The Dangerous Comfort of Being the Most Experienced Person in the Room

 After nearly three decades of working, I have acquired a useful professional skill. I can occasionally reach a conclusion before the younger people in the room have finished explaining the problem. Unfortunately, I have acquired another skill too. I can be wrong considerably faster.

I guess the challenge is figuring out when experience stops being an advantage and starts becoming baggage. And, preferably, figuring it out a little before it actually happens! There have been many occasions when experience has served me well. Looking at a project plan and knowing it was unrealistic. Suggesting building a premium into a proposal which the team was against. Recommending that we kill a product a year before we eventually did. Or, conversely, fighting to continue with one that everyone else had declared a goner. On all those occasions, my judgement turned out to be right.

Experience does that. It teaches you to recognise patterns, understand market dynamics, anticipate customer behaviour and occasionally see around corners. This is experience at work. Alas, experience takes you only that far.

One would like to believe that by the time one reaches a leadership position, the success rate should be close to 100%. I have some bad news. I think 7 out of 10 is pretty good! The trick, perhaps, is recognising the other three quickly enough before they become expensive monuments to one’s conviction. And it is precisely in those three—or perhaps just one for the exceptionally gifted! —that the bane of experience can set in.

Recently, I was in a meeting with my team discussing the time required to develop and industrialise a platform. Having built complex systems over the years, I had a fairly clear view of how long this ought to take. Yes, AI would make development faster, I thought, but surely the overall process would still take X months. A colleague proceeded to show me that development could potentially be 10x faster and the overall cycle perhaps half of what I had assumed. My experience wasn’t necessarily wrong. It was simply trained on the wrong era. The AI paradigm wasn’t coded into my experience. I was applying perfectly sensible pattern recognition to a pattern that had changed.

And therein lies the danger. Experience gives us pattern recognition. But eventually we risk seeing patterns where they don’t exist—or failing to notice when the pattern itself has changed.

The question then becomes. Am I recognising this problem? Or merely recognising something that looks like it? There is another curious privilege that seems to disappear as the hair turns grey: permission to ask stupid questions.

At 25, saying “I don’t understand” demonstrates curiosity. In one’s 50s, one occasionally worries that it demonstrates that the recruitment process made a terrible mistake a few decades ago.

I believe precisely the opposite. One privilege of genuine seniority should be the confidence to ask the embarrassingly basic question that everybody else in the room is avoiding. And let me tell you, I have been exercising that privilege quite liberally!

Just the other day, I was in a conversation with a prospective customer about processes that would form part of a transformational journey. I am relatively new to this industry, and perhaps that helped. As the discussion progressed, it seemed to me that we were complicating the proposed process while simultaneously diluting some of the very benefits the transformation was supposed to deliver. 

So, I asked the embarrassingly basic question, what exactly we were trying to achieve. Thankfully, the (in)experienced person’s plea was heard!

Perhaps that’s the paradox. Experience helps me question things because I’ve seen enough and inexperience helps me question things because I haven’t seen enough.

Maybe we need a little of both. As far as I am concerned, the real advantage of experience isn’t knowing more answers. It is having been wrong often enough to become suspicious of the obvious ones. And those numbers will only keep growing! Experience should shorten the journey to the question, not prematurely decide the answer.

In my earlier post, The Joy — and Humiliation — of Being a Beginner Again, I wrote about the unexpected pleasure of becoming a novice underwater.

Perhaps the challenge is to bring a little of that beginner’s mind-set back with us when we surface—and, more importantly, when we walk into the boardroom.

After nearly three decades, experience is something I value enormously. I just don’t want to be it’s prisoner…

The Joy – and Humiliation – of Being a Beginner Again

There is something wonderfully inconvenient about learning something completely new later in life.

At work, people almost always expect me to know what I am doing. Underwater? The fish have no such expectations! And my dive instructor certainly didn’t.

As careers progress, we gradually surround ourselves with things we know. Titles, experience and familiarity create a comfortable competence bubble.

