A technology leader listening to a couple during a difficult conversation.

Reflection 01

Listen Before
You Solve

The hardest leadership decision I ever made occurred long before I became a Head of Technology.

It wasn’t about AI or technology, it was about a family.

Earlier in my career as a Business Banking Manager, I met with a husband and wife whose business and finances had reached a breaking point.

After reviewing every possible option, I had to deliver news they desperately didn’t want to hear - their loan would not be approved.

The most practical path forward was to sell the family home they had lived in for over 30 years.

The husband was angry, and the wife was crying uncontrollably.

I remember walking away from that meeting, not questioning the decision, but questioning whether I could have handled it better.

Nine months later, I unexpectedly crossed paths with them.

The husband shook my hand and thanked me.

He shared that selling their home had been the hardest decision their family had ever made, but removing the financial pressure had changed everything.

The arguments had stopped, and their family had become stronger.

That moment changed how I think about leadership.

Leadership isn’t measured by how quickly we provide answers; it’s measured by how deeply we understand the problem before deciding what the right answer should be.

I’ve carried that lesson throughout my career—from banking into technology, and now as a Head of Technology in an AI-enabled world.

Today, we have extraordinary tools at our fingertips.

I use AI every day, not to replace my thinking, but to strengthen it.

It helps me tailor communication for various stakeholders/teams and challenge my assumptions.

However, AI cannot understand a room, earn trust, sense hesitation, recognize the emotion behind silence, or carry the responsibility of making a life-changing decision.

AI has reinforced one lesson I’ve believed for years: the better the technology becomes, the more intentional we need to be about staying human.

AI can accelerate analysis and amplify communication, but judgment, empathy, and trust remain leadership choices that begin long before we ask AI for an answer.

They begin by listening.