Great writers, Toyota and young kids tend to have something in common. They’re obsessed with the word “why?”.
Almost to the point of annoyance.
But in business, where you’d assume a certain level of curiosity would be richly rewarded, asking “why?” often gets you branded as a bit of a disagreeable troublemaker. A sceptic. A blocker. Which is ironic, given that entire companies have collapsed, gradually then suddenly, precisely because not enough people asked, “Hang on, does this actually make sense? Remind me why we’re doing it like this?”
Naturally, this felt like good territory for our next Sidebar chat.
The Problem with Questions in Business
A lot, maybe even most, big companies treat asking questions a bit like their strategy off-sites or special projects. One-off exercises that can be neatly contained within a specific window of time, unlikely to be revisited. Like when the new CEO is appointed and embarks on a “listening tour”, nodding sagely as the front line employees voice their opinions, and the management team carefully word their thinking. All too often, once the 100-day grace period is over, the time for questions is over, the plan is set, and anything that gets in the way of the plan is somewhat frowned upon.
We both said this during the conversation that we often find we don’t know the best, or maybe even the right questions when we’re starting out … and the most impactful ones tend to come up only as the first version of a proposition or a plan emerges when things are already in motion.
Questions at this point can seem a bit like a wrench, and too often end up going unvoiced. That’s a problem. Alternatively, the way questions get asked can be interpreted as someone trying to be disruptive rather than looking to improve their understanding or a constructive contribution.
The Social Politics of Asking Questions
It’s tough being the person asking a question about a plan, or a project, that is rolling. More often than not, they’re coming from a place that is intended to make the entire thing better, but they require some psychological safety. A lot of the time, questioning the status quo feels like a career risk, for as much as leaders often say they want constructive challenge, when faced with an uncomfortable question in a meeting, the reaction is more often defensive.
We’ve experienced this, for better or worse, in different ways … where the questions can come across as an irritation, but really shouldn’t. It’s perhaps a case of management consultants and how they’re taught what a ‘good meeting’ is … moving smoothly, avoiding tension and ending with clear next steps. Perhaps that focus on the meeting comes at the cost of how decisions get made. The best meetings are often somewhat messy, maybe someone asks an uncomfortable question that forces a pause for reflection. If consensus comes too easily, that might just be a sign nobody is doing enough to question the underlying assumptions.
When Distance Encourages Dissent
Now what if this has ties into the ongoing conversation about in-person, remote and hybrid working patterns. Are people more comfortable asking difficult questions when they are not physically present in the room.
It has us reflecting on a project a long time ago, when we were a bit more naive. While showcasing the work to the executive team, the most challenging participant was the one dialling in via video conference. The individual wasn’t particularly more insightful than the rest of the group (although he did have a particularly sharp Scottish wit), but perhaps because he was just far enough outside the group dynamic, felt emboldened to be a little bit more disagreeable.
In the moment, we as consultants found this rather frustrating like it was throwing us off track, in hindsight, what he was asking likely helped improve our own work and the bigger outcome.
This ties in nicely with a poll Charlie ran on LinkedIn. The results suggested that while most people feel comfortable dissenting in person, when asked whether other people were more likely to dissent remotely, they overwhelmingly said yes. So either we all think we’re braver than we actually are, or a lot of important challenges just aren’t being voiced.
The Art of the Well-Framed Question
This might be a bit of the reason designers love “How might we” questions, to soften the blow of what can be seen as dissenting. Rather than the direct “what do we do about x"?” or the combative “why isn’t this working?” you get a nice, gentle invitation to explore alternative ideas. We can trick the brain into feeling exploratory rather than defensive by changing how we set up the question.
It’s important to not rely on the “how might we” trick though, by asking a variety of questions that stretch thinking beyond conventional constraints. What if? questions, for example, are incredibly powerful in dismantling assumptions. What if we didn’t have to follow this rule? What if we designed this for a completely different audience? These kinds of speculative questions open up entirely new ways of approaching a challenge.
Similarly, more coaching style questions like “What’s stopping us?” or “What would need to be true for this to work?” force teams to confront hidden barriers, be they cultural, regulatory or a creative blocker for the imagination. Instead of asking whether something is possible, these questions assume possibility and instead interrogate the obstacles in its way.
With the abundance of technology, knowledge and resources today, better than we’ve ever had before, it’s these questions that can often get us to the uncomfortable truths of what inhibits progress. An ideal example for Iain to squeeze in some public transportation nerdery with transit tunnels.
So if Elon Musk’s Boring Company can tunnel cheaply and efficiently, what are the blockers causing public transport agencies to still spend billions on projects that take decades. Could it be because transit regulations dictate that trains must be a certain size. But why? Well, safety standards. But why? And if you keep asking “why?” enough times, you often find that the original rationale has long since ceased to be relevant, yet the rules persist.
Make Space for Unanswered Questions and Going Beyond the Illusion of Transparency
A bit of the challenge is making space for questions at the right times, so they’re not being limited to the likes of the first 100 days of a new leader, or the convening of senior leaders for a project update.
Throughout the chat, we touched on a variety of different theories and rationale around questions. One particularly interesting concept is the Einstellung Effect, which suggests that once we’ve learned a familiar way of solving a problem, we struggle to see alternatives even if they’re better. Organisations fall into this trap constantly by creating frameworks, dashboards and rigid processes, and then fail to challenge whether those structures are actually serving them.
Embrace open-ended questioning at all levels, not just in designated strategy sessions, counteracts that. As does the Zeigarnik Effect suggests that we remember unfinished tasks better than completed ones, a bit like a waiter remembers their open tables in much more detail than their paid up ones. This could be organisations treating decision making as a genuinely agile and iterative process rather than pseudo-waterfall approach where decisions are often treated as final and cannot be contested. ,
Most companies have become very good at the image of transparency, perhaps a bit less good at the act of it, but maybe there’s a touch of cynicism from us there.
Transparency isn’t just about sharing information in a town hall format and then inviting some questions, even if they haven’t been pre-screened. It’s more about creating systems where questioning is part of the process, not a scheduled event. Real transparency, a bit like asking some questions is a sorta uncomfortable, but it also means allowing for ongoing dialogue, not just controlled moments of feedback.
So What Can We Do About All This?
One of the most powerful techniques for asking better questions is flipping assumptions. Take any long-held belief and reverse it. Instead of asking, “How can we make our product cheaper?” ask, “What if we made it more expensive?” Instead of wondering, “How do we increase efficiency?” ask, “What if inefficiency is actually valuable?” By momentarily suspending conventional wisdom, you open up new possibilities that would have otherwise remained invisible.
One of the most powerful questions you can ask, at any level of an organisation is “What’s stopping us?”. Not the tactical obstacles, but the real, buried assumptions that dictate what is and isn’t possible. Sometimes, the best thing you can do when posing that question is without demanding an immediate answer.
Annie Duke, the poker player turned decision making expert, argues that the moment you’re presented with a decision, your brain has already started making it. The same goes for answering questions. The instant a question is asked, your brain rushes to generate a response. But what if we gave people space to sit with a question, rather than demanding an immediate reaction?
And therein lies the critical point of all this; for the best questions don’t have easy, let alone single correct answers. They likely unsettle and provoke a wee bit. Probably lingering long after they’ve been asked, and encouraging a change of perspective. Maybe best if not even answered right away. Which is, when you get right down to it, the way most interesting things ever happen in the first place.
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