A friend of mine, a great salesman, was giving advice to a colleague of mine who was new to fundraising.
His suggestion: if you don’t get thrown out of at least one meeting in your first year you’re not being bold enough in your asks.
This wasn’t conceptual advice – it meant actually physically being shown the door.
Now I admit in nearly six years of fundraising I haven’t actually been thrown out, but I’ve definitely made some pretty outrageous asks. At the same time, until I actually find the line I don’t fully know where it is.
You could be fundraising, you could be a freelancer, you could be selling just about anything – 9 times out of 10 we all are less bold than we could be and should be.
Yes be respectful, always, but find the line.