The Fear of Asking for Money Isn't About Money Part 2: So What Do You Do About It?

By Lori Zoss Kraska, MBA, CFRE, Founder & CEO, Growth Owl, LLC, and Rob Kalwarowsky

Moving from fear to confidence when it's time to make the ask

Earlier this year, Rob and I wrote an article together called The Fear of Asking for Money Isn't About Money.

The premise was simple.  For many leaders, the discomfort around asking for money goes much deeper than the actual dollars.

It can be fear of rejection.  Fear of being judged.  Questions about our own value.  A lack of confidence in our sales skills.  Or simply the discomfort that comes with doing something we haven't done very often.

That article generated enough conversation that we decided to keep going.

During a recent podcast conversation, we tackled the natural next question:

If you know fear is getting in the way, what do you actually do about it?

Whether you're an association executive asking a company for a six-figure sponsorship, a nonprofit leader seeking funding, an entrepreneur raising capital, or a professional negotiating compensation, we believe the path forward starts in much the same place.

It starts with you.

1. Start With Yourself

When someone lacks confidence around asking for money, the natural response is often:

I need sales training.

Training can certainly help. The key is finding training, resources, and tools that meet you where you are. Someone with an operations or finance background who has rarely been responsible for generating revenue has very different needs from an executive who spent 15 years in B2B sales before becoming a CEO. That's why we believe the first step should be a simple self-assessment.

Where, specifically, are you getting stuck? Researching prospects?  Initiating outreach?  Getting meetings?  Having the conversation?  Making the actual ask?  Following up  Hearing no?

Each of these challenges requires a different type of support. Too often, sales training starts with:   Here's what you need to know.

We think a better place to start is: What do you need help learning?

Meeting people where they are matters, particularly for leaders who may have spent years believing they simply aren't "salespeople."

2. Start Small Enough to Succeed

Once you've identified the skill you need to build, give yourself achievable goals.

We've both seen leaders leave a workshop energized and ready to build a list of 50 prospects and contact all of them immediately.

Instead, start with five.  Research one company this week.  Spend an hour identifying people you genuinely want to build relationships with.  Make one introduction.  Have one conversation.  Small wins matter because you're building more than a pipeline.

You're building a habit.

I’ve often described this as building muscle memory. The more frequently you engage in business development activities, the more familiar they begin to feel. What once required a tremendous amount of emotional energy eventually becomes something you simply do.

Consistency builds confidence.

3. Ask What You're Actually Afraid Of

This is where Rob's work with leaders goes deeper.  The key is finding the root cause(s) of the fear.  So, when someone says they're afraid to ask, the next question is:

What are you afraid will happen?

Maybe the answer is rejection.  Keep going.  What does that rejection mean to you?  That you're not good enough?  That you don't belong in the room?  That your work isn't valuable?  That you'll look foolish?  That someone will discover you don't know what you're doing?

Those beliefs can quietly influence how we show up in a revenue conversation. They can also influence what we ask for.

I recently saw this while working with a group of experienced creative professionals. These were established professionals with impressive portfolios, successful campaigns, and industry recognition.

Yet some still struggled with asking for their full value.  The question underneath the pricing conversation went much deeper than: What should I charge?

It became: Am I worth asking for it?

That question requires a different kind of work.  A better pitch deck can't resolve questions about your own value.

4. Know Your Why Before You Ask

One of the best antidotes to fear is clarity.  Why are you asking for this money?  What becomes possible if someone says yes?  Who benefits?  What changes?

Rob encourages leaders to connect the ask to the larger mission they're trying to accomplish. That purpose creates internal motivation when rejection inevitably happens.

I take that "why" one step further in sponsorship conversations.

Why this company?

• Why should this particular organization care about what you're proposing?

• Where does your mission intersect with its priorities?

• What are you uniquely positioned to accomplish together?

  
  

Your organization's value will resonate differently depending on the company or decision-maker sitting across from you.

The work is finding the people and companies for whom that value matters. When you understand that connection, asking for money begins to feel more like inviting someone into an opportunity that makes sense for both of you.

5. Tell a Story That Matters to Them

Data matters.  Emotion does, too.

Rob uses storytelling in his own speaking and coaching because people make decisions through a combination of emotional and logical processing. A strong case combines evidence with a story that helps someone understand why the information matters.

