Episode 227: The Psychology of Timing - When to Make the Ask and How to Know
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 Hallett Philanthropy, Randall Hallett.
I'm always humbled when you and or anyone takes a moment of their time to join me. Randall, on in particular this edition of around with Randall. Timing is important in the relationship building, donor engagement, donor movement process. Well, we're going to delve into today is the timing that's required to ask solicit at the right time, get into some pretty nuanced thoughts as to how you can better understand when is the right time, and maybe when it's not.
In previous episodes, we've talked about the importance when we are developing the relationship, making the ask around impact. That's episode 199. You can go back and listen to that and how to connect it to what's actually trying to be accomplished. Not going to spend a lot of time on that today. We're also going to avoid, because we've covered it in episode 2 or 4, about really knowing our donors and the passion that they should have to maximize gifts.
That's episode two of four. Will. You can go back and listen to that. Today is really about exploring the psychological, the emotional, the strategic indicators that reveal if a donors actually ready for an ask for solicitation for a major gift, ask and how we kind of evaluate that. So a high-level premise and all of this process is, is that I'm not talking about $100, to be candid.
I really believe there's no bad time to ask for $100, because basically it's going to be an email, a letter, maybe a phone call, and you just need to ask. I'm not saying don't have some small talk or be respectful, but at the end of the day, somebody's giving you $120 is just going to happen or it's not what we're talking about are the elevated gift opportunities, major gifts.
And I also want to stipulate here at the top, as I try to do often, that I don't classify major gifts as cash. Major gifts are a gift above a certain dollar figure that can include cash, pledges, stock, and most importantly, estate and plan giving options. I never have seen that as a separate category. It's part of the major gift portfolio or options that a donor has to maximize their giving.
So as we think about this, we want to delve into and ask the questions. Is it the right time? Should I wait? How do I recover? So let's get into the psychology. Kind of the high level stuff we start with and we'll get into the tactical. Why are we talking about this? Well, there's an emotional component. If done well, I'm getting a high enough gift level behind making a gift.
Particularly as we talk about transformational giving, which I can give you a whole series of episodes to go back and listen to, because if we're doing this correctly, we're elevating the connection that we have with our donors, with our prospects to elevate their gift, thought process. And transformational isn't a dollar figure. It's where that emotional core match is what they're trying to do.
That brings about the highest level of gift or series of gifts that might be possible when we maximize this conversation. To get to that ask, there probably four things I think about that we need to ensure. Number one is, is that donors feel that they're seen, i.e. that their values and their interests are clearly understood. You can't get to maximization unless their values and interests are recognized.
I think about being raised as a kid by my mom and dad, and how particular my mother and how important she said it was to always realize the emotional kind of place, the values and the interest somebody has in a particular moment. And it led me to better understand now what I teach my children, that people will forget what you say, but they'll never forget how you made them feel.
And this is important in the asking process. If people don't feel as if you are actually interested in them, their needs, their interests, their may give you a gift, but it's not going to maximize. So the psychology behind getting to that ask point starts with seeing. The second is safe. Do they trust the organization and do they trust the gift officer.
I'm going to hold off on this trust piece for just a minute. We're going to circle back to it and connect you to something else that might be helpful in developing that trust at a much higher level. Number three is, is that it needs to be significant significance. As we look at our four S's here isn't about the dollar figure as much back to that concept of is it meaningful?
Is it impacts people with resources who want to be philanthropic, don't make major gifts unless there's impact. Back to that episode. 199 and the last is secure of the four S's. So seem safe. Significant final want to secure are all of the financial ramifications clearly understood? If someone's making an incredibly large gift? And this is why I include planned giving in the major gift platform is particularly when it comes to plain giving.
They have to feel that the gift coming out of their life isn't going to affect negatively their life. There's an emotional psychological connection to this. So if you're not ensuring and this is why I think plain giving was something I naturally came to. Certainly going to law school and studying a lot of estate tax issues was part of that.
But from a kind of a relationship development process, I was always more interested in making sure they felt more comfortable about the gifts, particularly at the higher levels. Million, 10 million more, because if they felt comfortable making the gift financially, the gift came much more quickly, much more easily. But it wasn't about what I needed. It was based upon what their situation was.
So trying to make sure they knew I was on their side as well. So the four things, the four S's that donors need to feel, they need to feel seen, safe, significant and secure. All this is to lead that lead to the psychological well, I think of as a readiness pyramid that when we think about our ability to have donors ready for that ask, it's based on a pyramid.
So a triangle. And then at the bottom of that pyramid starts with trust. My daughter's doing a project at school, and she comes home every day. And at dinner we sit and chat and talk about the fact they're trying to build a pyramid, some kind of structure. I haven't even seen it. She talks about it every night, and if they're trying to be the tallest one and to hold weight.
And I finally looked at her and I said, you know, sweetheart, that if the base is the biggest, the most stable, everything else builds from that. And the next night she came back and she said, we changed our base. I went, well, that's good. That's what we're talking about here. If your base of the relationship, the psychology to get to that, ask isn't based on trust, you're not going to get to a gift, let alone ask.
