stevepb / Pixabay

Ever met an entrepreneur who doesn’t have to worry about deadlines? Me neither!

Being able to build our own schedules is such a privilege, but it doesn’t mean we have boundless timelines and flexibility for every task we tackle. Not by a long shot. And managing deadlines, timelines, and schedules becomes even more hairy when you throw a few team members into the mix.

You want to be reasonable and respect your contractors’ commitments to other clients (and work-life balance!) but also need them to complete the work you need on time and when you need it.

Luckily, today I’m sharing seven simple tips that will help you build and manage a shared schedule that works for your whole team!


Keep Team Schedules Aligned with Regular Check-ins

Schedules change. CONSTANTLY. It’s not something that can be stopped or mitigated because we simply don’t have control over all of the forces that influence our lives! People get sick, accidents happen, priorities shift, and sometimes we just plain forget things.

So my first piece of advice for you lovelies is to learn to love change and roll with the punches. Being rigid about scheduling matters will get you nowhere, fast.

Instead, communicate!

Send an email to your team every Sunday evening asking for any schedule shifts or updates by Monday at noon. Doing this shows your contractors that you know they have lives outside your business, and are willing to work around their needs so long as they share those needs freely.

It also gives you the chance to get the lay of the land on a week-by-week basis.

Manage Your Team’s Schedules by Creating a Shared Calendar

We all live by our calendars, don’t we? But sharing them with others can get dicey, especially if you pop your gynecologist appointments and reminders to buy cat litter on the same calendar with your work tasks. A shared calendar dedicated to your workflow and team assignments—and rigged to send helpful reminders—can be a great work-around, especially for teams spread across multiple states and time zones.

It would be so nice if a shared calendar cancelled out the need to send those weekly emails … but in my experience, it doesn’t. Contractors truly appreciate an active, personal nudge to share schedule shifts and update a collective calendar.

Create Realistic Schedules by Avoiding Rush Projects

OK, I know. Completely avoiding rush projects and last-minute work is impossible. Sometimes they just crop up, and there’s nothing to do but crank out the deliverables as best you can!

BUT if you’re the type of person who tends to wait until something has become urgent to give it your attention, you’re part of the problem.

Adjust your working style to allow for reasonable planning and chart out workloads a month or more ahead of time. It can help to reverse-plan: Start with the deadline, the work backwards to figure out which steps need to be completed by which dates.

Don’t Let Yourself be the Bottleneck in Team Schedules

Beautiful friend, I know how hard this one can be!

You trust your contractors, but may still feel the need to give a final sign-off on … well, everything. You may also be mentally ready to delegate, but emotionally clinging to control. Or maybe you’re just constantly scrambling to keep up with your own work, and push off addressing questions or requests from others until the very last minute. Natural, normal instincts, but ones that will make your team members deeply cranky.

If you realize that everyone else’s schedules are getting backed up because of your actions (or inactions!), be honest with yourself and willing to make change. This is a common issue for entrepreneurs, and a thorny one.

Find ways to let go of control and ease the flow of work past yourself.

Build Team Schedules with Wiggle Room

Down-to-the-wire timelines create unnecessary stress and allow zero room for error. As you build shared schedules for yourself and your team, make sure to include some padding. It’s always wise to allow time for unexpected issues so you can address them calmly and keep the project on track.

The bigger the project and the more team members involved, the more wiggle room you will need to allow.

Consider Hiring a Project Manager to Oversee Team Schedules

If you’ve got a larger team working on long-term, complex projects, even the best project management software in the universe might fall short. And if you’ve tried wrangling everyone’s schedule yourself only to create snarls and spawn catastrophes, it might be time to bring in a pro.

If you can hire a project manager—even in the short term—that person can maintain and update schedules, keep an eye on deadlines, and hold everyone accountable. Paying someone to tweak calendars and nudge team members may seem like a luxury, but if an endeavor or project is truly important, that investment will pay off in superior results and FAR less stress for your whole crew.

Create Flexible Team Schedules Through Cross-training

The best way to make sure nothing falls through the cracks? Always have backup ready.

When it comes to team dynamics, this means training different contractors to cover each others’ workloads. If a team member has a family emergency, are you just going to absorb her tasks yourself?

A much better way to keep the work going is to ensure at least one other contractor has been cross-trained to cover any gaps. This also creates flexibility for non-emergency situations like vacations and pregnancies.

Final advice? Don’t beat yourself up! Every team schedule has its hiccups, and even if you use all seven of these strategies things will still go sideways once in a while. Do what you can to keep things on track, transparent, and manageable for everyone … but don’t kick yourself when you hit the occasional bump in the scheduling road.