Email Writing Quick Wins to Raise More Money in December

Vanessa Chase Lockshin will share her email writing and storytelling tips that helped one of her clients raise more than $190k in September 2020.

Full Transcript:

Steven: All right. Vanessa, I’ve got a one 1:00 Eastern here. Is it okay if I go ahead and get us started officially?

Vanessa: Yeah. Sounds great.

Steven: All right. Awesome. Well, welcome, everybody. Good afternoon if you’re on the East Coast. Good morning, if you’re out on the West Coast. And if you’re watching the recording, I hope you’re having a good day no matter what time it is. We are here to talk about fundraising email writing quick wins, specifically how you can do that to raise some money here before the end of the year. Maybe a little bit in November, but mostly December. So thanks for joining us. We got a big crowd, no surprise to me for the topic and the speaker, but I’m excited to host you all. I’m Steven, I’m over here at Bloomerang. I’m at Bloomerang, but no one else is here. So I’m staying safe. In case you’re worried about me. That’s always nice to get those chats from you. But I’ll be moderating today’s discussion as always.

And just a couple of housekeeping items real quick. We are recording the session, and I’ll be sending out the recording as well as the slides later on today. So if you have to leave early, or if you’ve got another appointment, you get interrupted or toddler barges in on you, no problem. I understand. We’ll get all that good stuff to you later today. Just be on the lookout for an email from me with all those goodies. 

But most importantly, as you’re listening today, please feel free to chat in your questions and comments. There’s a Q&A box and a chat box. So you can use either of those. I’ll keep an eye on both, I promise. And we will try to get to as many questions as we can before the hour or so is up here. So don’t be shy. Don’t sit on those hands. You can also tweet us. I’ll keep an eye on Twitter every once in a while, if you want to send us a tweet. But we’d love to hear from you. Introduce yourself if you haven’t already because we also like to know a little bit more about who we’re talking to. 

And if this is your first Bloomerang webinar, welcome. We love doing these webinars. We do them a couple of times a week. We’ve been doing them for eight years. We’re zeroing in on like 1,000 sessions, some ridiculous number. We love doing them. Always educational, always informative. Today will be no exception by any means.

But if you’ve never heard of Bloomerang, just for context, if you’re wondering what the heck is Bloomerang, you know, we do these webinars, but our core business is a donor management software. So if you’re interested in that or just kind of curious about us, check out our website, you know, there’s all kinds of videos and stuff that you can watch. You don’t have to necessarily talk to anybody before you really learn about us. So check it out if you’re interested. But don’t do that right now because we got like 2,000 people who want to hear from one of my favorites, a friend of the program joining us from beautiful Vancouver Island, our neighbors to the North, Vanessa Chase Lockshin. Vanessa, how’s it going? Are you doing okay?

Vanessa: Yeah. Doing great. I can’t believe you guys are coming up on 1,000 webinars. I think it’s something fun to celebrate that.

Steven: I need a cake or something. But you’ve been a part of it.

Vanessa: I think I was part of that.

Steven: Yeah. I mean, you’ve been a stalwart. You know, you’ve been very gracious and generous to come on and knowledge. Have done numerous sessions for us. And this one I’m really excited about, because . . . A little bit about Vanessa, over the past few months she’s been tweeting. Every time she sends one of these emails she’s going to show you and it raises like $100,000 and like one cent. Like this is awesome. So we got to have Vanessa on. And she was gracious enough to spill some of these beans for us. And you’re going to want to connect with her after the session, especially after you see all this great advice. Author of one of my favorite fundraising books. It’s on here on my shelf somewhere. Well, yeah, let me get it. I’m going to grab it. I always say this. I have it on my bookshelf. So let’s check it out. “The Storytelling Non-Profit.”

Vanessa: Oh, exciting.

Steven: It’s beautiful. It’s got like . . . It’s a good book, but it’s got like lots of cool activities and stuff. So we’ll link to that. You’re probably going to want to buy that. But she’s got a lot of great clients. She’s been raising millions of dollars for her clients. Does a lot of copywriting, stewardship plans, lots of digital strategies. So check her out. She definitely, well, obviously, you know, talks the talk, but also walks the walk. So I’m excited to see all these. I got a peek at the slides earlier this week and this going to be a good one. So, Vanessa, I’ve already gabbed way too much and taken time away from you. So I’m going to stop sharing my screen and I’ll let you . . . 

Vanessa: Okay. I’ll share mine. And I’m going to try to do full screen so that folks can see things as I go through. We’ll see if that works.

Steven: Try and make it happen. Here we go.

Vanessa: Yeah, hopefully. Well, welcome to all of you. I am super excited to be here to talk about email writing. I have been fundraising since 2009, which seems like forever ago now, but I have to say, one of my favorite things about my work and about fundraising generally is definitely email fundraising. It is a very wonky sub-genre of direct response writing in the fundraising world. And there’s a lot of reasons why I love it. I mean, one of the things that I like particularly about email is the immediacy of being able to see results from things. I think that when you are running a digital program, the ability to see how things have done out in the world and out in the wild quickly is immensely helpful because it helps you pivot faster, it helps you make more decisions that are, you know, more data-informed about things that you’ve done, and just the ability to measure significantly more metrics in email and in digital, I think it’s just so helpful for all of us in this day and age with our fundraising work. And while I could kind of wax poetic about all kinds of aspects of email fundraising, one of the things that I really want to focus on for us today is actually talking about email writing, which I know is something, you know, a lot of folks struggle with, a lot of people are kind of always trying to figure out well, like how do we get, you know, how do we stand out in people’s inboxes? How do we get more eyes on our emails? All of these questions and, you know, of course, bottom line, how do we convert more donations from the emails we send?

