Episode 216: To Automate and/or Individualize Stewardship - Maximum Output with Outside Assistance
Welcome to another edition of Around with Randall, your weekly podcast for making your nonprofit more effective for your community.
And here is your host, the CEO and founder of Halette Philanthropy, Randall Hallett.
It's an honor to have you join me, Randall, on this edition of Around with Randall. We want to jump into something a little bit more technical today when it comes to philanthropy—covering everything from the donor management process to finance, gift officers, leadership, and strategy. This is all about figuring out the give and take, the yin and yang of personalization versus automation of stewardship.
Why am I talking about this? Because it's come up a couple of different times in the last 60 to 90 days. In various ways, it's kind of interesting how subjects seem to percolate when you pay a little bit of attention. One example is the listserv that I'm on—several, actually—where discussions have emerged about how to steward people, with recommendations, thoughts, and questions from different nonprofits around the United States. Then there's a personal friend who has taken a new job and is learning the rhythm and process of philanthropy in a larger organization. She realized that there are sub-parts within the organization, each with its own development operations or processes. A conversation arose about closing a campaign or mini-campaign within a certain part of the organization. The question was: How often do we steward? Someone suggested stewarding all campaign donors seven different times. But when asked how to do that and what it should look like, nobody had a clear answer.
I've also had a client recently begin talking about a campaign with concerns about whether they were prepared, as they may not have been stewarding their donors effectively. All of this highlights the ongoing push-and-pull, cost-benefit analysis of stewardship.
So let me start at the top with a reminder—why is stewardship so important? If you pay attention to this industry, you know that the largest gifts, which come from the top 5% of donors who provide 95% of the dollars, are rarely first-time gifts. They are typically second, third, or fourth-time gifts. This makes stewardship essential because if we want to elevate those donors, we need to build deeper, more meaningful relationships. My dear friend Nathan Chappelle calls this the "radical connection" in his book, which ties into the current state of philanthropy, sometimes referred to as a "generosity crisis."
But what about the other 95% of donors? How do we determine which of them have the potential to become major donors in the future, perhaps in two or three years, if stewarded correctly? Who among them will rise into higher-level conversations? We want to steward everyone, but the challenge is that personalized stewardship is time-consuming, requiring more hands-on efforts compared to broader communication strategies.
This brings us back to my friend managing a large organization's philanthropy through many smaller parts. Should everyone receive the same seven touches? How do we determine who gets what level of stewardship? There’s a wealth of information out there about stewardship’s importance, but not enough detailed discussion about what needs to be done practically. My goal today is to provide some tactical thoughts that you can apply, as I strive to do in every episode of Around with Randall.
Let's begin by defining personalization. When someone makes a gift, we want to tell them how their gift was used, why it was important, and what value it had. The more specific we can be, the better. For example, if their gift was restricted for a particular purpose, we should communicate that: "Your donation was used for X. The outcome of X was this. You played a vital role in making that happen."
On the other hand, what happens when we either over-personalize or don’t personalize at all? A lack of personalization results in generic stewardship, which can feel impersonal. For example, my wife often feels that some of our philanthropic efforts are met with generic thank-you emails that don’t acknowledge our interests. Let’s say I give to a law school, but the thank-you and stewardship come from the broader university, which I don’t have a strong connection to. That’s ineffective stewardship. Instead, organizations should connect stewardship to the donor’s specific interests.
Over-personalization can also be problematic. If too much time is spent on detailed personalization for every donor, it can become inefficient, leading to mistakes and unclear priorities. The goal is to elevate the right donors to higher levels of giving while providing general information to all donors so they understand how their contributions are being used.
When thinking about automation, we must balance efficiency with personalization. The benefit of automation is scalability, speed, and efficiency. However, the risk is that stewardship becomes too generic if not executed properly. Returning to the university example—if all stewardship efforts are at the university level rather than the specific school or program the donor supported, the donor may feel disconnected.
