For people new to the table: young officers advising at the two- to four-star level, and anyone new to the C-suite. Decide what your boss needs to hear, then build a brief they can act on.
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Know your principal
Same message, different delivery. Fill this in once.
Why this matters. The best answer in the room does nothing if it reaches the wrong person, at the wrong time, in a form they can’t use. Start with the person.
Why this matters. Trust comes before influence. Leaders weigh advice by what they think of the person giving it. Learn how they work before you try to change what they decide.
Read your principal (optional, deeper)
Why this matters. Two leaders can want the same outcome and need completely different handling. This section helps you name how your principal operates, based on what you’ve actually seen them do, and what tends to work with that style. Hold the read loosely. Advisors who label too early stop seeing. The read is for you only and never appears in the brief.
What are you bringing them?
Pick the situation. Each one has its own path.
Portfolio triage
List what’s on your plate. For each item, check what applies. The tool sorts each one into Tell nowWeekly update or Handle it
Why this matters. Sending more updates won’t make you more valuable. Your boss’s attention is the scarcest thing in the building, and part of your job is protecting it. The other part is making sure they never get surprised by something they should have heard from you first.
Crisis brief
Shape the conditions for their decision. Don’t try to make it for them.
Why this matters. In a crisis, your principal’s most valuable asset is decision space: enough clear information, and enough time, to choose well. Separate what you know from what you think. State your confidence out loud. Frequent updates only help if they change the picture.
Why this matters. Name the kind of problem out loud. If it’s clear, use the playbook. If it needs experts, bring two or three options with tradeoffs. If it’s complex, recommend small, safe steps and watch what happens. If it’s chaos, recommend one stabilizing move first: one spokesperson, one set of facts, and a set time for the next update. In chaos, stabilize first and learn as you go.
Why this matters. Get clear on roles first: who recommends, who has to agree, who decides, and by when. Being consulted isn’t the same as having a veto. If no single name is on the decision, it won’t get made.
Major recommendation
Answer first. Then make it easy to say yes, and clear who has to say it.
Why this matters. Leaders have minutes, not hours. Lead with the answer, support it with two or three reasons, and end with the next step and a named owner. A list of facts isn’t a recommendation.
Who decides
Why this matters. Sort out roles before content. Keep the list of people who can block it short, and give them a deadline. Being consulted isn’t a veto.
Stakeholders
Why this matters. Score each stakeholder on three things: can they affect the outcome (power), is their claim legitimate, and is it urgent for them? Those with all three come first. The loudest voice isn’t always the one that matters.
Why this matters. A goal nobody can check isn’t a plan. Write it so someone could confirm in 90 days whether it happened.
Ethics check (TARES)
Pressure test and delivery
Run these before you walk in.
Why this matters. Bad news gets worse when it looks hidden. If one of these boxes stays empty, that’s the part of your brief to fix before you deliver it.
If you disagree with where this is heading
Truth to power. Do it privately and early. Describe behaviors and consequences, not labels. Offer a fix that keeps their intent. Then tell them what you’ll do if they still decide the other way: you’ll make sure your concern is noted, and you’ll carry out their decision. Timing matters as much as words: raise it when it’s relevant to what they’re working on, when you’re ready with a remedy, and when they can actually hear it.
Built on my own time from almost 20 years of advising senior leaders. It draws on public frameworks including the Cynefin framework (Snowden and Boone), Boyd’s OODA loop, decision-rights models such as RAPID, and the pyramid principle (Minto). The principal read draws on research on organizational behavior and leadership: Downs (1967), Merton (1940), Davis, Schoorman & Donaldson (1997), Ferris et al. (2005), Brehm (1966), Hermann’s Leadership Trait Analysis (1980), Hambrick & Fukutomi (1991) and Tepper (2000).
