Why Business Leaders Need to Ask More Difficult Questions

Seth Goldenberg wants us all to be more curious. The designer and entrepreneur brings design-based principles and questions to a variety of enterprises. He runs a design-based management consultancy, and has worked with many companies, including Apple and Oprah Winfrey’s OWN to help rethink their business structures and processes.

Goldenberg, who also runs a Dickensian-sounding bookstore, Curiosity & Co., that doubles as a wine bar and cultural center in Jamestown R.I., has recently turned his attention to the role of curiosity—instead of just knowledge—in the culture and especially in the way businesses operate. His book, Radical Curiosity: Questioning Commonly Held Beliefs to Imagine Flourishing Futures argues that the workplace of the future needs to be asking a lot more fundamental questions if it’s going to thrive.

This interview has been condensed and edited for clarity.

What do you think the role of curiosity is in the workplace?

For me, it’s central. It’s the foundation. I mean, work is certainly turning itself inside out right now. We are having to recheck the questions we asked that put us on a path to create value. Curiosity, as a kind of leadership practice, is penultimate to determining what is even worth doing at all.

What do you mean by ‘create value?’

Radical curiosity is a practice that comes from my studio epic decade. We’ve had the pleasure of working with companies, organizations from almost every industry, and we find over and over that there’s a great deal of aspirational intent, but that work doesn’t always yield true, resilient value, meaning impact in the world, or the objective that we seek. I think a lot of times the transactions of the day supersede and can camouflage our original intent. In fact, some of the work we do is to help organizations re-engage and re-embrace the upstream process of why they do the activity that they’re doing. We need to return to questions—we need to embrace curiosity—to question the trajectory.

Can you give us an example of what a workplace that is focused on curiosity, or at least using it well, might look like?

In our studio we ‘slow down in order to speed up.’ If we believe [businesses] are not asking questions or are not embracing curiosity, we talk about slowing down the process. One of the things that we have introduced into organizations is moving from self-actualization to a collective actualization. We often think about performance and the notion of singular careers: we often have a learning plan, a career path, a trajectory that we are engaged in as our story. But slowing down in order to understand the collective actualization of teams or departments, or the ways in which different interfaces and intersections across complex organizations behave, allows us to kind of become systems thinkers.

There are a lot of businesses that need to make decisions quickly. What if they don’t have time to slow down?

I think we maybe have swapped urgency for value. And I think we need to ask harder questions about the roots of things. We don’t necessarily believe, many of us, that at a national scale, education as a social system is working, but we’re going to throw you in jail if you don’t attend for truancy. Wall Street is an easier one; there’s millions of transactions happening per minute. But is it creating value? I’m interested in radical curiosity as a kind of manifesto and a kind of urgent desire to, in fact, create more value or have greater impact, by slowing down and questioning the very roots of the assumptions.

How might curiosity be affected positively or negatively, by what seems to be an increasingly atomized workforce?

I’ve seen an interesting conversation emerging that has flipped the great resignation to this other conversation about the great simplification, which I found quite appealing. It just sounds wonderful to talk about, but I think that human beings need a hybridity. We need multiple models for ways of working, of connecting, of creating meaning, and finding ways to adopt purpose both individually and in teams. The digitization of working remotely, in the beginning, I think, was very challenging and people were certainly finding new rhythms to make that work for them. I think we’re going to enter a period of experimentation. We talk about in the book what I call cultural interregnum: this idea that we’re moving from kind of one era to the next era on a variety of social systems. There are these kinds of legacy narratives that work needs to happen this way and that is the kind of inherited normative behavior. And I think that in this era of interregnum, when we move from one model to another, in particular with work, we’re going to see probably dozens and dozens of models to iteratively figure out what works. And it’s going to take some time.

You write that “curiosity is the fuel of transformative leadership and value.” How?

I think we’re still healing; I’m not sure we have fully embraced the full kind of aftershock of how the pandemic will be a catalyst to reorganize the kind of operating system of culture. We’re going to need leaders who are full of humility, or willing to ask questions, and maybe courageous questions that felt untouchable in the past. When you face an existential kind of threat, things that you thought and assumed were fixed and no longer are, will require adaptive business models, adaptive growth models and leaders will need to be able to use curiosity themselves, but also to indoctrinate and kind of build cultures of curiosity, to encourage their teams to be willing to chart into the unknown.

