, the boat would stall in the turn, and then auger us back around into a run.  It didn’t help that at the northern end, the bowl of the lake caused the wind to swirl around from the west as well. Desperation was starting to set in, but we weren’t willing to consider jibing as an option.  If the boat wouldn’t turn with a gentle hand, clearly we needed more force.  I told Scott I wanted to try to turn fast this time.  He agreed, and I slammed the tiller to starboard.

The boat nimbly spun on its axis and we passed rapidly through the points of sail, passing through the head-on gale from the south.  The main luffed violently, so Scott pulled the main sheet in tighter to get the wildly swinging boom under control.  Our turn continued, and the tightly cleated jib suddenly backfilled and now began pushing us through the turn.  I couldn’t control the helm.  The boat continued to turn on its own: southeast, then east.  Scott suddenly realized the jib was on the wrong side of the boat, and uncleated it.  It luffed wildly in the wind, but released its hold on us allowing me to hold the course east-southeast, heading toward my house.  Scott got the jib on the port side and pulled it in tighter, by shear luck the main was set at the proper position for the close reach I had us on.

The boat lept forward, the strong wind pulling us rapidly across the lake, heeling like crazy we grinned and wooped for joy.  All too soon we reached the eastern shore in front of my house, and we needed to turn again.  I pushed the tiller rapidly to port, and we spun through the points of sail on the starboard tack.  Once again the jib wanted to hold us back from completing the turn, but we were moving so fast the boat was not to be denied.  We passed the midpoint, and the jib backfilled again, pushing us around westward.  The speed of the turn and the force on the jib carried us even further around into a port run…but the main was still set for a close reach!  The wind got behind the main, and suddenly we jibed!  The boom swung rapidly over our heads and we dropped down to keep from getting brained.  The boat heeled violently to the other side, and the turn continued, now being carried by the incorrectly set mainsail.  Northeast, then east, then southeast.  From my position on the floor of the boat, I couldn’t release the tiller.  We turned through the oncoming wind again, screaming in a strange combination of fear, surprise and elation!

The boat repeated the same maneuver again, with the jib spinning us around until the main jibed again, and flung us into completing the second complete circle.  I managed to get back on the seat, and pulled the tiller straight.  We were now heading west (exactly as I originally planned), cutting rapidly through the water and heeling more and more.  The sails, still set for a close reach were set too tight for the beam reach we were sailing.  The faster we went, the more the boat heeled, until the sail was parallel with the water.  We were going over!  I remember thinking I should jump off the boat, but wanted to avoid the sails and rigging.  I tried to clamber over the port side, and saw the wooden daggerboard pull out of the water.   Then we were too far over for me to clear the hull.  I turned back and watched the sail dig into the waves.  I chose a clear spot of water alongside the sail and jumped in.

Scott and I swam frantically around the capsized boat, calling each others names, prepared to dive under and rescue our trapped crewmate if necessary.  We finally spotted each other as the wind continued to push the hull over.  The mast sank, the daggerboard pointed skyward, and the two of us watched helplessly, all the while laughing like madmen.   Little did we realize at the time but my mother was out on the deck in front of our house, with binoculars, counting how many heads popped up around the inverted boat.  She was on the phone with Scott’s family right after that.

A few minutes later, Scott’s father arrived in the speedboat.  He circled around the now-turtled boat, shouting instructions for righting her.  First we had to dive under the hull and release the mainsail so it wouldn’t resist us.  Then we had to climb up on the hull and try to use our body weight to draw the mast upward.  Every time we tried to stand up, we would lose our grip on the slick fiberglass hull.  Every time we would reach for the daggerboard to get a grip, his father would shout at us to stop pulling on the board, or we’d break it!  Time and again we’d try to synchronize our leap onto the edge of the hull, then as the rim sank below us, tried to find something on the smooth round hull to grab in order to pull the boat over.  Each time we tried, we failed.  Each time we reached for the daggerboard, we were shouted down by the crazy man circling us and alternately encouraging and discouraging our efforts.

Finally his circling put him on the far side of the boat, out of line of sight with us as we tried our next leap.  This time Scott and I both grabbed the daggerboard and put all our weight on it.  The boat flipped upright, the mast covered in seaweed, and his father cheered in triumph that his advice had finally paid off.  We climbed back in the boat, and thanked him for his help.  Scott then started preparing to raise the sail again.  We were bound and determined to finish the trip under our own power.  Scott’s father had other ideas, and threw us a tow line.

As we were dragged back to shore, in utter defeat Scott and I looked at each other, and decided right then that we had never had so much fun in our lives.  Our sailing careers were both placed on hold by unanimous parental acclaim.   But I never forgot that experience.  And today I have my own boat.  Before taking her out, my wife and I took an official sailing class and learned how to sail.  More importantly we learned why the boat sails.  It is only through the benefit of that training that I can even tell this story in a way that will make sense to a sailor.  (Mind you, I’m not an expert sailor yet, so I’m certain it could be better.)

I’d like to explore this metaphor further.  Since beginning the Agile adoption at work, I have felt that same elation of barely knowing what to do, and having a tremendous time doing it.  I’ve had the authority-figure circling the crash site, trying to decide how to help, offering advice, but denying options.  As my own Agile education continued, and I began to see why failures had occurred, and how they might be avoided, I tried passing that knowledge on to others, only to find myself on shore watching them flounder in the middle of the lake.  Watching the parents circling the team in the water.

We do this all the time when we first train agile teams.  We teach them what sailing is.  We tell them how to sail.  Then we arrange them in groups of seven plus-or-minus two people, put them on a big sailboat, and tell them to sail together.  We often forget the necessity of the onboard coach, guiding the crew through the four “ormings”, until they can do it themselves.

Author: Michael Marchi

Michael Marchi CSM, CSPO, CSP-SM, CSP-PO, RSASP, AHF Management Consultant / Agile Coach & Trainer @ 42 North Unlimited ( Co-Founder and Board Member @ APLN Chicago ( Co-Host [here's this agile thing] podcast (