How to Brief Senior Leaders and Make It Count, Part 1

How to Brief Senior Leaders and Make It Count, Part 1

Briefing a senior leader on an important issue?
Want to hit a home run?
Read or listen to this article to learn how.

For a pdf of this article, click here

You’ve been tasked with briefing the Big Boss on an important issue, and you want to hit a home run. Or at least you’d like to not screw up.

That’s no problem if you know this person well—how they like to receive information; the problems they’re grappling with; and how they come across when they’re annoyed, intrigued, or just being polite. If you know all that, you’re halfway home!

But if not, consider these guidelines, which we’ve collected from several decades of experience in the hot seat briefing senior leaders, and which we refined by directly asking many executives: “How do you like to be briefed, and how do you not like to be briefed?”

Step #1: Define Your “Home Run”

A few years ago, U.S. Navy top leadership asked us to improve the process by which their daily brief was done. So we asked a few of their young Navy briefers, “What’s a home run for these daily briefs?” Unanimously they responded: “No questions. If we can get out with no questions, that’s a victory!”

But then we asked the same question of the 4-star admiral heading the meeting. His answer was different. He told us the brief was useful only when it enabled strategic-level conversations. Hmm. What an unfortunate disconnect on the whole reason for the brief.

Here’s our point. A clear and well-informed purpose—your “home run”—will set you up for success. Generally, you want to create a condition in which the boss can successfully decide or assess something. Maybe they need to pitch an idea to others and you’re giving them the ammo they need.

Never is your home run the tautology of giving them information for informational purposes. You’re there to make some thing happen. Name that thing and devote yourself to it.

Step #2: Gather Intel

Upfront digging prevents unpleasant surprises for you and your audience. Three kinds of intel will help you with that.

The first is about style—that of the boss and of the other key attendees. One good go-to for this is the boss’s executive assistant. The EA usually knows the boss’s style and will help you make the best use of their time, especially if you frame it that way! Here are five questions that will help you pull that thread:

  • First, What are their “tells”? Ask about the boss’s tells, such as, “What does she look like when she’s bored—and I oughta move on to the next point?” Likewise, “annoyed,” “being politely patient,” and so on. (Then go beat the boss at poker. No. Just kidding.)
  • Second, How do they consume the written part? Are you better off sending a point paper and then just taking questions in the meeting? If the boss likes slides, should your slide deck be the read-ahead? Is it okay to send an agenda? (You want a “yes” to that last question; agendas help you manage expectations and the meeting. Be sure the agenda includes a statement of the brief’s purpose.)
  • Third, Who should send the read-ahead? Maybe it’s you, or maybe it’s more appropriate for the EA to do that. Or, if the meeting has multiple participants, perhaps the boss would like to receive a draft agenda from you and then send it out under their own name.
  • Fourth, In what format do they like their visuals? Generally, the higher a leader is in an organization, the more they’ll prefer at-a-glance-type visual information. (We’re not talking clipart here; we’re talking about conceptual diagrams of ideas and relationships, charts, graphs, and the consultants’ old standby: the 2X2 matrix.) Senior leaders will incline less toward bullet points and even less toward great gray masses of words, but it depends on the issue and the person. Maybe the boss prefers whiteboards or flip charts. Find out.
  • And fifth, Who else is coming to the meeting? What are their roles, and—especially—which of them may need a little managing or extra attention? Who will have the boss’s ear on this topic? If someone derails your meeting, you won’t achieve your goals and it may even be seen as your fault. So, know what or whom you’re up against and have a plan.

A second kind of intel you need is on the boss’s interests, concerns, and annoyances, especially as they pertain to the topic of your brief. Here are a couple of ways to get at that.

  • First, What does their public face say? Have they given speeches, conducted interviews, or written memos that tell you what’s on their mind? You can likely connect your message to their concerns. Or you might learn topics to avoid, or how you should frame your message. At the very least, an awareness of the boss’s current world will increase your credibility.
  • Also, What do other attendees say? Another powerful source of this information will be others who are attending the meeting. As with the EA, ask a few key players for a brief conversation. The double payback of this preparation is that you get the information you wanted, plus a little advance rapport with key attendees. That’s a very good thing.

Lastly, gather intel on the meeting’s setting. You want to be comfortable with your venue so it doesn’t siphon your attention while you’re briefing the boss.

  • Will your venue be a videoconference? If so, make sure your software has the latest updates and you know how to operate it, especially if you plan to use slides or other visual aids. If you get to choose between a teleconference and a videoconference, we’d recommend the latter. That’s because, with visual cues, it’s easier to pick up on—and convey—nuance.
  • Or is your venue it face-to-face? If the meeting space is physical, you should ask to see it and learn how it’s going to be set up. Will you be using a podium? A mic? Where’s the boss going to sit? If it’s not practical for you to see the space, ask a friendly soul to text you some pictures. It’ll help. Really.

Step #3: Build the Brief Around Your “Home Run”

Consider that the sequence in which you captured and outlined your thinking may not be the same sequence in which to unveil your message — if you want your audience to grasp your message.

In addition, although you do want to make your brief easy to follow, don’t do that by boring your audience with baby bites they don’t need. You’ll lose their attention and pigeonhole yourself as a low-level, tactical (i.e., not strategic) person.

