The Art of Making Clear Asks: A Guide for Startup Founders

As startup founders navigate their journey, the ability to make clear, effective asks becomes a crucial skill. Whether seeking investments, partnerships, or mentorship, how you frame your request can make the difference between success and silence.

The Three Types of Asks

• Quick Ask (1-2 minutes): Simple, straightforward requests that require minimal time investment. Example: "Would you mind making a quick intro to [specific person] via email?"
• Five-Minute Ask (3-10 minutes): Requests requiring brief consideration or action. Example: "Could you review this one-page pitch deck and provide your top three observations?"
• Long-Term Ask (Extended engagement): Substantial commitments requiring ongoing involvement. Example: "Would you be interested in joining our advisory board, meeting quarterly for strategic guidance?"

Elements of a Clear Ask

• Be Specific and Definitive: State exactly what you need, when you need it, and why it matters - context matters here.
• Minimize Work for the Recipient: Provide all necessary context and materials upfront
• De-risk the Ask: Address potential concerns and demonstrate you've done your homework

Common Pitfalls to Avoid

• Vague Requests: "I'd love to pick your brain sometime" vs. "Could we schedule a 30-minute call next Tuesday to discuss our go-to-market strategy?" Bonus points: if you can provide material upfront for the meeting it gives the participant an opportunity to see the quality of how the meeting is going to go before the meeting occurs (they will be more likely to help you longer term).
• Incomplete Context: Making the recipient hunt for essential information
• Misaligned Time Expectations: Labeling a complex request as "quick" when it requires significant effort - you will blackball yourself from a lot of circles this way

Best Practices for Making Asks

1. Do your research first - understand who you're asking and why they're the right person
2. Present clear value proposition - explain what's in it for them. Not completely needed, but give a bigger picture - for those in the know they understand the early game.
3. Provide an easy out - respect their time and right to decline (if you hold this above your own you will make a lot of friends)
4. Follow up appropriately - be persistent but not pushy (this is an art form as well: I’ll do a blog post if you ask nicely on it)

Remember: A well-structured ask demonstrates respect for the recipient's time and increases the likelihood of a positive response. By being clear, concise, and thoughtful in your requests, you build stronger professional relationships and improve your chances of success.