How to Deal with Double Booking and Other Scheduling Headaches
At the end of a long day, you check your schedule for tomorrow only to discover a scheduling issue: you’ve double-booked two jobs.
What do you do? Do you rework your schedule? Do you call one of the clients to apologize and postpone? Or, do you try and split up your team to tackle both jobs, (even if it’ll negatively affect your reputation if you get it wrong)?
Read on to learn about how to handle double booking and what to do to avoid this common scheduling mistake.
Overbooking vs. Double Booking Scheduling Issues
Double booking is where you accidentally or purposefully book two jobs for the same time slot. It means your team has to be at two places simultaneously. Double booking can protect your income if someone cancels, but if not, you’re in a pickle.
Overbooking is where you book more jobs than usual in a day, which means there’s less time between jobs and or even an overlap. The idea is to secure more work to make more money. Overbooking can work if used sparingly, but the wheels will fall off if used all the time.
There’s very little room for error, and if one job runs long, it can negatively affect subsequent jobs. It also places unnecessary demands on your team, can lead to an unhappy workforce, and contributes to burnout.
Should You Ever Double Book on Purpose?
The short answer: No.
Double booking may be common for some businesses like hotels and spas. But it’s generally bad business practice for service professionals like arborists, landscapers, painters, commercial cleaners, and plumbers—even if they have plenty of cancellations.
The drawbacks of double booking outweigh the benefits. Double booking puts unnecessary stress on you and your team to figure out what to do when clients don’t cancel and can lead to unhappy customers and lost profits.
You could argue that double booking is okay if you manage the process well on specific jobs. For instance, if you’re busy with a big job, why not schedule a smaller one with another client that only requires one employee? There will invariably be a gap where an employee can slip away for a few hours, so what harm could that do?
Plenty, in fact.
Some clients may not like this, both jobs could end up taking longer, you’re risking your overall workmanship and customer service, and it can make you look unprofessional if employees keep “disappearing.”
If you’ve ever been tempted to double-book to make up for cancellations, there’s a more serious issue you need to address: preventing cancellations in the first place with a strong cancellation policy.
READ MORE: The 8 best scheduling apps for small business owners
How to Handle Double Booking
There’s no perfect way to handle a double booking. You’ll have to assess each scenario individually to make an informed decision. That said, there is a blueprint you can follow to guide you through this tricky process.
Step 1: Decide Which Customer Takes Preference
Decide which client takes preference. Making this decision means you only have to deal with one unhappy client: the client who you tell about the issue and whose booking will invariably be moved.
A few considerations that will drive your decision include:
Whose booking was first? The fair thing to do may be to honor the client who booked with you first, but things are rarely that simple…
Is the project time-sensitive? A project that’s on a tight deadline may take preference.
What is the revenue for each job? When you approach a client and inform them of the scheduling issue and that you can’t help them on that day and time, you need to be prepared for the worst: They may cancel the job altogether. That’s why you need to ask yourself if you’re willing to lose their revenue and even their business. The smart business option may be to honor the bigger, more lucrative job but do consider the next point.
Is the job for a loyal customer? If the job is smaller, but for a long-time customer, you may decide to keep their booking to maintain the relationship because you know you’ll get repeat business in the future.
Similarly, a loyal customer may also be more understanding of the odd scheduling mistake, so you may be able to simply tell them and let them know you plan to move their appointment. On the flip-side, if one of the customers is new, you may want to keep their booking to start the relationship on a positive note.
Deciding whose job to move is tricky as there’s plenty to consider. You’ll need to choose based on your circumstances and what you feel is right for you, your business, and your customers. Just make sure you make the decision quickly so you can start communicating and resolving the issue.
Step 2: Communicate with the Customer
Sending a text message is certainly better than no communication, but it’s impersonal and can exacerbate the issue. The better option is to communicate in-person or via a phone call.
If you can’t immediately get through to the customer, leave a message, send a follow-up email letting them know you tried to contact them, and set a reminder to call them a little later.
When communicating, provide a genuine apology. If you fail to offer a sincere apology for double booking a job, the customer may take the other road to another business. Make a short, clearly worded apology to appease the customer, and let them know that you want to find a solution to the scheduling issue.
Step 3: Offer a Solution to Fix the Situation
First, suggest moving the client’s booking. Just make sure the new booking is at a time and on a day that’s suitable for you, and most importantly, convenient for your client.
Don’t make the mistake of immediately offering some sort of financial incentive (e.g., a discount). Instead, try to find a way to provide value that doesn’t affect your bottom line. For example, provide even more personalized service than before. Communicate better and often, send follow-up emails, be attentive, be on time, respond promptly to questions, and do those small things which take very little time and cost you nothing, but can “wow” your client.
If you do decide to offer a financial incentive, keep it small, or provide an offer that depends on the client using you again. For example, bundle together a free service with one of your service packages.
How to Avoid Double Booking and Other Scheduling Headaches
When you have a lot of leads, it’s easy to double book a job and make other scheduling errors when you’re juggling many other business tasks. It becomes even easier as your business grows and, with it, the number of scheduled tasks, jobs, clients, and employees.
But you can avoid scheduling issues by using the right software
Jobber’s Scheduling Software, gives you the flexibility to book tasks, jobs, or other appointments on the fly. When a new job comes in, use the drag-and-drop calendar feature to avoid double booking.
The calendar has five different views, and you can assign different colors to each employee, so you can easily see who’s already scheduled to work. These views include Month, Week, Map, Grid, and List.
Both Grid view and Week view are great for showing availability on a day-to-day or weekly basis, so you don’t overbook, underbook, or double books yourself or any crews. And, once you’re ready to book a job, simply select the suitable time slot and tap to notify employees via a push notification.

Double Booking Doesn’t Have to Give You a Headache
Double booking a job happens to most service professionals at some point.
It certainly doesn’t have to be a nightmare to handle, as long as you communicate the problem immediately, offer a genuine apology, and provide a solution to fix it.
In fact, you can avoid this scheduling nightmare altogether by investing in scheduling software to reduce human error, improve organization, and better manage your schedules.
This article was originally published June 2016. It was last updated in October 2020.