Major Gift Challenge #5: Not Asking for Enough Gifts?

Oh my, here’s a common complaint: “My major gift team is not asking enough!”

Do you ever feel like this? You may have a team in place, but the frontline fundraisers are not making enough asks?

Or – could it be that they are just not making effective asks?

Whatever is happening, it’s certainly holding your fundraising back.

And, in this chaotic and fearsome world we are in right now, asking donors for help is more important than ever!

Let’s get it right.

Let’s bolster everyone’s asking skills, so gifts and contributions can flow in your door.

Here’s how to help your team grow their asking abilities, so they can raise the funding that’s needed so urgently.

1. Building Confidence Around the Ask

Talking with major donor prospects can be scary.

People tell us that they are hesitant to approach donors, because they don’t have confidence. Major gift officers are often worried about a lot of things:

• Is the ask amount the right size for the donor?
• Has there been enough cultivation and relationship nurturing so that the donor is ready?
• Is the timing really right? Are you rushing the donor?
• Does the specific project really excite the donor or will their reaction be lackluster?

Your solution:

Confidence can be learned! You can build up your team’s confidence by giving your fundraisers ongoing training and practice.

Teach them the Conversational Ask and permission-based questions can make an ask easier and more organic. It creates an atmosphere of discussion rather than an ask-and-response dialogue.

This is what they can learn in our 2025 Major Gifts Intensive. They will learn 5 different models of asking successfully, based on the unique donor. These techniques allow fundraisers to move to gift discussions in more natural ways, and with greater confidence.

2. Creating More Opportunities for Actual Asking

The truth is Asks need to be a routine part of your team’s workflow.

Fundraisers may focus too much on social engagement with donors – that does not lead to a professional, businesslike relationship.

We all know that philanthropy is a very personal act for each donor. And, building up a trusting professional relationship is a huge success factor in the solicitation process.

Better relationship-building leads to deeper understanding of each donor’s goals and opportunities for gift conversations.

When your fundraisers are better attuned to donors’ values, motivations and interests, they will be ready when donors indicate readiness, and say, “Yes! I’d like to support this!”

Your solution:

Although many major gift programs focus on the Ask, the solicitation itself is just a moment in the donor’s relationship with your organization.

The more opportunities a donor has to get to know the mission impact, avenues to be involved, and opportunities to get to know the leaders, the greater their affinity grows.

That could mean setting up regular donor meetings (in person or virtual), hosting small gatherings where donors can engage, or creating cultivation events where your major gift officers can deepen connections and build trust with donors.

Need help? Your team can learn a systematic approach to building relationships when they join the 2025 Major Gifts Intensive. They will be able to build trust, move quickly when donors are ready, and close gifts much much faster.

3. Are You Focusing on a Metric Like “Asks per Month?”

We are all for setting clear metrics!

However, some fundraisers will send proposals or make lukewarm Asks simply to hit the metric for the month.

Or the fundraiser bases an ask on a wealth rating but has not built the donor’s affinity – so they make an Ask outside of the target Ask amount.

And, fundraisers may be unsure about how often to ask, what size gifts are realistic, or what qualifies as a “good” ask. It can be so confusing!

Your solution:

What kind of metrics really work? Set clear, actionable goals that speak to relationship building activities – cultivation, solicitation and stewardship, not just Asks.

Leadership can clearly set forth what is expected and should consider adding relationship-building metrics into the mix.

This could include monthly or quarterly targets for making Asks and ensuring that they are aimed at the right range for each donor’s capacity and affinity.

That’s one of the important areas around donor and prospect relationships we teach in the Major Gifts Intensive.

Teams learn how to create donor plans, provide actions and phrases for easefully moving into conversations with donors, and finally – make an Ask at the right time, at the right level, and for the right area of support.

4. Lack of Training in Major Gifts

We hear how difficult it can be to hire a major gift officer with sufficient training.

Are you in the situation where you must hire someone with less experience than desired?

Fundraising isn’t sales, it isn’t marketing, and it isn’t passively waiting for gifts to happen.

Remember, the major gift donors and prospects supporting your organization are happy to work with professional fundraisers!

Fundraising is part of an ongoing relationship-building process. If you haven’t invested in your team, you may be experiencing the fallout from the lack of investment.

Our solution:

First, we encourage leadership to understand the value of relationship building at every level of donor giving.

With major donors and prospects, the expectations may be very high for building professional relationships that can meet the goals of the organization and the donor’s hopes and wishes.

Expecting major gifts fundraising to come naturally to everyone at your organization is unrealistic.

That’s why we encourage teams to take the Major Gifts Intensive professional development training together; so they can learn and work together more cohesively and effectively as a team.

Bottom Line: Not Asking for Enough Gifts?

If your team is struggling to make enough Asks of your donors and qualified prospects, it’s likely a combination of mindset, strategy, and leadership.

The good news: all of this is fixable.

With the right training, expectations, and accountability, your team will be making stronger asks – with more confidence – in no time.

If you want to support your team in asking more and asking more effectively, we encourage you to join the Major Gifts Intensive.

Our 16-week program has a proven record of success and provides the tools and coaching that teams need to transform their approach to major gifts.

Check it out here, and we look forward to speaking with you!

The deadline to apply is February 20!