The key is finding a balance. Not every organization has the same resources. A three-person fundraising team will have different scalability options than an academic medical center with extensive staff and resources. Attending large conferences can be enlightening, but smaller teams may find it unrealistic to implement the same strategies as large organizations. What’s important is building a stewardship plan that is both strategic and achievable.
The purpose of personalization is not just to provide information but to elevate donors. Fundraising is about generating philanthropic revenue to drive the organization’s mission. Understanding which donors have the potential to give more is crucial. This is where data and prospect management come into play. Organizations should screen donors and analyze the results. Good donor screening doesn’t provide definitive answers but offers direction—helping identify donors who may have the capacity to give more.
For example, if a donor gives $500 but has the potential to give $25,000, or if a donor’s overall philanthropic history suggests they could contribute significantly more, that’s a donor worth elevating into more personalized stewardship efforts. Tools like artificial intelligence (AI) can assist with this. My friend Nathan Chappelle’s DonorSearch AI, for example, can analyze donor data and generate lists of prospects with higher giving potential.
However, even smaller teams can implement a basic version of this. A two- or three-person shop can use spreadsheets to sort donors by past giving and potential giving capacity. Identifying these prospects quickly allows organizations to focus stewardship efforts where they matter most.
Once donors are categorized, the next step is determining what to do with them. Here’s where tactical planning comes in. If you’re building an individualized stewardship plan, start by selecting a manageable number of donors—perhaps 25 to 50—and develop customized cultivation plans for them. Because in reality, stewardship is cultivation.
I talk about that in the trainings and when I’m working with gift officers, but stewardship and an individual plan are about individual communication and connection—bringing people in for tours, getting them to meet the CEO or someone important in this process, having a couple of cups of coffee with them, talking about why they made this gift, really honing in on the "why" and less about the dollar figure. Telling them the story of what their gifts did—that's one-on-one or small-group stewardship. It’s time-intensive, so if you're a small shop, you pick 25 to 50 donors. Do a little research—take all the gifts over the last three months, compare what they gave versus a screening, and pull that number out in Excel. By adding and subtracting quickly, you can see the differential between what they can give versus what they actually gave. The larger that gap, the more individualized the opportunity.
If we can figure out if they’re connected, remember—the connection piece is more important than the monetary piece. But we need to do some science to take it down to a number we can work with. I have a sheet I use with clients that serves as a planning device for individual stewardship opportunities. You can use something like that to create a plan, which, by the way, becomes a subset of your annual plan—your prospect management plan. You're planning how many meetings you can have, a portion of which may lead to a second gift the following year. So if they gave $500 this year, you’re going to increase stewardship because they have significant potential—they might give $2,500 next year, then $25,000, and eventually an estate gift. That’s part of your planning process if you’re a gift officer, managing donors, prospecting, or handling data. You’re helping gift officers focus on the right people—the ones who can give more and are already engaged. We need to figure out why they are giving and build on that.
That is the individual stewardship process, and there are countless ways to execute it—tours, meetings, coffees, meet-the-professionals events, opportunities to see and experience the organization firsthand. There are all kinds of ways to individualize a stewardship plan. The greater conversation is about the tactical side—what should be automated. Let’s say you have 1,000 donors, and you've elevated 25 to 50. That leaves you with 950 to 975 donors you still need to steward. If you're a small staff of two or three, it feels impossible to reach all of them. It’s a proportional issue—the more donors you have, the larger the organization, but the same general problem exists. That leads us to automation.
Over the last 10 to 15 years, technology has allowed us to engage much more effectively with donors through automation. Sometimes, we need a third party to help with this process, which we’ll discuss at the end. What we do know is that automation helps with the basics—thank-you letters, thank-you emails—these things can be easily automated in CRMs. I’m always amazed when I audit organizations and see people doing tasks manually that could be automated. People are our most valuable asset, so we should be taking tasks off their plate that can be automated, allowing them to focus on higher-value activities.