So I really want to talk today about, you know, the structure of a good email and things that you can really think about as you work on your emails, you know, in December and hopefully beyond December, of course. So let’s see if I can get my slides going forward here. Steven already introduced me, so I’m not going to go through this. I’ll just go ahead and click on through. But I’m curious for some of you, you know, thinking about, you know, this year or even past years, what’s been your best month for email fundraising? You know, how much did you raise from your email program? I would love to know just kind of where some of you are at, so feel free to chat us and I’ll take a look at those as some of you share in. I’m not sure I can pull up the chat on mine. Let’s see. Well, I don’t know. Steven, maybe you can read some off to me if there’s any coming in.

Steven: Yeah. Lots of people are saying December, December, November. Lots of fourth quarter, I’m seeing here. Yeah. November to December. Few people are saying they’d like to try it for the first time this year. So, yeah.

Vanessa: Oh, that’s awesome. That’s great. Yeah, definitely. I mean, yeah. Unsurprisingly, like last quarter of the year, December, is a great month for all of us for fundraising. I’m sure many of you have seen the stats about, you know, just how much money comes in the last two days of December. It’s something like I think 12% of all annual giving donations are made in the last two days of December. So lots of opportunity in December. I always think that it’s like, of course, one of the easier months to raise money in because you have sort of the context of the holidays like the end of the tax year deadline, so the lift of making your case for support is sometimes a little bit of a lighter lift, but, of course, it’s still important to, you know, make a good argument for giving and give people compelling reasons beyond just those two kind of obvious ones that might already be moving folks forward towards their donations.

So we’re in, what? November of 2020. It seems like we’ve going in 2020 forever. I will say my best month this year so far was September. One of my clients did $193,000 in email. And for them, since July 1st, we’ve done $294,000 in email fundraising. And I have to say, I’m very excited to see what we do in December based on some of these numbers. These were an anomaly for them, and hopefully not now that we’ve really started investing in how they’re doing email in their digital program. Prior to September of this year, their last best month for email was $33,000, so a significant difference. A lot of that came from changes to our send frequency, but it also came in changes about how we were writing fundraising emails, which I think is one of the biggest differences and one of the most important differences in getting these kinds of results.

I often have conversations with people when they ask me about like, “How frequently should we send emails?” The answer is always more than you think you should be. And the line of diminishing returns for how like too many emails sends is way further away than you need to think it is. I think when we did 193,000 in September, we sent something like, I think it was like 13 emails total that month, which probably seems like a lot to some of you, but we were doing a very specific one-week campaign and there was another sort of micro campaign we ran during that month. Not everyone got every email, which is an important part of thinking about how you’re doing your digital program, but, you know, that was like what it took in terms of send volume for us to get to that kind of a number for their email program. 

It might be something that you want to think about as you’re moving into December and thinking about, you know, ambitious goals you might be setting or maybe even if you think about like good, better, best goals for your yearend fundraising, you know, what’s it going to take to get to that like best level goal or maybe exceeding that goal? You know, maybe it’s only like one or two more emails than you think you need to send will get you there and will make the difference in, you know, not reaching your goal or maybe reaching it and exceeding it. So that’s something that I just wanted to kind of mention here at the top of this session. 

But I just want to say like bottom line about getting to some of these numbers, there’s a lot of parts and pieces in email fundraising, but I just want to really emphasize that, you know, it’s worth never underestimating the power of good writing in an email. Like it really is such a fundamental part of converting people who open those emails into donors and into additional donations, which is, of course, what we’re going to talk about here today.

So one of the numbers that I lean into when I think about email analytics that might be helpful for some of you to think about is the amount raised per email sent. M+R Benchmarks does this number every year as a part of their industry indexing around how email is performing and how digital programs are performing. If you want to calculate this for yourself, it’s a pretty simple number to calculate out. So let’s say you raised $10,000 from an email list of 10,000 people, you know, you’d be looking at it like a dollar raised per email sent. This year with some of the emails I’ve written, my clients have been doing, you know, in the dollar to dollar or three raised per email sent, which is pretty exciting for them. 

But I like this number for a lot of reasons. Like there’s obviously a lot of analytics that you can measure in email, but for somebody who are trying to really give accurate projections or think about like what is realistic for us to raise in our email program, this is a really good number because it will really ground you in, you know, the response rates that you’re getting from your emails and whatnot. And over time, you can keep measuring this number and keep getting more and more accurate with what you’re able to project in terms of, you know, what you want to raise through an email fundraising program or even just campaign-specific emails.

And I’ll just add to that too. You know, one of my best pieces of advice for people usually around analytics is to benchmark yourself against yourself. There’s, of course, you know, useful industry averages, you know, there’s things like I shared at the beginning about how much some of my clients are doing in their email programs. Everyone’s program is different. Your list looks very different than, you know, some of my clients’ list, you know, it’ll look different from the other lists of people who are here on this webinar. The best thing you can do for yourself is pick a couple of metrics that matter in your email program and really think about measuring those over time. I found that for one of my clients, you know, we’ve really turned things around since July for them. And even just in the amount of data we’ve collected and measured since July, it has radically changed my ability to understand what’s working in that email program, and that’s only like five months’ worth of data at this point.

So, you know, even if you haven’t really figured out like how to measure things or what to measure, even just started measuring things in your email program, December is a great time to start doing that and really make it a habit going into next year so that you can start collecting data points about your email program that can really help you understand what’s working and what’s not working, which is something that I emphasize to people all the time, which is that knowing what works for your organization, your digital program is really like what the goal should be. There’s lots of industry advice about, you know, what you can do with your email programs, how to write good emails, all of these things, but ultimately like the best thing that you can do is test things and figure out what’s working and how to keep doing that for your organization for as long as it’s working and when it suddenly stops working, you just keep exploring and keep figuring out what can work and what else can we do to keep getting the kind of results that we want to see in our email program.

So I don’t want to take up too much time with this, but I just wanted to share those couple of things before we talked about kind of the writing of emails themselves. I think it’s a useful kind of context to think about the analytics and how much we’re talking about when we talk about how we raise money from email and whatnot. But I want to talk about writing, specifically, because that’s what you all came here to talk about with me. So I want to ask you guys a question. And feel free to chat in your answers to this. True or false, the copy from your direct mail letter and your email should be exactly the same? And let Steven, and I know. And Steven, maybe you can just let me know what folks are saying.

