Don’t ask strangers to…
1. Acknowledge that they received your email
Electronic return receipts are a thing of the past, and I know many people who interpret them as a sign that you (a) are paranoid, (b) have an inflated sense of your own worth, or (c) have just emerged from a 20-year coma and are unaware of mailer-daemons and delivery status notifications. If your message goes unanswered, you can always resend it a couple weeks later.
2. Share your content on social media
What if they don’t like your material? An explicit request to circulate puts people in an awkward position: they can say no and look rude, or drop the ball and look disorganized. It’s more polite to just send them your content along with a sentence about why it’s up their alley, and end it there. If they like it enough, they’ll share it—and they’ll do it more enthusiastically, because it’s based on intrinsic motivation rather than obligation.
3. Provide feedback on something you’ve created
If you’re seeking input on a product, service, technology, document, or idea, it’s an awful lot to ask a stranger to engage with your work and comment on it. Whereas feedback requires a lot of effort, advice can be much less time-consuming. Try asking for guidance on a specific question or dilemma that you’re facing, and you’ll be more likely to get a response.
4. Jump on a call today or tomorrow
If you’re asking the favor, the onus is on you to be flexible. Ask if they might be willing to talk sometime in the next month or two, and let them suggest some times.
5. Name some times for a meeting
It’s a red flag when people feel entitled to a face-to-face conversation. A friendlier option is to ask strangers if they’re willing to meet, or if there’s a more convenient way for them to communicate with you.
6. Introduce you to specific people in their networks
It’s not fair to ask people to put their relationships on the line for someone they don’t know. Instead, ask if they know anyone who might be a good source of insight on a particular topic, and they may suggest a person who they feel comfortable connecting.
After strangers respond to your initial message, don’t…
7. Email them every day—or even every week
Stalker alert! People sometimes interpret a polite reply from a stranger as an offering of friendship. If you’re tempted to reach out too regularly, try saving your points in a draft email, and then prune at the end of the month. Intermittent reinforcement can be a powerful thing.
8. Immediately introduce them to someone else
This can come across as using your newfound access to gain status or influence with the third party. The safe bet here is to simply ask for permission first: “I thought you two might enjoy a chat for the following reason. Are you interested in connecting?”
9. Invite them to collaborate
You just proposed marriage on the second date. Try having a dialogue first, and explore whether working together might prove mutually beneficial.