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Listen to this week’s podcast episode, Ep.230: Start With What If - Creating Immediate Change in the Everyday Moments That Matter, with Doug Fleener, click here to listen now.

Most people wait for major events to create change. In reality, the direction of our leadership, businesses and even our lives is so often shaped by the ‘smaller’ moments we overlook every day. In this week’s episode of Leading with Integrity, I spoke with Doug Fleener, a speaker, coach, former Director of Retail for Bose Corporation, and author of Start With What If: Weekly Questions to Spark Immediate Change and Growth.

Doug’s focus on change is at a practical, everyday level (so it obviously appealed to me, and I hope to you). Rather than discussing transformation as something dramatic or distant, he explores how meaningful progress often begins with much smaller shifts in thinking and behaviour. Much like how we talk about leadership more often than not, on the podcast.

Throughout the discussion, Doug challenged the assumption that change has to be large-scale to matter. Many people wait for the “right time” to improve a situation, make a decision, a reset, a pivot or to approach leadership differently. But in doing so, they often miss the opportunities already sitting inside everyday interactions and routines.

We explored the role curiosity plays in leadership, why “what if” can become a powerful starting point for growth, and how leaders can create immediate movement without waiting for perfect conditions. At the centre of the conversation is a simple but important idea: change becomes far more accessible when we stop treating it as something distant and start recognising the small moments where it can begin right now.

Whether in business or personal life, there’s a tendency to believe that improvement requires a major breakthrough, a complete reinvention and/or the perfect set of circumstances. As a result, people postpone action while waiting for certainty, confidence, or more time. It’s similar to the way a lot of overwhelmed leaders will hold off on making a decision (any decision) until they have the much-anticipated-never-materialised ‘perfect’ information. Or just more information. Or one more bit of information… etc. etc. etc.

Doug speaks about how this mindset quietly keeps people stuck. The challenge isn’t (usually) a lack of awareness, most people already know there are areas where improvement is needed, they know conversations that need to happen, habits that need attention, situations that need addressing or decisions they have been avoiding. The difficulty lies in the way change itself is framed, it can feel big, scary, risky, uncomfortable, all of the above, and when change feels too large in these ways, it makes people hesitate.

This is where Doug’s “what if” approach is incredibly useful. Instead of focusing immediately on major outcomes it introduces curiosity into the process and creates space for possibility without demanding immediate perfection, which matters because curiosity reduces resistance. So rather than forcing people into dramatic action, it encourages exploration, opens the door to movement.

Real, tangible leadership is shaped in ordinary moments, not high-profile situations or ‘top of the mountain’ speeches. Doug reflected on how many leaders underestimate the influence they have through everyday interactions. Small responses, brief conversations, subtle acts of support and routine decisions all contribute to the environment people experience around them.

This is easy to overlook because these moments rarely feel significant at the time. Leaders tend to focus on major presentations, strategic decisions, the big show or the high-pressure situation as their defining moments. But culture, trust and engagement are often built far more quietly.

A leader’s response to a problem, the way they handle frustration, how present they are in conversations, whether they create encouragement or tension in routine interactions.

Over time, these behaviours accumulate and shape how people feel about their work, how safe they feel contributing ideas and how connected they feel to the organisation. Doug’s perspective brings leadership back to something practical and immediate: don’t sit around waiting for opportunities to make a major impact, because the true leaders begin by paying closer attention to the moments already in front of them. Especially the moments that may appear small individually, because collectively they define the experience people have working with and around a leader.

In many workplaces, people operate from a position of certainty and soon begin to seek out this certainty in every scenario, like the crew of the Enterprise seeking out new life in every episode.

Processes become fixed, assumptions go unchallenged, routines settle into place, thinking becomes stagnant (dare I say, lazy..?). Over time this can reduce energy and limit innovation, even inside successful organisations.

Doug described curiosity as a way of reopening possibility. The phrase “what if” sounds simple, but it changes the direction of thinking, moves people away from automatic assumptions and toward exploration.

What if this process could be simpler?

What if this conversation went differently?

