You have five minutes on an executive agenda and six weeks of work to explain. If you start at the beginning, you'll still be describing activity when someone interrupts to ask whether the project is on track.
This article gives you a structure for spoken updates, written updates, risk escalation, and follow-up questions. Draft the one-sentence headline first, then choose only the details leadership needs to understand the outcome or make a decision.
The advice comes from Wes Kao, co-founder of Maven and the altMBA; Shreyas Doshi, who led product at Stripe, Twitter, and Google; and the Mochary Method's guidance for issue and decision meetings.
Write the headline before the update
Your first sentence should answer the question a leader would ask after hearing everything else. Common versions are:
- "The launch remains on track for September 4, with security approval as the only open risk."
- "Activation is improving, but the experiment has not recovered the acquisition cost."
- "We need a decision today between protecting the date and including the enterprise workflow."
Don't start with the calendar, the meeting history, or a list of completed tasks. Those details can back up the headline when someone needs them.
Give leaders the information that lets them help
Wes Kao says strong managing up keeps a boss informed without sending every detail. The amount of context depends on how reversible, expensive, or consequential the decision is.
Choose the right amount of context. The player below is queued to 32:58, the exact moment Wes Kao explains proactive communication and judgment. Watch on YouTube.
"One really big way of doing that is keeping your boss in the loop on the kinds of decisions that you're making and what you're working on... proactively giving the right amount of context for your manager to be able to weigh in on what you're doing and to be able to give feedback."
A routine green project may need one sentence. A project that just went red needs the evidence, the consequence, the options, and an owner. If a decision is expensive to reverse, give enough of your reasoning that someone can challenge your assumptions.
Why silence scares leadership. The player below is queued to 101:40, the exact moment Matt Mochary explains why not sharing your status makes leaders assume the worst. Watch on YouTube.
"If you don't share it, they think you're irresponsible, that you're blind, that you have no idea what's going on. You have to allay that fear by saying, here's what I see."
Use outcome, state, risk, and ask
The four-part leadership update
- Outcome: the result the work is supposed to produce.
- State: where that result stands now, including what changed.
- Risk: the condition most likely to change the outcome.
- Ask: the decision, help, or awareness you need.
Example: a 45-second update
"Our outcome is to move 80% of enterprise customers to the new billing system by October. We're at 52%, which is six points behind plan after two large customers paused. The main risk is migration support capacity rather than product readiness. We can recover by moving two implementation specialists for three weeks. I need approval from Sales and Services today; Priya owns the revised customer schedule by Friday."
That update tells a leader what success means, what changed, why it matters, and where they can actually help. Keep the supporting numbers handy, but wait until someone asks before going through all of them.
Separate activity from impact
A status update can make useful work visible. It can also become a polished list of activity that says little about results. Shreyas Doshi calls status reporting an optics activity and warns against rewarding the update as though it were the outcome.
Don't mistake the update for the work. The player below is queued to 1:00:23, the exact moment Shreyas Doshi explains why a status update isn't an accomplishment. Watch on YouTube.
"Do you appreciate a launch? Do you appreciate results? Do you appreciate an awesome status update that somebody sent? So a status update doesn't on its own accomplish anything. I mean, they are important, but a status update is an optics activity."
Swap the activity language for evidence that something moved:
Rewrite the update
- Activity: "We held four customer calls." Result: "Four calls confirmed that setup time, rather than price, is blocking adoption."
- Activity: "Engineering completed the API." Result: "The API is complete and passed the two load tests required for partner launch."
- Activity: "We are working through legal review." Result: "Legal cleared data retention; the indemnity clause remains open and threatens Friday's signature."
See how long it takes you to reach the headline
Work Coach times your update and marks the second where a leader was still waiting for the point. Run the 45-second version against a simulated exec until it fits.
Start Free Trial2-week trial, no credit card needed. Your data is never shared with your employer.
Lead with the bad news
When a project changes from green to yellow or red, say so in the headline. Don't spend two minutes on progress before mentioning that the date is likely to move.
