How Can Nonprofit Leaders Ask Better Questions?

The best nonprofit organizations work to solve some of society’s biggest problems, but they can’t do that without asking the right questions. Why? Because questions help us to understand problems. They allow us to relate to others better. Questions forge solutions. 

A nonprofit team asking the right questions.

​Asking questions helps drive everything from program offerings and fundraising initiatives to the organization’s overall strategic mission. So, that begs the question, how can you ask better questions?

​Hypothesize Instead of Assuming
Too often the process of asking good questions is stalled by making assumptions or holding too closely to existing viewpoints. In discussing critical thinking in business, John Coleman explains, 

As a former analyst at McKinsey & Company, one of the first things I learned was ‘hypothesis-driven thinking.’ Based on the scientific method, this process is what allows McKinsey teams to work through problems quickly and efficiently. It involves formulating an early answer to a problem and then digging into the data to seek to improve and refine it. Core to this approach, however, is holding your hypothesis loosely. If you are too attached to your initial answer, you may refuse to let it go, no matter where the data leads. But if you treat your own answer as a strawman, holding your assumptions loosely, you’ll be willing to totally abandon it if the situation calls for it.

​Taking a hypothesis approach is especially important in group settings where there is a tendency for groupthink to take over. Otherwise, it’s easy for the loudest voice in the room to drive the narrative and shut out a proper examination of the ideas being discussed. No matter what the problem is or where you are in the process of trying to solve it, always leave the door open for questions. These questions will allow your organization to find the best solution!

Embrace Discomfort
There are times when asking questions isn’t easy. In these times it’s key to not shy away from the uncomfortable. Transparently address questions and concerns being respectful to different communication styles and cultural differences. Don’t forget to consider the value that personal experience can bring to the conversation as well. As our team explained in an article assessing the effectiveness of nonprofits today, 

Often times the most zealous anti-racism advocates at organizations are white employees campaigning for the rights of their BIPOC colleagues without a true understanding of their colleagues’ lived experiences or the outcomes they are hoping to achieve. These kinds of efforts are well meaning, but often misplaced or unproductive… While it is great when all employees want to support each other’s rights for equal treatment, listening to the loudest voices instead of the most relevant voices can be dangerous. Do not let a vociferous faction upstage the voices you are trying to protect, or you will play into the marginalization you are seeking to overcome.

​When needed, be willing to stand alone as an organization or a leader within an organization to challenge the status quo, but do not close the door on asking questions and having healthy conversations.

Foster Conversation
The goal of asking questions is to create dialogue. Ask open-ended questions to get a broader perspective on what you are trying to understand. Then ask follow-up questions to dive deeper instead of just letting an answer end the conversation. Remember, asking questions shouldn’t feel like a standalone activity (like a 1-on-1 meeting or a focus group). It should be an ongoing initiative. Embed asking questions into your organizational culture to include it in everything you do.

Engaging in ongoing dialogue is incredibly important at all levels, but especially between the Executive Director and the board. Board members asking questions helps nonprofit leaders to see what they are doing or planning through the eyes of someone who doesn’t live and breathe that work every day. As such, it not only strengthens their relationship but also provides great perspective and helps to foster a deeper understanding of how the organization is perceived. The board can speak on behalf of the community, acting as the outsider’s eyes and ears for leadership that is enmeshed in the day to day of the organization’s work.  

Listen Well
It’s important not to forget though that asking better questions is only half of effective communication. The other half is listening well enough to get an answer! Active listening is one of the most important skills for nonprofit leaders, especially in relation to equipping board members to help the organization succeed. If you want advice on how you can improve, take the leadership assessment now!

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​Take the time to truly listen to your employees, supporters, and program participants to understand their perspectives. In the same way that asking questions should meet all employees where they are professionally and personally, listening must consider differences between employees as well. With a diverse workforce there may be vast differences in how employees communicate, and each voice deserves to be heard.

Move Slowly
Of course, we ask questions to better understand something so we can act. However, this shouldn’t be done too quickly. Take it slow to ensure that your organization is executing its mission effectively. Acting too quickly runs the risk of creating mission creep, which can derail even the best-intentioned organizations. Ensure that any action being taken based on your conversations furthers your mission in some way.

When you need interim nonprofit leadership or board advisory services, we can help! Our nonprofit consultants have guided countless nonprofits through changes and difficulties to help them come out stronger on the other side. We have the kind of experience needed to provide strategic support no matter what your organization is facing. Contact us today to find out more!