Steven: I’m seeing a lot of false, and that’s what I thought too, so I’m hoping . . . 

Vanessa: Excellent. Yeah. I’m finally seeing the chat here. Yay.

Steven: Okay. Good.

Vanessa: Great. Yeah. Claire, you say, guessing false, but not sure why. Yeah. Cindy, false. Okay. Great. You guys already know something super important about email. I am so pleased to hear that. Yeah. Absolutely. You guys are all right. It is definitely false. There’s things about your direct mail campaign and if you’re running like an integrated direct response campaign that involves multiple channels for asking, there, of course, should be some through lines, right? Like you should have some similar messaging, there should be probably a similar, you know, kind of conceptual ask for these campaigns, but ultimately, like you do not want to copy and paste your direct mail letter into your email. Like that’s not effective. And there’s a lot of things about how direct is written that is not applicable to email and will probably slow down some of your results in your email.

So I would say generally one of the things that I often underscore for people when we talk about email fundraising is that email writing is really its own wonky sub-genre of fundraising writing. Like different from anything else you probably write just like kind of grant writing is very different from other things that you may be doing. And it’s useful to know what some of these principles are in writing good emails because then you could start getting better at them. 

I often say to people that I find with fundraising writing, you know, it’s so much more of a science than it is an art, of course, like, you know, kind of massaging what you’re writing and like figuring out the best ways to say things and communicate things is like definitely the art part of it, but there is a lot about direct response copywriting that when you know what to do and like how to structure things, how to get into an ask, all of that, it’s much easier than you might anticipate. And over time when you keep practicing at it . . . like I really do believe you can get better at it and it can be a learned skill that you can improve on over time. 

And I say that because I know some people, you know, have wavering confidence in their ability to write well. And I just want to say that it is very possible to become a better writer with practice and with time, and so I just want to encourage you, if you’re feeling like, “Oh, I don’t know if I can do this,” especially for writing emails for the first time this year, you can absolutely do this. And I hope that what I share will be helpful for you in figuring out what you want to say in those emails.

The other rule of email fundraising that I want to just share as well is that no fundraising email is truly a standalone. You’re always building narrative. And this is probably a much bigger conversation than just this webinar. But when you think about emails that you send in December, I would encourage you to think about them as like a connected chain of beads or however you want to think about them being connected, they’re really never a standalone piece of copy or a standalone fundraising piece. You’re building narrative over time and when people are reading these emails, you know, you’re building up their understanding of what you’re doing, you’re building up your messaging, hopefully you’re building on your case for support over time. 

And I think it’s a really useful strategic decision for you as a fundraiser and as somebody who’s working on your digital program to understand that interconnectedness and to start seeing them as like an ecosystem of copy and an ecosystem of fundraising collateral. And rather than just thinking about like, “Oh, we’re sending out an e-blast like that has to go out on the state.” You know, like, no, like we’re sending out multiple things and like here’s how we are like moving the trajectory of our argument for giving forward over the course of these, you know, several emails that we might be sending.” So hopefully that’s helpful context for some of you thinking about email and just some basic things and principles that I think about kind of like holistically around email that I think is really useful.

So let’s get into thinking about actually how we write emails. So one of the things that I teach people when I think about emails is that emails should really have two asks and you should treat each of the asks in your email as a mini case for support. So I just put the screenshot in here of this one and I’ll show you some closer shots of it. So if we could actually read it together. But hopefully . . . My slides are advancing too fast for me. Hopefully, you can see it. 

So there’s two hyperlinked asks here, one in the middle and one at the bottom. So you can see those are the two asks. I think having a to asks structure works very well for a lot of reasons. One, it’s extremely skimmable. And as we all know, when we read things online, we’re not really reading them, sometimes we’re reading them quickly and trying to like get past what’s going on and get to the point of things. 

I also think that for most organizations, a two-ask structure in email is helpful because it allows you to break down complicated information so that it’s easier to digest. So many of our organizations work on things that feel like complicated or wonky to explain and by instead giving yourself two shorter chunks to explain things, I think it helps us stay out of the weeds of potentially communicating a really complicated explanation about what’s going on or what’s happening that ultimately like makes people think too much and really like makes you lose momentum going into an ask for whatever it is you happen to be asking for in that email.

The other thing about two asks structure that I think is really important to say as well, and I’ve noticed this in some of the emails I’ve worked on this year, is that I definitely see a higher click-through rate on the top ask in that email more so than the bottom one, which I think surprises me a little, I often think that people open email and just like scroll right to the bottom of it. Not always the case. And I think that I’ve actually been able to capture more conversion on some email because we’re making multiple asks and so we’ll get people clicking on the first one, we get people clicking on the second one, which is always a great and really useful thing from an email conversion perspective.

I really want to talk about the first task. So let’s get into that for a few minutes and just talk about some of the principles of how do we write a strong opening in our email to really get into the first fundraising ask that we have in there? So some general guidelines that I would share, I think about writing, you know, somewhere between 120 to 150 words before the first ask in my email. I always think about short, skimmable paragraphs, of course. I would say one of these is a little long and now that I’m looking at it, but generally what I’m trying to do in my first ask is I’m trying to communicate what’s happening, like, you know, what’s the problem and the context for what’s going on and what can donors do in response to what’s happening. So getting into that ask very quickly. So you can see here in this email, I’ll just talk a little bit about, you know, how those things kind of apply and play out in this one, in particular.

So this was from a campaign that I ran with one of my clients back in September. And this was, I think, the first email that we sent in that week-long campaign. So the first sentence of email, “Variety BC is often the last resort for families who are trying to get their special needs kids the resources and support they need, and these days that need is overwhelming.” Like right away, if we’re getting to what’s going on. And I think this is a really important thing in digital in general, is like we never want to bury the lead. We never want to make people really hunt around for the most important information. We just want to get to the point and communicate it really quickly. 

