Question Everything

“The ability to ask questions is the greatest resource in learning the truth.” – Carl Jung 

I’ve just finished reading Questions Are the Answer, by Hal Gregersen. This terrific book has inspired me to scribble more than usual. I’ve been jotting down questions on scraps of paper, adding questions to our staff meeting agendas, and peppering client presentations with even more questions. During a recent strategy session with our team, we reflected on whether we’re striking the right balance between giving our consulting clients the answers they need and teaching them how to raise—and resolve—challenging risk questions themselves. We want to be responsive to our clients’ wants and needs, but we also know that leaving an organization with answers to today’s questions about risk or ERM, won’t necessarily fortify them with the skills to cope with the disruption around the corner.

This is Your Crucible Moment

Gregersen turns to dozens of esteemed colleagues and clients for wisdom and insights on the topic of questions. Although published in 2018, his advice seems poignant and truly relevant at this moment in world history. I especially loved the references to ‘crucible’ experiences and the work of management gurus Warren Bennis and Bob Thomas, who explored how leaders are transformed by “intense episodes of adversity that push them into periods of self-reflection.” In their article published in the Harvard Business Review in 2002, Bennis and Thomas write that “A crucible is, by definition, a transformative experience through which an individual comes to a new or an altered sense of identity.” Here is the article’s powerful ending:

“It is the combination of hardiness and ability to grasp context that, above all, allows a person to not only survive an ordeal, but to learn from it, and to emerge stronger, more engaged, and more committed than ever. These attributes allow leaders to grow from their crucibles, instead of being destroyed by them—to find opportunity where others might find only despair. This is the stuff of true leadership.”

Be Vulnerable, Not Competent

Last week, our number 6 from “Take 10: Resume and Thrive Strategies” touched on the quality of vulnerability as a prominent trait for superb leaders. It emerges again here when Gregersen rails against a leadership style where the leader professes and pretends to have all the answers, all the time. He explains that claiming (or faking!) all-knowing expertise is, in fact, the opposite of authentic leadership. He interviews numerous successful leaders whose experiences recall familiar themes: listening is more important than talking, questions are more important than answers, and striving to understand others is fundamental to making connections at work and in life.

He reminds us that: “If you want to find a new angle on a problem and ultimately find a breakthrough solution, you must rid yourself of the impulse always to display deep competence. For the right questions to surface, you must spend more time feeling mistaken.”

Change is Here

Change is hard, it’s painful, and it’s coming, ready or not. During the past several weeks, we’ve heard from leaders of nonprofits across the vast charitable sector about the difficult changes they are making to save and renew their missions. Some of these changes are a direct response to the inability to continue normal operations. However, we suspect that many of these changes may have been a long time in the making. Business and financial models must be built to flex when inevitable external risks emerge. An external risk is one that your nonprofit doesn’t control or influence; your only course of action in the face of such risks is to pivot by implementing your business continuity plan and pausing to ask tough questions about how your agency must change to survive and thrive.

Gregersen observes: “My observation is that top executives’ legacies come down to whether, across their tenures, they have been able to spot the moments when big change is called for—what Intel’s Andy Grove famously called the ‘inflection points”—and marshal the energies that only they can marshal to bring about the transformation.”

Burst Your Own Bubble

Gregersen shares insights from Simon Mulcahy, chief marketing officer at Salesforce, on the not-so-safe world inside the executive’s ‘bubble.’ Mulcahy shares: “Many CEOs have this staff that basically creates a ‘ring of steel’ around them. They’re all complicit in doing their very best to support the CEO, but they create an absolute cocoon, a vacuum of feedback. The CEO only gets presented what the direct reports tell him or her, and it leads to an incredibly stilted decision-making based on very nuanced feedback.” Gregersen explains: “Too many leaders get their information catered—picked, prepared, and plated for them in a way they’ve already indicated they’ll find palatable. To fight back, they need to get out into the field, gathering raw stuff on their own.”

The NRMC team has observed the executive bubble at work in some of our nonprofit consulting clients. We nudge these organizations to double down on ‘psychological safety,’ a culture where all team members feel included, safe to learn, safe to contribute, and safe to challenge the status quo—all without fear of being embarrassed, marginalized, or punished in some way. (See The 4 Stages of Psychological Safety, by Timothy R. Clark and The Fearless Organization, by Amy C. Edmondson.)

Another way to ‘burst’ your own bubble is to expect and welcome sharp poking from your board of directors. How? We all need boards comprised of leaders who support our missions and work with us in a constructive partnership. But a board of ‘yes’ men and women is downright dangerous. Genuine board leadership emerges when members feel comfortable discussing existential threats and posing questions to the CEO and one another that are difficult, and sometimes impossible to answer. If your board isn’t asking questions that you can’t answer or questions that make you feel uncomfortable, you’ve got the wrong type of leaders on your board.

I Have a Few Questions

Your post-COVID-19 world:

  • In what ways have you been utterly wrong about how a pandemic would affect your organization?
  • What is your organization doing to build resilience so you can capably respond and bounce back from the impacts of a future disruption to ‘normal’?
  • What has been the most important lesson you’ve learned about your organization? About yourself?

Your executive bubble:

  • When was the last time a direct report or junior colleague told you that you were wrong?
  • When was the last time you received unfiltered, bad news?

Your board as a team that challenges you:

  • When was the last time a board member asked a question that made you think twice or even feel uncomfortable?
  • What are you doing to encourage board members to candidly talk about the biggest challenges facing your organization?

Your engaged (or demoralized) workforce:

  • What are you doing to make the work of your team more meaningful?
  • What are you doing to inspire hope?
  • What will you do to support your team’s progress and minimize setbacks?
  • What are you doing to tap into the creativity and bold ideas that exist in every member of the team, from the newest or freshest member of the team to the seasoned veterans?

When I’m immersed in a thought-provoking book like Questions Are the Answer, I sometimes feel like I’m drowning. My brain wants to go straight to the application of the text’s wisdom and insights even before I’ve reached the concluding pages. I scribble ‘to do’ items in the margins of the pages. I have to consciously remind myself to slow down and let the questions sink in before I wrestle with action steps and answers. In a time of truly unprecedented uncertainty, I sense that we all need to give ourselves permission and safe spaces to ask the toughest questions we can imagine. Vow to unite against this storm; invite the colleagues who bring your nonprofit’s mission to life into that space. Pop the bubble protecting you from bad news and resolve to surface the most difficult challenges you’re facing now and into the future.

Melanie Lockwood Herman is the executive director of the Nonprofit Risk Management Center. She welcomes your questions about questions and can be reached at or 703.777.3504.