Ask Culture vs Guess Culture

Ask culture and guess culture.

Sometimes an idea or perspective from outside the world of Fundraising can help you see the work of Fundraising more clearly. 

That’s what happened when I heard about “Ask Culture vs Guess Culture.”

Here’s a quote from when this idea first appeared online

In some families, you grow up with the expectation that it’s OK to ask for anything at all, but you gotta realize you might get no for an answer. This is Ask Culture.

In Guess Culture, you avoid putting a request into words unless you’re pretty sure the answer will be yes. Guess Culture depends on a tight net of shared expectations. A key skill is putting out delicate feelers. If you do this with enough subtlety, you won’t even have to make the request directly; you’ll get an offer.

When an organization is operating in Guess Culture, here are three of the behaviors you see:

  • Over-stewarding of donors
  • Never asking, or Asks that aren’t direct or clear
    • Perfect example: I did a “creative review” for an organization where I looked at twelve pieces of their fundraising.  In all those pieces they never actually asked the donor to give a gift. 
  • Under-communicating out of a fear of “donor fatigue”

You’re also seeing Guess Culture at work any time you hear a Major Gifts Officer say something like, “If you do a great job of stewarding a donor, you won’t even have to ask.”

Guess Culture and Fundraising

I think the unique demands of nonprofit fundraising cause people and organizations to operate in Guess Culture more than they normally would. 

Asking for money is a vulnerable experience, and it’s hard to be vulnerable.  Many times, for many reasons, it’s emotionally easier to shower donors with stewardship and give them the occasional “opportunity” to give… instead of boldly preparing a specific offer and asking the donor to make a gift.

And of course the Guess Culture approach works sometimes.  Because donors are generous, any approach will work sometimes.

But looking at the performance of the nonprofits we’ve worked with over the years, an Ask Culture approach to major gifts fundraising (and to direct response fundraising) works better.  It results in raising more money and keeping more donors year-over-year.

Ask Culture major gifts fundraising looks like:

  • When setting up a conversation or meeting, telling the donor in advance whether you’re going to ask for money or not
  • Being willing to ask major donors for more than one gift a year
  • Asking for a specific amount
  • Asking directly with phrases like, “…so I’m asking if you’ll give a gift of $10,000”
  • After the ask is made, being silent and letting the donor speak next

Of course there will be a few “no”s.  Of course there will occasionally be an uncomfortable silence.

But you’ll get a lot more “yes”es and you’ll raise more money for your cause.

Change the Recipe, Change the Results


When a nonprofit is first founded, its fundraising letters / emails / personal asks tend to have high response rates and high average gifts.   

But in my experience, the response rates and average gifts tend to go down as the organization grows. 

Here’s my theory to explain this…

The recipe for fundraising right after an organization is founded is remarkably simple and goes like this:

  • The founder talks about whatever “the situation” is that caused him/her to start the organization
  • They describe what needs to be done to help, and how it will help
  • They ask the donor to give a gift to fund what needs to be done

Works like crazy.

But as a nonprofit ages and expands, it develops its own programs, approach, and expertise.  It develops an organizational ego.

In a nutshell, this results in fundraising that talks more about the organization itself than it used to.  The recipe changes to:

  • They talk about the work they are already doing
  • They describe how they do that work
  • They ask the donor to give a gift to fund their ongoing work

This fundraising recipe does not raise as much money.  It lowers donors’ awareness about whatever “need” the organization exists to serve because “the situation” is rarely mentioned.  And it lowers response rates and average gifts because the fundraising is mainly focused on work that has already been completed – most of the compelling reason to give a gift today has disappeared.

I don’t enjoy this truth, but it’s still true: fundraising to individual donors that talks about “powerful work that’s already done” will cause less money to come in than talking about “powerful work that needs to be done now that the donor can help make happen.”

Organizations that stick to the original recipe will grow faster.

Individual donors tend to give because there’s work that needs to be done.  Not because the organization is already doing the work.

Do you know Sofii?


If you don’t know, you should.

It’s a website for Fundraisers, by Fundraisers.

