Okay, let’s say you buy into my premise that communication is truly the one biggest key in successful telecommuting from my last post.

1:1s are one of the best ways for you to develop great communication. It does not matter whether you are currently working from home and just want to improve your perception, or you are still in the process of convincing your boss to let you work remotely.

One On One Meetings

I’ve been fortunate in having been able to have one on one meetings with my boss during my last two jobs. Ideally, all of us should have these weekly one-on-one touch points with our boss. Unfortunately, I found that these types of interactions are far less common than they should be.

So, let’s assume you are one of the many who does not currently meet on a weekly basis with your boss. The first thing you should do is ask your boss to set aside that time and have a one-on-one meeting with you. Odds are, since you’re not already having those meetings, that your boss may wonder what the purpose of those meetings is.

This is another one of those cases where it comes down to understanding your boss’s needs. Your boss needs you to get work done and perform that work with a high level of engagement. By requesting the dedicated weekly time you are demonstrating initiative and engagement. That, of course, is a weird reason to give for a meeting, right? So what you should say instead is the following.

I was hoping we could take a little time every week so I can make sure I’m on track and working on the things which are most important to you. If possible, I would also sometimes like to discuss some questions I have about the company and challenges where I might be able to contribute.

That is pretty open ended, but it also sends a strong message about your engagement. That is especially true if one-on-one meetings are not currently taking place.

Your boss may still be skeptical. She may even suggest simply using email. Should that happen, you should simply suggest that you would prefer a conversation because the direct interaction would be more productive. I feel that one on one meetings ideally should be a half an hour. Nonetheless there is nothing wrong with a shorter one on one time to get started with the concept. Perhaps 15 minutes would be more suitable. If that seems too long, then perhaps 10 or even 5 minutes will work. That gives you less time and would only be for getting the ball rolling. Remember, this is to help you with increasing your visibility to your boss. It serves to build a stronger relationship that will help ease a potential decision on allowing you to work from at home.

Once you get going with the 1:1 meetings, there are a lot of ways for you to shine. Here are my personal suggestions on making the most of that time.

  1. Keep it high level. Remember your boss has a lot of demands and you should be respectful of his time by avoiding unnecessary minutiae. Besides, by keeping it high level you strengthen the understanding that you don’t need a lot of feedback on fine grained items. Higher level employees are more likely to get to work from home.
  2. Make sure to ask for feedback on priorities. This lets you show follow through the next week. Just make sure you do follow through. It won’t look great if you keep showing up without accomplishments.
  3. Be prepared. This should go without saying, but it’s important. It shows respect and that you truly value that 1:1 time.
  4. Bring some big questions. This lets you demonstrate that you are engaged. There are a lot great topics to ask about, but ideally you will ask things that show you are engaged and not just heads down in your little world. Your boss may not know how or be prepared to answer questions like “How could we help make sales more effective?” or “What do you think about trying a new approach to the weekly team status meeting?” Don’t worry about that. Ideas are generally well received and ideas like that will most likely produce good discussion.

Whether your trying to score some remote time or feel like you might be a little out of the loop, the weekly 1:1 with the boss will go a long way to cementing your position and demonstrate value to the organization. Heck, you might even try setting an occasional 1:1 with a teammate or other colleague you enjoy working with and learning from.

Let me know if you have any experience with 1:1s or you’d like to talk more about it.

I love working uncaged.