The Art of Asking: How One Question Led to a $10,000 Check (On the Spot!)

I make ambition easy.

Hey Reader,
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Sometimes the best pitch isn’t a pitch at all.

When I ran marketing & fundraising for a non-profit, I once got $10,000 on the spot and it forever changed the way I saw self-advocacy.

I was meeting with a potential sponsor and for whatever reason, decided to drop the carefully crafted presentation about our non-profit and make the meeting all about them.

Here was the question I asked that gave me what I needed to tailor my ask by the end of the meeting:

“When you think about the gaps in your team and all of the goals that you currently have, if you could hire people to fill those gaps, what would they be doing?”

This question served multiple strategic purposes:

• First, it invited the sponsor to envision their ideal future state.
• Second, it revealed their current challenges and aspirations.
• Most importantly, it allowed me to position our organization’s services as a cost-effective solution to their needs – far more affordable than hiring full-time staff with benefits.

I shifted the conversation from what we wanted to what they needed, making them feel listened to in the process.

By encouraging them to dream big about their goals and then presenting our organization as a practical pathway to achieving those dreams, I transformed the dynamic.

The sponsor no longer saw my request for money as a charitable donation but as a smart business investment.

What seemed like a substantial donation to us appeared as a bargain to them.

Here are the key takeaways:

1. Prioritize listening over pitching. Your questions can be more powerful than your statements.
2. Focus on the other party’s vision and challenges. Help them dream big, then position yourself as the bridge between their current reality and their aspirations.
3. Demonstrate value in terms that resonate with their perspective. When you can show that your ask is actually an investment that saves them money or resources, you’ve created an irresistible proposition.

Whether you’re seeking funding, closing a sale, negotiating a salary, or even just interviewing, these principles can transform your approach and your results. It also feels a lot less awkward.

Sometimes, the most powerful pitch isn’t a pitch at all – it’s simply asking the right question.

Now go get paid 🤑

x Claire
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In this week’s newsletter:

✍️ Really Good Work Advice: Get Ahead Without Getting Burned

🎧 Podcast: How to Get the Raise You Deserve

📝 Steal this script: How to answer the interview question, “What excites you about this position?”

🗣️ Join the convo: Hate selling yourself? This one’s for you.

How to Get Ahead Without Getting Burned

An excerpt from last week’s edition of Really Good Work Advice,

a digestible deep dive into what makes a good work-life.
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The summer I turned sixteen, I was a Senate Page, a kind of glorified gofer whose main tasks included running errands, fetching water, and setting up lecterns. I was technically assigned to Senator Ted Kennedy but any Democrat who needed assistance, I was theirs. We mostly loitered on the Senate floor, ready to spring into action at the drop of a hat (or more accurately, the wave of a hand), and we cherished our station as the bitches of the libs.

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I have many formative memories from that time, but one stands out among the rest. It shaped so much of my worldview on not just politics, but office politics and gave me a taste of what it takes to be a woman at work. It was this: the female Senators (of which there were very few), were DYNAMOS.

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But perhaps not in the way one might’ve expected. They were quiet dynamos.

Because I had a front-row seat (literally), I was privy to covert conversations, watching as they sidled up to one another; things were whispered, then a smattering of laughter, and finally, a shaking of hands.

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Here’s what stood out: they made the men feel listened to. In what they said but also what they didn’t: their body language, their laughter..they didn’t have the luxury of bulldozing their agendas through, so they had to deploy a special kind of charisma.

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They truly personified the saying, “Ginger Rogers did everything Fred Astaire did, but backward in heels.”

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You might be thinking, “Claire! What a terrible message! Are you suggesting that to get ahead, we have to be charismatic?!”

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Every single successful person, regardless of their gender, has to be charismatic. However, the way that women play the game can’t always be according to the same rules, otherwise, we’ll be burned.

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Known as the double bind, women can be penalized if we act outside our expected norm; i.e. accommodating or nice. This of course puts us in direct conflict with getting ahead: how can we advocate for ourselves without seeming self-centered?

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Here’s the good news, if done the right way, these things don’t have to be mutually exclusive. What you want doesn’t have to be at odds with what someone else wants. Strategy and authenticity can co-exist and multiple agendas can be married.

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It may take some dancing backwards in heels but when you master the moves, it feels so 👏 damn 👏 good. Here’s how.

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“What excites you about this position?”

From the Get Hired Dashboard, your job search command center with scripts, tips, and templates.
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💫 Pro-Tips:
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• Focus on how your existing strengths align with the role’s challenges
• Reference specific findings from the research you did on the company
• Emphasize what you can contribute rather than what you’ll gain
• Example: “I’ve developed expertise in [specific skill], and I’m excited to apply that to [company’s specific challenge or project]”

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Here’s an example a Product Manager Role at Spotify might use:

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“What really excites me is the opportunity to tackle Spotify’s podcast discovery challenge. In my current role, I’ve developed a recommendation engine that increased user engagement by 45%, and I’ve been following your recent acquisition of AI startups focused on audio recognition. I’m particularly intrigued by the challenge of helping listeners discover niche content that matches their interests. Having led personalization projects for both music and video content, I believe I can bring valuable insights to how Spotify approaches podcast categorization and user experience design. I noticed in your recent engineering blog post about the challenges of podcast metadata – this is an area where I’ve developed specific expertise in implementing automated tagging systems.”

How to Get the Raise You Deserve
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“I’ve Been Stuck in the Sam… Jan 30 · Money Rehab with Nicole… 37:33   ​

In this conversation, I share the exact language you should use when negotiating a compensation package at a new job or a raise, what perks you can ask for if a company can’t afford the salary you want, and many more tips to help improve your work, wealth and worth.
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PS Interested in being coached by me? Book a free exploratory call here!​

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Hate “selling” yourself? This one’s for you.
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You’re going about it all wrong.
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Instead of looking at it as self-promotion, see it as SERVICE promotion 🤯
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There are people out there who desperately want you. They want to hire you. They want your product. They want your services, and they will never get help if they don’t know that you are there.
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And so everything that you put out there, it’s not so much about, here’s why you’re great, but it’s, here’s how I’m going to help you. For example, a lesson that you’ve learned that they can take with them.
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What this boils down to is relationship building. Whether it’s with a customer, a client, or a company. A relationship is built on the foundation of trust and how do you build trust?
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By showing who you are and what you’re capable of NOW.
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​So every time that you put yourself out there, reflect on: how do I bring value to the other person? ​
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Not only will the experience feel a lot less 🤮, you’re going to get a lot more out of it. Tell me what you think! 👇

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x Claire I help you reach success without self-sacrifice. Learn more here.​

PS Want to reach 50k people and support my work? It’s easy, sponsor this newsletter! ​