Have you ever hear bosses ask this question? I've heard it, but not very often because it's kind of an embarrassing question to ask. Still I think many leaders wonder this. Unless you're standing over your people, micromanaging everything they're doing (please tell me you're not doing that), there's no way you can really know, is there?
Sure, there is.
You set goals and you measure them. Sounds easy, but many leaders want their people to do the work and do it the way the boss would do it. Oh, please! You've heard the phrase, "there's more than one way to skin a cat", right? Well, that's true at work. As long as your folks get the tasks done on time and nothing illegal or immoral took place during the completion of the tasks, you should (within reason) be OK with how they chose to get it done (within reason).
Hence, the main point. Whether your people sit in the same room with you or they're spread all over the world, the answer is the same. Set goals and measure them.
Let's say that you have a project to complete by September 1 so since it's August 4, you have almost a month to get it done. You give Lisa the project as one of her tasks to complete (for the sake of the example, it's a one-person project). What are the steps that you might take to help Lisa successfully complete the project?
Hmmm? Well, what are they?
Here are a list of possible steps:
1. Sit down with Lisa and let her know of the project with details and deadline.
2. Ask Lisa her initial thoughts on how to complete the project or brainstorm with her on that if she's willing.
3. Once Lisa has a clear understanding of the requirements and has no questions, send her on her way.
Are you done?
No. There is one more step...and this is the one that bosses fail at most often...
follow-up.
4. Since I know you'll be meeting with Lisa every week for your 1:1 sessions (because you're such a communicative, proactive boss), you'll be able to review the project with her (along with any other tasks she has) to see how she's doing, offer any guidance you feel needed, answer her questions and ensure she stays on the right track. With this example of a September 1 deadline, you should have 3 times already scheduled where you can follow-up with Lisa (add more meetings if you need to, but these are already set).
The regular 1:1 meetings are key to ensuring you know that your people are taking care of business. Like I said, not only can you ensure Lisa's project is completed successfully, but you can help your people prioritize based on current reality and guidance you receive from above.
It comes down to
communication. People ask me about their team members working from home. I say, "more power to them". As long as you've set clear expectations, are available to support them, and check in on them periodically to ensure they're OK, then you should be good to go. Of course, every now and then you need to meet face-to-face with all your team members to reconnect, but you won't have to worry about the work getting done.
If you've got a good follow-up system in place, relax and focus on your own tasks. I'm sure you have plenty to do yourself.