But First: Let’s Talk About That Contractor Who Ruined It for Everyone
You know the one. They were brilliant at D365. Absolute wizard with configurations. Then one day they just… vanished. Poof.
Three days later they resurface with some story about their internet being down. The client’s eye starts twitching. Trust is broken. And suddenly every D365 contractor after them gets treated like a flight risk.
Don’t be that contractor.
Look, I get it. You chose contracting for the freedom. No boring meetings about meetings. No corporate BS. No mandatory fun committees. But here’s the thing – your clients are betting their careers on you showing up. The least you can do is tell them when you won’t be around.
This guide is about the stupidly simple communication habits that keep clients happy and keep you busy. And those extensions rolling on.
Rule #1: The “No Surprises” Policy (Unless It’s Cake)
Your client finding out you’re off on Friday… on Friday morning… is not the kind of surprise anyone enjoys.
Here’s what works:
- Monday morning: “Here’s what I’m tackling this week” (30 seconds to type, saves 30 minutes of panicked client emails)
- Doctor appointment next month? Tell them now. Why wait?
- Big request comes in? Even just “Got it, will dig in after lunch” beats radio silence
Real example that actually happened: “Hey team, dental appointment Thursday November 20th, 1-4pm. The reconciliation scripts will be done and documented before I abandon you for my root canal. If anything explodes while I’m gone, blame Dave.”
Client’s love this. And it’s so simple.
Rule #2: Yes, We Know You Have Other Clients (We’re Not Idiots)
Your clients aren’t children. They know you’re not sitting around waiting for their emails like a golden retriever. Well, not ALL the time! They know you have other clients. What drives them crazy is not knowing WHERE they fit in your world.
Just be straight with them: “Cards on the table – I’ve got another client who gets my Tuesdays and Thursdays. You get MWF and my full attention those days. If something catches fire on a Tuesday, I’ll handle it, but my standard response time is MWF. Cool?”
You know what clients say to this? “Cool.”
You know what they say when you’re mysteriously ‘busy’ every Tuesday without explanation? Nothing good.
The worst excuse I ever heard: “Sorry, I was… uh… walking the dog all day.” Dude. At least make up something believable. You have a Pug.
Rule #3: Taking Vacation Doesn’t Make You a Bad Contractor
Taking vacation WITHOUT WARNING just isn’t cool.
The 3-2-1 Countdown:
- 3 weeks out: “Hey, heading to the Bahamas first week of December”
- 2 weeks out: “Remember that Bahamas thing? Here’s my coverage plan”
- 1 week out: “Bahamas next week! Everything’s documented, Dave knows what’s up”
The message that makes clients love you:
“Heads up – I’m off March 1-5 (finally using those airline credits from 2020 🙄). Here’s what’ll be done before I go:
- User permissions audit – DONE by Feb 26
- Month-end close documentation – DONE by Feb 27
- Dave’s briefed on everything (he owes me one anyway)
- My phone works in Mexico if something literally catches fire
Anything else you need before I abandon you for tacos and questionable tequila?”
Rule #4: When Life Punches You in the Face
Kid projectile vomits at 3am? Car battery decides today’s the day to die? Life happens.
The “Oh Crap” Protocol:
Send this immediately (yes, even at 6am):
“Morning [Client]. Life happened. [Brief truth]. Need to handle this until ~2pm. The warranty report will still hit your inbox by 5pm today. Will update you at 2pm. Sorry for the disruption – my [car/kid/cat] apparently hates project deadlines.”
What NOT to say:
- “Something came up” (They’re imagining you at the beach)
- Nothing (They’re imagining you at the beach)
- An elaborate lie about food poisoning (We all know you’re hungover, Steve)
Rule #5: The Friday Insurance Policy
Every Friday, spend 5 minutes writing this email/Teams message. It’ll save you from Monday morning panic texts.
The World’s Simplest Status Update:
“Friday wrap-up:
Done this week:
- Fixed that weird bug in the payment terms
- Taught accounting how to actually use the reports
- Prevented Dave from breaking production (again)
Next week:
- Month-end close prep
- That integration thing we discussed
- More Dave damage control
Need from you:
- Approval on the warranty config
- Someone to tell Dave to stop touching things
Have a good weekend! 🍻”
Takes 5 minutes. Prevents 5 hours of “where are we on…?” emails/Teams.
The “I’m Getting Swamped” Conversation
When every client suddenly needs everything yesterday (usually in December, because of course), here’s how to not implode:
The message that shows you’re a pro:
“Hey [Client], being transparent here – I’m getting stretched pretty thin across all my clients. Your D365 project is important to me and I want to make sure I’m not dropping balls. Can we do a quick call to prioritize what absolutely needs to happen this week vs. what can wait? I’d rather be honest now than disappointing later.”
Clients LOVE this. Know what they hate? When you say yes to everything then deliver garbage because you’re running on 3 hours of sleep and coffee fumes.
Tools That Make You Look Like You Have Your Sh*t Together
Bare minimum:
- Calendar that shows when you’re available (doesn’t need detail, just “Available” vs “Booked”)
- Surprise out-of-office that doesn’t say “I’ll respond when I return”
- Slack/Teams status that isn’t permanently set to “Away” (we see you, Kevin)
Next level:
- Phone reminder every Friday at 3pm: “Send status updates, dummy”
- Template folder called “Excuses” (kidding… call it “Client Communication Templates”)
- At least one contractor buddy who’ll cover for you (and vice versa) in mega situations
The Bottom Line (The Part Where I Get Serious for 30 Seconds)
You’re not an employee, but you’re not a ghost either.
The D365 contractors who survive long-term aren’t necessarily the best technically. They’re the ones who answer their damn emails and tell people when they’ll be gone.
Your clients don’t need you to be available 24/7. They need to know WHEN you’re available and trust that you’ll show up when you say you will.
It’s literally that simple.
Your Homework 😀
- Right now: Send every live client a status update. Even if it’s “Everything’s on track, no blockers, talk Monday.”
- Check your calendar: Any time off in the next month? Tell your clients. Today.
- Set a phone reminder: Every Friday, 3pm – “Send weekly updates or clients will panic”
- Save this message template: “Hi [Client], emergency came up, will be back online by [time], [deliverable] still on track for [deadline]. Will update you at [time].”
- Forward this guide to that one contractor friend who needs it (we all know who it is)
“The void created by the failure to communicate is soon filled with poison, drivel, and misrepresentation.” – Some smart person who probably got ghosted by a contractor
