Tag: Leadership

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 Most Expensive Words in Business: “We’ve Always Done It This Way…”

One of the more fascinating observations after nearly three decades across industries and roles—largely centred around technology—is this, it’s not how much technology has changed that surprises me. It’s how little human behaviour has.

Every organisation has that one sentence capable of stopping innovation and progress in its tracks with “we’ve always done it this way.” I sometimes wonder if it is engraved—perhaps in invisible ink—right at the entrance of every office.

A few months back, when I joined my current organisation, I noticed something interesting. Every proposal to a prospective client included a “pilot phase.” In fact, it was so institutionalised that it existed as a milestone in the sales CRM. Naturally, I asked why.

The answer was simple and familiar, “that’s how it’s always been done.” We decided to remove the pilot phase from our proposals. Almost immediately, the conversation with clients changed—and so did the order values.

Only later did I understand the origin of this practice. A few years earlier, when the organisation was still evolving, the pilot approach helped us learn, de-risk implementations, and avoid over-commitment. It made perfect sense then. But over time, that thoughtful precaution had become… hard-coded.

Today, the word “pilot” has quietly exited our lexicon—and our revenue cycle has become meaningfully shorter.

Going back a few years, I recall a conversation with my Executive Assistant—fresh out of business school—who asked a simple question: “why are we so conservative in our social media communication, especially when we’re trying to attract young talent?” Our instinctive response? Yes, you guessed it right, “we’ve always been this way.” That’s when it struck me that I was part of “this way.”

The irony was that we had built a genuinely vibrant workplace, with strong employee engagement and plenty of recreational initiatives. But none of this was visible externally – or for that matter, perceived internally! Within a month, we changed course. We expanded beyond our internal portal, became active on Instagram and Facebook, and began showcasing employee stories and experiences.

The result? A noticeable shift in how we were perceived by potential hires and, interestingly, even by our own employees.

Let me go further back about two decades to my time at one of India’s largest banks. We were evaluating outsourcing a significant operational function (incidentally, I was leading the initiative). The move promised substantial cost savings and a clear improvement in service levels. But the reaction was… dramatic. “It’s like selling the family jewels,” someone said. Here’s the quiet irony: most of the sub-activities were already outsourced. All we were proposing was to consolidate them under a single partner. Yet, reframing the same reality proved far harder than analysing it. Eventually, the decision went through. Today, that model is not just accepted—it is standard industry practice.

So, what’s the essence here?

1.      Experience is invaluable… until it becomes inertia. The very experience that helps us solve problems can also convince us there is only one way to solve them.

2.     Technology changes faster than habits. We talk about AI, automation, and digital twins. Yet many organisations still make decisions exactly as they did fifteen years ago.  (Tsk tsk. Ironically, some now find it easier to converse with AI agents than challenge their own processes. I’m still somewhere in between).

3.     Great leaders don’t have all the answers. They simply ask better questions. (I’m still working on that).  One of the most powerful questions I’ve come across is “If we were starting this company today, would we build it this way?

And perhaps this says it best: “Progress begins the moment experience becomes a guide instead of a prison.”

To summarise – its’ about letting go of yesterday’s certainty. Innovation isn’t always about inventing something new. Sometimes, it’s simply having the courage to stop doing something old.