What if the obstacle is not as fixed as we believe?

What if we look at this from the opposite perspective?

Questions like these create movement because they interrupt habitual thinking patterns and encourage people to look at situations from a different angle rather than repeating the same responses. Importantly, Doug didn’t frame curiosity as abstract positivity or endless brainstorming. The focus remains practical, and in this way curiosity matters because it helps people take action.

When leaders create environments where questions are welcomed rather than dismissed, teams become more engaged in problem-solving. People feel more ownership over improvement because they’re invited into the thinking process rather than simply being told what to do. Done by us, not to us.

One of the most grounded ideas from the discussion I had with Doug is that immediate change rarely begins with massive transformation. More often, it starts with small adjustments that shift momentum over time. I love this concept for several reasons, but primarily because 1. it makes change less scary and more achievable, and 2. it closely mirrors the way I see great leadership too; the everyday, the small moments.

Doug emphasises that people frequently underestimate the impact of small behavioural changes because they are looking only for dramatic results. But leadership, culture, change and personal growth are usually shaped through small repetitions (there’s probably another parallel here to physical fitness but I’m not the one to write about that..!).

A slightly better conversation…

A more intentional response…

A willingness to pause before reacting…

A decision to approach a familiar problem differently…

These changes may not feel significant in isolation, but over time they alter patterns and patterns ultimately shape outcomes.

Large goals can become overwhelming because they create pressure to solve everything at once, smaller shifts feel manageable, they allow progress to begin immediately rather than remaining trapped at the level of intention.

What stood out throughout the conversation was the balance between practicality and responsibility. Doug isn’t suggesting meaningful change is effortless, but he was highlighting how people often already possess more ability to influence their situation than they realise.

Doug spoke about leadership as something active and ongoing rather than occasional. The way leaders show up consistently shapes the emotional tone around them, the quality of communication inside teams and the level of trust people experience.

Making (as I’ve already hinted) leadership less about isolated moments of inspiration and more about intentional presence.

It also reinforces why small moments matter so much, if every interaction reinforces something, every response teaches people what to expect and over time, these patterns become part of the culture itself, then it becomes crucial for the leader to recognise and be intentional about those small moments; an important responsibility.

It means understanding that influence is happening constantly, even when no major decision is being made and it means understanding that meaningful change often begins much earlier, and much smaller, than we assume.

This weeks episode, my conversation with Doug, offers a refreshingly practical perspective on change, leadership, personal growth, maybe even life itself.

Rather than treating transformation as something distant or dramatic, it brings attention back to the everyday moments where direction is actually shaped. The conversations we choose to have, the questions we ask (or don’t ask!) and the small decisions we repeat all influence the environments we create around us.

The discussion also underlined for me an important leadership truth: progress rarely begins with certainty. More often, it begins with curiosity and a willingness to explore what might be possible.

For leaders, that means paying closer attention to the moments that are easy to dismiss as ‘ordinary’ because in the long run, those moments are rarely ordinary at all. They become the foundation for trust, culture, momentum and meaningful change.

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Listen to the full episode on your preferred podcast platform, find the links (or a web-player) here: https://smartlink.ausha.co/leading-with-integrity/ep-230-start-with-what-if-creating-immediate-change-in-the-everyday-moments-that-matter-with-doug-fleener

If you prefer video then you can watch on YouTube too: https://youtu.be/RHRUYRG_2dw

Join us again next week when we’ll be exploring the lessons of leadership and management from a career in Firefighting and Emergency Medicine, with my next guest Mark Andrew.

I know I say this every week, and you might be tired of reading it, but it’s important to me to keep saying it anyway: THANK YOU for reading, for listening, for supporting Leading with Integrity. There’s no show, no newsletter, no future of leadership without each of you.

Be a Leader Not a Boss,

- David

In case you don’t know me that well, I’m David Hatch and I’m here for new managers and first-time founders working in tech or specialist driven teams to help with their leadership skills, so they can become leaders not bosses, lead with integrity, and build happier, higher performing teams, more effective organisations, and, ultimately: successful teams.

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