Instead, try this little thinking hack: Use questions to organize your brief.

List the key questions your audience needs answered, and then decide the best sequence in which to answer them. When you frame your brief this way, the sequence will become obvious to you.

You can also use these questions to provide your audience the intellectual scaffolding to follow your reasoning. You could say something like, “Here’s what I hope we can accomplish and the six questions we’ll answer to do that.”

Or, if you’re a good storyteller, you could begin with an engaging anecdote that tees up the goal of the brief and the topics to be discussed to achieve it.

If you’re using slides, put any details or supporting data that you might need at the back of your brief in a section labeled “supporting information” or “backup slides.” Be sure to reference them by page number in the main body, as you would with endnotes, so people can flip back and forth with ease.

One more thing: Wherever possible, make the abstract concrete.

For example, if you’re expressing safety concerns about a new device on the market, you should cite statistics that make your case, but back it up emotionally with potent anecdotes about real people. Bonus points if you can hold up an object related to your message—say, a broken fan belt or a deceased victim’s name badge. That’s powerful.

Step #4: Be Present

Having mastered your material, it’s time to master the room.

It’s easy to withdraw into your own head with a flurry of self-talk. Instead, tell your brain to be quiet and tell yourself be present.

Take the attitude that you are there to benefit these people, so put your attention on them. It will calm your nerves and sharpen your aim if you shift from “How am I looking?” to “Are they getting what they need?”

Adjust as you read the room. It’ll help that you’ve learned a few of the tells already. The boss may give you a look that means, “Got it. Let’s move on.” So you ask, “Shall I skip to the next point?” Or maybe you’re getting a squinty, semi-frown—so you ask, “Is this making sense?” And so on.

Demonstrate that you’re engaged with them and not merely robo-briefing them. In virtual environments where sensing body language is more difficult, check in a little more often. This might be as simple as pausing to allow for comments or questions.

And in any environment, be willing even to set aside your presentation materials and just have a conversation if that’s what will serve them best. Be present.

Step #5: Close the Loop

If the session played out as you expected, then wrap up by asking for the decision or whatever your home run included. At the very least, confirm that the boss got what they were looking for.

You may not get closure right away. Maybe you’ve introduced new information that prompts further investigation. Or maybe the boss would like to confer with others.

Even so, what you can do before the meeting ends is ensure that next steps are clear—yours and theirs. This will give everyone a sense of closure and confidence that the topic of the brief will be effectively managed to the desired outcome.

In summary, you’ll find that your most effective briefs occur when you have a clear goal, which then becomes your North Star that guides your research, intel gathering, content development, delivery, and ultimate closure with your target audience. With this structured and thoughtful approach, you’ll hit the ball out of the park every time.

How to Brief Senior Leaders and Make It Count, Part 2


        • Dan Kilhefner

          A good tip that I have picked up through the years when briefing Senior Leadership and Executives, is understanding how to read the room. Understanding the basics in human behavior is key like understanding someone’s affect! If the room is quiet and making you uncomfortable ask the audience a question to provoke conversation which can lead towards engagement. Asking for feedback during a brief helps the exchange of ideas flow, making building rapport smoother. Great article!!


        • @Dan Kilhefner. Nice point, Dan. I think it’s easy for briefers to go into “safety mode,” and not take the move of interacting with their audiences. It might feel risky, but it’s actually lower risk than not checking in with your audience. Thank you!

      • John Harvey

        I’ve always thought a good brief told a story and if you need more than 8-10 slides to help tell your story, well then you don’t know your story well enough. Bombarding a senior leader with a mega-slide brief to cover every possible angle of the topic and demonstrate your master of the subject matter only serves to show you don’t know what is REALLY important and have no real idea of the message you’re trying to convey.
        Get to the point right away – tell them why they’re there and give them the bottom-line, tell the story and then tell them what you just told them!
        Bill and Wendi’s advice absolutely nails the essential issues relative to the brief. One important addition – DO NOT EVER JUST READ THE SLIDES TO THOSE ATTENDANCE – they can read for themselves.
        The slides should not be a “dense-pack” of tightly packed bullet points. Project the key ideas that you can expand upon in your voice-over.
        If you have to say, “I know this slide is an eye-chart…,” then your slide is screwed up! Pull only the data you need, make sure it’s legible from the back of the room for “older” eyes and ensure it supports the story you’re telling.
        Data dumps don’t help, they only hurt. I remember saying to one briefer, “It’s going to take me 20-30 minutes to figure out what you’re trying to tell me on this slide.” Not good because there was only 5-10 minutes left to get through the rest of the material!
        Bottom-line – this is great gouge from Wendi and Bill!!!!


      • @John Harvey. Thanks, John! Wendi and I love all your points — and especially share your loathing for “eye charts”!

    • Herb Koplowitz

      I’ve never seen this topic addressed before. It’s important and your advice looks practical to me. I also think here of Jaques’s notion that an employee owes their manager their best advice. I expect much (though likely not all) of this piece would also apply to the usually more mundane employee-to-manager best advice.


    • @Herb Koplowitz. Thanks, Herb. Yes, this is certainly an example of “best advice,” and in a vein that Jaques surely would have approved. Of course, “best” has to be aimed at a particular, thoughtful goal or purpose. That may be where more senior execs can be of more help to their junior-level briefers.

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