What are these courageous questions that have never been asked before?

For example, cities are saying, let’s have a community-wide conversation about what safety is. It’s not “fund or not fund the police”. It’s “Let’s have a civic imagination forum and procedure and process to explore us collectively redefining what the police and the role of the police can be in our community.” This is very constructive. For me civic imagination moves far beyond a kind of critique and begins to experiment with models that seemed not possible before. So what does equity look like? What does help look like? I often use the example around Obamacare. For me much of Obamacare was a debate over who paid for it, who got the invoice for healthcare, but we weren’t actually having a conversation about what we mean by health. Do we want to live to 100? Do we want a model where 90% of our dollars are spent in the last 5% of our lives? We need to have, at this kind of wonderful moment where we’re doing this operating system reboot, very core human condition questions: What is learning? What is safety? What is travel? These are all these questions that we’ve just assumed are on autopilot. There’s this exciting moment to say, what do we really mean by these things? We have kind of skipped over that stuff and just made the plumbing of how to move the invoices in the procurement system.

It feels like what you’re saying applies for certain leaders in certain industries at certain times. Is this across the board or is it more a seasonal thing, at a certain point in a business’s or enterprise’s lifecycle, that curiosity must be a key value?

I think it’s true that questioning everything cannot come at the expense of action. But I think that there’s probably no time in an organization that embracing curiosity would leave a net negative legacy. Questioning our commonly held beliefs within the organization, within our sector, about our audience or customers about how we create impact and value; that for me is always healthy and is almost a precursor to just great leadership and value creation. Maybe embedded in your question might be a sub question which is, maybe not so much the lifecycle of where an organization or business is, maybe it’s the lifecycle of where culture is. I just think that in some ways, the pandemic has kind of jump-started a requirement to recheck our assumptions. I think a lot of people are saying, it’s not so much getting back to normal. It’s questioning what we want to learn from this and to design what a new normal may look like. Any organization that is not asking radical rooted fundamental questions, they may have a time period in which they are doing okay, but it will come back to haunt them if they don’t embrace such deep questions sooner rather than later.

How would radical curiosity change the way we learn?

I would argue that this is a time in which the future of work depends on how learning enters the organization. An organization can be a full time learning identity—and embracing learning as part of the daily activity of the workplace may actually, ironically, bring a sense of awe and wonder and purpose that feeds that curiosity and may be the antidote to the great resignation.

What are you suggesting? More of those learning modules where I’m taught not to let Gremlins come and steal my data?

The world is filled with all kinds of fantastic learning experiences. They’re just unaccredited. I think one of the opportunities here is to disrupt the typical format of credentialing. Every day, somewhere in New York City, there are 500 learning experiences happening that Fortune 500 companies are unaware of. I think finding a way to get these two spheres to speak to one another—the corporate objectives of professional development, and the extraordinary world of culture and the arts and all of the discovery that happens in the real world—for those languages to kind of be reconnected could unearth an extraordinary, much more open curriculum of the real world.

What would you say to this business guy who says this is way too pie-in-the-sky unremunerative?

In my experience, money and profit is the result of creating culturally relevant value and it’s very difficult to create cultural relevance if an organization is fundamentally disconnected from active culture. Think about it from a multi stakeholder point of view: if your employees are disconnected, if your customers are disconnected, if your brand is disconnected, it will be very difficult to make money. We all know the kind of examples—whether it’s the Blockbuster Videos of the world or the organizations who are losing billions of dollars market cap value, because of their fundamental disconnect from the cultural zeitgeist.

Where have you seen great examples of radical curiosity?

I have great inspiration for the sea and avalanche of social entrepreneurs that I think are emerging and will emerge as a kind of reparative movement of this moment. I think there’s this kind of fascinating era of re-healing and reordering that is already unfolding, and I see that increasing in its velocity. It turns out if you want to make a billion dollars, you might need to ask social questions like, what is the future of water? And how are we going to feed 9 billion people? Actually, those more core Maslow’s hierarchy of needs issues, for me, these are the big terrains of opportunity. And there’s not necessarily a single company but I think there’s a persona of the radically curious challengers that are questioning those basics.

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