One assumption that’s easy to make but can really damage your career is that your boss knows what you’re doing and how well you’re doing it.

After all, they’re your boss. It’s their job to know what’s going on and to look out for team members, right?

Unfortunately, most bosses aren’t perfect and they’re definitely not mind readers. They’re busy people with worries of their own.

That’s why the best strategy is to take charge of keeping your boss updated on what you’re doing and to do it in a way that serves both of you well.

Why It’s Important to Keep Your Boss Updated

When done well, keeping your boss updated is one of your career secret weapons (more on that in a moment). And there are four reasons why it’s in your interest to make it a regular part of your routine.

1. Helps you with your workload

When you keep your boss updated, you provide them with insight into the volume, complexity and impact of your work. When they know what’s on your plate, this makes it easier for you to get the resources you need, and it can also keep you from getting dumped on with more work than you can handle.

2. Makes your boss a better advocate for you

When your boss is informed and armed with your accomplishments in real time, they’ll be able to advocate for you more effectively and on an ongoing basis. And when it’s time to negotiate for more resources, they’ll be in the know about what you need and why you need it. In essence, the more informed your boss is about you, the better an advocate they will be.

3. Helps your boss pave the way for you

If you’re keeping your boss regularly updated, they’ll be in a better position to help you at the more senior levels of your organization. You’ll also be able in a great position to direct your boss to help troubleshoot or pave the way with senior people you can’t (yet) get to easily, whether that’s in your client’s organization or in your own.

When you find appropriate ways to involve your boss, it gives them an opportunity to feel part of the effort and, best of all, it’s easier for them to see you in action. They can see your successes and how you handle challenges first-hand and are then in a position to brag about you authentically.

4. Enhances your visibility with higher level managers

Your updates are fuel for your boss to use in keeping their bosses updated on all the great things going on across the unit. Just like you, your boss is interested in looking good with his or her boss too!

When you help your boss look good, they’ll feel more secure in their role. This in turn makes them more likely to be generous in sharing some positive press about you with senior management.

It’s Easy to Get It Wrong

Just because keeping your boss updated is important doesn’t mean everyone does it. And it’s possible to get it badly wrong. So much so that it backfires.

Take my client – let’s call her Linda – for example. Linda was proud of the thorough briefings she prepared for her update meetings with her new boss. Her one frustration was that their supposedly hour-long meeting was often cut short to 15 minutes or even canceled at the last minute.

Since she was often traveling to meet with clients but still wanted to keep her boss updated, she switched to an email update. By reading this one comprehensive document, her boss would know everything that was going on. She felt confident this would show her boss that she was working hard and staying on top of things even when she was away from the office.

When I met with her boss, I got a different story. He was frustrated with Linda because she couldn’t seem to get to the point. He dreaded their long update meetings and felt she was wasting his time with all that unnecessary detail. For him, even 15 minutes was a long meeting.

As for the emails, they were just as bad. He hated to read long, dense emails that you had to scroll down multiple times to get to the end.

Instead, he preferred a few bullet points or an informal “fly by” update and wondered why she couldn’t just “stop by and poke her head into my office with a quick ‘oh, by the way, we got that deal today’ or ‘I need your input on X’ like everyone else?”

Fortunately, Linda was able to change the way she updated her boss and they got back on track. But it almost derailed her career.

How to Update Your Boss Well

The “how” will be different for different bosses, and it’s your responsibility to get clear on what will land best with yours.

If they’re a micro-manager, you’re probably better off with more frequent updates and greater detail. If they’re “laissez-faire” or have a short attention span, then a few well-placed bullet points will do.

As an example, the best team member I’ve ever worked with, Charlie (not his real name) somehow knew my preferred update was in person. I had way too many emails and was always behind.

Charlie would stop by in the late afternoon and ask if I had a moment to speak (how did he know that I hate getting interrupted in the morning, which is my most productive time?!).

Then he’d sit down next to my desk and tell me the projects he’d finished, the ones that were still in progress, and the requests he had for me. Then he’d ask if there was anything else I wanted him to work on. If not, he’d be heading home after he finished his last tasks.

