Stop Perfecting Your Pitch Deck. Start Learning How to Ask.

If you watch “Shark Tank,” you’ve seen founders ask investors for cash in exchange for a bite of their business. But those rehearsed polished pitches that have come to epitomize entrepreneurship in popular culture represent a sliver of the requests founders make while launching new ventures.

“Asking is not just about requesting resources,” says Darden professor Saras Sarasvathy, an authority on high-performance entrepreneurship. “Every entrepreneurial activity — from testing ideas and getting legal advice to finding customers and reliable suppliers — depends on asking.”

Sarasvathy defines an ask as an “entrepreneurial interaction consisting of three components: an asker, an askee, and the possibility of a venturing relationship.” Her research shows that a founder’s ability to ask, and to do it well, is not just another skill. It is the core competency that makes everything else possible.

Unfortunately, novice entrepreneurs struggle with asking and tend to default to conventional but less effective approaches. “They often focus on building pitch decks and writing business plans because business schools emphasize those methods,” says Sarasvathy.

The good news is that asking is a learnable skill that improves with practice. To help founders develop this capability, Sarasvathy’s longtime collaborator and visiting research professor at Darden, Tiago Ratinho, along with Heidi Neck, Professor of Entrepreneurial Studies at Babson College, wrote “Dare to Ask!” published in Developing Entrepreneurial Mindsets, Ideas, and Opportunities: A Guide for Educators. Their article offers practical tips on what to ask for, whom to approach, and how to frame requests effectively.

Start With What, Not How Much

When aspiring entrepreneurs think about resources, they typically jump straight to money. But this narrow focus can paralyze progress, notes Ratinho. Before you've validated your concept, built relationships with potential customers, or understood your market, obsessing over funding makes little sense.

In “Dare to Ask!” Ratinho and Neck give examples of early actions of successful founders that didn’t revolve around asking for money.

Reed Hastings of Netflix didn't raise millions before testing his concept — he mailed DVD packages from various California locations to see which ones survived USPS shipping. Joe Gebbia and Brian Chesky launched Airbnb with a simple webpage listing their own reconfigured living room. Stanley Tang validated DoorDash by going door-to-door in Palo Alto, talking to small business owners about unfulfilled delivery orders.

None of those critical early steps required outside funding or any funding at all. What those entrepreneurs needed early on was information, feedback and access.

What to Ask For: Focusing on Specific Relation-Driven Resources

According to Ratinho, your early stage asks should focus on four categories of resources:

Transactional resources with low commitment, which include advice, information and feedback. These are one-time interactions that don't require the provider to have skin in your game. Ask a designer about prototyping options. Request a lawyer's perspective on intellectual property basics. Seek opinions from potential customers about the problem you're solving.

Ongoing support without major commitment, which encompasses mentorship, coaching and regular guidance. These relationships provide sustained help without requiring the provider to commit significant resources. University incubators, industry mentorship programs and advisory networks often fall into this category.

Transactional resources with high commitment, which include formal investments, grants and subsidies. Here, providers commit substantial resources, but the relationship remains primarily transactional. Angel investments and government grants fit this category.

Ongoing relationships with high commitment, which represent the ultimate goal: paying customers, reliable suppliers, co-founders, and long-term partners. These stakeholders have both invested resources and established, ongoing relationships with your venture.

A balanced ask-list should span all four categories, says Ratinho. If you're only seeking low-commitment resources, you're likely staying within your comfort zone. If you're disproportionately focused on high-commitment asks, you may be moving too fast for your stage of development.

Whom to Ask: Map Your Network Strategically

Once you've identified what you need, the question becomes: whom should you ask? This requires honest assessment of your network across three levels: first-order connections, second-order connections and strangers.

First-order connections are people you know directly — family, close friends, classmates, current colleagues, and others in your immediate circle. These relationships offer the easiest access but may lack the specific resources you need.

Second-order connections are people your first-order contacts know and could realistically introduce you to. This is where your network becomes exponentially more valuable. That former professor might know the exact manufacturing expert you need. Your college roommate's parent could work in your target industry.