Risk update script
"The October migration is now at risk. Two customers paused after the security review identified a logging issue. Engineering can fix it by Friday, but that leaves only three days for validation. I recommend moving the migration one week. If we hold the date, I need Security to approve a reduced test plan today."
Say when you first knew about the risk, what you did after that, and what would put the work back on plan. The playbook for telling leadership a project is delayed covers that conversation in detail.
Make written updates easy to skim
Wes Kao puts the most important point at the top and moves the reasoning below it. That way anyone who already agrees can stop reading there, and anyone who wants to check the decision can keep going.
Put the point first and the context underneath. The player below is queued to 36:34, the exact moment Wes Kao describes the format. Watch on YouTube.
"I'll usually put the most important point at the top, the TLDR, if you will, the gist. And then I'll say, context colon. And then there might be multiple paragraphs of context below for anyone who wants additional thinking."
In writing, the same order holds. Copy this into your weekly note.
Written update template
Bottom line: One sentence on outcome and current state.
Changed since last update: Two or three bullets.
Risk: The risk, trigger, consequence, and owner.
Decision or help needed: The named person and deadline.
Context: Links, data, and history for readers who need it.
Create a cadence that prevents surprises
Lenny Rachitsky describes a weekly "State of Lenny" email with three sections: current priorities, blockers that needed help, and things on his mind. It kept his manager up to date and got blockers in front of her before they turned into emergencies.
A simple weekly update. The player below is queued to 34:23, the exact moment Lenny describes the format in his conversation with Wes Kao. Watch on YouTube.
"I sent my manager a State of Lenny email every week... and it had basically three sections: my priorities currently, blockers that I need their help with, and then just things on my mind currently that week."
Match the cadence to the risk. A stable project may need a weekly note. A red launch may need a daily written update plus a short live decision meeting. When the risk changes, say out loud that you're changing the cadence.
Answer leadership questions without restarting the presentation
Give the direct answer, then one supporting fact. If you don't know, say what you do know and when you'll come back with the rest.
When asked, "Are we on track?"
"The date is still achievable, but I'd call it yellow because security validation has no buffer. We will know by Thursday whether the risk is resolved."
When asked for a number you don't have
"I don't have the seven-day retention figure in front of me. Weekly activation rose four points. I'll send retention by 2 p.m."
When asked to go deeper
"The main cause is implementation capacity. I can walk through the customer-by-customer data if that would change today's staffing decision."
If your answers keep growing, use the structures in the playbook for concise meeting answers.
Frequently asked questions
How long should an executive status update be?
A routine spoken update can often fit in 30 to 60 seconds. Use more time when leaders need to understand a new risk or make a decision. Put the conclusion in the first sentence either way.
How many metrics should I include?
Include the few measures that show whether the outcome is improving and whether the plan still holds up. Keep the diagnostic metrics handy for follow-up questions.
Should I include completed tasks?
Include a task when completion changes the outcome, removes a risk, or allows another team to start. Put the full activity log in the linked context rather than the spoken headline.
What if leadership wants a different format?
Use their format but keep the same information underneath: outcome, current state, risk, and ask. Ask them what they want to know and how often they want it.
The status-update checklist
Prepare
- Write the one sentence leadership should remember.
- State the outcome and what changed since the last update.
- Name the largest risk, its trigger, consequence, and owner.
- Make the decision or help needed explicit.
Deliver
- Give the headline first.
- Connect activity to a measurable result or learning.
- Pause after the ask and answer the question that was asked.
Follow up
- Send decisions, owners, and dates.
- Put deeper context below the summary or behind links.
- Increase the update cadence when risk rises.
Sources
- Lenny's Podcast: Persuasive Communication and Managing Up, with Wes Kao (Aug 2022)
- Lenny's Podcast: The Art of Product Management, with Shreyas Doshi (Jun 2022)
- Mochary Method: Meeting Guidance Sheet and Writing and Video vs. Talking
- Mochary Method: The Value of Issue/Proposed Solutions and RAPIDs (Mochary Method Class 3) (Nov 2021)