Strategists Should Be Entertaining Too

In his autobiography, ‘Windswept and Interesting’, comedian Billy Connolly makes a remarkable admission: his performances, often several hours long, are fundamentally improvised, grounded in an almost unfathomable ability to perceive and then respond to the audience’s energy.

This notion of give and take when performing is fascinating to me; it’s a fragile premise that demands razor-sharp observational skills, an instinct critical to the role of anyone in the business of persuasion. Within advertising, I sometimes feel there’s this default mentality that entertainment sits firmly within the round pen of the creative department – but the story starts with strategy. So we are as duty-bound as our art director and copywriter friends to employ charm, provocation, and even crowd-work to breathe life into what would otherwise be a boring pile of facts.

SICKDOGWOLFMAN creative director Jess Wheeler, while rival by name, is a kindred spirit in humour. I admire Wheeler's snappy, facetious LinkedIn commentary, insightful and distinctive approach to writing, entrepreneurial ambition with sunblock brand Slather, and the consistently punchy and delightful creative outputs of SICKDOGWOLFMAN.

I wanted to get Wheeler’s take on performance style, breaking out of rigidity, when to talk, and, more importantly, when to listen.

In his advocacy of 'good' presenting, Wheeler claims it’s not about cultivating a ‘signature style’ but more about "showing enthusiasm for the work, irrespective of the vibe in the room." It's a balancing act, and for strategists, it starts with resisting the urge to equate value with volume and investing your energy and intention toward "getting to the fun bit quicker."

When a project has seeped into every weird little crevice of your brain, dominated your shower thoughts, and encroached on martini Fridays, the act of distilling down weeks of painstaking analysis into a pithy handful of slides feels... anticlimactic. But this is the magic act where real skill and craft are revealed, and while there are contexts in which demonstrating the "heft" is necessary, we should all be trying to tell a story that is compelling in its simplicity.

Once you’ve cracked a few solid presentations, it becomes tempting to descend into a formulaic view of the whole process. Still, legendary, culture-informing work arises almost exclusively from the unforeseen and unorthodox. "Every brief is different. Every industry is different. Every CMO is different, all with their own specific problems and challenges. So, of course, there's not a paint by numbers answer that you can always wheel out."

While a tried and true foundation of principles and provocations offers a solid base from which to jump, I’m finding the ideas most worth pursuing often emerge from digging into unfamiliar ground and drawing on seemingly abstract, disparate influences. This applies to research, storytelling, strategic design, creative briefings and most outputs or touchpoints along our journey of discovery.

When starting out, going off-book and breaking free from a methodical frame of mind can be a tricky concept to grasp. Even recently, when managers and co-workers introduce a new way of expressing, framing, or analysing something, I’ve found myself saying, “Huh, I didn’t know we could do that.” It’s an ongoing experiment: making, breaking, and re-making.

It’s something you can only really improve through experience and solid mentorship, which Wheeler notes is becoming harder for juniors to access due to the stretched capacity of senior leaders in the industry. A steady obsession with what makes work truly great – paired with the humility to know you’ll be humbled repeatedly – sets you up not just to get to better work faster, but to do it without everyone thinking you’re a d-bag along the way.

"I was probably too opinionated as a junior. It’s been a double-edged sword – the foundation of my career, but no doubt a source of frustration for a few along the way.” As someone who both self-identifies and has been told on multiple occasions that I’m somewhat annoying, this speaks to me on a spiritual level.

Working in this industry demands a commitment to entertain, which, in turn, demands a commitment to shutting up so you can listen. I’m learning to be more observant, more receptive, more empathetic, and more open to being wrong. It’s made me a better strategist and, dare I say, a better person.

As our founding comedic father, Sir Connolly, once said, “Before you judge a man, walk a mile in his shoes. After that, who cares? He's a mile away and you've got his shoes.”