My husband, who’s also my business partner and sometimes my writing partner often says that like one of his tricks for kind of making sure that that’s true in an email is tacking on a sentence, “Let me get straight to the point,” right at the beginning of the email, just for like editing purposes. And if after that phrase, “let me get straight to the point,” you did not get straight to the point, it probably needs some editing, and there’s probably a faster way for you to get into that email, especially if you ended up kind of meandering to the point. 

I think that this is one of the things too that feels very divergent for me about email and direct mail, which is that in direct mail we’re often like kind of, I think in kind of traditional direct mail copy, we’re often like building a lot of rapport. We’re sort of meandering our way to the ask. And I think some of that’s a little bit about just the demographic of donors and what they’re used to. But I think in email we have much more leeway to just kind of get into things quickly. And, in fact, I think that that’s a really good practice to be doing in your emails. 

I just want to speak a little bit more to some of the other things here in this email quickly and then we’ll talk about writing great first sentences because that is definitely an important part of the first ask in an email. In a first ask, there’s also other things that you want to think about. I always think about kind of having these pivot sentences into the asks, so where you’re really making the connection between the problem and what donors can do and why it’s important that you’re going to make that ask. 

So, you know, in this email, it says, “Since the spring we’ve funded virtual therapy as counseling and tutoring to ensure kids don’t lose the progress they’ve worked so hard to achieve.” That’s a really important kind of point and making their case for support and helping donors understand that, you know, there’s something at stake, like we want to communicate the stakes of the problem. So if this problem goes unsolved, here’s what’s going to happen. And I think that that’s a useful device in writing in any kind of fundraising writing, being able to communicate the stakes of the problem. And I think that that often makes for a very good pivot sentence into an ask where we kind of like, again, reiterate, you know, why it’s so important that donors, you know, kind of meet the moment and help address this problem that we’re working towards.

So I feel like the first sentences of emails are so important. It’s such an essential part of, you know, getting people into the message and getting them engaged with what we want to talk about. You know, I think that in general, when I think about writing a strong first sentence, you know, it’s something we want people to immediately understand. Like we want them to be able to connect with it very quickly. Sometimes it’s about communicating the stakes of what’s going on, like . . . It also goes back to that last slide. The second sentence of this email does that very well. You know, “And these days, the need is overwhelming.” Like it’s a very clear communication of what’s going on. 

You know, there’s a lot of ways of much like using sometimes like clichés or like, you know, sort of like cultural truisms to a certain extent will help people understand what’s about to happen and help them really get into that email a little bit more. So just some examples. And this one here. So these are actually all independent first sentences that I just grabbed from some emails that I’ve written. So this one, the first one, they say, “It takes a village to raise a child, and that’s especially true if you have a child with special needs.” I really liked the sentence. And interestingly enough, I took this from an email that my client had written way earlier in the year, and they actually had buried the sentence in the middle of the email somewhere, but it’s such a powerful way for people who are reading this to really understand something important about the organization’s work. If they’re a parent themselves, they can immediately kind of like connect with this like slight cliché about like, you know, taking a village to raise a child, but also kind of understand, “Oh yeah. Like it probably would take even more if I had a child who had special needs.”

Let’s see what else. Let’s see. The third one here, the third example I have here on the slide, “Every special needs child deserves to get the support necessary to live their best life and reach their unique potential.” It’s like a really simple statement of fact that again, like just kind of pulls people into what’s going on and helps them really understand quickly what we’re about to talk about. 

I don’t have this example here on this side, but there was an email that I wrote, gosh, probably like four years ago now for a rape crisis center that I worked with in Vancouver for a number of years. And I still remember the first sentence. It’s probably to this day one of my favorite first sentences in an email that I’ve ever worked on. We sent this email shortly after a very high profile verdict came out about like a nationally televised like court proceeding on a sexual harassment and sexual assault case in Canada. And I remember the first sentence of the email said, “When I heard the Jian Ghomeshi verdict, I was sad, I was angry, but I wasn’t surprised.” And that was such a powerful sentence for that community and for that email list because it really captured the mix of feelings that people were themselves probably feeling.

They were probably sad about it, they were angry, and yet, like there was this fundamental, like, “I’m not surprised like there’s often not justice, you know, in the legal system for women around sexual harassment and sexual assault cases.” And that was a really . . . like that was a very well-performing email for a number of reasons, but I think to me like the power of that first sentence that just really like connected with people right where they were like in that emotional moment was a really big part of what worked well in that email. And I think that that’s something that you can also think about. 

You know, I often think about the context in which we’re sending emails like the cultural moment, the political moment, the social moment, whatever it is. Like if there’s something that connects to your cause about what’s happening right now that you can tie together with what’s happening in the broader world so that people can kind of contextualize the importance of your work and what’s happening in their lives, that’s often a really powerful way to get people engaged in the message and in your work and in the email itself.

So all of this stuff just to say, I just want to reinforce this point and you get to the point quickly in your email. And I feel like if I could share one other piece of advice for you on the first ask, you know, don’t bury your best information way down in your email. So often this is the mistake I see organizations make. They have great points to make about their organization, their work, the importance of why people should support it, and yet like that most important, most impactful sentence is like way in the middle of the email where nobody can really see it easily. 

So as you edit and as you read your email drafts and you think about like, “What can I do to improve this?” I would really encourage you to read through and just think about like, what is like the single best sentence in this email? And if you find that it’s somewhere not obvious and somewhere not easy for people to read quickly in your email, think about ways to just rearrange your copy and move it up so that people can see it fast and so that you can really make that strong point way earlier on in your email and not make people, you know, work for it and also, you know, not like lose the power of some of your best writing way down in the middle of that email.