Above trust comes the idea of alignment. We're going to talk about this here in a moment in the tactical about two ways to look at alignment, not just the alignment with the donor, but alignment with the organization. Are you ready? We're going to break this apart here in the tactical in about a minute and a half. The third is readiness.
The top of the pyramid is readiness. And that's what we're here to talk about today, because you can't be ready to ask. You can't have them ready to be asked unless you have built alignment on top of trust. If you're looking for ways of starting at the bottom and building up this pyramid with trust, you can go back and listen to episode 214, where I spend an immense amount of time of the things that are required in the trust building process with donors.
So this is our theoretical that there's an emotional component, that it's not transactional, that particularly as we get more complicated assets, the donor has to feel those things that are seen safe, significant and secure, and that we're building the relationship based upon the idea of trust at the bottom. Then do alignment and at the top readiness. Which brings us to our tactical.
How do we know for ready to ask? I look at these in three dimensions. This is your tactical. And I think there are eight questions we have to ask ourselves and be honest about to know that we actually are ready to ask for eight transformational major give principle gift. Large gift. Opportunity. So the first dimension is the rational readiness part of someone's thought process, the donor thought process in terms of their readiness.
Here are the three questions. Have they shared personal or emotional connection to the mission, to the purpose, to the impact? This is all the way back to episode 2 or 4 and passion. I didn't think about when I laid these out, and I try to work ahead a little bit the connections in these podcasts, but if you don't have passion, we're not figuring out what they want, which we talk about an episode 2 or 4, then how are we going to maximize gift?
So have they shared their personal emotional connection? Number two, did they respond to an invitation and follow up somewhat proactively, or are they being drug into this? There's an enormous difference from someone showing up on their own, and they're wanting to engage versus you dragging them and you're throwing that proposal for them. We really got to have you.
We're going to talk here and probably about five minutes about what happens when you don't have a yes to all eight of these questions. So are they responding and initiating proactively some type of engagement. Number three, have they referenced their future involvement or deeper engagement. Do they understand what it will mean for them personally? They're indicators that we can know to answer these three questions.
Do they tell stories about how they're connected? Grateful patients talk about the health care, the you know, oh my gosh, this physician or this nurse or this care tech, did this business or was in the hospital. Alumni do it from the perspective of maybe an experience when they were on campus many years before, or somebody who made a big difference.
Do they tell stories? Number two, do they use you ownership language? Do they include themselves? We're trying to accomplish something that's different than, well, you're trying to do it because they're not now on board. And it may seem like a simple difference in pronoun, but it's a completely difference in perspective. Do they include themselves as part of the solution, the outcome, the impact?
The answer to the question? Number three do they ask incredibly good, detailed questions about the work that's going on and the impact? Are they inquisitive or are they just you're going to do great things. That's great. That means that they're not they're not engaged. So do they tell stories? Do they use themselves as a part of the solution?
Do they ask good questions? There are also red flags that come from this dimension in terms of rational readiness is are they guarded? Are they only focused on recognition, which we've talked about before isn't the worst thing in the world. But that's not where we're gonna get the highest level gifts. And was there something significant life change? There's the old adage, you shouldn't change 1 or 2 major things in any one time.
Making a $5 million gift for someone who has $10 million shortly after a retirement or loss of a significant loved one, or something of that nature. That's one too many. So those are some red flags or things to think about. So the first is, is rational readiness them. The second is institutional readiness us. And here we start talking about whether or not the organization not just use the gift officer maybe, or the CEO, the organizations.
Right. So the first thing is, does it align with a clear priority that the organization is trying to accomplish? Does the donor's interest match up? I have a client that I'm working with where this is an enormous problem. We were testing out options for them to raise more money, and they keep saying, but we need this. And I'm like, yeah, but your donors don't want to give to that.
And then they say, but we need more money. And it's just like a bad circle. And I and I'm, I'm not angered. I'm frustrated not with them, but on their behalf. They need the money, but we have to reposition it. So when you think about individualizing this as an individual donor asking the questions, are you ready to ask, do the two line up?
Number two are they're in internal champions aligned. So this could be people that have to use the money, particularly on larger gifts. Now if it's a party campaign and obviously that's probably more clearly defined. But if you're creating an endowment, a chair or something of that nature, are all the internal people ready to use that money when it's available?
There's nothing worse than being looking at a donor and saying, okay, we got your money. We haven't done anything with it. And believe it or not, have a client who are dealing with that where they've accepted a gift like three years ago, and it's not $50 and they haven't spent the money, and there's a million reasons why the donors finally saying, I don't really care anymore.
They weren't ready to ask because they weren't ready to spend. The third question is, is the stewardship team ready to deliver what's promised now that stewardship team shouldn't be just aligned to the fundraising office, or to the organization's foundation or office, or the development? That's a part of the previous question. Stewardship is not just about communication and recognition, it's about usage.
And so are you. Aligning the internal readiness. If you can't answer all three correctly, the answer is you're not ready to ask because you're not doing something. You're not ready. You're either not aligning its priorities or you're still disconnect. Number two is, is that the internal champions, people using it aren't ready to use it. And number three, stewardship teams are not ready.
