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TAMPA BAY • FEBRUARY 23-24 2026

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What Makes For A Helpful Question?

Welcome to Helpful Questions Change Lives. Let me begin this first post with a question. One that stopped me in my tracks and changed my life for the better, just a few years back. It was…

Why do you experience life the way you do?

For the first 55 years of my life, the answer seemed obvious. Where I was born and my upbringing had a lot to do with it. Sweet, bitter, and extreme life events like the birth of children, divorce, and the death of loved ones too. The hand life had dealt me and how I played my cards were in the mix. Other people I’d met, the circumstances I found myself in, and how much money I had seemed to matter too. Also, how I thought about what had happened and what could happen in the future, all helped explain why I experienced life so far as I had.

Until, that is, the story all these explanations added up to, felt a bit too much to cope with. It made me unwell. Depressed.

In my search to restore mental health, I discovered a bigger story in which mine was but a small part. Its many chapter headings remained unwritten. Each took the form of a question. Some were old and required revisiting, others were brand new. They included…

…How possible is it to experience life differently from our norm when it’s turbulent or unhelpful?

…What elements of experience can and can’t we influence?

..How might our understanding of, say, truth, well-being, life shocks, love, leadership, anxiety, well-being, addiction, curiosity, criticism, difficulty with others, redemption, parenting, conflict – and much more – be helped, by a deeper understanding of why we experience life as we do?

Questions like these inspired this series. My posts here will explore them in more depth. I hope you’ll join in too.

Perhaps, what we discover together, may not only help how you experience life but also seep into the conversations you have with someone else you care about. And beyond that maybe, into your wider family, workplace, and society at large. Who knows?

Before we go any further though, I thought it might help to look at what constitutes a helpful question, as well as why it might not appear helpful to everyone.

Einstein’s useful insight about questions

Take a look at this well-used quote from Einstein:

If I had an hour to solve a problem and my life depended on the solution, I would spend the first 55 minutes determining the proper question to ask, for once I know the proper question, I could solve the problem in less than five minutes.

What could he have meant by “proper question”? To me he’s pointing to what’s fundamental – the principles that are foundational to understanding a topic. Why thrust, drag, weight, and lift are fundamental to our understanding of flight, for example. And to what’s essential – the necessity of something for a specific purpose or outcome to arise. For instance, we need oxygen to breathe if we’re to stay alive!

Einstein encouraged inquiry into what’s at the heart of the matter. Once identified, the question allows you to see the problem more clearly and find a direct path to a solution. He’s highlighting the idea that understanding the problem and defining it correctly, is often more than half the battle in problem-solving. Once you have the right question, the solution becomes more apparent. Our attention on what comes next can be more acutely focused.

Suppose, for instance, family members are troubled by the behaviour of their neighbours. Compare these two ways of framing a question for this situation: What could be the reasons behind our neighbours’ behaviour, and how can we foster better communication with them? Why are our neighbours terrible people and always causing problems?

Or in a workplace setting where a business is facing some headwinds: What helps employees reach their full potential to deliver what those who depend on them really value? What’s the quickest way to cut costs and increase profits?

A content family and a healthy business, respectively, are the desired outcomes, but can you see how the first question in the pair takes us to what’s fundamental and essential in ways the second does not?

A family at its best can overcome many concerns that are seemingly caused by others, including what good neighbourliness could mean. Similarly, a workforce that enjoys learning and adapting to what those who depend on them value, is likely to thrive even in the most testing economic conditions.

A ‘proper question’ it seems to me, not only gets to the heart of the matter but is asked in good faith too. It’s intended to elevate our sights, broaden our understanding, and make us better people. That’s why it’s helpful. Not just to its originator but to those who will help answer it too.

Helpfulness, however, like beauty, is in the eye of the beholder Of course, I realise a helpful question to me, may not be to you. It may never be. Perhaps because you’ve already considered a question deeply and are comfortable with the answers you’ve discovered. You’re not up for looking at it more broadly and in more depth. Maybe, it isn’t of help just now. I get it if your mind is busy with other stuff or it’s just not the right time for you. I too had no time for what once seemed like difficult, dumb, and demanding questions.

You might also be wondering who am I to be asking them, and whether I have an agenda. I don’t. At least not in the sense that I’m here to convince or cajole you into particular answers, and persuade you to follow prescriptive actions. That’s not my thing. I am here to create a space for human inquiry though. With fellow, curious detectives, keen to explore why we humans do what we do, why we are the way we are, and what change possibilities might arise for us as individuals (including me) as well as those around us.

