For as long as I can remember, I didn’t like rules. I’ve mostly respected authority, but I struggled with enforcers who had a rigid, black-and-white approach. I wasn’t always very popular with people in positions of authority—especially those who couldn’t (or wouldn’t) answer my “why” questions. Most of the time, my resistance was justified—at least from my perspective—because the rule didn’t seem to make sense.
I partly blame my dad for this attitude. He wasn’t too phased by certain rules. He’d often brush them aside and say something like, “It doesn’t apply in this case.” He allowed me to do things I was arguably too young for—mostly because he didn’t have many alternatives. But that’s a story for another day…
I remember having a disagreement in Grade 9 with my Religious Studies teacher. She was irritated by this schoolboy challenging her understanding of certain rules. In front of the whole class, she said I wasn’t “qualified” to question her because “she had read the entire Bible from front to back at least three times before I was even born.”
Then, as a young staff trainer in a large insurance company, my first personal development plan, requested by my manager, was to learn how to communicate in ways that made people in authority more open to my input, because I didn’t always “play by the rules.” The golden guidelines I learned were:
- When you challenge, challenge with care.
- Don’t challenge for self, but for the greater good (company, team, client).
- Speak respectfully and listen to understand.
That exercise was invaluable. It made me aware of how others perceived me when I disagreed and became a cornerstone of my growth as a professional. It prepared me for leadership, and for that I’m grateful.
I entered the corporate world in the early ’90s at age 24. In the insurance industry back then, a tie and jacket were non-negotiable—even if the jacket was just slung over your shoulder, just in case you bumped into a client or a senior executive.
After being promoted to Head of Skills Development at head office, I started questioning the dress code rule. It affected productivity, especially for staff who were in development roles, worked behind desks, and never saw clients. They were dressed for the boardroom while facing computer screens.
One day, I showed up not wearing a tie and got a reaction from someone who was dressed by the book but looked like something the dog dragged in. Ironically, I was far more presentable and client-ready than she was. This strengthened my resolve, and I began advocating for staff, especially advisers, to dress appropriately for their audience. Instead of one picture of a professional image, match your client’s style, just one level up. Avoid being underdressed, but dress to build rapport and connect with clients from other industries.
As I grew older (and hopefully wiser), I realised that even though I didn’t appreciate ‘rule-focused’ living, I dislike unruly people even more. It sounds like a contradiction, but I reframed my thinking. Everybody knows, rules exist for important reasons:
- Improve our standard of living.
- Keep us safe.
- Make society work and promote responsibility and accountability, ensuring individuals and organisations adhere to expectations.
- Ensure fairness and justice by establishing equal treatment and consequences for actions.
- Streamline processes, reducing confusion and increasing productivity.
- Prevent chaos and disorder, providing a framework for behaviour and decision-making.
This is where someone made me aware that our focus should never be the letter of the rule. Even though we need to know this too, our biggest drive always needs to be to understand the “reason for the rule”. We need to know and understand:
- The intention of the rule.
- The principal foundation of the rule.
- The reason why authorities decided to go through the trouble of drafting the rule.
A memorable moment that humbled me happened at the Cape Town International Airport. I had several good reasons to bend the rule that day. My brother had just landed, and instead of parking and walking to arrivals, I decided to time my arrival and just remain in my car until he walked out through the sliding doors. (He had to time it to exit when the one-way sliding doors open for passengers entering departures). I hadn’t been there two minutes when a security guard approached me:
“Sir, are you dropping someone off?” Looking through the cabin for people and luggage.
“No,” I said. “I’m picking up my brother. He’ll be out any moment.”
“But this is the drop-off-zone, sir”. he said, pointing at the massive sign right in front of me.
“I know,” I admitted. “But he doesn’t know where to go. I’ll move if it gets congested.”
“Sir, that’s my job. If I do it well, it won’t get congested.”
He was right. I had no leg to stand on. I left the zone and made alternative arrangements. In the end, it took more effort, wasn’t cheaper, and my brother didn’t get lost.
Let’s think about it:
- How might a more balanced approach to rules improve our relationships, leadership, or decision-making?
- As a parent or a leader, do I make the effort to explain why certain rules are introduced?
- When I disagree with a rule, how can I do so in a way that invites dialogue rather than defensiveness?
- And in that disagreement, am I challenging for personal gain, or for the greater good?
As leaders, we carry the responsibility of understanding the rules, both in letter and spirit. It’s not enough to enforce them; we must interpret and teach them wisely. When rules are clear, purpose-driven, and enforced with empathy and context, they don’t restrict—they empower. The best leaders know when to honour the rule, when to bend it for the right reasons, and most importantly, how to communicate why the rule exists in the first place. When we lead this way, we don’t just build compliant teams—we build thoughtful, responsible, and values-driven communities.
Love and respect,
Stefan Lessing
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