Here’s a GREAT post to start with:

The post is about a successful donor acquisition letter written by Harvey McKinnon, a pro who I’ve had the pleasure of meeting a couple of times.

There’s a lifetime’s worth of fundraising wisdom in this post – seriously, get a cup of coffee and read it.  You’ll get so many ideas.  If your next piece of fundraising isn’t better, I’ll eat my hat. 

Sofii and Harvey – you can’t go wrong!



Quick story.

A few years ago I wrote a letter for a large, national organization you know the name of.

The letter was a huge success – it doubled the number of gifts they projected, and the average gift was higher than expected, too.

The President of the organization was pleased with the letter’s performance… and thought it would have raised even more if it was more in his voice.  So he wrote the letter the following year. 

His letter brought in half the number of gifts. 

The president is a very smart person and a great public speaker.  But his communication style – his “voice” – was not effective in direct mail.

There’s no judgment here; there’s absolutely nothing wrong with his voice.  But no one voice is always the best voice for all contexts. 

Quick common example: an organization decides that as part of their voice they will always describe their beneficiaries with one particular phrase, and that phrase is highly academic.  That phrase is perfectly appropriate in a grant application to a foundation with subject-matter expertise.  However, in a fundraising email to individual donors who don’t immediately know what the phrase means, the phrase will usually cause the organization to raise less money.

A nonprofit’s “voice” needs to be flexible enough to be modified for whatever context it’s communicating in.  To be most effective, a speech to a state legislature should sound a little different than a direct mail letter to individual donors, which in turn should sound a little different than a grant application.

If your Executive’s voice, or your brand voice, isn’t flexible enough to be adapted to meet the requirements for success in whatever context you’re communicating in, slavishly following any voice is costing you more than it’s helping you.

If you use the appropriate voice for each context, instead of using the same voice in every context, you will raise more money.

How to Take a Successful Email to the Next Level

Next level.

Say you’ve sent out an appeal and it was successful.  And you’re sold on the strategy of “sending it out again at the same time next year.”

It’s like you’ve discovered a new “tool” that works really well, and you’re wondering how to get the most out of it.

Let me tell you a story to tell you how we normally do it…

A decade ago we were serving an organization that helps mothers and children who are experiencing homelessness.

They didn’t have any fundraising planned for summer, and we didn’t want them to “go dark” for a couple of months.  So we asked them if they did anything for the children of their beneficiary families when it was time for them to go back to school.

Turns out the organization provided each child with a new outfit, new shoes, and a backpack filled with school supplies.  (This organization knew that kids who had been homeless had experienced more than enough trauma, and didn’t want the kids to feel like “the poor kid on the first day of school.”  We love them for this!)

The organization was low on budget, so direct mail wasn’t an option.  We put together an e-appeal that asked donors to provide an outfit and backpack for a child. 

It worked great.

And we worked under the assumption that if more people saw this offer, more people would give.  So here’s what we did in the subsequent years to turn a successful piece of fundraising into a full-blown campaign.

  • Year #2, we sent the email again and we did a direct mail letter with the same offer.  We raised even more.
  • Year #3, we sent the email and letter, and added a 3-email series on the last 3 days before the first day of school.  We raised even more.
  • Year #4 we did all of the above, plus updated their website to feature the campaign for the entire month of August.  We raised even more.
  • Year #5 we did all of the above, plus we asked a major donor to provide a match.  We raised even more.
  • Year #6 we did all of the above and used the campaign as a way to increase major donor giving over the summer.  We raised even more.

Today, this campaign is a pillar of the organization’s fundraising plan.  In addition to raising several buckets of money, it raises awareness about what happens to kids who experience homelessness.  It’s brought new donors into the organization.  It brought some donors deeper into the organization’s programs.

And it all started with one email that worked. 

So if you send out something that works, do two things:

  1. Notice what the campaign asked for.  In this case, it asked donors to provide a new outfit and backpack with school supplies for a child.
  2. Then ask yourself how you can get that same ask in front of even more people, even more times, at the same time of year.

After you go through this process a few times. you’ll have multiple proven campaigns with predictable, increasing revenue.  These campaigns become very real “assets” that reliably raise money year after year.

