Making the (Career) Ask…Advice from a Former Fundraiser
It's safe to say we've all faced those pivotal moments in our career, from asking for a raise or promotion, to negotiating your job offer, or perhaps asking for investment capital for that big idea. Whatever the ask, it's typically high-stakes, potentially career-transforming, and usually completely nerve-racking.
As a former major-gift fundraiser for over 20 years who planned, executed, and closed six and seven-figure gifts, I'm here to share the key factors that go into a successful ask. But wait — you might be wondering what fundraising has to do with career negotiations? The answer is simple: an ask is an ask, regardless of the subject matter.
Read on to learn how to utilize connection, authenticity, and impact to create career asks that cut through the noise and position you above the rest.
The Three Pillars of a Powerful Ask
1. Connection: The Outline That Holds the Ask Together
Let's face it. If two candidates are equally experienced and deserving, and imagining a perfect world where all inequities, bias, and barriers have been removed, there is still one component that gives a person the edge: connection. The person who takes the extra steps to create a meaningful relationship with the decision maker is the one who wins.
2. Authenticity: The Secret Sauce That Differentiates the Ask
This is the intangible element and the quality that makes people lean in, trust you, and root for you. Authenticity can't be faked, but it can be cultivated through preparation, self-awareness, and genuine gratitude for the opportunity in front of you.
3. Impact: The Main Ingredient
Your track record of results is the backbone of any ask. Without it, connection and authenticity alone won't close the deal. Impact is your proof and it needs to be front and center.
How to Craft Your Ask:
Start with no surprises
The first rule of any successful ask is to never surprise the decision maker. Let them know in advance:
That you'd like to have a conversation
Why you're requesting the meeting
Generally what you'd like to discuss
This gives them time to prepare, and signals that you're thoughtful and professional.
Lead with the bigger picture
Open by sharing where you want to be and the ambition driving you forward. Nobody will fault you for expressing your professional aspirations. Most importantly, make sure you're translating your future goals into what success looks like for the team — the ROI of saying yes to your ask.
Highlight your wins
Your Impact is the heart of the ask. Come prepared with specific examples of:
Key projects you've led or contributed to
Measurable outcomes and results
Recognition, kudos, or milestones achieved
One tried-and-true method is maintaining a "My Wins" folder of your key projects, achievements, and praise. It's invaluable when crafting your ask and will serve you well in future interviews and negotiations.
When highlighting your impact, don’t forget to acknowledge the role they have played. You're not giving away credit for your work, but sharing that their support, advocacy, and guidance have been impactful on your professional journey.
Use the "Cool Kids" strategy
Another very effective strategy from the fundraising world is painting a picture of what others are already doing. This technique builds credibility, eases concerns about risk, and helps decision makers see themselves in your vision. For example:
Reference Fortune 500 companies that offer full relocation packages and highlight their employee satisfaction levels or low turnover rates
Share data on the cost savings companies realize by promoting from within versus filling a role externally
Always tie it back to your specific value by keeping it personal, relevant, and compelling.
Closing the Ask with Confidence
Embrace the silence
As uncomfortable as an awkward pause can be, embrace the silence that follows your ask. Allowing for that moment gives the other person time to calibrate, and it signals that your confidence level is high. Resist the urge to fill the space.
If the answer isn't yes
If you don't receive a definitive yes, express your ongoing ambition and desire to revisit the conversation. Something like:
"If it's OK with you, I'd really like to continue this conversation again when the timing is right. I genuinely value your guidance on this."
Ask if they'd be open to outlining the steps that would get you closer to your goal. It shows intention, maturity, collaboration and that you're in it for the long game.
Always say thank you
Last and definitely not least, remember to thank them. Thank them for their time, for their willingness to hear your presentation, and for their ongoing relationship. A handwritten note, email, or text goes a long way in reinforcing the authenticity of your ask and helps document the conversation for future reference.
The career ask is rarely easy. But with the right support and preparation, it becomes one of the most powerful tools in your professional arsenal. Visit Grateful Career Coaching’s Services page to see how we can support your next big career ask. You've done the work. Now go make the ask.
