Underground Railroad by Colson Whitehead book cover

Dear Maya,

I delegate a hundred little things in a week. How can I make sure every single one of them got done? Should I go through my sent mail once a week to see what’s still out there?

Outbox Checker

Dear Outbox Checker,

I feel you. Delegating is among the hardest skills we must master to succeed. Whether at home or at work, we have to get a significant number of tasks off our plates in order to devote enough time to our high-priority, high-value activities.

Successful delegating requires three things: competent people to delegate to, clear instructions and expectations for the work we’re dispatching, and fail-safe systems for reviewing delegated work at well-timed intervals. Luckily, two of the three are totally within our control and we can heavily influence the third.

As a culture, we’ve come to view email as a kind of Swiss Army Knife of digital productivity and inevitably many assignments are issued through this medium. But email is just email. It’s simply a correspondence tool. We are the multi-tool that can scale fish, drive screws or lift caps (metaphorically speaking). We are the ones with the power to make an email a suggestion, an order or a reminder.

If you are delegating to great, experienced workers during a great week, you won’t have to revisit your sent box to remind you of outstanding tasks. They will work steadily and communicate updates regularly so the dialogue remains open. But in the real world, we’re often delegating to less-than-great or inexperienced workers during less-than-great weeks and some fail-safes are required.

The clarity of the instructions and expectations that you set in your initial email can help. Embed updates in the assignment to impose regular communication from people who might not take the initiative to provide it. That is, ask your correspondents to reply confirming they’ve received the messages and to send updates when they hit certain milestones. This way, you’re really assigning two things for them to do: perform specific tasks and communicate progress as they go. As confidence and competence develop over time, you can ease up the communication requirement.

“Trust, but verify” is an axiom to live by in management (and journalism, incidentally). Even when delegating to the best of the best, you’ll still need a personal system for tracking progress. Below are some suggestions for specific systems. But first, you need to think about what type of task you’re assigning to determine the kind of follow-up it requires.

There are two kinds of tasks people delegate: Those that are ends in themselves and those that are steps in a process. The former include things like adding a photo to a blog post or sending a retirement card to a former employee. They must be done (if not, why delegate?), but failure to do them isn’t preventing someone else from doing their job.

By contrast, the latter category of tasks has a direct impact on the next person in line. If someone doesn’t report payroll, the bank can’t transfer the money to employees’ accounts and the workers can’t pay their bills. If someone doesn’t conduct the research, the analyst can’t write the report and the manager can’t make an informed decision or argument.

Tasks in either category can be urgent or not, important or not. But you must consider the distinction when determining the urgency and frequency of your progress reviews. It’s not enough to check your sent box weekly if something needs to be done tomorrow or should have been done yesterday to keep other work on track.

The goal is to review a select number of things when you need to. That means considering each task individually, making a call about how aggressively you want to follow up, and scheduling a reminder or recurring reminders if necessary.

Here are a few ideas on how to use technology to help you:

Note it.

Create a “Waiting For” list as David Allen advises in “Getting Things Done” and keep a running list of what you have requested from others. I recommend doing this in an online task manager like Wunderlist so that you can schedule reminders. Tying a deadline or reminder to the pending items ensures that they will rise to your attention (your Today list) when you want them to.

The wisdom in such a system is that you don’t have to wade into the muck of your email account to see who needs to be pushed, prodded or encouraged. If you dive into your task list first thing, as opposed to your email inbox, you’re taking control of your workday and are less likely to get pulled off track.

Of course, if any of your tasks require emailing someone a follow-up note, you’re back in the inbox and susceptible to distraction all over again. But this is the answer less often than you think. Often, you can do said pushing, prodding or encouraging by phone or (gasp) face-to-face. Sometimes the medium is the message.

Boomerang it.

Now, if it’s a one-off thing that you don’t want to trouble your to-do list with, using an email resend service like Boomerang, which works with Gmail and Outlook, is a viable (but not ideal) solution. Once installed you simply hit a Boomerang button to schedule the message to return to you at a specific day and time. Envision yourself flinging messages into cyber obscurity, only for them to return a day, a week or whatever timeframe you choose later. That way, you can reply within the same email chain to request an update. All without having to sort through your sent box.

The problem with this approach is that it increases email volume and dependency.  Now you’re checking emails from others and from yourself.  But it’s slightly better than scouring your outbox.  Baby steps.

File it.

Another option for the email-dependent is just to create a specific label or folder within your email program for items that require follow-up. The relevant messages are segregated, which saves you time sifting through all of your sent mail. You can review them easily on a weekly basis as you originally suggested. Once the task is complete, you can remove the label or re-file the message.

Again, this works, but we can do better. With the filing method, you still have to remind yourself to check the label or file on a consistent basis. Technology is ready to help you achieve just-in-time notification as described above in the Wunderlist example. It’s just smart to use it to your advantage.

How do you stay on top of the things you’ve delegated to other people? What technology, processes or other tools are you using to close the loop on outsourced tasks?