Strangers are people completely outside your network. While reaching out to strangers feels intimidating, many successful entrepreneurs built their networks from scratch. The key is being strategic about which strangers to approach and how.

Take an honest inventory of your ask list. If most of your potential askees are strangers or celebrities unlikely to respond, you need to either adjust your asks to match your network or commit to systematically expanding your connections.

Consider reframing your needs. Instead of “I need a trademark lawyer” (which might require reaching out to a stranger), think “I need legal advice on trademarks from law faculty at my university” (which could tap into second-order connections). Rather than “I need a software engineer” (generic stranger), try “I need coding help from recent graduates in computer science” (accessible through alumni networks).

How to Ask: Master the Art of the Open-Ended Ask

How you frame your request matters as much as what you request and whom you ask. Most aspiring entrepreneurs make a critical mistake: they structure their asks as closed yes-or-no questions that box in both parties.

Consider a typical pitch ending: “Will you invest $10,000 in our company?” This approach makes several problematic assumptions. It assumes the listener wants to be an investor. It assumes $10,000 is the right amount. It assumes cash investment is the best form of help. Most importantly, it forces a binary decision that's easy to decline.

The alternative? Use open-ended questions that invite dialogue and broaden the range of possibilities. For example, asking, “What would it take for you to help me build this prototype?” shifts the dynamic entirely by avoiding a simple yes-or-no response and prompting a more constructive conversation.

This approach works for three reasons. First, it expands the opportunity space. The person in front of you might not want to invest $10,000, but they could connect you to a makerspace, introduce you to someone who could redesign your product more cheaply, or offer resources you haven't considered.

Second, it eliminates assumptions. You might think someone wants equity returns when they're actually more interested in lasting social impact. You might assume someone has no relevant connections when they're connected to exactly the right people.

Third, it starts a dialogue rather than triggering a transaction. Instead of negotiating terms you've proposed, you're exploring how you might work together on terms they find acceptable.

Other effective open-ended phrases include:

- “How can I make this a win for you?”

- “What hoops do I need to jump through to get you on board?”

- “What would you do if you were in my shoes?”

- “What are possible ways we could work together?”

Take Action Systematically

Understanding these principles is valuable, but improvement comes through deliberate practice. Treat asking as a skill you develop through repetition and feedback, just as athletes improve through drills.

Start with low-stakes asks to build confidence. Request informational interviews from second-order connections. Ask classmates for feedback on your pitch. Seek advice from professors or program coordinators. Each successful ask builds your comfort level for more challenging requests.

Set concrete targets for network expansion. One approach: attend four networking events per year, send ten thoughtful LinkedIn invitations monthly, and strike up conversations with strangers in appropriate settings. The specific numbers matter less than creating a consistent practice.

Focus on actionable outcomes. Rather than collecting business cards or LinkedIn connections, aim to secure specific next steps from each conversation: an introduction to someone specific, feedback by a certain date, or agreement to reconnect after you've completed a particular milestone.

Identify multipliers in your network — individuals with extensive connections and high credibility who can amplify your reach. These might be successful alumni, well-connected mentors, or active community leaders. Building strong relationships with a few multipliers can open doors to dozens of valuable connections.

The Path Forward

Becoming comfortable with asking doesn't happen overnight. You'll feel awkward. You'll hear “no” frequently. But each ask provides immediate feedback and builds your skill.

Remember that entrepreneurs who excel at asking become better entrepreneurs overall. It's through asking that they attract mentors, enroll partners, win customers and secure financing. The ventures that succeed aren't necessarily those with the best initial ideas — they're often those whose founders most effectively mobilized resources by asking for what they needed.

“Your next step is simple,” says Ratinho. “Identify your five most immediate needs, determine whom to ask, and craft open-ended requests that invite dialogue. Then make your first ask today.”

The only way to get better at asking is to start asking.

You can find more practical insights about asking in “Dare to Ask!” a chapter written by Tiago Ratinho and Heidi Neck in Developing Entrepreneurial Mindsets, Ideas, and Opportunities : A Guide for Educators.