The Job That Made Desmond Hale Start Taking Notes
Before Checkmate Movers existed, Desmond Hale spent eight years running crews for a big-box moving franchise. He’ll tell you straight that most of those jobs got improvised. A couch would get carried up three flights of stairs, come back down because it wouldn’t clear a turn on the third-floor landing, and go back up again, twice, on the same move, because nobody had walked the stairwell first. Trucks got repacked on the sidewalk more often than they got loaded right the first time. Boxes got walked into doorways sideways because nobody had measured. The plan for the day was whatever the first mover through the door decided to do.
Desmond started keeping his own notes on load order and room sequencing, even on jobs that weren’t his to run. Watching a move go sideways bothered him more than it should have. By 2013 he’d seen enough repacked trucks to start Checkmate Movers on one idea: a move gets planned like a chess game, every piece worked out before anyone touches a box, not improvised in the doorway.
Nine trucks and eighteen people later, that’s still the whole business. Checkmate doesn’t run day-labor crews or subcontractors picked up for the week, and the walkthrough is the same first step on every job, whether it’s a studio apartment or a full four-bedroom house.
What Happens at the Walkthrough
Jamal Whitfield, our in-home estimator, walks the property before crew day, not to eyeball a number but to build the actual load plan. He looks at stairwell turns, doorway widths, whether it’s a two-flat with a narrow gangway or a downtown building with a specific loading zone, and which rooms need to come off the truck first at the other end. That plan gets written down and handed to the crew, not improvised at 8am in the driveway.
What It Looks Like on Crew Day
Crew chief Tomasz Nowak runs the loading off Jamal’s plan: heavy furniture and awkward pieces loaded in the order they need to come off, not just whatever’s closest to the truck. That’s the difference between a couch clearing a stairwell turn on the first pass and a couch coming back down for a second run at it. It’s also why our trucks don’t get repacked on the sidewalk halfway through a job. The load order was set before the truck backed in, not worked out box by box as the day went along.
Why This Matters More Than It Sounds Like It Should
A move that gets replanned mid-job doesn’t just take longer. It’s when things get dropped, walls get dinged, and a four-hour job turns into a six-hour job because the crew is solving a puzzle it should have solved before the truck arrived. Desmond built Checkmate around not having that problem, because he spent eight years watching it happen to other people’s furniture, and it never sat right with him.
See It for Yourself
Every move Checkmate books starts with Jamal’s walkthrough, whether it’s a one-bedroom in Wicker Park or a four-bedroom house in Naperville. Call (312) 508-3947 and Michelle will get one on the calendar.