Time to get in touch with your printer…


Here’s a quick public service announcement: the sooner you get in touch with your printer about your fall mailings, the better.

A lot of mail is going to be sent:

  • In the couple of months before the election by both sides 
  • In the couple of months after the election by the losing side

So contact your printer now.  Tell them your drop date, your mail quantity, your paper needs.

When you start hearing stories about nonprofits not being about to send out their mailings on time this fall, your future self will thank you!

Make Your Fundraising Offers Accessible

Simple offer.

Finding an accessible offer for an annual giving donor can be one of the most difficult challenges in fundraising. 

Here’s why: Your annual giving donor doesn’t have all day to read about all your programs. She might have just $30 to contribute, AND she still wants to make a difference.

An accessible offer will show her the incredible difference she can make with just her $30 and a few minutes of her time. 

An accessible offer is:

  • Direct – It’s a clear solution to the problem presented.
  • Specific – It tells her exactly what her gift will do.
  • A Good Deal – It’s affordable, and the donor feels her gift will go a long way.
  • Urgent – It demonstrates why her gift is needed now.

Here are some examples:

  • $35 provides a night of safety and care
  • $7.50 provides a meal for a college student who can’t afford it
  • $55 provides a day of summer camp
  • $37 provides 1 art class for a middle-schooler

An accessible offer requires the donor to understand less about your organization.  Most nonprofits work under the incorrect assumption that a donor “must know all about all the things we do, and that we are good at it” before the donor can be asked to give a gift.

But offers that present ONE compelling part of what your organization does are more accessible to your $30 donor.  Offers like this will increase your appeal results, and your donors will feel amazing knowing the incredible difference they can make!

PS — You might be thinking, “OK, so our offer is $7.  Are we going to get a ton of $7 gifts?  Aren’t we going to raise less money this way because our donors are going to give less?”  Check out page 24 in this free Offers E-book to learn the answer!

Make Your Appeal Letters Accessible

Accessible typewriter.

We want to help you create appeal letters that are accessible for your donors.

You may have heard that the average donor is a 65-year-old woman.  She receives a LOT of mail.  To get through it all, she’s scanning and in a hurry.  But that doesn’t change the fact that she wants to make a difference.

The easier it is for a donor to read and understand your appeals, the more accessible your appeals are, and the more likely your donors are to give.

Here are some ways to make your appeals more accessible for your donors:

  • Use font size 12 and up.
  • Indent the beginning of each paragraph.
  • Write in high-contrast colors (black text on white paper).
  • Write at a middle-school grade level.
  • Use underlines and bolded sentences to show donors the most important sentences.  Each emphasized phrase should be understandable without reading the whole letter in case the highlighted sentences are the only ones she has time to read.
  • Use a double-space after a period.  It will be slightly easier for her to separate your sentences.

Writing accessible appeal letters will help more of your appeals get read, and show your donor the incredible difference she can make for your beneficiaries.  But your donor won’t know the difference she can make if the appeal is written in small text she can’t read, or if it uses colors she can’t see clearly.

It’s little changes like this that will make your appeal letters accessible, and help you raise more money!

There Is No Secret Meeting

Secret meeting.

For small nonprofits that are struggling to raise money, it’s tempting to imagine that there’s a secret meeting.

You know, the meeting where all the donors from your town get together on Zoom and decide not support your organization.

If your fundraising life feels that way, you might consider asking yourself a couple of questions. 

  • Does your fundraising make it clear what will happen when the donor gives a gift, stated in concrete (not conceptual) language?
  • Have you told people how a gift to your organization will improve a situation that they care about?
  • If donating to your organization might feel risky to donors, what can you do to make it feel less risky?
  • When donors have given to your organization in the past, did your organization take the credit (“Look at what our team accomplished!”) or did you give the credit away to donors (“Look at what you and your generosity accomplished!”)?
  • Does your fundraising make it clear that you need their help?  If not, are you able to boldly and vulnerably ask for support?

When a nonprofit feels like the biggest secret in town, it’s usually something about their fundraising that’s keeping it that way.