You start answering a question and hear yourself searching for the point. Somewhere around the third sentence you find it, so you say it, then keep going, adding background nobody asked for, until you trail off with "so, yeah."
This article covers why that happens, a three-part shape for answering on the spot, a 60-second prep routine, and clean ways to stop once the point lands. Practice the structures in low-stakes meetings first, so they are available when the stakes go up.
The advice comes from Matt Abrahams, who has taught strategic communication at Stanford's Graduate School of Business for 25 years; Wes Kao, co-founder of Maven and altMBA, who coaches executives on communication; Tristan de Montebello, co-founder of the speaking school Ultraspeaking; and Lauren Ipsen, who recruits senior executives at Daversa Partners and General Catalyst.
Why you ramble in meetings
Rambling looks like a speaking problem. Usually something else is causing it, and three causes show up constantly.
You haven't decided what your point is
Wes Kao points out that the standard concision advice, "don't bury the lede", "cut to the chase", "bottom line up front", all assumes you already know what your point is. In her words: "You can't cut to the chase unless you know what the chase is." Her diagnosis is that long-winded answers come from unclear thinking, and word count is just the symptom (19:28 in the episode, which is embedded further down).
Real-time conversation already asks you to listen, process, decide, and speak at once. If you haven't picked the headline yet, you're doing all of that while everyone listens. Most rambling is just thinking out loud in front of other people.
You're performing instead of answering
Matt Abrahams sees a second cause: the pressure to sound impressive. Judging every sentence as you say it uses the same attention you need to actually form the answer. His fix has a name that lowers the stakes on its own.
Dare to be dull. The player below is queued to 12:31, the exact moment Matt Abrahams explains it. Watch on YouTube.
"I often say strive for connection over perfection. By daring to be dull, just get the task done. Just answer the question. Just give the feedback. Just be engaged in the small talk. By doing that you dial down the volume of self-evaluation, freeing up resources that can be used to really help you succeed."
Dull doesn't mean boring. It means trying to be useful instead of trying to sound brilliant. The phrasing can be ordinary, and the answer usually comes out better because you spent your attention on the question instead of on how you sound.
Silence feels like failure
Tristan de Montebello spent years training speakers at Ultraspeaking, and he treats filler words and rushed speech as symptoms rather than the problem itself.
Filler words have a root cause. The player below is queued to 13:43, the exact moment Tristan de Montebello explains it. Watch on YouTube.
"The root cause of having lots of filler words or racing in your speaking is that you probably struggle to feel comfortable slowing down, relaxing, or even pausing when your mind is racing and you feel pressure. Solve that, and not only do the filler words take care of themselves, but the racing takes care of itself."
People repeat themselves because stopping feels abrupt when you're the one talking. A pause feels much longer to you than to anyone listening. On a video call, look up while you gather your thoughts; looking down looks like you're checking your phone. If anxiety is what makes the silence feel dangerous, the guide to being more confident in meetings covers that side of the problem.
Answer, example, relevance
For questions you did not see coming, Abrahams teaches a three-part structure he calls ADD:
- Answer. Lead with the bottom line: "I recommend moving the launch to next Thursday."
- Detailed example. Give one fact or example that supports it: "Payment failures are running four times the normal rate."
- Describe the relevance. Connect the evidence to the decision: "Three more days gives the team time to fix and retest checkout."
The ADD structure. The player below is queued to 1:04:20, the exact moment Matt Abrahams lays it out and then demonstrates it in a mock interview with Lenny. Watch on YouTube.
"It's called ADD, for adding value. You answer the question cleanly and concisely, you then give an example to reinforce the answer, and then you explain the relevance or significance of the answer."
In the demo, Lenny asks how many students he has taught. Abrahams answers the real question underneath (his experience: 25 years, thousands of students), gives one example (he teaches in both academic and corporate settings), then states why it matters to the person asking (he can tailor material to their students). His warning: we assume listeners will connect the dots, and they usually don't. Connect them yourself.
Here is the difference in a launch meeting:
Before
- "So, there are a few different things happening, and I know we originally said Friday, but engineering has been looking at the payments issue and there are also a couple of smaller things..."
After
- "I recommend moving the launch to next Thursday. Payment failures are four times normal, and three more days gives the team time to fix and retest checkout. I can walk through the recovery plan if useful."
That last sentence matters. Offering more detail lets the group decide whether they want it, so you don't feel like you have to include everything up front. Then stop.
For updates and presentations rather than direct questions, Abrahams uses a sibling structure in the same episode (39:04): What, So what, Now what. Say the thing, why it matters, and what happens next.
See how long you talked before the answer
Work Coach flags the timestamp where you buried the point and shows how many seconds of background came first. Answer it again, leading with the point this time.
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Prepare the sentence you want them to remember
Kao is blunt about what actually fixes rambling, and it is not a delivery trick.
The unglamorous fix. The player below is queued to 20:49, the exact moment Wes Kao says it. Watch on YouTube.
"The only solution I found consistently to being concise is preparation. It's not a very glamorous solution by any means, but the clearer I am going into a meeting, going into a conversation, going into a pitch, the better I am at being concise."
She is not talking about hours of prep. Even a couple of minutes before a weekly meeting makes a difference, and most people spend zero because they arrive still unwinding from the last call. De Montebello is specific about what those minutes should produce:
Prepare what you want them to remember. The player below is queued to 1:38:35, the exact moment Tristan de Montebello explains the mindset behind his Bow and Arrow method. Watch on YouTube.
"The mistake that most people do when they're preparing a talk, a presentation, an all-hands, a meeting, whatever it is, is we tend to focus more on what we want to say than what we want our audience to remember."
