The Art of the Ask

Put Your Investors to Work

You did the hard work getting great investors into your company. Why wouldn’t you spend just as much time putting them to work for you?

Investors want to prove that they can add value—in fact, they need to. Investors that last for decades win based on relationships and reputation. Positive interactions snowball, leading to more connections and more deal flow. Use this to your advantage.

Not all asks are created equal.  Learning how to level up your investor asks will not only save you time, it will unlock the full power of all your key stakeholders.

Help Them Help You

For better or for worse, how you ask for help goes a long way in determining what type of response you’ll get. Your investors want to help, but they’re constantly context switching from one opportunity or portfolio company to the next. Consider how you can help them take action in the five minutes of downtime they have before their next Zoom meeting. Be specific and make it turnkey.

Be Specific

You want to make your ask as specific as possible. Remember: your individual ask is likely one of many responsibilities that an investor has, so the more you can empower them with specific information, the quicker they can assess whether they—or someone at their firm or in their network—can help. If an investor has to clarify what you meant by an ask, it’s probably a sign you didn’t appropriately context-load them ahead of time. Avoid back-and-forth. Take the time to include everything necessary in the first outreach so your investors can get right to work.

Consider a common example of asking for potential customer intros.

  • Don’t: Ask for an intro to Acme Corp.

  • Do: Ask for an intro to the VP, Digital Marketing Analytics at Acme Corp, who you happen to know your investor is connected to on LinkedIn.

As a B2B entrepreneur, you’re not selling into a company — you’re selling into a specific org, department, segment, or persona at a company. If you can’t identify who that person is, then it’s unlikely your investors will be able to. Tell your investors why you’re targeting a specific person at a certain company and give them the background information necessary to be useful.

Make it Turnkey

Turn-key means actionable with all the necessary information at hand. In other words, it’s “forward-able”—and while it may seem silly, details make the difference. You want to reduce the work required on the other end as much as possible and while trivial, re-formatting an email is still work.

What does this mean in practice? Let’s use an example of a talent ask, something almost all founders need help with at some point. 

  • Don’t: Ask for intros to full-stack engineers.

  • Do: Ask for intros to full-stack engineers with a specific background. Provide a forwardable link to a job description.

  • Extra credit: Find 2-3 Linkedin profiles of dream candidates in your investor’s network. Ask the investor if they’d be willing to reach out to those candidates on your behalf, and then send individual, forwardable emails for each of them including context on the company, role, and why you’re interested in meeting. 

Doing this right requires much more upfront work, but that extra effort is the difference between getting something done and having another ask die on the vine.

Competitive Spirits

Investors are competitive. Keep that in the back of your mind as you structure how and where you make your asks. Give credit where credit is due—give shout-outs to investors who have responded and were helpful to asks. There’s a difference between needlessly creating competition and sparking investor’s natural desire to go above and beyond; choose the latter.

Quaestor's Investor Update tool allows you to centralize all of your updates and asks by bringing your investors into a single, shared space where you can manage who is actually being helpful from a simplified vantage point. This tool helps you track and monitor your asks, but you still need to make sure the asks are effective. 

If you’re sending investor updates with email today, book a time here for a 1:1 onboarding session for your next investor update. We’ll discuss best practices, help you craft your narrative, and share templates!

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