I always think it’s such a shame to read nonprofit emails that I get in my inbox where, you know, it’s a cause that’s great. I know they’re raising money for something really important and yet like the ask is like just not quite there or they maybe did sort of like beat around the bush of it, but they didn’t just like really make it concise and just really boil it down in a way that felt as powerful as it could be. And so I’d encourage you to just think about that in your own writing if you find that you’re kind of like meandering around and you’re like, “Oh, like, I don’t know if we should just come out and say this.” Trust me, come out and say it. It’s much better to do that than to make people try to connect the dots themselves when they may not necessarily connect the dots about what matters and why it’s important.

Okay. Let’s talk about this a little bit more here in the email structure. So one of the other things I think about both in the first ask and the second ask of the email is that you often need a strong connection sentence between what you are saying leading into your ask and then actually getting to the ask itself. And I think about this connection sentence as sort of the pivot into your ask but it also does a really important function of building your argument for donating and sets you up for an ask that makes sense and doesn’t just like come out of left field, right? Like we want people to understand that like, yes, we like, you know, we’re making an ask. It makes sense, like we’ve like done the legwork to get people to that point.

So I’ll just read you the one from this email. So the sentence before the asks says, “It breaks my heart that we’ve had to say no to special needs children and their families asking for help because I know the support we provide is life-changing.” And then it pivots into the ask, “This week we have an incredible opportunity to turn things around. Your donation will allow us to say yes to one more special needs child looking for help.” So you can see there’s kind of this transition into it. 

And this is one area where I think a lot of emails can be quickly improved, is just having that really smooth, seamless transition into the ask, both the first ask and the second one that you make in your email. So if you’re reading and editing yours and you find like, oh, like, you know, “We got into the ask, you know, for people to donate, but . . . ” you know, it felt kind of clunky. Like maybe it just kind of like transitioned really roughly from like one thing to another and there wasn’t a lot of smooth flow, you probably need some sort of connection or transition sentence between the paragraph above that and the ask itself. And it’s really just about kind of like threading the needle and making it, you know, kind of, as I said earlier, like connecting the dots between what you’ve told people is the problem, why the problem matters, the stakes of the problem, and then getting into why making a donation is the solution. Like you just need that one or two sentence connection that connects those dots for people and just makes it really smooth and really apparent.

Okay. So I want to talk quickly it just about the second ask and look at a couple more examples and then I want to leave plenty of time for questions because I think that’s probably the most helpful thing I can do for a lot of you, is to answer some questions. The second ask is, for me, personally, I always find the easier one to write of the two. It’s a continuation of the first ask and I always see it as an opportunity to get into more details and specifically more of the wonky, like more wonky or like more complex details of what you might be working on. So if there’s things that are difficult to explain or like concepts that just seem like you could get more into the weeds of like policy or something you may be doing, you know, like use the second part of your email to explain those so that, you know, if people have read that far, they have some groundwork already, and hopefully it’s going to be easier for them to understand when you start getting into the second part of that piece.

Sometimes in the second ask as well, like I will use this as an opportunity to get into, you know, specific examples, specific stories, all of that, where I feel like I can just sort of extrapolate and expand on the groundwork I laid in the first ask of the email to really kind of give people some additional context and some additional reasons for giving. 

Again, like it doesn’t have to be a long part of the email. I would say a lot of the emails I’m writing these days are probably somewhere between like 400 and probably like 700 words max. Seven hundred seems like a long email to me at this point. But, you know, it’s just really about providing people those additional pieces of information to help them kind of nod along and say, “Yes. Like I’m understanding this, like the reasons are there. It seems important, and I want to help this organization.” Like the more we can get people nodding along as they’re reading, probably, the more likely we are to capture those people as donors and have really successful emails.

So I’m going to ask all of you, just a true or false question. So I know a lot of people know that I do a lot of work around narrative and storytelling in fundraising. So true or false, for some of you, you know, the story, a story about an individual has to be the lead in your email? Like it’s the starter part of your email, you’re using that as sort of the center piece of what you’re talking about. And curious to see what some of you say. I’m just going to grab the chat so I can see. Yeah. Megan. So, false. That can be a strong lead, not always. Andrea, but it always is true on some . . . Yeah. True to some extent, right? Yeah. Doug, can be a strong lead. Yeah. 

So, yeah. I think I agree with a lot of you. I think it can be an important part of an email, like telling a story about an individual giving people like a specific example. I don’t think it has to be the lead of your email. I don’t always think it’s the most compelling information that you can share sometimes like just the more grounded, factual case for support type information is more useful the top of your email than the story and like meandering through the details of an individual story. So I think, I mean, it’s one of those things where like you could test and see what works very well for your audience and on your email list.

I personally feel like this year things that I see that have been working better on one email list that I’ve been working with is using the stories at the second part of the email, so in the second ask. And I’ll just show you an example of that for one of the ones that I worked on here this fall. So this is just a screenshot of the whole . . . Oh. Goodness. The whole email. So just so you can see the whole thing and that’s why . . . Sorry, my mouse pad is apparently very sensitive today. 

So over in the image on the right-hand side, that is all the second ask part of this email. And you can see here in this email, like it gets into a story pretty quickly. So coming out of that first ask, it says, “We know the help we provide can change someone’s life, and in Karissa’s case, it saved her life.” And it gets into a specific example of how this organization was able to help a child with counseling support. 

And, you know, to me, it was like a really like touching important story for this organization to tell about some of their mental health and wellness work. You know, could it have made a really compelling opening to this email? Like probably. In fact, I don’t remember writing a version where this was the lead in the email, but I think ultimately, for me, like why I decided to use it in the second part of the ask was because I wanted to get to other information that seemed like it would be more compelling and more urgent first and then get into actually sharing the story about an individual and contextualizing it in the organization’s impact and ultimately in donor impact as well.