Thank-you letters and emails are simple to automate. You can set up CRM reports to handle data analysis—it’s not complicated. This kind of automation shortens response time, increases consistency, and reduces human error. It also allows you to sort donors strategically. For example, if you have 25 different gift accounts tracking where donors give, automation can ensure that people receive thank-you letters specific to the purpose of their gift. If you use a standardized thank-you letter with tax information (which is required for gifts over $250), you can also send a second letter based on the gift area. If they donated a certain amount, another report can trigger a follow-up phone call from a volunteer or staff member, ensuring the donor feels appreciated without necessarily elevating them into an individualized stewardship plan.
The next step is creating a calendar—a schedule for donor engagement. Donor anniversaries are often overlooked, but they’re a crucial stewardship tool. Reminding donors of their gift anniversaries instead of lumping everyone together in generic messaging is key. Automation makes this easy—sending emails or physical mail on their gift anniversary or incorporating other personal touches like birthdays or long-term donor recognition. Identifying patterns in donor behavior allows you to automate messaging in a meaningful way.
Events are another opportunity for automation. If donors have attended events, find ways to follow up with them. If they attended because someone else purchased a table, determine if they have a further connection to your organization beyond that event. The goal is to make data meaningful—are we thanking them effectively? Are we reaching out again? Are we personalizing communication based on their level of engagement? Maybe the CEO sends an automated email to all donors who gave over $5,000—that’s a second or third touchpoint that enhances stewardship.
All of this leads to donor recognition, an area where simple automation is often underutilized. Some organizations do this well—about three months before the annual report is published, they send an email saying, "Hey, you may have made a gift last year. Please check the list to confirm your placement in the correct giving category." You might think this is unnecessary, but even high-level donors—those giving $5,000 or $10,000—care about their recognition. They check to see if they are in the right category, and sometimes they realize they forgot to give and make a gift to ensure they are included.
Recognition can be elevated beyond the annual report—through plaques, naming opportunities, or acknowledgments in programs. Another overlooked opportunity is social media. While not my expertise, I’ve seen how a well-placed post thanking a donor—even one who gave $5,000—can significantly boost engagement. That donor may feel more connected and, in time, increase their giving to $5 million. Strategic donor recognition plays a crucial role in growing relationships.
As we analyze our donor base, we must determine which donations should be elevated. Out of our group of 950, maybe 20 donors are prime candidates for special recognition. Over the next year, their stewardship can be automated—expressing gratitude in meaningful ways while ensuring that higher-touch engagement is reserved for key prospects.
Ultimately, all of this leads to a larger conversation: How do we maintain relationships effectively? Automation is a crucial piece of that puzzle, and yet it’s often overlooked.
Most often are volunteers now they're human capital human assets great job but if you have people that you can come in and just do thank you calls or just do outreach calls I've got a number of clients that I'm always just pleased and an an odd by they've got one or two or three volunteers that all they do is come in for a couple hours a week and just make calls and say thank you. I'm a part of the organization I work with CEO chief Roman officer we're just calling to say thank you for your amazing gift that's an automated process with using some human capital.
One of the neat things I did many years ago when I worked at the St Ed St Thomas Academy in Mendoza Heights Minnesota Catholic military all-male college prep institution loved working there is we started a thank you night campaign every every semester a week each semester multiple nights the kids and I've talked about this from a stewardship perspective and other podcasts that originated from when my dad got a phone call from an Nebraska football player thanking him and my mother for being donors. He talked about it for years turned up it started quarterback point was is that you can automate some things with personnel what we tend to figure out is is that we probably when we look at this needs some help.
So I'm going to give you some examples or places you can go look. I'm not going to singly endorse any of them to think that's unfair I may not have all the details and I certainly haven't worked specifically with them but I've heard of these organizations through my clients and friends and colleagues who are having good luck. They're outsourced there's a cost to them but the cost I'm finding out is minimal in terms of what they can deliver.
So let me give you some categories. Email marketing i.e. what are we doing to get the email into people's inbox you probably know some of these but MailChimp constant contact HubSpot are all ones that are used. If you work in healthcare in particular HIPAA is an important component of making this decision to making sure they're KIPAA compliant. If you want to chat you can email me at podcastedhealthlinthweep.com I'm glad to talk about this for hours but the HIPAA compliance piece you want to check for everybody else it's pretty clean you can use any one of them and constantly be sending when you have emails updates segmented in different ways different messaging depending how much you want to play with it but using a tool to send all that information so you don't have to do it yourself.
