When we seek to understand the complexities of human behavior, leadership, or even the way we manage our daily lives, we often fall into a familiar trap: asking about the future. “Would you use this feature?” “Could you see yourself making that change?” We aim to predict, believing that tapping into someone’s imagined future self will yield insights. But the future is a fantasy, shaped by hopes and biases, and inherently unreliable.
To uncover meaningful truths, we need to look backward. “When did you last face this issue?” is not just a concrete question – it’s a gateway into specifics. It gets to the root of what drives decisions, how problems were approached, and what solutions actually worked. We are who we have been, not who we hope to be. In management, this becomes clear. Teams often talk big about what they’ll do next – how the upcoming quarter will be different. But to truly understand performance, you don’t look at their plans; you look at their history.
How did they handle the last big push?
What happened when deadlines loomed?
How did they communicate under pressure?
Past behavior is one of the best indicator of future performance, and not just what someone claims they’ll do. This, I would contend, holds true in business, leadership, and life.
The Trap of Hypotheticals
Why, then, are we so drawn to future-based questions? Perhaps it’s optimism. We think that by asking someone to imagine their future self, we’re tapping into their ideal self – the disciplined, driven version. But that’s the trap. Hypotheticals offer comfort because we can’t be held accountable for a future that hasn’t happened yet.
It’s all smoke.
In my experience coaching international students navigating complex systems in new countries, the power of asking about past actions is undeniable. Instead of asking, “Would you prioritize education over a job?” the more revealing question is, “When did you last choose between work and school? How did you decide?” This uncovers their true priorities. Once you see their patterns, you can guide them where they need to go, helping them see themselves more clearly.
Past as Prologue
Focusing on the past isn’t just practical – it’s free from the bias of future hopes. When you ask someone about what they’ve done before, you force them to recall specific moments packed with context, emotion, and action. These reflect real decisions and consequences.
In leadership, I remind myself that leaders aren’t defined only by their future vision but by how they’ve acted when times were tough. When did they last navigate a crisis? How did they communicate under pressure? These are the moments that reveal a leader’s style, not the aspirational speeches. Having worked with many leaders, I’ve learned more from their reactions to challenges than their promises for the future.
In professional development, this backward glance is even more powerful. When I mentor or coach, the most transformative conversations emerge from past experiences – the highs and lows, the struggles and triumphs. It’s not about what someone might do, but about understanding what they have done, and why.
Reframing Success
Let’s take this further. The past is our greatest teacher, yet we often avoid it, preferring to shape a shiny narrative of growth. But it’s in the missteps, the failures, the unpolished moments that the richest lessons lie. When did you last miss a deadline? What did you learn from it? These aren’t just questions; they’re opportunities for insight, invitations to examine what works and what doesn’t.
Asking about the past also reveals the drivers of behavior. In business and life, people are often motivated by incentives they aren’t fully aware of. When you ask when someone last acted on a decision, you uncover not just what they did, but why. What pushed them? What motivated that choice? This is key not only for understanding performance but for inspiring change or improvement.
So, the next time you’re tempted to ask a hypothetical, resist it. Ask about the last time. The most recent example. Anchor the conversation in the real, the experienced, the lived. You’ll get clearer answers and open the door to a deeper understanding of what drives people – and how to lead them forward.
Living in the Reality of the Past
While we anchor ourselves in the truths of the past, it’s also crucial to recognize that the future holds promise and potential. This article is not about dismissing future vision or planning but rather about balancing the present by grounding decisions and expectations in what we know – our past experiences. In doing so, we ensure that future aspirations are informed, realistic, and achievable, rather than being celebrated simply as imagined possibilities. We need to celebrate what the future can become, but not at the expense of the hard-earned lessons from the past.
While the future is a canvas on which we love to paint, the past is where the masterpiece already exists. It holds our truths – unvarnished, raw, real. The future offers promise, but the past offers clarity. As you seek to grow, lead, and guide – whether in management, business, or life – let the past be your guide. Ask the right questions, and you’ll find the answers were always there, waiting to be discovered.