Purpose-driven organizations have an enormous advantage here.  You already have stories.  The people you're helping.  The careers you're advancing.  The industries you're strengthening.  The communities you're changing.  You are closest to the work you're seeking to fund, which means you already know many of the stories worth telling.

The skill comes in packaging those stories in a way that connects with the decision-maker.

The story has to matter to the person hearing it.

A story that resonates beautifully with one audience may fall flat with another.

Before the conversation, research the person sitting across from you. Understand what they care about, how they communicate, and what they're trying to accomplish.

Then package your story accordingly. As we discussed on the podcast, the way your message lands with the other person matters tremendously.

6. Consider Leaving the Pitch Deck at Home

This one may make some people uncomfortable. For an initial 30-minute conversation with a prospective corporate partner, I often tells clients:

Bring nothing. 

Have a conversation.  Ask questions.  Listen.

Demonstrate that you understand your organization, your industry, and the opportunity well enough to have a thoughtful discussion. There will be time for a pitch deck later if one is needed.

Decision-makers want to work with people who understand what they're doing. A genuine conversation can demonstrate authority in a way that marching through slides sometimes cannot.

Something interesting often happens when you remove the presentation.

People relax.

The meeting starts to feel like two people exploring whether there's something worth pursuing together.

That is often exactly what a strong first meeting should accomplish.

7. Learn to Appreciate "No"

Nobody likes rejection.  I like to remind clients that no is your second-best answer.  A clear no gives you information. Maybe the budget isn't there.  Maybe the timing is wrong.  Maybe the decision-maker isn't interested.  Maybe there simply isn't enough alignment.  Repeated rejection can provide even more information.  

• Your message may need work.  

• You may be approaching the wrong people.

• Your value proposition may need refinement.

  
  

Rob experienced this himself when he initially marketed leadership coaching to audiences that either lacked the budget or organizational influence to purchase it. The rejection eventually helped him refine whom he should be serving.

That's why rejection can become useful data. And the more no's you experience, the better you become at distinguishing between this isn't right for them and something about my approach needs to change.

There's another important point:

No doesn't necessarily mean no forever.

Budgets change.  Leadership changes.  Priorities change.  Timing changes.

A relationship handled well after a no can become an opportunity a year later.

8. Make the Ask, Then Let It Land

This may be the hardest part.  You've done the research.  Built the relationship.  Made the case.  Asked for the money.  Now you want the answer. That desire for an answer can quickly turn into frequent follow-up and unnecessary pressure.

There's a difference between professionally managing a business development process and trying to force an outcome. Once you've clearly articulated your value and why the opportunity makes sense, give the decision-maker room to think.

People can sense the energy we bring into a sales conversation. Confidence and desperation land very differently.

Confidence says:  I believe in what I'm offering. I believe there's alignment here. I've made the case. Now I'll give you space to decide.

As I said during my guest conversation on Rob’s podcast, sometimes you have to let it land.

The Ask Gets Easier With Practice

That's ultimately where our second conversation brought us. Getting better at asking for money involves much more than developing sales skills.

It's about understanding your value. Knowing why the work matters. Learning how to communicate that value to the right people. Becoming more comfortable with rejection.

Building confidence through repetition.

And trusting yourself enough to make the ask while allowing the other person the space to respond.

Whether you're asking for a sponsorship, an investment, a donation, a contract, or a raise, some vulnerability will always be part of the process.

The goal is reaching the point where fear no longer gets to make the decision for you.

Know your value. Know your why. Make the ask.

Then let it land.

Lori Zoss Kraska, MBA, CFRE, is the founder of Growth Owl, LLC as well as a national expert in corporate sponsorship strategy and a fractional CSO in the area of revenue generation. With more than 25 years of experience in corporate sponsorship, revenue generation, and executive advising, she helps organizations and entrepreneurs secure transformational corporate support.  She's an Amazon best selling author, speaker, and trusted advisor.  Contact Lori at lori@thegrowthowl.com 

Rob Kalwarowsky is a world-renowned executive coach, author of best seller Capitalizing on Chaos, and keynote speaker.  Rob’s TEDx talk is an international hit with over 315,000 views.  With a client roster including Fortune 500 executives, entrepreneurs, and Olympic Gold Medalists, Rob only works with top performers who want to dig into the work so they can achieve huge results.  Rob has foundations of high-performance as he graduated from Massachusetts Institute of Technology (MIT) and he was a 3-time Academic All-American in NCAA Water Polo.  Contact Rob at rob@robkalwarowsky.com