That’s it. Inquiring together. That’s all. So, what kind of helpful questions?

As mentioned above I will start with a series of questions that spin off from the why-we-experience-life-as-we-do one. This will give us a foundation from which to explore so much more.

The world of groups next – families and workplaces – a question like What sits behind a family or workplace culture people love being in and is free of toxicity? could help many of us it seems to me.

In the worlds of science and business, I’m keen to explore What makes innovation engaging and widespread? – as in how the answers to one question can lead to more. For instance, Alan Turing once asked Can machines be programmed to mimic human intelligence? Marvin Minsky and Dean Edmonds wondered How we design a machine that can learn from experience. Later Joseph Weizenbaum asked How can computers understand and process human language? By the late ’60s John McCarthy and Pat Hayes were asking Can machines reason and make logical decisions? Then there was David Marr and How can computers visually perceive and interpret images? A decade later Richard Sutton and Andrew Barto pondered Can we create machines that can adapt and improve their performance over time?

See where I’m going with this? Questions about systems that can…

  • recognise patterns in large datasets,
  • converse with humans,
  • assist with autonomous driving,
  • simplify complex tasks,
  • make interplanetary travel possible,
  • make accommodation worldwide affordable, and
  • revolutionise logistics and shopping experiences
  • …have all led to the creation of the largest companies in the world who created technologies that enabled this image of me and Ted, taking a moment together, to be available to all.

Not to mention a technology called Artificial Intelligence that could transform what it means to be human!

Now, you may have noticed the emphasis on innovative tech here. I’m not a tech geek though, far from it. And I recognise innovations aren’t disruption-free. They may not all be a force for good either. The hubris and misaligned incentives that are attached to many of them can mean their impacts have us wincing, squirming, and shuddering sometimes. My point here though is to simply illustrate where a powerfully framed question can lead us. To the point of being able to help billions of us, yet simultaneously pose an existential threat to our species and, as I say, what it means to be human.

Just think. There are questions that may help many of us that haven’t been framed yet. Who knows? Perhaps, in this space, we might stumble across a few.

Finally, the wider societal perspective.

In his inaugural speech in 1961, President JFK said “Ask not what your country can do for you, but what you can do for your country.” In my head, the world over, even today, this call to personal responsibility and civic duty still resonates. It sparks many questions that help us inquire into the fundamental principles and essential outcomes we all seek. Replace ‘country’ with ‘people and planet’, for instance, and what emerges? Similarly, how could polarisation spur innovation? What could turn the rise in mental ill health around? How could we reduce crime and reoffending simultaneously? How can new technologies help create societies we love living in? What makes our species a net positive to other sentient creatures?

Questions begin the process of stepping into the unknown, being curious, and becoming voracious inquirers.

You are warmly invited to join me in this inquiry. Together, let’s uncover the potential that helpful questions have to change our own and others’ lives.

In the next few posts, I’ll focus on…

  • The questions that voice in your head raises
  • Being present in each moment and its implications
  • What’s mysterious about the way we experience life
  • What we can and can’t influence with respect to how we feel

…and much more about the way we make sense of what’s going around us.

I do hope you’ll join me.

Kindest,

Roger.

Roger Martin
Roger Martinhttps://www.rogermartin.me/home
Though unique to me, parts of my life story may resonate with you too. I’ve worked in toxic cultures and helped craft those in which people thrive. I’ve been divorced twice and learnt much on both occasions. I was estranged from my children for over 20 years but no longer am. I’ve suffered much anxiety and depression but don’t to the same extent anymore. Professionally speaking I qualified as a management accountant. But, driven by a desire to help people’s experience of workplaces be fulfilling, not demoralising, I soon switched to the world of leadership and team development. Over the last 37 years, I’ve had the privilege of working with thousands of leaders and see myself as a student of what works and what doesn’t for them. Variously I play the role of sounding board, critical friend, coach, mentor, consultant, and speech writer. Nowadays I write more and record audios and videos too. I have a Substack called Helpful Questions Change Lives. It’s a friendly place in which to inquire into why you, and the rest of us, experience life the way we do, with all its ups and downs.  Do join me there if this is up your street or, perhaps, someone you care about.

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