Jack is Perhaps the Best Leader that Ever Was


Bill Cooper, Chief Executive Officer

When I was younger, like many I am sure, I was taught by my mother the expression ‘Jack of all trades, master of none’.  Well I do not know who that Jack fellow was, but he was on to something quite powerful.

‘Jack of all trades and master of none’ is a phrase that, with the benefit of some perspective and retrospect, I now know applies exceptionally well to me. Whether one chooses to highlight my unerring willingness to try most things or my propensity to never fully grasp any of them, there is no doubt the phrase’s two core meanings apply.

But what never dawned on me until recently was that such a quirky, dated expression could represent the underpinnings of effective leadership.

I say this because I believe I have evolved into an effective leader. And I have done that in no small part through acknowledgement of the benefits of deferring to those who have mastered their respective area of expertise more so than I. And that is not an insignificant evolution because it requires the humility to accept that no matter how prideful I might have been in my capability in a certain area, inevitably delegation and/or empowerment to a person that can focus on and master the task will likely generate an output equal to or greater than I would have. This approach also allows me to keep my attention on the broader project.

In short, I have found that the farther I get in mastering humility, the farther I get in mastering leadership.

I have been a workplace leader, both figuratively and as depicted in organizational structure, for some time now. And while I have not led enormous teams, I have led teams that, in my view, have done enormous things. The most recent example was a leadership role I undertook with the HSBC Canada Sevens rugby tournament in Vancouver, wherein a small team of four of us were the catalyst to staging the largest rugby event ever held in Canada. It was also arguably one of the most successful inaugural annual events the sport of rugby has ever seen.

So how did a group of just four realize something so enormous? We did it through hard work, humility and collaboration with a huge array of masters of their respective specialty. Be they colleagues at Rugby Canada, contractors, team members at our agency, Board members, strategic partners or volunteers, it was our collaboration and sharing of tasks with a much wider team that brought the project to life.

We were Jacks (and Jills!) of many trades and relied frequently on the mastery others to bring success to the event.

The courage to get things started

As a Jack of all trades you have the capacity to generate and act on many ideas. And by initiating, you often start to benefit from a more realistic view of the time and resources required to bring the idea to fruition. But if you take a task too deep into the weeds, it can dilute your ability as a leader to remain focused on the bigger project. This is when the courage to enable members of a wider team to carry initiatives forward with adequate empowerment and autonomy is critical to your success.

The courage to step back and let them get it done

Early on when you are learning to ride a bike, it is hard to imagine what would possess you to let go of the handle bars. You grip them with a mix of both determination and fear. But if you can persuade yourself to loosen your grip and enable somebody else’s determination to advance the task, you can re-direct your focus on the larger project. So take your hands off the handle bars and feel the wind rush past – that sense of nervous exhilaration is the feeling of your team propelling the project with no more than some balance and gentle guidance from you.

The courage to pose questions, influence but not dictate

If you’ve been selected as a leader you are likely pretty competent in some of the key areas that will bring success to the project, so you’d be remiss not to look under the hood and kick the tires once in a while. The key when doing so, though, is to have the courage to accept that your team will have listened and learned from your questions and observations and they will inevitably invest that enriched perspective into how they are delivering a given portion of the project. If you suffocate their autonomy with too much assessment and guidance, there is a risk they will leave and/or start to rely on you too much and draw you away from the larger direction you are intended to give.

The courage to look in from a distance

Perhaps the greatest challenge for somebody who has been in the middle is realizing you must stand aside and let somebody else take your place in the middle. And this is where, as a Jack of all trades, you must leverage your advantage and readily see how delegation and empowerment can generate an output more efficiently than would have been the case had you retained the task. In stepping back and observing others bring elements to life, you will enjoy the aggregate view of the whole project coming together.

The courage to manage your distance

The tough part now that you have started to master the avoidance of micro-management though, is ensuring that the pendulum doesn’t swing so far over  that you ‘macro-manage’. While each team member will vary in terms of the optimal level of management they require, in general you want to give them enough autonomy such that they can rise to their potential and the project can enjoy efficiency, but not abandon them so much that progress is slowed by lack of direction. Myself, I lean too far into the macro-management style and have seen project hiccups as a result over the years. As each project and team will differ  in terms of the optimal approach, however. The key takeaway is to be always monitoring and self-aware as to whether the approach is well-suited to the project and team at hand.

The courage to acknowledge

Now here is where that Jack guy really kicks you in the teeth. Because on the tail end of having embraced so much humility, stepped aside on tasks you think you may have done quite well at and empowered others to drive the ship forward, you must acknowledge and celebrate their pivotal contribution to the project. If this were a meal; they are the main, the side, the appetizer, the wine, the table, the chairs, the service and the company while you are but a portion of the intangible atmosphere. And how often do people comment on the intangible atmosphere when reviewing a meal? Ensure your circle of ‘masters’ of their respective area are acknowledged and adequately thanked so that the table is set for the next meal.

When the HSBC Canada Sevens’ inaugural edition came to a close, I received a wide variety of congratulatory emails about the event we had staged. However, without the benefit of having fully digested lessons learned, I now realise my answers were largely deficient. In most cases I thanked people for their kind words and I enthusiastically acknowledged how wonderfully Vancouver had embraced the event. But what I now realize I forgot to mention is that I had not staged the event. I was merely a Jack who helped get some ideas started; it was the team of masters that truly staged the project to rave reviews.

I sincerely hope these lessons learned might help you master the art of being a Jack.

Bill Cooper was seconded by The TwentyTen Corp to serve as the inaugural HSBC Canada Sevens Series Tournament CEO.