So there’s lots of ways that you can kind of integrate these like anecdotes, these sort of smaller vignettes about specific aspects of your work and your impact as an organization. I’ve been finding, for me personally, that, you know, in the second part of an email seem to be performing a little better. But as I said, I think it’s one of those things with email where testing is always useful. And so if you are thinking, you know, as you write an email, “Oh, like, you know, the story actually seems very compelling. There’s a really good first line in that email, like maybe we should try this story this way instead.” You know, you can test it, you could send two versions to your email list. 

In fact, as I’m just looking at this email again, I know exactly which line it was that I originally thought about using as a first sentence, that line, you know, “We know the help we provide can change someone’s life, and in Karissa’s case, it saved her life,” was one of my options for the original first sentence of this email. And I still think it’s a very strong, had a profound and like, I would say like a punchy sentence that really like gets to a point and is very impactful and would have potentially worked well as a first sentence in the email.

Okay. So I just want to share some other kind of like, hopefully useful, but I kind of categorized as like miscellaneous tips about email writing with all of you before we go into some questions. So just in terms of readability and whatnot, I would really encourage you to hyperlink entire lines so they’re really easy for people to find and click on, especially in mobile. You know, lots of people read your emails on their phones and just hyperlinking the word Donate or Donate Now is often very difficult to find and click on, on a phone. So as you can see, like in my emails, we hyperlink entire sentences, sometimes entire paragraphs, just so that it’s really easy for people to find those links and click on them. 

You know, use a readable font for mobile. Don’t go crazy with the design inside your email. Like it needs to be readable. It needs to be a big enough font that people can actually see it. And, you know, kind of like with direct mail, I would encourage you to bold your most important points so that, again, we can kind of encourage skimming. We can encourage people to read some of them was essential things we want them to know in that email. And I have just, actually, for me, like as an editing tool, I find the act of figuring out what to bold in my email is a really useful tool for figuring out like, what are the best, most important things I’ve said in this email? And it will often help me figure out, you know, are there things I want to cut out? Are there are things that I need to revise and figure out how to say more concisely as well?

All right. Things you’ve been stop doing this year and hopefully beyond. You do not need to include a graphic of someone’s signature in your email. Not necessary. Like you can just type the name, nobody needs to see like the digital version of someone’s signature. And similarly, like you don’t necessarily need to have the signatories’ headshot in your signature line if you’re doing an email from a specific person at your organization. I have to say, I am generally like a minimalist when it comes to like the design of emails. I’m generally like a fan of the header or like two by two images in there, but there’s a couple of things about images that I would just flag, like one is that like practically speaking, they often slow down the loading time of your emails and also not all email programs will auto-download those images. So if you are overly reliant on an image with text to convey your call-to-action, some people may not see that because it may not actually download in their inbox. So it’s useful and good practice to actually be hyperlinking text in addition to images, if that’s something that your organization has done in terms of formatting for a long time.

All right. One final, I guess, unsolicited piece of advice I can give you, we haven’t talked really much about open rates on emails, but if this is something you want to work on if you’re thinking about like how do we get more people to actually open them, how do we increase like the average open rates on our emails, of course, subject line is one thing that you can think about. 

I have to say, my least well-performing email in September on one of my campaigns was the one that I included the word donate in the subject line, which was unsurprising to me, actually. I don’t know why I use that one in retrospect, but most of my other emails did not include a reference to donating and they performed significantly better than that one. 

But separate from the subject line, you can also periodically consider running sender name tests where you try changing up the sender name of your emails, so maybe you always use your organization’s name or your CEO’s name. You might want to try something different. People respond to seeing things that are unexpected in their inbox, like a name that they don’t recognize, or what have you. It might actually bump up your open rates in a good way for you. So that’s something that you can also trying December. That’s for me like a natural part of what I bake in to email strategy in yearend, is thinking about, you know, who are these emails coming from and how can we make sure we try some different names or different combinations of things so that people continue to pay attention to what we’re sending them? And don’t just see that it’s another, you know, email from such and such organization and they think like, “Seen this all before. I don’t need to read this one.”

All right. Last thing before Steven and I get to some questions. I just want to encourage you not to procrastinate writing your emails. Time for editing is where the real magic happens in all kinds of fundraising writing. I can’t even tell you how bad some of my first drafts are sometimes to me personally. And they get so much better when I have the time and space to massage them and make them better through the editing process. 

I know it’s something that I do professionally and something that I just spent probably large amounts of time on probably compared to some of you, but, for me, the more time I have to kind of take a step back from a draft that I’ve written, the more I can come back to it with fresh eyes and actually make some significant headway in making that email better. So you might be thinking, “Oh. We’re not going to send emails until December 30th or 31st, and that’s like a month and a half away.” Don’t wait to write those emails, like write them now. Write them this week or next week. So, one, you have time to do other things that might come up, other fire drills that you inevitably have to run in December, but, you know, you have time to like make those emails a lot better and you can kind of sit with them and work through the editing process on them because that really is where email can get significantly better.

Okay. So I’m very happy to answer questions and talk more about email copywriting and all the things. If you have questions you’d rather reach out to me personally about, I always answer emails. You can reach me at [email protected]. You can find me on Twitter at Vanessa E. Chase. And I also have a number of writing tutorials over on my YouTube channel. This is the Bit.ly link to get to that, bit.ly/vclyt. There’s one on writing better emails and also one on year-end fundraising letters if you’re just looking for some other writing tips to keep working on your fundraising work this year. So, Steven, with that, I will turn it over to you for some questions.

Steven: Yeah. Wow. That was awesome. There were so many good tidbits in there. I love what you said about the hyperlinking more than just a couple of words. That’s a good one. Wow. That makes total sense too. It’s just more realistic to click. 

Vanessa: Yes. 

Steven: And I want to back you up on one thing, not that you need me to back you up on anything, but you said something in the middle about contextualizing, how maybe COVID or the crisis has impacted your work specifically. Folks, she’s right. And she doesn’t need my validation, but I have the data to prove it. We actually looked at that amongst Bloomerang emails, we looked at emails that did that versus the ones that didn’t and overwhelmingly the ones that did mention the crisis and contextualize it in some way. It was like by huge margins. So if you take anything away from Vanessa, that was a big one, for sure. So don’t be afraid.

