How to Keep Your Head-in-the-Clouds Clients On Task

You’re a highly self-motivated contractor or assistant. You always finish your homework before playtime, and you finish your dinner before you have dessert. You know that deadlines are real, and playing hooky has consequences.

Your clients almost certainly hold these values, too. But as their businesses grew from day-to-day grunt work to big picture planning, they may have lost their knack for staying on top of their ever-expanding to-do list. That’s why they hired you.

As their subordinate, keeping your client on task probably isn’t the easiest job in the world. You may feel, because of the power imbalance, that you don’t have the agency required to keep the trains running on time. You probably hate feeling like the bad cop—though not as much as you hate being behind schedule.

Good news, taskmaster! You’re about to learn about three areas you can monitor to keep clients on task: planning, proficiency, and accountability.

1. Planning

Even the most self-motivated clients benefit from the reassuring structure of a daily to-do list or weekly routine. If your client is struggling with time management, the problem could have to do with planning. Do any of the gripes below sound like you?

“My client has trouble coming up with monthly goals, project ideas, or content topics.”

Without clear direction or a sense of purpose, productivity grinds to screeching halt. Strong planning begins by establishing annual goals, which then inform monthly goals, which can be broken down into weekly and daily tasks.

If your position allows you to do this kind of big-picture planning with your client, seize the day! Talk to your client about where they see their business at this time next year. Talk through what you’re currently accomplishing each month, whether that’s in terms of revenue, content published, speaking engagements booked, pages written, or episodes recorded. Ask if they’d like to see that level of output increase, whether in quantity or quality. You don’t need to wait for a new calendar year to revamp your planning, either—June is just as good a time as January.

If your client creates content for their business and is overwhelmed by the responsibility of producing fresh material week over week, propose a few hacks. Plan out monthly themes to narrow your scope of topics—January could be Productivity Month, February could be Networking Month, etc. Repurpose your client’s greatest hits, whether by republishing an oldie-but-goodie blog post or converting a popular video into a new media format.

If you don’t have the keys to the master calendar, don’t despair. Keep a running list of ideas and topics inspired both by your client’s own work and the work of their industry competitors. Have these solutions at the ready anytime your client acknowledges they’ve hit a roadblock—they’ll appreciate it!

“We have a project management tool in place, but my client seems overwhelmed by it or forgets to use it.”

If you’re a contractor or freelancer, you’re used to juggling dozens of tools at once. You likely have strong feelings about which platforms make the most sense to your brain. However, it doesn’t matter how much you adore Slack or Trello or Asana—if your client hates it, drop it like it’s hot.

Tool buy-in is an essential part of team productivity, especially if one or more of you works virtually. Testing out project management platforms can be annoying, but your future self will appreciate the long-term benefits of finding the perfect tool. Make time for training, too—don’t assume that any software will feel as intuitive to your client as it does to you.

“I depend on certain deliverables to do my work, and my client is often late handing off those deliverables.”

Learn which flavor of procrastination your client is practicing. If they start their share of the work too late to deliver in time, consider creating both a “start this task” reminder and a deadline reminder. Move your own deadlines to allow for a generous time cushion. You may not have control over when you client procrastinates, but you can prepare for it, and save yourself from a few gray hairs in the process.

And if your client is always, always, always late with the hand-off, read on—there’s more you can do.

2. Proficiency

Smart clients delegate the tasks they shouldn’t or don’t want to do. If you see your client forever dragging their heels with a particular type of task, it may be time for you (or an outside hire) to take over.

Those tricky tasks could be the good kind of challenge: something outside your client’s comfort zone that pushes them to grow. Clients facing these kinds of challenges might simply need to grin and bear it, along with plenty of encouragement and positive reinforcement from you. But if your client is holding onto a task they just don’t have the skill for, it’s time to triage a solution.

If your client is holding onto the task reflexively, out of fear that no one else could possibly do it right, collaborate on a workflow checklist that will allow you to take over the task. This can grant them the peace of mind that it’s being done correctly.

If they’re worried that delegating tasks like writing means their content will sound impersonal or phony, reassure them there are plenty of ways to keep their content authentic. Good ghostwriters are experts at matching their voice to their client’s or transforming rough outlines into polished final products. Your client could dash off something rambling and off-the-cuff, and a good writer will transpose that raw material into something publishable.

If a particular medium or channel gives your client trouble, analyze whether or not they need to be active in that space at all. Podcasts are powerful, but not everybody needs to get in front of the microphone—make sure you’re not chasing after diminishing returns in an attempt to “be everywhere.”

3. Accountability

Holding clients accountable to their commitments can be stressful, particularly if there’s a substantial gap in authority between the two of you. You don’t have to enter the fray empty-handed, though.

Recruit your planning tools to send reminders. Set your project management tools to emit deadline and past-due alerts. These serve as your first line of defense in keeping your client on task.

If something’s late, don’t be afraid to check in on its status, no matter how small the task is. If your client knows they’ll hear from you if they don’t deliver on the little things, they’ll be less likely to let the big things slide, too.

If you don’t already have periodic check-in meetings, schedule them, and make progress reviews part of the agenda. Deadlines will be easier to remember once you’ve confirmed them verbally, and meetings add social pressure to honor commitments and make the team proud.

Get comfortable with your “accountability style.” Are you the friendly alarm clock? The business-y bad cop? Be direct about what you need and when and you won’t have to worry about being passive-aggressive. Frame these strategies as being for your benefit, rather than your client’s, if necessary—your client probably doesn’t like feeling scolded or nagged, however justified the nagger may be.

Finally, remember that your client hired support because they need and value your brainpower. Being gentle on deadlines and lax on productivity only hurts their business goals. Stay respectful and intentional when keeping your client on task, and they’ll love you for it!