Video messaging I think is critically important. I'm going to give you two to maybe just play with or google to check thank you so that's thank vi e w is one that I hear a lot another one is bomb bomb and what this is is a way that you can record messaging and send them out three emails. I was touched by this one in particular in late November early December with a gift that we made and I got a very quick 45 second video from the head of philanthropy from the organization we made the gift from that I'm sure took her about a minute to do but I watched it a couple times I was like that's that's outreach that stewardship you got my attention.
Give you another one so that could be just reviewing but there's a platform so you very simple to do. Another one is I get a interestingly a sung birthday message around the first of the month in my birthday month from another organization that we give to. Now I'm not sure the voices are all that great but I appreciate the effort but they're sending out to anybody they have the birthday of in that particular month it's not individualized again another great way to use video mass segmentation to masses that's not individualized great way to appreciate people.
Same is true of the holidays via religious organization or Easter or other things that you might be connected to what a great way of messaging people do you want them to know you care about them because you generally do just do not have people in time to do it all.
Another one is social media management and this is not my expertise but I have been watching the growth of individualized messaging as well as group messaging or telling the story through places like Hoot Suite that's HOOT Suite S U I T E and Buffer. They offer a couple platforms again I'm not endorsing any of them but that can help you automate a lot of messaging in a really interesting way.
The other place I would recommend is doing a deep dive into your CRM whether it sales force razor's edge bloom bloom meringue or donor perfect whatever many of them have tools to help with at least some basic standardization as well as a little bit of automation when it comes to processing. All of those things can help you figure out how to do more with what you're trying to accomplish.
It's a balancing act just remember that when we think about the tactical takeaways is is that automation is not a replacement for stewardship and personal relationship building it's a tool to do more of it with less resources but it's not going to replace the top couple people again depending on your size and your pipeline and needs who are the people you need to build the individual pull those people out first do that automation doesn't replace that.
But what automation can do is get you better communication with the masses who you don't have as much resources or time to spend time really working with. The second thing is is that when you create these automations it actually is all about size and scale. You can't try to do everything hit the things that work best for you.
If you happen to use a third party like we talked about one one of these particular recommendations and we're really just mentionings like the video messaging of thank you or bomb bomb you have to choose the things that you have value for that you have money for that actually you can use. There's nothing worse than working with a third party and then not doing anything with it.
Remember when we talk about automation we talk about stewardship we talk about individualized personalized relationships it doesn't make a difference donors don't want to feel like numbers they don't want to be forgotten they want to be appreciated appropriately for what you do and so you have to find the right balance. It's an up and down figure it out but the more you do the better off you are as long as it's the most important word you take from this podcast genuine.
Automation can be genuine individualization can be should be and has to be genuine. When you do it in the right way sizable and scalable you can do both and put some resources behind it to maximize its impact.
The tactical call to action don't just overlook it talk about it strategize about it build a plan for it build a three year plan that every year you do a little bit more start small and build what you'll find is donor stick around longer they'll elevate their gifts and they'll make a bigger difference in your organization.
Don't forget to check out the blogs at Hallettphilanthropy.com. Two a week rss feed right to you if you'd like and if you'd like to email that's podcasted helifelanthropy.com.
As we move into 2025 I think there's some interesting things that may happen in the world and that philanthropy may play a bigger role in the various sectors that we all work in education climate the health care social service all kinds of places. But philanthropy fills a gap. That gap between the commercialization free enterprise where there's not a profit and government which is inefficient.
That middle ground is what we do. Don't forget my all-time favorite saying: Some people make things happen, some people watch things happen, then there are those who wondered what happened. We’re people who make things happen you're someone who makes them these things happen for the person's people places that are wondering what happened and there's no better way to spend a career than working to make the world a better place.
I'll look forward to seeing you the next time right back here in the next edition of Around with Randall. Don't forget make it a great day.