Vanessa: Yeah. Definitely. I mean, I would say even like what some of the emails that I showed you all on the slides from Variety, you know, there’s so much to talk about with their work with special needs kids and, you know, why it matters and why it’s important. But when I worked on the September campaign emails, like one of the most important points that got buried very far down in, I think a direct mail letter version of what they said was that, you know, for the first time in their 54-year history, they had a waitlist this year that was directly related to people’s financial challenges about being able to provide what their kids needed to thrive. 

And to me, like that was just so like relevant and important in this moment of people like understanding themselves, like how the pandemic is affecting everyone and being able to say like this year has like been particularly challenging for families with special needs kids. And well, I went back and forth about like, you know, was that actually the most important point that we could make and like an important message in the email, you know, sequence that we sent out. I do really think that it was a very like powerful, very impactful thing that helped people kind of stop when they read that email and go, “Oh, like, yeah. That is something like an anomaly and something different for this organization. And like, tell me more about that.”

Steven: Yeah. I love it. Well, geez. We got a lot of good questions here. Probably won’t get to all of them. A lot of folks, Vanessa, this come in earlier, when you were mentioning that, that email, I think you sent maybe 11 or 14 emails in a month and you mentioned that not everyone on the list got every email, and some people have been asking about that segmentation. Can you talk a little bit about maybe who got what emails and maybe what the strategy was there?

Vanessa: Yeah. For sure. So there was a lot of things that happened when I thought about this segmentation of those emails. So in one of the examples on . . . I’m going to go back and find it for you all under these slides. Yeah. In fact, I will. Let me just go back and I’ll find it for you. Guys, you can all bear with me flipping back through these slides. Here we go, this email. So you can see this email ask, in an email is an ask for $1,250, which is a very big ask. I’m not going to lie. I was nervous about sending an email that asks for over $1,000 donation. This email did not go to everybody on their list. I very strategically wanted to test a larger amount. I had seen this work in another context and I thought, “Well, you know, if we have a large enough universe of people in this segment, like, why not? Like let’s give this a try and see if this ask makes sense.” 

And there was a lot of thought put into this number, specifically. It made sense in the campaign context and it turned out when we ran some numbers inside their CRM, they had think about . . . I think it was about 500 people in a segment where it made sense for us to run a $1,250 test task. And so that was like a very small subset of the email list. This email and a follow-up when we sent about a $1,250 donation, I think about $20,000 total in donations and did something on average like $34 per email send, which is very high and due to the high ask amount in this.

But in terms of non, like high dollar ask segmentation for this email list, there were other things we did, like we obviously sent out love emails to people who had not yet donated. One of my long time things that I often do is send, like what my partner calls a kicker email to people who did not open an email. So I’ll often resend the exact same copy and subject line to people again and we’ll see a good portion of the original open-end click-throughs just by resending it and kicking it back up to the top of people’s inboxes. 

So not every email, but I write in like a campaign sequence will be completely unique. We’ll often send one or two kickers like that. It’s something I’ll definitely be doing on Giving Tuesday and then probably on like December 31st as well. But that’s like . . . And a good example of not a full list is getting that email. But we’re, you know, sending multiple emails over the course of that campaign sequence.

Steven: So things like gift them out for the different asks and then obviously the campaign activity, if they’ve opened it but not clicked or maybe not opened, those kinds of things?

Vanessa: Exactly. Yeah.

Steven: Yeah. That makes sense. You piqued my interest with December 31st. So you recommend an email on New Year’s Eve. Can you talk a little bit about that?

Vanessa: Yeah. So there’s lots of great data that shows that a good chunk of all annual giving comes in the last couple of days of December. So being able to send out those couple of like last chance, like it’s the end of the tax year deadline, like make your donation now or like wait until next year kind of thing. Like there’s a lot of urgency about like a hard deadline of December 31st that works very well for donors. So I would say, as you plan out your email calendar in December, definitely including, you know, December 30th and December 31st email is a really good thing to do.

Steven: Yeah. We see that every year amongst the Bloomerang users. There’s just always a spike in revenue, even since the tax change. Like for some reason there’s still this weird ingrained thing in people’s heads, you know, about the last day of the year. They like to get it in before the end of year, I guess. A lot of people, Vanessa, have been asking about subject lines. And we could probably talk for an hour, at least on just subject lines, but any quick ideas there or maybe things that you’re going to try between now and the end of the year? You mentioned one, like kind of that last chance, kind of last, you know, last day of the year type thing. That makes sense?

Vanessa: Yeah. I mean, for me, like one of the things that I think about in writing subject lines is, you know, really thinking about like what is like an important key point that I made in the email itself? Like something that I want people to pay attention to, to capture their attention on. And trying to even just sometimes like pull direct copy from the email itself to use as a subject line, something that I felt like it was a really important point that would make a good short subject line, you know, obviously something that’s not like sentences long. 

I have generally found this year emails that had the word donate, or impact in them, or underperforming compared to other subject lines that I sent. So I am personally . . . I mean, that like might be unique to one of the email lists I’m working on, so I would add that as an asterisk. That’s something that I am testing in December just to see if that’s still holding true. But I do think that like, you know, being able to write good subject lines that pique people’s interest is obviously something of an art form in email. But I think that, you know, taking a cue from the copy itself in the email, like if you can find a good like phrase or way to kind of like rephrase something that you think is really important in that email, that can often work very well as a subject line.

Steven: A couple people have asked about the personalization. Have you tested kind of using their first name in the beginning of the email? Or do you avoid that or what do you think?

