Package Up Before You Message Up

Everyone who works an office job has experienced it: that terrible moment mid-meeting when the decision maker’s eyes glaze over and they stop paying attention. It could be because they just got a heart-stopping email from their boss. It could be that they just realized they need to place their lunch order now to receive it and wolf it down before their 3 p.m. Or it could be because they’re bored. Whatever the reason, that glazed-over look in the eyes of a decision maker is the death knell for any kind of proposal or plan that requires sign-off.

As someone who regularly presents to decision makers, observes others presenting to decision makers, and gets presented to as a decision maker on a regular basis, I’ve seen my share of the “oops, just lost ’em” moments. In fact, there’s a little game I like to play in my head in the meetings I’m not running: I try to catch the very moment a key participant mentally checks out. Now that many of us work from home, “meetings” are video calls, so presenters are competing with Slack, browser tabs, kids, pets, and doorbells for attendees’ attention. It’s not surprising that these moments happen sooner and more often than ever. 

“A boss loves a good summary.”  —my boss

Know your audience

No matter how distasteful, there are political realities of corporate life that all participants have to deal with. They include:

• Corporations are hierarchical. At work, you’re always talking to people up, down, or across the organization.
• Everybody has a boss. Every boss has a boss. Even the ultimate boss answers to clients, boards, investors, and shareholders.
• Everyone is separated into functional groups, and their role is concerned about different aspects of the work.
• Senior leaders and executives oversee the whole shebang, and ultimately sign off on initiatives and budget.
• Senior leaders are the farthest away from the nuts and bolts of how work gets done. They have spent about 2% of the time you have thinking about the details of the matter at hand.
• Senior leaders skim across every single thing going on in the org. They are spread thin and are constantly switching contexts.

This means senior leaders will show up to discussions seeming scattered and forgetful. You’ll have to repeat yourself. They’ll ask basic questions in the last five minutes of the conversation, which will make you wonder if they understood anything you said at all the entire time. Almost every time you see them, they’re still mentally tied up in a terrible meeting about something completely different that just ended two minutes ago. 

Given these realities, how does any honest, hardworking, well-meaning human being ever effectively communicate anything up the chain?

There’s a specific kind of managing up in communication, and that’s packaging information in an easily digestible way, minus the fluff, to get to a conclusion. When you package up, keep this in mind: The higher the altitude of your recipient, the lower the fidelity your presentation should be—and the broader the context it should include. 

It’s the most basic premise of Communication Strategy 101: Know your audience. But so many people in professional settings miss it, especially when they are communicating up the chain. Here’s a refresher on how to master upward communication—no matter your position in the org.

Set the stage and drive to clear takeaways

Don’t assume anyone has read the meeting title, description, or agenda when they show up to a meeting. The first thing any busy executive secretly wonders about any meeting is, “Why are we here?” On bad days, in big meetings, they think, “How much is this meeting costing the company?” 

When you start a meeting, set the stage as clearly and concisely as possible, e.g., “As a reminder, we’re here to discuss Project X, which is the initiative to better address Q and R. Last time we met, we decided A, B, and C. The purpose of this meeting is to gather feedback/make a decision/review the status of D and E.”

Then, firmly guide the discussion to its clear conclusion. Shut down tangents with “we can take that offline” or “that can be a different meeting” or “that’s out of the scope of this particular discussion.” If you want to really impress, wrap up the conversation sooner with clear takeaways and next actions before the meeting is scheduled to end.

Brevity is better

When you’re presenting a plan or an idea up the chain, draw the picture in broad strokes and leave out the details. A mistake I see often, particularly by more junior folks, is sharing all the details of everything related to the matter at hand as proof of work. (No one, except maybe your direct manager, wants proof of work.) Sometimes midlevel people think that by sharing all the details, they’re justifying their existence or bolstering their case. The opposite is true: They’re creating more noise. Clear, plain English is your friend. Acronyms and legalese and jargon make you sound like you’re trying too hard to sound smart, or hand-waving.

Another pattern I’ve observed: Good leaders will spend the front half of a meeting quietly listening to a presentation with a bone-chilling lack of any reaction or response at all. They want to hear you out completely. When you’re done, they spend the back half interrogating. That question and answer part is when you can drill down into the details they actually care about. Be prepared to go a level deeper on any point, but only one level. A common question I’ve heard from leaders looking for more detail is, “Can you summarize XYZ?” They’re saying, “Explain this part further, but keep it short.”

Focus on the why

Leaders are less focused on the details of the how but care deeply about the bigger-picture why. Leaders want to know how the matter at hand connects to the business goals they specifically are responsible for. And leaders are always looking out for risks on the horizon, around their areas of responsibility. When you’re presenting a plan to a leader, make sure you address the risk by answering the question “What happens if we don’t do this?”

Finally, when someone key can’t make the meeting, or to make sure everyone who has doesn’t forget, make sure to share the executive summary after the fact.

While you ultimately may lack visibility into a leader’s decision-making process, the best thing you can do to influence them is to give them the information they need—no more and no less—to make a call and move on. Good luck. 

Gina Trapani (@ginatrapani) is a Managing Partner at Postlight. Want to talk? Get in touch: hello@postlight.com.