Building Software Together

Chapter 5: How to Talk People Into Things

Persuading people to do things is almost as essential to teamwork as running a good meeting. These simple rules have served me well.

If you have to talk someone into something, odds are that they don't really want to do it. Respect that: it's almost always better in the long run to leave some particular thing undone than to use guilt or any underhanded psychological tricks that will only engender resentment.
Be kind.
I don't know if there actually is a book called Secret Tricks of the Ninja Sales Masters, but if there is, it probably tells readers that creating a sense of obligation or guilt increases the odds of a sale. That may work, but it only works once and it's a skeezy thing to do even then. If, on the other hand, you are genuinely kind and help other people because it's what good people do, you just might inspire them to be good people too.
Appeal to the greater good.
If you open by talking about what's in it for them, you are signalling that they should think of their interaction with you as a commercial exchange of value to be bargained over. Instead, start by explaining how whatever you want them to help with is going to make the world a better place, and mean it. (If what you're proposing isn't going to make the world a better place, propose something better.)
Start small.
Most people are understandably reluctant to dive into things head-first, so give them a chance to test the waters and to get to know you and everyone else involved in whatever it is you want help with. Don't be surprised or disappointed if that's where things end: everyone is busy or tired or has projects of their own, or maybe just has a different mental model of how collaboration is supposed to work. Remember the 90-9-1 rule and set your expectations accordingly.
Don't build a project: build a community.
There is a softball team here in Toronto that never actually plays games: their practices are just an excuse for members to enjoy each other's company. You probably don't want to go quite that far, but sharing a cup of tea with someone or celebrating the birth of their first grandchild can get you things that no reasonable amount of money can.
Establish a point of connection.
"I was speaking to X" or "we met at Y" gives them context, which in turn makes them more comfortable. This must be specific: spammers and cold-callers have trained us all to ignore anything that starts, "I recently came across your website…"
Be specific about what you are asking for.
People need to know this so that they can figure out whether the time and skills they have are a match for what you need. Being realistic up front is also a sign of respect: if you tell people you need a hand moving a few boxes when you're actually packing up an entire house, they're probably not going to come back.
Establish your credibility.
Mention your backers, your size, how long your group has been around, or something that you've accomplished in the past so that they'll believe you're worth taking seriously.
Create a slight sense of urgency.
"We're hoping to launch this in the spring" is more likely to get a positive response than "We'd eventually like to launch this." However, the word "slight" is also important: if your request is urgent, most people will assume you're disorganized or that something has gone wrong, and may then err on the side of prudence.
Take a hint.
If the first person you ask for help says "no", ask someone else. If the fifth or the tenth person says "no", ask yourself if what you're trying to do makes sense and is worth doing.