Ops Insights #072 - 3 Leading Questions to Ask Your Leader Today
August 22, 2025 | Read Time: 5 minutes | Written by Jenny Kleintop
It’s fabulous to have you as a reader. Thank you so much for tuning in and taking the time to lean into the growth and development of you and your team. So glad you are here!
One of the two main reasons I went to work for my second nonprofit was to report directly to the head of development. This way, I could learn how to report to and interact directly with the leader. As I’m naturally an introvert, at the time, I didn’t have the skills I knew I needed to acquire this skill. So, this gave me the opportunity to learn.
I read books, listened to podcasts, watched webinars, and observed others. I was eager to learn anything I could about leadership and how to report to a C-suite executive. Between this approach and interacting directly with the leader, I grew tremendously in my skill set.
Now I’m super comfortable interacting with, understanding, and supporting CEOs, CDOs, EVPs, VPs, and leaders. Over the years, I have learned to ask three leading questions to leaders.
What are our top 3 priorities as an overall fundraising team?
What story are you trying to tell about our fundraising progress?
What keeps you up at 3 am?
ONE: What are our top 3 priorities as an overall fundraising team?
Ideally, you already know, as your leader has shared the strategic plans with the team. However, it’s good to check in every so often to ensure you still understand them in the same way, and that they remain the top 3 priorities today.
Then, determine how to utilize the data, database, or processes to better support those priorities. For example, if total dollars raised toward a certain initiative is a priority, what data, dashboards, or reports are needed to tell the story that the team will meet that target? If you already have something in place, take it a step further.
Rather than simply showing the dollars raised toward the goal, provide the amount still needed to raise, identify opportunities likely to close within the timeframe, and help pinpoint where the gaps lie. This is moving from a reactive operations professional to a proactive operations professional, and leaders need team members who are proactive.
TWO: What story are you trying to tell about our fundraising progress?
Often, there is a lot to unpack with data and sharing the narrative regarding fundraising progress. Providing only lots of statistics, dashboards, or reports can often be overwhelming to comprehend. Rather, ask what your leader is trying to convey to others, and find the data to support that story. Give the leader bullet points to support the dashboards or reports you are sharing.
For example, if your leader is trying to share how the team made an active effort to obtain more recurring donors, help the leader tell that story. How many recurring donors did you have each year over the past 5 years? How many are you trying to get this year, and where are you at toward that target? Tip: Do not only pull by the Recurring Gift type, as the data integrity may not be there. Rather, do an additional pull of all donors and the number of gifts each donor has made per month. Then, if you have recurring monthly donors who have given throughout all the months so far this year, they are considered recurring donors. This typically finds additional recurring donors, such as those from your employee payroll.
Then, be proactive, analyze, and share insights on the data you provide to help the leader tell the story they want to tell. If you notice a significant increase in recurring donors 3 years ago, but then a drop in the next 2 years, examine the data from 3 years ago. Perhaps you were in a capital campaign or had a huge employee giving push? Either way, provide the leader with bullet points to support the statistics they are reviewing. Then they take it from there to tell the story, and when they do tell the story, listen.
Listen to:
How did they tell the story?
What data points are they weaving into the story?
What narrative did they include that is not shown in the data?
As you listen, learn how to improve next time with providing bullet points to the leader. This will help you move toward becoming a proactive operations professional, which leaders find valuable and need on their teams.
THREE: What keeps you up at 3 am?
This is one of my favorite questions to ask, as anytime I hear it’s related to the data, database, or operations, I lean in to listen extra carefully. In data and ops, we are best positioned to be the solution maker as the data, database, and operations touch all aspects of fundraising efforts. Listen closely and take note of how you can help fix these things. Don’t let our area be the thing that’s keeping the leader up at 3 am.
Take Action
Now take action. Take the following three steps to ask leading questions to your leader.
1 ➡ Take note of the 3 questions above and start asking them. You don’t have to ask all 3 at once. Find the appropriate moment and start with one.
2 ➡ Ensure you do the follow-up. Ask the question and then be the person who can solve it.
3 ➡ Don’t let being overwhelmed, behind, or bottlenecked in work tasks stop you. If you need help with the load, figure out what you need to push through it, and ask the leader for it.
👋 See you next time,
Jenny
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