Vanessa: For one of the email lists I work on right now, we haven’t been doing that. Like the personalization of the first name, like where it might say like, hi, Steven, or something like that in the email, that’s partially because we have an email list that also has a mix of like corporate donors and other things, other like means and entities that like might make the merge field a little wonky. So we haven’t been doing that at all. And I have to say, I haven’t seen too much of an impact on donation rates, which I think is something, you know, like interesting to note. I think you certainly can try personalization. I think I have done that a couple of times this year on some tests and saw, you know, not ultimately like not much of a difference in like email performance.

Steven: Interesting. What about fonts and . . . Oh, go ahead.

Vanessa: I was just going to say, I think on the note about personalization, like there’s a lot of ways to understand personalization and marketing and fundraising. And like yes, merge fields are obviously like one way that you can think about that, but I think the more important personalization is like often segmentation around like the ask amounts or the like specifics of the ask. Like the $1,250 ask that I shared with you guys is a really good example of personalization in fundraising. Like that obviously wasn’t going to go to somebody who made a $20 donation last month. But it was a really targeted, specific personal ask to people that we knew were good candidates for it and it worked really well. And so if you’re thinking about like the gamut of what it looks like to personalize a fundraising experience, I personally would prioritize that over some of the other, maybe less important things like a first name field in an email.

Steven: I love that. You’re speaking my language. That makes total sense. And if the data goes wrong and that merge field looks weird, it’s like, no matter what comes after it, right? So, yeah.

Vanessa: I’ll tell you guys . . . I feel like this was probably only for people who are fellow like email fundraising nerds. My husband told me one of his favorite like email mishaps one time was they didn’t put a merge field in and like in the test version of the email copy it just said something like, “Hi, Zack,” and then it went out to everyone on the email list with that instead of like the merge field. And then they sent a follow-up email, the subject line said, “We know your name isn’t Zack,” but they forgot to suppress the Zacks from the list.

Steven: Oh, no. Poor Zack. Yeah. All seven Zacks. I love that.

Vanessa: Anyways, nerdy email data problems.

Steven: That’s amazing. Oh, wow. I wouldn’t put that in my book if I heard that story. That’s perfect. That’s so good. Wow. Couple other things before we wrap up. What about fonts and sizes? Do you kind of go bigger like maybe you would on a direct mail? I think that’s kind of the conventional wisdom there, but . . . 

Vanessa: Yeah. I mean, I always aim for at least like size 12 font. If not. Like more like 15, sometimes 16, I think. I mean, there is a point where it gets like too large. Like obviously you’re not going to run an email with like size 20 font. But, you know, this is where like sending yourself or colleagues test emails to see like what it looks like on different devices and for people with maybe different like eyesight abilities will be helpful for you to understand, like if it’s readable and if it’s easy to read. 

You know, I think one of the other things, I mean, one of the more finicky things about like readability and emails is the line height and line spacing in an email. So if you have things that are like really close together, like no line spacing, it can just be really difficult to read because it looks like the lines are all kind of like so close together, it’s hard to skim. It’s hard to see. So I think I usually do like at least 1.5 line spacing just so that there’s some like white space between, well, lines and email and you can actually like see things and it’s not like too difficult to read. Like, to me, like it’s often like more of a readability challenge for most organizations than font sizes. But I would also say like the color choice of hyperlinks is another one too. Like, you know, don’t use yellow, like yellow is probably going to be hard to read on a white background.

Steven: Yeah. That makes sense. Yeah. You don’t want that wall of text. It’s all scrunched together. That’s good. So many good tidbits. Maybe a good way to end it, Vanessa. I know we didn’t get to all the questions, but we got Vanessa’s info there. Giving Tuesday.

Vanessa: Yeah. Definitely reach out to me.

Steven: Yeah. Any quick tips for Giving Tuesday? It seems like probably everybody’s going to get, you know, an email. How do you stand out there?

Vanessa: I mean, I would focus on probably your subject line because that’s going to be one of the biggest determiners of people paying attention and even opening it in the first place. But I would also say, you know, like this probably more like a bigger conversation about frequency of email sends, which is that if people aren’t used to seeing your organization in their inbox, you know, they’re more likely to unsubscribe or report it as spam because they might’ve forgotten that they’re even on your email list. So if you are an organization who thinks that sending an email a month or an email a quarter is the right frequency, now is the time to send more emails to Giving Tuesday so that people remember who you are and remember that they’re on your email list. 

So that’s probably one thing that you can do because the biggest determiner of people’s desire to take action on an email list is a recency of last action on an email. So like if they have opened emails frequently and clicked emails frequently and recently, they’re more likely to make a donation when the time comes. So getting people used to that, working on your basic list health is probably something good to do between now and Giving Tuesday. You know, you might want to think about sending an email this week and an email next week to kind of get people warmed back up. And, you know, you can use those emails to start building your narrative and your messaging arc leading yearend campaign so that you’re sort of like planting the seeds for what it is you’re going to make an ask for, come Giving Tuesday.

Steven: That makes sense. Great advice. Geez, this was a good one. Thanks, Vanessa, for doing this. This has been awesome.

Vanessa: Yeah. Absolutely.

Steven: Reach out to her, obviously a wealth of knowledge. Check out her book too. I’m going to plug it even if she’s not going to. It’s okay. I’m not shy about it. And hopefully we’ll catch you again on another Bloomerang session. So if you want to review any of the content, don’t worry. We’re going to send out the sides, the recording. I’ll get all those good things to you today, I promise. And hopefully you’ll join us on another Bloomerang webinar soon. We’ve got a lot coming up even before the end of the year. I think we’ve got maybe four or five sessions before the end of the year. So just visit our website, click Resources. There’s a webinar tab there, and we’d love to see you again on another session. 

So we’ll call it a day there. Have a good rest of your . . . I guess it’s Wednesday. Time has no meaning, but it is Wednesday. Good Wednesday, have a good rest of the week. We have a session on Friday. So if we don’t see you on Friday, have a good Thanksgiving. Be safe if you’re celebrating here in the States, and we will talk to you again soon. Bye now.