How to Brief a Senior Executive
You can always count on outside circumstances to affect your pitch to a senior leader, so prepare to get your point across under pressure by understanding the interpersonal dynamics at play in advance. What are your boss’s “tells”? How do they engage with material? And whom do they look to for endorsement? Knowing these things ahead of time will help you react effectively to pushback and pivot when necessary while you’re in the room, either in person or virtually.
Briefing a senior executive is an art and adept White House staffers do it every day under the most stressful of circumstances. They’re masters of compressing the right information into the right amount of time, no matter how complex the topic or short the briefing. The skills needed to brief the chief executive in the Oval Office are directly applicable to briefing any executive in the C-suite.
There’s no shortage of advice on how to brief a senior leader: keep it short, front-load the message, and so on. These are solid pointers, but they undervalue the interpersonal elements that are critical to a successful briefing. Your presentation can fail or succeed before it begins and your odds are worse if you skimp on the personal in favor of the PowerPoint.
The following tips are based on battle scars from serving twice in the White House and from years of briefing senior corporate, nonprofit, and government leaders, as well as teaching briefing skills in seminars around the country. They’re important whether the briefings take place in person or virtually.
Identify the “crucial nodder.” At a critical moment in the briefing, the president will turn to a trusted advisor and look for a facial expression to affirm what you’re saying. You need that person to nod “yes.” It’s a quiet gesture that gives the boss comfort; it shows that your idea is sound and all of the right people have been consulted. Anything short of a supportive nod will invite follow-up questions and sow doubt in the room. Even worse, a look askance or a non-endorsement from a chief advisor can spell the quick death of your pitch.
Before you present your idea, figure out who the crucial nodders are (it may be multiple people and it may vary based on the issue) and consult them in advance. While the executive you’re briefing may not have a crucial nodder, chances are they do have people whose opinions they trust more than others. You need their support — or at least a sense from them that you’re facing an uphill battle.
Know your boss’s “tells.” If you spend a lot of time with the senior executive, then you should know the nonverbal cues that indicate things like “go deeper on that point” or “speed it up.” If not, seek out people who regularly brief and interact with them. Ask what to look for to know if the boss is annoyed and whether there’s any way to determine if it’s because of something you’re saying or if it’s unrelated. Also ask how best to respond to negative signals to try to shift the mood. Advance understanding of your boss’s body language will help you keep your cool and pivot in the right direction during the briefing.
Find out how the boss engages with the material. People vary in how they react to and absorb information. A senior leader I briefed in the White House would question and push back (hard) on every point, large or small, in every briefing. Some colleagues found this intimidating and eventually turned into “yes” people and lost his respect. Other people jumped into a fight every time; they appeared closed minded and agitated him. The colleagues who earned this leader’s respect were the ones who picked their battles wisely. They went with the “yes” where they could and judiciously pushed back when it counted most, showing flexibility but also confidence in their views. If you go in with an awareness of a leader’s engagement style, you’ll be better prepared to effectively convey information and respond to pushback.
Plan for gradations of success and failure. Of course, you should identify what you need from a meeting before walking in the door. But here’s a twist: Don’t think of it in binary terms of success and failure. Walk into the meeting with your “ask” but also with contingency plans for multiple scenarios of success and failure. If the conversation is trending toward “no,” you can offer a scaled-back version of your proposal. Likewise, if your idea is succeeding, have some additional ideas for add-ons or offer ways to accelerate the timetable. In short, think of how you can achieve a limited victory instead of a complete failure, keep an idea alive to fight another day, or, in the best case scenario, go bigger and faster in implementation.
Read the room, not your notes. Whether the briefing is in person or virtual, you need to read cues and body language. You should know your material cold by this point so that you’re not fumbling with your notes; your mental energy should be focused on reading the room, looking for openings, and watching out for pitfalls. If there’s a corollary to this rule, it’s “take cues, not notes.” (In fact, when possible, have someone else take notes so you can be fully in the moment.)
Stay laser focused on your task. Time pressure, competing interests, and unforeseen circumstances can threaten to pull you off task during the meeting, but don’t lose focus. Your ask is your priority and why you’re there, so dedicate all of your mental energy to looking for opportunities to advance it. If the conversation gets off track, a question causes the meeting to digress, or someone starts to rant about a pet topic, pre-plan several ways to redirect the conversation and get what you need. It’s a rare talent to be dogged but deft at the same time, and of course, you don’t want to look like a stiff or a robot. In a fast-paced work environment, though, meetings often get interrupted or cut short. Try not to deviate or raise unnecessary details to reduce the chance that a briefing will be interrupted before your ask is addressed.
Practice the art of staying silent. You’ve floated your idea or posed your question. The discussion has taken off and now you need to be exceedingly strategic about whether and when to chime in. The executive is engaging others in the room or thinking aloud. By speaking at the wrong moment, you risk derailing the line of thought or annoying your boss. There’s no need to unnecessarily affirm something said or show off your knowledge. Alternatively, if the discussion is trending against you, take your best shot — rather than all the shots — at jumping in to try to get things back on track. Often, not speaking at the wrong time is just as important as saying the right thing at the right time.
No matter how well you prepare, circumstances beyond your control, from an unrelated crisis to the boss’s stress level that day, will affect your pitch. While you cannot guarantee success, focusing on the interpersonal dynamics ahead of time and improving your situational awareness once in the room will make you more effective. You’ll be better placed to communicate the right message under pressure, whether you’re briefing the president of the United States, a C-suite executive, or any leader.
How to Brief a Senior Executive
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