Pitch perfect: ten tips to ace your next ask

Do you ever wonder if you’re getting the most out of your ask? This is the part of the meeting many fundraisers feel most nervous about, but it’s not something you need to leave to chance!  

If you were at the IDPE Annual Conference last month, you may have caught Annarosa Muscatelli and Kurstin Finch Gnehm’s major gift solicitation masterclass. If not, or if you’re ready for a refresher, we’ve rounded up their top tips in this ten-point guide to help make sure your next ask hits the mark. 

1. Prioritise preparation 

The ask is the tip of the iceberg – if things don’t go to plan, it’s likely not because of the ask itself, but all the things leading up to it. Successful solicitation is built on everything that happens before you enter the room: understanding your donor, shaping the conversation, and preparing yourself and other stakeholders. 

2. Assemble your ask team 

A key question to consider is: who is the right person to make the ask? Who can bring institutional credibility, financial insight, or first-hand knowledge of the project’s impact – and what will your donor be most motivated by? Aim to keep numbers in the room at a minimum – the more voices in your conversation, the more variables.  

3. Prepare your leadership 

Even for leaders with a strong understanding of your office, a clear briefing is key to ensure they’re comfortable with the flow of the meeting and the part they need to play. Include donor information, objectives, meeting roles, and talking points, and tailor to the member of staff in question (short and sweet, or detail-oriented? Written or verbal? Both is ideal!) 

4. Prepare your donor 

A donor should never walk into an ask conversation without knowing that some kind of request is coming. Plant the seeds early and set expectations by framing your meeting beforehand. Clarity builds trust, and trust underpins every donor relationship. 

5. Embrace the timeline 

Treat the ask as a process, not a single moment. Nurture the relationship, allow time for reflection and discussion, and use different touchpoints – be they meetings, introductions to members of your institution, events, or other engagement opportunities – to explore values, motivations, and readiness. This process isn’t always linear, and you may need to pause, repeat, or pivot along the way. Ideally, your ask should feel like the natural next step.   

6. Ask to ask – at every stage 

Today’s major donors often want to ‘co-create’ a project with you which they will then fund. Asking for their input, feedback and expertise along the way is a way of respecting their availability to contribute more than money. For example: ‘Can I share the project budget with you? I’d like to make sure you think it’s reasonable. Could you see yourself getting behind it?’ 

7. Ask in the right way 

To decide how to ask, start with what’s in your toolkit. Do you have proposal templates that are easy to personalise, an impactful Case for Support that’s ready to go, or a Principal/Vice-Chancellor who loves to be involved? Then consider your donor – some will prefer a detailed proposal they can take away and digest, some will value a discreet one-to-one conversation, while others may respond best to an ask from senior leadership. Tailor your approach to what works well for your donor and for your institution. 

8. Expect objections 

You will get objections – be ready! Often they’ll be linked to external factors such as VAT, personal reasons, or the gift/project itself. Try to anticipate and address objections in advance, and remember they can arise at any stage of the cultivation process, so it’s helpful to always have objection-handling strategies in your back pocket. 

9. Handle with care 

Address objections with care, curiosity and creativity, using four key steps:

• Acknowledge the objection

• Ask questions to clarify it (consider asking to ask questions so the donor doesn’t feel grilled)

• Reframe your direction

• Continue: whether that means continuing with cultivation, pausing and addressing the concern, or finding a new avenue for partnership. 

10. Own your confidence 

Finally, do what you need to do to feel personally confident in your ask conversations. Know your objectives, do your research, bring your passion for the cause, and remember that you’re inviting someone to make a meaningful difference – and that’s a wonderful thing. 

At Cairney & Company we work with lots of fundraisers to help them make confident asks, get the most out of their relationships, and take their fundraising to the next level – from workshops, to coaching, to engaging with leadership.  

If this sounds like something that might help you or your team, book in a call with Annarosa and chat it through! 

‘The ask is the tip of the iceberg’