“When a door opens, go through it!”

That’s famous advice by the late great comedian Joan Rivers. Many young creatives rightly follow it. But I’m not really sure that Joan meant you shouldn’t ask any questions.

You should ask questions. Just be sure to ask the right ones.

This week, I was contacted to do a ‘motivational speaking’ gig at a men’s shelter in Brooklyn. They needed me to ‘talk for 90 minutes.’ Then the young woman said they wanted ‘a bid.’

Taking Joan’s advice, despite the fact that I have exactly zilch experience working with the homeless population, I expressed interest. “Oh really? That sounds great. How did you find me?” (Translation: It would be good to know whether there was something in my online presence that framed me as a candidate, and what on earth it may have been.)

“I just found you online.”
“I see. So what about me made you want to reach out? I’m just trying to ascertain what you’re looking for in a speaker.”
“You do life coaching, right? We need someone who can help ‘them’ find a job.”

And a speech will do that? (This would have been a wrong question to ask. Rhetorical questions are rarely a good idea.)

“Is this a new program?”
“No, the woman who was doing it had to move.”
“I see. So is this ongoing?”
“Yes. Three times a month for three months”

Ah. Now we’re getting somewhere. We’re talking about group coaching, not ‘a speech.’

“I see. Can you tell me the budget? I don’t want to pitch something totally outside the realm of possibility.”
“I don’t know.”

Welp, long story short, I got the caller’s contact information and told her I’d get back to her this week. And then I did some outreach to people who may have experience in this realm and could offer some advice. What I got was: Ask more questions.

In my research I even learned what questions I needed to ask, because in a new situation, it isn’t always apparent: How many people are they contacting? If it’s 25 or 30 it won’t be worth my time because I really am an arbitrary number. What about my experience makes me seem relevant? (That will allow me to focus my offering.) Again, if it’s just that I’m a coach, they probably are reaching out to a bunch of people–in which case I really am an arbitrary choice, which is not worth my time. Plus, I really do need to know the budget before making a bid–it’s a government program. Can they put me in touch with someone previously involved so that I can get a sense of expectations? I proceeded to submit all of these clarifying questions in a polite follow-up email to my contact at the Department of Homeless Services.

See, the old me would have been afraid to ask anything: aped the old, ‘just say yes’ attitude drummed into so many creative professionals, undercharged to make sure I got hired, and if I did, kamikazed my way through the experience from a totally needy, fear-based place–possibly doing more harm than good. Just what a bunch of homeless guys need, a nice middle-aged lady coming in without a clue. Now, if I do get the gig, I’ll still be a nice middle-aged lady without a clue…but I’ll be grounded in my approach, not be afraid to ask them questions, and feel good about the compensation.

And if that’s too much to ask my potential employers then, to quote a wonderful 12-step platitude, rejection is protection.