This made things easy for me as a new manager. And hearing Charlie’s update felt like a nice break. I was regularly amazed by how calm he was and how quickly he was able to handle his work without any hint of panic. It was also a smart way for Charlie to leave when he was finished with work without worrying that he was letting me down or feeling like he was sneaking off.

Not only did Charlie do excellent work, his updates helped me feel in control at work because I was never caught off guard. As a result, I was always happy to brag about Charlie and what a great job he was doing. If I was ever moving to a different part of the firm, Charlie would have been the first person I’d ask to come along.

Tailor Your Update to Your Boss

Bosses come in many sizes and flavors and you want to make your update easy for your boss to consume. Just as vitamins come in different forms (e.g., gel cap, chewable, liquid), your approach needs to suit your boss’s preference.

If you’re not sure, then ask them or someone else who knows. And then experiment with formats to see which lands best and is easiest for you to produce.

I like to think of it along the lines of content, framing, frequency and format.

  • Content: What to update your boss about
  • Framing: How to position the things in your update
  • Format: How to communicate your update
  • Frequency: How often you update your boss

Content – What to update your boss about

The key here is to make a conscious decision about what to include in your updates.

First, figure out what’s important to your boss. What you include will give him or her clues about whether or not you see the bigger strategic picture. For example, the organizational “housekeeping” that’s taking up most of your time this week may not deserve top billing whereas the insights from a 5-minute client call could be big news.

Second, think about the content from your own perspective. What are the accomplishments or milestones you’re most proud of? What issues or challenges are on the horizon, how are you handling them, and what help do you need from your boss? Where do you want to start planting some seeds for the future, such as workload and how close your team is to full capacity?

As a boss, here are the things I would want to know:

  • What you and your team have accomplished since the last update
  • Any challenges you’re facing (especially flagging potential future issues) and how you plan to deal with them
  • Any assistance or input you need from me

Framing – How to position the things in your update

From a framing perspective, think of it as a story or narrative that you’re communicating to your boss. What’s the overall impression you want to give, and what’s the language and phrasing that best conveys it?

For example, if you want to come across as competent and capable, then the way you frame issues and challenges needs to be matter-of-fact and include your proposed solution.

If you need your boss’s help, direct them rather than sound like you’re adrift without any idea of what to do. For example, “At this stage in the project, it would have a big impact if you connect with the head of the client team” instead of “Can you call the client? I’m worried they think I’m too junior.”

Finally, consider what you would want to include if your boss happened to forward or repeat the contents to a more senior person in the organization. Make sure it represents you well.

Format and Frequency – How and how often to communicate updates

Format and frequency are things for you and your boss to decide. I preferred weekly updates but biweekly or monthly could suit your situation better.

Depending on how often things change and how much detail you provide, I’ve found these three update formats can work whether they’re in writing or in person:

  • Very short and to the point – this is great if your boss has a short attention span and is very busy. The more senior your boss is, the more likely they are to fall into this category.
  • Reasonably detailed – this includes some charts or spreadsheets that capture key information such as pipelines or project updates. The broader a group you need to update, the more likely it is you’ll need an update like this. Also, a newer manager or a boss with micro-manager tendencies will like this. With this format, I’d recommend having sub-headings and bullet points to make it easier to digest.
  • A hybrid – this is an executive summary with the three main points along with the action or decision you need from your boss. Then everything else can be below your signature or attached as an appendix. When you’re not sure, this is a good way to go.

Updates Are Your Opportunity to Increase Your Visibility

Remember, your update represents you with your boss and potentially with more senior management. They’re a great opportunity for you to be more visible with people who matter in your career.

That’s why given the choice, I would go for shorter updates (as in three bullet points), in writing, sent weekly via email with the same subject line so it’s easily searchable as you get closer to review time. This is especially useful if you don’t get to see or speak to your boss frequently.

And while you want to take your updates seriously, don’t get bogged down with trying to make it perfect. The point is to get it going. Then you can get feedback and adjust.

As the saying goes, done is better than perfect!

So how about you?

If you’re already updating your boss, how has it helped your career?

And if you haven’t been doing it yet, how will you get started?

Leave me a comment and let me know.