The Big Story: 5 Questions to Help Your Team Make Better Decisions
“We might recognize that better questions lead to better decisions but aren’t sure exactly what to ask.”
Question-Framing for Complex Problems
By Melinda Church
3-minute read
Healthcare philanthropy is having more than a moment. It’s a movement.
Over the past five years, giving to health systems and causes in the U.S. has increased by well over one-third—from $41.5 billion in 2019 to $60.5 billion in 2024 according to the latest figures from Giving USA. And, that growth is being fueled by large gifts.
With all that’s at stake, today’s transformative fundraising solutions won’t be created using yesterday’s methods. Enter, the “How might we” construct.
Taken together, those three words are an unmatched combination to help unlock solutions for mission-driven healthcare leaders seeking philanthropy to fortify and expand their operations.
Asking early can prevent false starts. For instance:
- How might we deeply engage clinical and administrative leaders in philanthropic campaign planning?
- How might we announce a $30 million gift to spur additional investment?
- How might we generate philanthropy to fuel our new health sciences college?
The power of this question-framing came to mind recently when working through several client challenges and reviewing HBR’s “5 Questions to Help Your Team Make Better Decisions.”
Each word opens possibilities:
- “How” – Unlike the word “can,” “how” implies that answers exist; they’re just waiting to be developed.
- “Might” – In contrast to its second cousin, “would,” “might” signals openness to broad, even unorthodox thinking and fresh ideas.
- “We” – “I” begins and ends with one individual’s life experiences and creativity; “we” brings exponentially more possibilities.
Here are some thoughts about applying this question framing for maximum impact.
Start right: Peel the onion to the core issue
First, some background on “How might we.” Its origin links to Procter & Gamble’s famed innovation lab, the Clay Street Project, so we reached out to Michael Luh, a former innovation leader at P&G.
“In the past, we’ve looked at questions all wrong, and that can have negative consequences,” Luh said.
Leaders, he said, are not thinking broadly enough. Time is wasted winding down unproductive paths. And even in answering fundamentally wrong questions.
Too often, teams jump into problem-solving, simply accepting that the issue, as defined, must be correct. “That’s how you get incremental solutions,” Luh said.
He cited a lesson from a project to bring clean drinking water to a small African village. To start, the team believed the problem was technical. (In fact, that was simple enough: a powder that removes disease-causing waterborne pathogens.) Soon, they understood the real issue was a business problem: how to make the technical solution market-based and sustainable. Addressing the business challenge meant jump-starting entrepreneurship, ensuring everyone made a profit, providing pricing assistance and building local demand.
Assemble the right team, then deploy smart tactics
False-start analogs for healthcare philanthropy abound. One silent scream-inducing example: “Can I just get clinical leaders’ sign-off after we’ve planned the campaign?”
Let’s play out that example of philanthropy campaign planning that’s merely box-checking instead of immersing clinicians and experts in defining priorities.
Putting clinical and administrative leaders in the campaign-planning driver’s seat is all upside. But it’s not simple. And it’s not necessarily easy.
A one-page visual outlining your approach and timing is a good starting asset for leadership discussions. Once you have the green light, it’s time to map the process in greater detail.
Consider these path-smoothing tips:
- Invite participants into a structured, clearly defined process. Scheduling time with oversubscribed faculty, physicians, leaders and researchers is tricky business. But we can’t define compelling philanthropic priorities for healthcare without their vision and insights. Be clear about the time frame and number of meetings.
- Think beyond the usual suspects. The benefits of a diverse team compound when generating ideas to address complicated healthcare and medical research issues. Include some unexpected but well-respected colleagues by asking each leader to invite an emerging star, even standout trainees in areas prioritized for fundraising. The group’s ideation powers can be ignited by early-career participants with different life experiences and mindsets.
- Let others hold the baton. The system’s CEO needs to charge the group and launch the fundraising visioning work. Then it’s time to shake up the hierarchy a bit more. Teams grow accustomed to a leader’s preferences and naturally calibrate ideas to the boss’s typical flight path. Sessions could be led by a skilled facilitator or could alternate among the clinicians and researchers.
- Support every step of the work with fundraising team members. Clinicians and system leaders spend their lives caring, innovating and educating. Development professionals offer complementary expertise to gain clarity about today’s distinction. To capture the 10-year impact that will inspire transformational philanthropy. To articulate how donors will advance the cause.
So, how about that upside?
The funds you raise will be thoroughly linked to your strategies and aspirations, and your fundraising priorities will have baked-in expert champions. That big idea for new cell therapies was conceived by leaders in leukemia and lung cancer, immunology and stem cell biology, among other fields. They’re day-one ready to talk with donors.
Other pluses: You will likely raise more money. You will definitely elevate your organization’s culture of philanthropy for lasting benefit.
“How might we” question framing can help tackle any thorny problem. At this turning point in healthcare, the balance of advantage will surely go to organizations addressing the toughest challenges—in the most effective ways.
Editor’s Note:
If you’re involved in healthcare philanthropy, we invite you to participate in our national survey about the future of healthcare philanthropy. Help shape the discussion.
Contributor: Emme Nelson Baxter, David Jarrard
Image Credit: Shannon Threadgill


