#085 Trust Nothing, Question Everything
March 6, 2026 | Read Time: 6 minutes | Written by Jenny Kleintop
I know a heavy topic for a Friday, but stay with me. I woke up in the middle of the night, and this phrase popped into my head, trust nothing, question everything. I’m working as a system lead to bring 8 foundations into one fundraising database. We’ve been at it for a year and are close to the finish line.
Bringing together 8 separate databases into one is not just about the database. You know me, I say this all the time, Philanthropy Operations is not just about the database. When you are bringing together 8 different databases, you are bringing together 8 different teams, 8 different philosophies, 8 different ways of doing business. It goes well beyond the database - people, processes, and change management.
This leader had the people under her to tell her this. As a leader, she listened. Hence why I am there. Clicking the button to merge the databases together is one step. Yes, a big step, but one step. It’s all the planning, preparation, and activities that happen before that will lead to a successful database of ONE implementation.
Database migrations is not the focus for today’s Insights, but hopefully the backstory gives you some insight into my train of thought to trust nothing and question everything. That is hard for most, especially those of us in Philanthropy Operations. We spend days, months, years pouring into our databases to update, regulate, and fine-tune, right? Then you have some outsider come in and question what feels like everything. Your way of thinking, your way of doing things, and all those years that led up to today.
All those years have not been wasted. You did what you had to do in the moment. You learned, you implemented, you did. It wasn’t a waste of time. It all led to today. Rather than seeing the question as “I don’t know what I’m doing”, reframe it. See it as an opportunity to build upon what you’ve done, to adjust to today’s best practices, and get that support you’ve long waited for. I learned a long time ago that things change. Tech changes, people change, leaders change, needs change. It’s perfectly okay and necessary to adjust, evolve, and learn new ways.
I say trust nothing, question everything, as someone nudging you to say just because we’ve always done it that way doesn’t mean we have to keep doing it that way.
Let me give you an example. Number of constituents. The question I was asked: Can you help me think through how, in the new database, I would pull the number of new constituent records added MTD or YTD by each location? Meaning, with 8 separate databases, she can get separate counts now, but when we're in one database, how will she know how many records were added for each location?
My first response was to see how she would respond. While preparing the databases for migration with the teams, I’m also building future leaders. I’ve always believed you don’t need a title to lead, and in philanthropy operations you have to get comfortable asking questions, even to your leader. My response: Yes, happy to. The first larger question is why? Why are we pulling these stats? What story is it telling? Who is looking at them? What next step does this help them take?
After she responded: "I know it isn’t a good reason for continuing to do things…because we’ve always done it.” Then she went into detail on how she is asked for these numbers and how she reports them. I knew it was safe to take her to the next level.
My next response: Thanks for elaborating. The short answer is you will still be able to pull it, whether it’s by cons code or attribute. We’ll touch on this during our call next week. Although if you are using date added, they will all revert to the date they migrated into the new database.
The long answer is I don’t expect you to have all the answers. The takeaway is we need to be asking these types of questions if we are going to get to a place of operating as ONE. It’s an example of us helping our leaders and teams tell better stories and utilize the data more effectively. Today is not the right time to have this exact conversation. We should roll it into overall reporting/dashboard/metrics conversations. Some smaller conversations have happened and others are in motion, but we’ll swing back around to the larger discussion down the road. The teams are not ready yet.
For example, the board doesn’t care about how many new constituents we added. The board cares about how much money we are raising. What will help us raise more money? Not more “new constituents”, but who are those new constituents and how are we working to close more and larger gifts?
Here are 7 other stats I can think of off the top of my head over new constituents:
How many new donors? How many dollars came in from those new donors?
How many new recurring or sustaining donors? How many dollars came in from them?
How many upgrades, downgrades, renewals, lapsed, and lost donors did we have?
How many new referrals? How many turned into engaging with us? How many turned into donors?
How many new prospects? How many turned into gifts closed?
How many new names did annual giving pursue? Did that increase our dollars?
How many new names were given to mid-level, to major, and to principal pipelines?
With all those 7 stats, what’s our strategy to retain and/or upgrade them? Plus, with all those, we don’t need a code to get the data. We can get at it from other areas on the record.
I do agree it helps you to have and report the number of new constituents, not just from a gift processing perspective, but from a gifts and constituent data management perspective. However, not necessarily by location but as ONE entity working together. If we say # of new records by location, that doesn’t give an apples-to-apples story. One location adds thousands of records to the database, while some of the other sites add only hundreds. We know they are smaller, and do we really want to remind them that they are smaller? That’s a constant reminder that doesn’t sit well from their perspective. Plus, what happens when we have cross-over names? For example, a gift goes to one location, and they are already in our database from another location. They were not added to the database, but they are new to that location. How do we report that?
And if we say we added 8,986 new records to the database, that doesn’t necessarily mean much. But if we take it a step further and say of those 9K, X turned into donors, X attended our events, X, we are pursuing a 1-1 relationship via prospecting efforts, etc., that carries more meaning.
Okay, that’s it for now… stepping off my soapbox. All this to say, that is my stream of thoughts to include along with your thoughts. This way, when the time is right, and we have this conversation, we can remind ourselves what in the world we talked about all those months ago. In the short term, yes, you’ll be able to pull the same stats. That works for today, and where we will be for this year. Next year, we graduate to the next level, to help us meaningfully grow together as ONE.
All this to say, when you have an opportunity like migrating to a new database or launching a certain project or implementing a new feature, or feel like today’s the day, trust nothing you’ve “always done” and question everything about how you can do it the best way.
Take Action
You don’t necessarily need a big migration or project to practice this. Rather start small and follow these 3 steps:
1 ➡ Take a step back and become an observer. Like you are starting new. Remember that feeling, the newness, the uncomfortableness of starting fresh? Sometimes when we’ve been at a place for a long time, it’s time to take a step back and look at the bigger picture. It’s okay to change. It’s okay to learn, evolve, and lean into new ways of doing things.
2 ➡ If you are not able to do #1 yourself, bring in someone who can. Whether it’s a team member from another area, someone new to your fundraising office, or outside support. To keep growing fundraising results in exponential ways, it’s important.
3 ➡ Find 3 tools, processes, or reports. Question their current use and lead with why. Why are we using or doing this? What story is it telling? Who is using it or looking at them? What next step does this help them take?
Trust nothing, question everything.
You’ve got this!
👋 See you next time,
Jenny
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