The lost art of asking questions
Opinion
We have become too solutions-oriented. We need to stop and ask questions — and the most powerful questions come from consulting with a range of lived experiences.
Do you remember when failing fast was a thing? Its origins can be traced back to a Stanford University speech in 2001 by Carol Ann Bartz (former CEO of Yahoo). It was adopted by the tech bros in Silicon Valley as a mantra for rapid progress and innovation.
While I can get on board with the test-and-learn philosophy that’s at the heart of this business management concept, I’m much more cynical about its intrinsic pace and focus on “doing”.
There is a lot we can learn from our failures (and I do believe we shouldn’t fear them), but failing fast with continuous repetition doesn’t leave us time to reflect.
With current market conditions somewhat sluggish, leaders have become more risk-averse and “failing fast” has fallen out of favour. But we haven’t seen a new organisational psychology theory surface to replace it.
Stop, reflect, ask
I believe asking questions has become a lost art that we all need to relearn.
We have become highly solutions-oriented — often there is not enough time to stop and ask questions. We are expected to jump incredibly quickly from problem to solution and many businesses are designed to deliver ready-made solutions to clients — it’s more efficient and profitable that way.
The trouble is, when everyone is being given the same solution, creativity and competitive edge are diluted.
The art of questioning starts with fostering natural curiosity. It requires us to stop, look up and reflect; to resist the urge to jump to solutions. It’s a shift in mindset — one that is OK with not knowing the answer straight away.
Critical thinking
In qualitative research (where I started my career), you learn the practice of asking open questions, the skill of laddering and probing, and — of course — avoiding leading questions.
The hardest skill to master, however, is the power of a pause. Not many people are comfortable with silence. So, if you leave a beat, it will be filled — and that’s where the most interesting insights are hidden. I use this technique with my clients all the time.
Susi Castle, a marketing consultant and neurodivergent business owner, agrees: “What I’ve noticed is that struggles that can be superficially othering can become enormous advantages when you reframe them. My dislike of small talk drives me to seek more meaningful insights and I naturally question what others take for granted — I hear the subtleties in language and the spaces between words.”
For me, it’s the experience of midlife that has allowed me to perfect the craft of asking questions. The cacophony of motherhood alongside supporting a partner with ill health, followed by grief and perimenopause, has taught me so much. I’ve learned to be more vulnerable.
And I’ve realised this is at the core of asking good questions.
My journey with grief has made me even more determined to be my authentic self. This has enhanced my ability to connect with other people on a more meaningful level. When you connect, you get to the questions that really resonate.
I see this same skill among my peers in the industry, many of whom are operating as consultants and small business owners like me. It’s midlife women and men, neurodivergent talent, black and brown entrepreneurs, and people with different lived experiences who are asking the most challenging questions right now.
These individuals have expertise that comes from their experiences — expertise that offers an alternative to the tech bros and is more in keeping with the times. As AI capabilities get more deeply embedded into businesses, we need to realise that, yes, we can use technology to harness speed, and even some of the thinking and creation, but the human in the loop is going to need to get much smarter at critical thinking.
A new kind of courage
And asking questions is a foundation skill to critical thinking.
Those with tougher lived experience may have faced challenges, felt vulnerable in the most everyday of situations and been forced to learn to be OK with not being OK.
These experiences can perpetuate throughout life but, sometimes, with enough time, the right support and the strength of a community, a new and powerful type of courage is unlocked. A courage that means you are more comfortable with not knowing the answer, well-placed to be empathetic, can listen to your instincts and let your voice be heard.
As Nick Sami, another consultant and business owner, tells me: “Being on the receiving end of stereotypes (both brown and gay) has only made me work harder to both earn respect and also show respect and empathy for others. I’m unafraid to challenge, but this is balanced by my enhanced listening skills. You need both to ask powerful questions.”
Singular view of progress
As we herald in another era of Donald Trump, this will have ramifications on the world stage and in business. This new reality carries a real danger — that, in the pursuit of progress, we will settle on an even more singular view.
Economic progress to the exclusion of other types of progress is Trump’s mission. He’s made it abundantly clear that diversity, equity and inclusion, as well as sustainability, are in direct competition with this manifesto.
Shazia Ginai, a business growth expert, challenges this singular view as a Muslim, South Asian woman. She says: “I bring a different perspective into decision-making spaces — questioning things that perhaps a more homogenous group would miss. Alas, exclusion still exists, with tight-knit exclusive groups holding power — questioning is discouraged. How will we ever drive progress if we don’t encourage curiosity?”
Media prides itself on being a progressive industry, but the definition of progression is shifting, with economic progress being decoupled from all other types of progress including equity and inclusion, health and the environment.
The truth is we need to decide which side we’re on. I will be keeping an eye on the All In Census, but anecdotally the latest wave of redundancies does not feel even-handed to me — the axe seems to be falling more readily on marginalised groups.
Acknowledging that we don’t have all the answers isn’t a weakness; it’s a strength. Vulnerability can be a superpower.
In our industry, we don’t always reward vulnerability, but we should. It’s what creates the conditions for powerful questions and, ultimately, for inclusive leadership that listens, learns and grows.
Anna Sampson is a consultant