Have you been hoping for a way to build your relationship with someone more senior who can become an advocate for you in your career?

Specifically, wouldn’t it be great to find a way to have a direct connection with your boss’s boss… without upsetting your boss?

Well, that’s the exact happy situation that came true for one of my coaching clients – let’s call her Tanah. She got on an assignment working directly with her boss’s boss – let’s call him Charles. And best of all, Tanah’s boss was the one who asked Tanah to step in and take on the project because he was too busy to do it.

This was Tanah’s big chance to impress her boss’s boss and show herself in a senior light. But the problem was twofold. First, Charles was busy and often hard to reach. Second, the project was mostly process-oriented and therefore not something that would help Tanah show up as more senior.

That’s where we came up with three steps to help Tanah show her potential through this project:

  1. Make it strategic
  2. Have an opinion
  3. Be succinct

When you’re faced with keeping your boss’s boss updated in the best possible way, these steps will help you too.

So let’s start with the first step.

Challenge yourself to find a way to make your project strategic

If you don’t see a project as strategic but your boss’s boss is paying attention to it, then it’s almost certainly strategic. And it’s vital for you to figure out why so you approach the project in the right way – one that’s motivating and helps you show up as a senior and strategic thinker.

In Tanah’s case, her boss’s boss deemed the project so important that he insisted on being at the first several meetings with key stakeholders. So it was time for Tanah to adopt a different perspective so she too could see the strategic nature of it, even though the underlying tasks were process-oriented.

You can look at any project from a variety of perspectives

Using a building analogy, it could be a ground floor view, the rooftop view or the helicopter view and so forth. When Tanah zoomed up and out, she started to see how the project could unlock tremendous value by getting people in various business unit silos to collaborate and share resources. Her part of the project was step one, which was to document what was happening currently and look for the opportunities to connect people across departments.

So even if your project is process-oriented like Tanah’s, don’t focus solely on the tactical aspects. Find the reason why it is strategic and keep that in mind when you do the job and report on updates.

Every job has a ground level view and a rooftop view

Being able to adopt both vantage points allows you to be effective in carrying out the project and also communicating it as a senior person would.

So think about the projects you’re working on. How do they contribute to your unit and the bigger mission and strategy of the organization?

That brings us to the second step.

You have to have an opinion

When you’re trying to step up and show you’re able to be senior, it’s important to have an opinion, be able to articulate it, and also identify next steps.

So when you’re updating a senior manager, don’t just report the facts and figures. Instead, paint a picture and state your opinion. Create a storyline or narrative that makes your point. Make observations and use the data to back it up.

In Tanah’s case, she was going to send Charles a regular email that described the actions she and her team had taken each week. And then ask what he wanted to see them do next. But once she started thinking about the project from the strategic perspective (also Charles’s perspective), she realized that he wasn’t looking for an activity report. He would want to hear her higher-level views on the data and what they had learned through their conversations with stakeholders that week.

Tanah also realized that she needed to propose next steps rather than ask questions about what to do next, which would make her appear more junior. So she started writing, “As a next step, I propose we…”  instead of “here’s what I’ve done, what would you like me to do next?”

This brings us to the third step.

When you’re updating someone senior, it’s important to be succinct

Develop the reputation for never wasting the senior person’s time. For a meeting or call, ask for just 10-15 minutes and be done in that period of time or less. Generally, that means less preamble and more of “getting to the point”. But adjust that to the culture of your organization and the way your boss’s boss likes to interact.

One area where you can save time is to keep your answers short and to the point. Resist the urge to give too much detail. As a senior manager, the meetings I dreaded were the ones where my team member rambled and kept talking way past my attention span. It not only made them appear more junior, it also made me less impressed with their abilities and less likely to advocate for them.

As one of our top managers like to say, “if you’re in my office for more than 10 minutes, that means you’re in trouble.” For him (and many senior people), the shorter the meeting the more successful it is.

In writing, that means having an executive summary version in the body of your email or memo with more detail below your signature if it’s needed. In Tanah’s case, she decided to keep her email updates to no more than a few bullet points, ideally three.

But what if you’ve been providing succinct email updates and getting no reply?

Sometimes, no news is good news. Other times it could mean they haven’t had a chance to read your email or they’re not happy with your updates.

Find out what their silence means, ideally from your boss’s boss herself. You could ask the next time you’re both at a meeting, either before it starts or at the end by asking her to stay on for a moment. Or it may be easier to ask her assistant or others who know her well such as your boss.

That leads us to the mistake that you won’t want to make

Which is forgetting to keep your boss informed. Ideally, discuss this with your boss directly. They may want to get cc’ed on everything (if they’re a micromanager) or ask you to keep them informed when there’s something significant, otherwise update them before their meeting with their boss (if they’re busy and they trust you). Tailor your approach to meet your boss’s needs.

So when you need to update your boss’s boss (or someone in senior management) and want to sound more senior, remember to take these steps.

  1. Make it strategic – think about how your project or work ties into the bigger goals of the organization
  2. Have an opinion – make observations and use the data to back it up
  3. Be succinct – keep your answers short and to-the-point and resist the temptation to give too much detail.

Which of these steps would most help you sound more senior when you brief your senior managers?

Leave a comment and let me know.