I don't think I answered one question very well, though: How do you convince the boss?
I don't have a short answer. I don't KNOW a short answer. I only know a longish answer, but it's foolproof.
For the first 10 years of my consulting life I was a partner (the copywriter) in a small marketing agency: direct mail, PR, ads. Our very first client -- a medical practice -- taught me an extremely important lesson: you have to DOMINATE opinionated people, or they will not let you do what you feel is best.
The question posed in the session was: how do I convince the boss? But the REAL question is maybe: how do I, as a self-described professional, get to do what I'm learning to do?
I'll be blunt so I'm not misunderstood: you have to know SO much about how to get good and improved results that it silences every untrained opinion in the room. There's NO easy, alternative route that I know. There's no "just add water" and your boss likes what he's hearing.
Our method -- and we were eventually a successful agency winning international awards opposite competition from Disney and Boeing -- was to go in and LISTEN. Listen until the client had said everything they had to say. Let the silence ring.
Then start taking over, slowly, with smiles and with zero aggression. "I like your idea." Always start criticism with a compliment. "But there's some new research on that that could effect sales. May I explain?" BY ALL MEANS was the usual response from the sane (that did not describe all our clients by a long shot).
For the first few years we got push back. But I was secretly following the advice of a major guru to consultants.
He'd told me, "If you read one hour in your field every day, within a year you'll be an expert. If you do that every day for three years, you'll be a national expert." And I did it. Then I start speaking and writing books.
In "managing up" mode, maybe fundraisers should view themselves as consultants. If you do commit to something like that schedule of daily reading, then, when you go to your boss, you'll be saying things he'll want/need to hear, because they'll connect directly to increased revenue.
Money is the trump card. When someone asks me, "Tom, what do you do?" I answer, "I help charities make a lot more money." When the discussion's about money, the discussion gets serious instead of frivolous.
If the discussion's about who's right, you lose. If the discussion's about which version is better from a "I like it, I don't like it" standpoint, you lose. Those are NOT professional-caliber or -relevant discussions.
Talk about income instead. Have the body of knowledge under your belt. Change jobs regularly if you have to, learning a little more each time. And one day, maybe three years from now, you'll be on easy street.
I couldn't hide behind the Verbatim Rule ... I wouldn't now attract the clients of my dreams (which describes ALL my current clients) ... if I didn't know how to actually do what they want done.
It's not about getting permission. It's not about being right. It's about intellectual domination.
My self-confidence is off the charts when I speak with clients. You have to be the smartest person in the room in your field ... and in your head.
Treat your boss as a client. Listen.
Then mention money. Then dominate.
There is no shortcut I know. There is no spray for this. There is no herbicide. Your boss (despite appearances) is not a noxious weed.
To dominate, you have to be knowledgeable. And then you can slay.