Even when I don’t know something, there is usually a logical thought process that, if followed, will hopefully get me to the answer. I spent a significant part of my career in banking and payments and now find myself focused on retail and manufacturing. The industries, requirements and even the lingo may change, but somehow, they remain within the “known realms.”

Then I decided to do something where grey hair had absolutely no significance—and, if anything, the rigidity that came with it probably didn’t help! I became determined to get my Open Water scuba certification along with my children. There was just one small problem though, wwimming. For someone who could sink almost instantaneously in a swimming pool, I must have been every instructor’s dream student – or would it be a nightmare? With considerable effort, sweat and persistence, I eventually managed to swim 20 metres non-stop.

The big blue world beckoned.

The first dive into the ocean…

We started with the e-learning modules, which I attacked with great dedication. I was the first in the family to finish and scored 90%. A small confession: probably one of the few times in my life that I have ever scored so high! So, there we were, academically qualified and ready for our first practical session. Along came our instructor, probably a little more than half my age, who proceeded to explain to me how to breathe.

Breathe?

Surely, after all these years, that was one skill I could confidently claim to have mastered.

Then came the pool. With all the gear strapped on, a frightening thought suddenly entered my head, what if I drown? Pat came my daughter’s reassuring response that “scuba is basically professional drowning.” This was anything but sobering.

Our instructor then gave us what, to him, were probably very simple instructions. The rest of my family seemed to understand them effortlessly. I thought I did too. Theory was easy. Practice involved remembering to breathe, equalise, check my air, monitor the pressure and somehow control my buoyancy—all at the same time. And I wondered why something supposedly called “neutral buoyancy” felt anything but neutral. On land, I always multitask. Underwater, breathing alone seemed a perfectly adequate contribution. Then there was equalising. And ensuring that water didn’t keep seeping into my mask. And remembering my newly acquired skill of clearing it when it did. A small discovery much later: during my last two dives, I realised I hadn’t been tightening my mask sufficiently in the first place!

Experience, apparently, arrives after you need it.

And then there was my fascination with the air gauge. My instructor politely explained that I had “big lungs.” Once we surfaced, it was only natural to compare how much air everyone had left. My instructors and daughter: 90–110 bar. My son, who was initially a little nervous: 70–80.

Me? Hovering majestically around 40–50.

Apparently, I had not merely been scuba diving. I had been personally supporting the compressed-air industry. In my defence, apart from one 35-minute dive, I managed not to shorten everyone else’s underwater time, and we completed our full quota of around 40 minutes.

Then there was the small matter of my eyesight. Apparently, having difficulty seeing on land wasn’t challenging enough. I decided to try it 18 metres underwater. And strangely, this is where scuba became even more fascinating. Underwater, everyone has limitations. Everyone depends on a buddy. Everyone communicates differently. There is an interesting equality to it. Of course, following everything my instructor was trying to communicate was that much more challenging for me.

Maybe I couldn’t even know that 90% of the creatures were even there around me. But the 10% I could was more than worth it. And my success rate improved dramatically when it came to sharks! With a dedicated instructor guiding me, I was taken to a spot where two white-tip reef sharks were nearby, and I saw one of them.

Face-to-face with a predator

All of this left me thinking about something much bigger than scuba. When did we last willingly become bad at something?

Children do it constantly. Successful adults? Well, perhaps that’s an altogether different topic best avoided! As we grow older, we gravitate towards things we are competent at because it is comfortable. 

Beginning again isn’t. For it means asking stupid questions. Making mistakes, feeling foolish, and accepting instructions from someone who may have a fraction of your age and several times your expertise.

And perhaps that’s precisely why we should do it. Beginning again teaches humility. The older I get, the more I value occasionally doing something that reminds me how much I don’t know.

I started scuba because I wanted to explore another world. What I unexpectedly discovered was the pleasure of being a novice again.

I still have a lot to learn underwater. My buoyancy can improve and my air consumption most certainly should! 

And that’s exactly the point. After nearly three decades of being paid for experience, it feels surprisingly good to be a beginner again. Onwards—and downwards—to 30 metres…