So you can see some of these red flags if you get these answers. The third dimension that we were talking about here in terms of the eight questions, is really just two questions. And this is the external personal timing series of issues to be concerned about or be aware of. Is there something that's a time frame? You have to be incredibly aware of your end bonuses, liquidity of an event, selling of a house, but you don't as an organization may not get to control when that is, which means you may have to speed up one and two in the dimensions.
The rational readiness by making sure that they're ready. And number two, more importantly, what you're doing internally, which you have more control over, because if they're going to sell a business and this is part of that process, or they reduce their capital gains, they are not going to hold it up on you because they may lose that sale.
So you got to get everybody aligned in terms of timing. The second thing is what I would call transitions. Is there a natural transition coming for the donor or their family from retirement to we mentioned a sale. Maybe there's an inheritance coming. Maybe there's a child's graduation, maybe there's a terminal illness and they're trying to get things settled.
This is to say that there is some emotional context to these two questions. Is there something that's time oriented to that, to the calendar and or to their life? Number two, because these events may cause urgency. Eight questions you have to ask. Just a quick review. Are they sharing their connection? Do they respond to invitations on their own?
Are they engaged? Are they doing so affirmatively? And number two is they reference their future as a part of this deeper engagement. Do they do they see that we're doing something? Number two is the internal. It's the internal people spending the money and all the things that go along with that. Number two is the alignment with the internal leadership.
Dean of a law school or program leader. How are we going to make sure that they know the value and we're ready to use that money effectively? And number three is stewardship more formally with naming opportunities, things of a nature, but includes a lot of different things. The third dimension, external timing, calendar or personal data. Make sure if you can't answer all eight of those questions, to be candid, you're probably not meant to ask for that large transformational gift that I complicated.
Questions. Well, there are things we don't talk about. We're into the weeds of how to get to those major transformational gifts. I do want to spend one second talking about holding in ask because there's a chance you ask these questions. And two of the eight maybe not positive, you can reformulate all of this. Before we explore this gift, I want to make sure I best understand what you want most.
That's handling maybe an issue with the relational.
We're working internally to make sure we maximize your desires, wishes, and dreams. Can we have a month to get it all organized so you feel great about it? How important is the timing issue? Sale of company? Something else that we're working with so that I make sure I align this correctly. Remember you can say things like, you know, it's important to rush, but it's more important to get it right.
This is such an important moment for you. You've expressed such interest in all of this. I want to ensure that this is one of the great feelings, emotions, experiences that you'll go through outside of your family. You want to respect them. And in doing so, what you get is an all this connection. It's the that were the Sherpa this term I use for relationship match lots different analogies or metaphors.
The point is, is we got to bring lots of things together. Today I wanted to get into just the absolute nuances of when to ask, how to know when to ask, and maybe a little bit about when it's not ready to ask what you can do to maximize and ask at some near future point. Getting it right is better than getting it fast.
And all too often our metrics are incentive based compensation. Other things really speak more toward doing it quickly rather than right. And what I'm advocating is doing it correctly, slowing down, getting seven answers to your questions because it's not a milestone. Asking is not a milestone. It's a moment. Moment based on trust. And it's something your our organizations need.
And at the end of the day, maybe something you can consider is going through your portfolio, hopefully smaller other episodes of the podcast and find your top ten donors and say, have I got all these answers? Any questions? And if I don't, how do I pause effectively to get to the answer being yes and every case, that's how you're going to maximize gifts.
That's how you're going to create more transformational giving opportunities. That's going to make a difference for your organization. And the donor, and also for you. Don't forget to check out the blogs at Hallett Philanthropy two a week. I write all kinds of things. I find it fun. In fact, I tend to write too much because I think there's a lot to be said about leadership, about experiences in life, how they how they may help others kind of look at life in a more meaningful way.
Check them out@philanthropy.com, blogs 92nd rate. The other thing is you want to email me it's podcast to help find to be.com. We are feeling like we're maybe on an airplane bouncing around a little bit at about 33,000ft up down every day. Sometimes our to our, our nonprofits are trying to figure out financial issues or trying to figure out impact issues or trying to figure out strategic issues.
And wherever you are in the organization, whether you're the CEO, your gift officer, your board member, you're a staff member, whatever. We're bouncing along. The reason I use that analogy is, is that I want you to know how important it is, what you're doing. The bouncing is not going to stop. I hope it gets a less, but it's not going to.
We're going to have a lot of questions over the next 5 to 10 years. We're going to have solved philanthropy and nonprofits serve that gap. I always talk about between free enterprise, which some things they don't want to do because it's not profit possible. And government, which is not always the most efficient philanthropy nonprofits, fits the middle. We take care of people and things that are really important, that are really struggling.
Some people make things happen. Some people watch things happen. Then there are those who wondered what happened, where people who look for others like ourselves, who are people who make things happen to take care of, to deal with, to work with, to help those people and organizations and things in our community that are wondering what happened. It's a great way to spend a life, make an impact.
I hope you can enjoy a moment or two today and every day to know how important you are to that process. I look forward to seeing you the next time, right back here on the next edition of Run with Randall. And don't forget, make it a great day.