I used to race weekly on a 30-foot sailboat many years ago while living in California. I remember the first time I raced in the cold waters of San Francisco Bay, with the winds so high that I could not walk in a straight line as I headed to the marina.
That first race was incredibly exhilarating, and I learned more about sailing during those years than I ever did sailing for fun. However, what I learned the most was about people and their behaviours while under stress.
I was fortunate enough to be a crew member on a boat that embraced being a supportive team. We were not a team that wanted to cross the finish line first each week. Instead, we were a team that enjoyed the ride.
There were more than a few times where we had a lousy start and made a quick consensual decision to turn the boat around and sail in the opposite direction with music blaring, snacks, and fishing poles not far behind.
It was a team that not only enjoyed being out on the water, but we learned how to optimize our collective skills. We all had strengths to contribute and the skipper who owned the boat knew it. The only time voices were raised was when we were about to hit another boat…or an innocent sea lion.
When we made mistakes, which we all did, we figured out what went wrong together instead of just focusing on just one crew member’s actions. Then we discussed how we could improve the next time which allowed the entire team to reconnect as the humans we were, who make mistakes and move forward.
When I was earning my degree in Health Services Management, we studied the classic and timeless Harvard Business Review article written by William Oncken, Jr and Donald L. Wass called “Management Time: Who’s Got the Monkey?” It was originally published in 1974 and reprinted in 1999.
This article resonated with me and discussed how well we use our time and skills within the business world. My favourite quote from this article is “Most managers spend much more time dealing with subordinates’ problems than they even faintly realize.” Some may call this micromanaging, or others may even call it being controlling.
I was surprised to learn the history of the phrase. Some believe it originally referred to a “monkey on your roof” which was the burden of carrying a mortgage. The roof changed to a back sometime in the 1940s. It means you are unable to easily shake something off to move forward with your life.
The journey we are all on, whether we are racing a sailboat or working in a large corporation, is completely unpredictable. Trying to control it only makes for a long and sometimes painful ride. And along that way there will be lots of mischievous monkeys trying to catch a free ride.
An astute leader identifies the most skilled person, delegates responsibility, and instils confidence for them to proceed independently. Then happily hands them the monkey’s leash.
Whether on a sailboat or in a boardroom, is a leader really in charge of everything? No. Does the leader need to be involved in every tiny little decision? No. Embrace everyone and the contributions they bring with their talents, gifts and skills.
There may be those who can strategize the next step just by closing their eyes, feeling the wind on their cheek. There may be others who may be inclined towards logistics, and can picture the boat crossing the finish line at exactly the right spot.
There are others who may be so intuitive they can sense when the boom is about to hit someone’s head, and quickly alert them before it happens. Trust that the monkey is on the right back and being fed and cared for adequately.
As a project manager I could plan my teams so tight that we all end up in a dark closet and never find our way out to the light. The analogy of a monkey on your back is about removing that which burdens you and allows the monkey to gracefully land on the team member that can do the job.
Then simply trust in that person and their abilities, and be there for them when they need help. This is teamwork. And remember that sometimes the most invisible have the most knowledge to share, and they could change the outcome with their words in a short instant.
Do you feed your monkey well, and then choose the best skilled person to take over their care? Or do you just keep accumulating a troop of monkeys on your back?
With 20+ years project management experience, Barbara Kephart has led projects across industries like medical software, clinical trials, and cybersecurity. With experience teaching technical project management and stakeholder engagement, Barbara is dedicated to helping companies pivot, prioritize, and complete projects with Chief Project Officer-level expertise, project professionals, practical training, and hands-on management—without the executive-level price tag.