His claim, based on running this exercise with hundreds of speakers, is that people remember roughly one thing from a talk. Choose it on purpose. Before the meeting, spend 60 seconds on five questions:
- If they remember one sentence tomorrow, what should it be?
- What decision or action do I want?
- What is the most likely objection?
- Which example or number best answers that objection?
- What is my first sentence?
Write the first sentence out and leave the rest as bullets. A fully scripted answer makes it harder to listen when the conversation moves.
Buy time before you answer
When someone asks you something and you haven't got the headline yet, do not start talking to fill the space. Take one breath and decide whether you understand what is being asked. A clarifying question is faster than a polished answer to the wrong problem. Lines that buy you time without sounding evasive:
- "Give me a moment to organize my answer."
- "Yes, with one important timing caveat."
- "Are you asking what happened, or what I recommend we do next?"
- "I see two issues. Let me take them one at a time."
- "I need to check the data before I answer confidently. My current hypothesis is..."
De Montebello's point from earlier applies here: when you pause on purpose, people just assume you're thinking. Look up, breathe, and begin when the first sentence is ready.
Put the headline first, keep context in reserve
In her 2022 conversation with Lenny, Kao describes how she structures written updates, and the same shape works out loud.
Point first, context below. The player below is queued to 36:32, 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,' and there might be multiple paragraphs of context below for anyone who wants additional thinking on how did I get to this decision."
The logic: people who already agree get the gist and move on, and people who want your reasoning can keep reading, or keep asking. Spoken version: give the recommendation in one sentence, then let questions pull out the context. You keep the background; you just stop volunteering it.
One caveat from the same episode: a student of hers opened a customer email with "Bottom line:" and came across as aggressive. With your own team, lead hard with the point. With customers or executives you do not know well, add a sentence of warmth first.
Rehearse the stories you tell often
Kao has a test for her claim that clarity comes from preparation: think of your go-to story, the one where you know exactly when people will laugh. You tell it concisely because you have told it many times. Work anecdotes almost never get that practice, which is why the same project story wanders every time you tell it.
Lauren Ipsen sees the expensive version of this in executive searches.
The tenth-interview problem. The player below is queued to 54:19, the exact moment Lauren Ipsen explains it. Watch on YouTube.
"Practice telling your story. So often people don't do that, especially when they're not looking for jobs, and then it's not until their 10th interview that they know how to tell their story and what they did and what they impacted and why they were someone to be missed when they moved on."
The meeting version: the launch story, the outage story, the customer problem, the recommendation you keep making. Say each one out loud once before you need it, built around the decision:
- Situation: one or two sentences of context.
- Tension: the conflict, risk, or constraint.
- Choice: what you decided and why.
- Result: what changed.
- Lesson: what you would repeat or change.
Unnecessary background becomes obvious the moment you have to say it in real time.
How long to talk, and when to stop
Concise does not mean short. Kao's counterpoint to all of the advice above:
What concise actually means. The player below is queued to 18:33, the exact moment Wes Kao makes the distinction. Watch on YouTube.
"Being concise is not about absolute word count. It's about economy of words. It's about the density of the insight that you're sharing. And so you can have a 300-word memo that's meandering and long-winded and a thousand-word memo that is tight and concise."
A complex decision can deserve three minutes. The test is whether every part earns its place, and whether you stop when the question is answered, the relevance is clear, and everyone knows what happens next.
Kao's rule for agreement that arrives early, from the same episode (18:07): take the win. She used to keep presenting after executives had already said yes, and learned that more examples can only reopen a decision that has already been made. As Lenny puts it in the exchange, if you've sold them, stop talking.
Deliberate closing sentences make stopping easier:
- "That is why I recommend option B."
- "Those are the two risks I would solve before launch."
- "The decision I need today is whether to proceed."
- "That's the headline. Where would you like more detail?"
Frequently asked questions
Is rambling caused by anxiety?
Often, yes. Anxiety adds cognitive load and makes silence feel dangerous, so you talk to fill it. Preparation, a written opening sentence, and permission to pause all help. If nerves are the main driver, start with the meeting confidence guide, and consider coaching or clinical support if it persists.
How do I stop rambling in virtual meetings?
Keep a small note near the camera that says "answer, example, relevance, stop." Hide self-view if it distracts you. Look up while you think, so the pause looks deliberate instead of like you're reading something.
Will short answers make me sound abrupt?
Clear answers can still be warm. Add a brief transition such as "My recommendation is..." and invite questions after the headline. Kao's caveat applies too: with people who do not know you well, one sentence of warmth before the bottom line goes a long way.
The one-week plan
Before each meeting
- Spend 60 seconds on the five prep questions. Write your first sentence and the decision you want.
When someone asks you something
- Answer, give one example, explain the relevance, offer more detail. Then stop.
- If the headline has not formed, pause or ask one clarifying question first.
After each meeting
- Note one moment you buried the point, repeated yourself, or kept talking past agreement.
Daily practice
- Record a 30-second answer to "What are you working on?" once a day.
- At the end of the week, pick one recurring filler phrase to drop.
Sources
- Lenny's Podcast: Become a better communicator, with Wes Kao (Apr 2025)
- Lenny's Podcast: How to speak more confidently and persuasively, with Matt Abrahams (Mar 2024)
- Lenny's Podcast: Why most public speaking advice is wrong, with Tristan de Montebello (Oct 2024)
- Lenny's Podcast: Lessons from one of the world's top executive recruiters, with Lauren Ipsen (Nov 2022)
- Lenny's Podcast: Persuasive communication and managing up, with Wes Kao (Aug 2022)