Contractor Best Practices: When working with a 3rd party in support of my book (artist, formatter, editor, PR, PA, etc.) what's one thing I do to make my life and theirs easier/make the project more successful?
Set expectations upfront--on both sides.
It amazes me how many folks enter into a business arrangement while operating on a host of assumptions that are never shared with the other party(ies). There is no way that ends well for anyone.
Ask questions at the get-go. Get the answers you need to be a good partner. Even if you think you know the answer, ask anyway. Confirmation will save you heartburn. This is one part due diligence and another part documenting commitments between two parties. Don't be afraid to not know an answer. Don't fear looking like a newb or unprofessional. Setting and receiving clear expectations is a foundational element of professionalism.
A Sample of Questions: What do I need from them? What do they need from me? When? In what format? What are the deliverables? What are the milestones? What happens if dates need to change--on my end or theirs? How much lead time is needed? What is a reasonable turnaround time? Payments: invoices sent at the end of the project, at intervals, portion upfront and another on completion? What method of payment is preferred? When is payment due/when will I be paid? Who is my point of contact and what are their contact details? Etc.
Whether dealing with a freelancer, small business, or corporation--regardless of industry--take the time to set expectations upfront. If the party with whom you're planning on working doesn't agree to do this, bitches about doing it, or doesn't answer your questions to your satisfaction that is a HUGE red flag. Do not proceed.
If someone asks to set expectations with you, take the time to do it. Yeah, yeah, not everyone will say "Hey, I'd like to set expectations with you." It might be as casual as "Hey, yeah, your project sounds interesting. Let's chat about details." If you use new contractors frequently, you might even create an expectations worksheet/FAQ in advance with the questions you need them to answer and the answers to questions you anticipated being asked/info you want them to have.
If shit goes south during the course of business, you're going to be on much better footing if you have the details documented. Especially if things go so badly that lawyers get involved.
A Bonus for Setting Expectations: As creatives, we know dates for deliverables are the first casualty of...well, life. Many of us dread telling our partner that we're not going to make the agreed-upon date. The longer we take to inform our partner, the worse the consequences for everyone. However, because we set expectations at the beginning and because date-slippage is so common that we included the "what-if" in our initial conversation, we've spared ourselves the anxiety-inducing, panic-attack spiraling, shame levying distress of telling our partner that we're not making the deadline. We know what to expect by missing the date and we know how to get the project back on track. Similarly, when we're told that a date is being missed, we've covered our ass by informing our partner of the consequences of slippage. (Hopefully, we've added a slippage cushion to our overall project schedule so a missed date isn't catastrophic to the entire project. Right? RIGHT?).
Good business communication starts with setting expectations.
May your partnerships be fruitful and your projects successful!