Choosing the right tool: asking for a meeting

So, you've got your pitch prepared, and you've mustered your courage, and you've shellacked your ruefully thin skin so that you won't be terribly damaged by inevitable rejection (as one of my first fundraising mentors was fond of saying - if no one is telling you no, you're not asking enough people.)...

Go forth and ask for some meetings!

And for some people, that brings them to a screeching halt.  Break it down further.  

OK.  So, you've got a lot of choices when in comes to the mode of communication you'll be using.  How do you sort through those?

Let's start with some reasonable criteria you can use to select the right tool from your toolkit.

1. You're likely to be limited by the contact information you have for your prospect.  If you only have a phone number or a mailing address, well, you use what you have, and don't look back.
2. What feels natural/most comfortable for you?  Are you the kind of person who would rather have the immediate give and take of a live conversation, where you can tell jokes and gauge the response (instead of being terrified they'll be misread in an email), where you can purr and pluck your voice to make sure your message stands out?  Pick up the phone.  Are you terrified of accidentally getting caught like a deer in headlights unless you have time to write everything out?  Email sounds good.  It's a great idea to default to whatever method lets you relax and shine.
3. On the other hand, you need to balance that with what you know about your prospect.  Take every person as an individual, of course...but if you're dealing with a Millenial whiz kid who's made a couple of fortunes already as a tech entrepreneur, email is probably your best bet, if not some other kind of electronic medium.  If you're approaching an old school, noblesse oblige philanthropist in their late 80s, a handwritten note on good stationery might be the way to go.
4. What's your time horizon?  Let's say you live in Boston and have to be in New York a week from Thursday, and you're looking to meet with a couple of people while you're there.  The US Postal Service is not going to do it for you.  Let's say you're looking to connect with a Forbes List billionaire who has a home two blocks from your headquarters, and it's less about when and more about making the best possible impression.  That's a great time to take the long view and get your board member's spouse's great aunt (who plays bridge with said billionaire on Wednesday afternoons) to finagle an introduction.  (Obviously, those kind of machinations do not turn on a dime!)

So what should you have in your toolbox, anyway?  For starters (and I've gone with bullets instead of a numbered list, to help you remember that I'm not listing these in any hierarchy...you have to decide which is best for any given situation):

• Email.  Useful and commonly accepted.  Often has a very swift turnaround. Spam filters can be a hazard.  Keeping it short is *essential* - no one scrolls down too far for someone they don't know.  You can include links, which, if done right, can be very engaging (without having to write more in that initial email).  If you don't have a formal record-keeping system where you save and categorize all your outgoing communications, you now have a record of what you sent to the prospect.
• Snail Mail.  Can help you stand out - people don't get a whole lot of actual person to person mail anymore.  Has to be opened and read...so you have to make sure not to look like a piece of junk mail.  You can send brochures or one-pagers or other pretty/graphic items that help tell your story, or even tchochkes...IF you think it helps your case.  You can type a longer letter or send a handwritten note for greater personalization.  Takes a couple of days at best to arrive.  Much harder to get someone to send a letter back than to click "reply."  Think about whether to mail to someone's home or office (what message does that send?).
• Social Media sites (LinkedIn and Facebook are the two big ones currently; there are others and fashions will evolve - this advice remains constant.)  Many of the advantages of email, but with the added benefit that the recipient can immediately see that they have x friends who already support you.  Usage is less normalized than email - e.g., some folks may be on Facebook 24/7, while others have virtually forgotten that they have the account and their inbox is not set up to alert them that they have a new message.  Some folks think Facebook is a place where they socialize with friends rather than interface with the public.  Some folks treat LinkedIn as a place for their business networking...rather than a place where folks might find them and solicit funds.  Note: a request for a meeting should always be done in a private message, even on these sites.  DO NOT place such a request on a public forum, even on one of these sites.  It would be terrible etiquette.  Potential exception: Twitter.  If you've developed a back and forth with someone on Twitter, go ahead and tweet an invitation as an extension of your conversation, but remember that it's not a private chat and adjust accordingly.  But it might be better to form a relationship via twitter and then email.
• Phone. Patented in 1876.  Pretty useful since then and still a great way to reach out and touch someone.  No worries about someone misreading the tone of your writing.  You can prepare all you want, but you can't be entirely scripted the way a written invitation is.  You can adapt on the fly as you talk to the person.  Very immediate.  You need to be equally prepared to have a conversation or to leave a message.  
• In person.  No, this isn't a case of scheduling a meeting to make a meeting...quite.  Let's say you see someone at a cocktail party - you can ask them for a meeting, get them to say yes, and arrange to call their office on Monday to figure out the details.  And if you think that's an approach that will work, this is a great long play - getting in the same room with someone for the purpose of catching their attention long enough to get them to agree to an actual "first date."  For folks who are (or are virtually) public figures, this might be the most successful way to open that door.  Biggest con: these are hard to manufacture/navigate, and you've got the additional pressure of a potential rejection happening real time, in your face, that you must deal with gracefully. 
• Friend of a friend set-ups.  If you can have someone who knows you and your organization open a door for you, that's almost always the best way to introduce yourself and ask for that first meeting.  But most of the time, that'll take the form of an introduction at an event you're both at, or an email of introduction where you're cc'd (and then need to follow up directly), or your friend giving you contact information for your prospect and allowing you to use their name ("Jane Doe told me I should give you a call because you might be interested in what we do...").  Some times, that friend will arrange a meeting for you...could be one on one, most commonly is a lunch or coffee where that friend will be present along with your prospect.  Going back to our dating metaphor, this one is definitely matchmaking.  It takes as long as it takes.  And for better and worse, you hitch yourself to the reputation of your matchmaker (could be great, but not everyone with access to wealthy philanthropists is liked by them...tread cautiously, using your gut).  Some matchmakers are terrible meddlers (if they're at the meeting, some will insert themselves in the conversation - again, for better and worse...depends on the person!).  You have to really be on your game and exceptionally charming at that meeting, because unlike the rest of these approaches, where the person has said yes because of something you have done, they may only be at that meeting because of social pressure and obligations to someone else entirely...so you've got more work to do to win them over!

Not on the list:

• Texting.  For the moment, this still seems too informal in most scenarios, for a first point of contact with someone you've never met.  How do you introduce yourself and ask for a favor in 140 characters?  But younger generations are eschewing email and phone for texting, at least statistically...so think about using texts if it makes sense, but only in connection with another method.  For instance: go "speed-dating" at a young philanthropists conference, and secure both phone numbers and permission to be in touch for a coffee date "some time soon."  Then it might be OK to text a followup the next day and suggest a meeting.  Just make sure it makes sense and feels like the best way to communicate...novelty alone isn't necessarily the best way to stand out.

What are some of the most effective ways you've asked for meetings with cold (or at least cool) prospects?