speak up!!!!!!!!!

WELL . . . landing words could change your life

One of the best pieces of advice I've received about moving up in the world is that you should aim to speak at least three times in every meeting you join. If you're not speaking up, you're not adding value—and if you're not adding value, you probably shouldn't be there.

I like this advice because I’ve found that many people approach meetings as consumers rather than contributors. They think “I should attend because I'll learn something” instead of “I should attend because I can move this conversation forward.” But generally, you will be much more successful if you orient yourself around how you can be of high value to others rather than what’s in it for you. (I’m reminded of another good piece of advice when cold outreaching: “make it an offer, not an ask.”)

When I share this advice, I can immediately spot what's holding people back. These obstacles usually fall into two categories: legitimate skill issues and what I call “head trash”—self-limiting thoughts and narratives that provide convenient excuses to avoid discomfort. This distinction matters because skill issues and head trash need different solutions. Once you recognize your head trash for what it is, you can focus on building actual skills.

wait what do you mean by head trash

Here are examples of things that might go through your head when reading this newsletter that I would consider head trash:

• I don't want to speak just for the sake of speaking.

• I don't want to be like those people who love hearing themselves talk.

• Everyone else is probably thinking the same thing, so I don't need to say it.

• I'm not 100% confident in my idea, and if I say something wrong everyone will remember it.

• I'm just here to absorb information. I don't know enough to contribute.

• I like to think before speaking, and by then the conversation has moved on.

• If someone wanted my input, they'd call on me to speak.

• I'm an introvert, so I naturally speak less in groups.

• I don't want to derail the meeting with my comment.

• Nobody cares what someone at my level thinks.

As I wrote in the self-promotion horror show, you know you’re dealing with head trash (as opposed to, like, a fact) because it crumbles into nothing when reframed properly:

I don't want to speak just for the sake of speaking. → This assumes your contributions would be meaningless. Of course, they do not have to be! Challenge yourself to find valuable ways to contribute: ask a clarifying question, summarize a key point, or connect ideas from different speakers.

I don't want to be like those people who love hearing themselves talk. → There's a huge difference between contributing thoughtfully and dominating a conversation. If you're worried about this distinction, you're already unlikely to become “that person.”

Everyone else is probably thinking the same thing I am. → So what? Articulating a shared thought moves the conversation forward, validates others who might be hesitant to speak up, and can help drive consensus.

I'm not 100% confident in what I have to say. → People learn all the wrong lessons in school. The goal of speaking up in a meeting isn't to, like, prove to the teacher that you know the secret correct answer. When tackling real-world problems, there's rarely a single “right” answer anyway. Most complex challenges have multiple valid solutions, each with different trade-offs. Dialogue is about collectively figuring out the best path forward. Different perspectives help us get there.

I'm just here to absorb information. → Even as a learner, your questions and perspective are valuable. Fresh eyes often spot connections or gaps that others miss.

Etc.!

Of course, not all self-doubt is head trash. It's good to recognize the specific ways you struggle or even fail to communicate effectively in meetings. If you're working on speaking up more, you probably won't be great at it initially. But you can improve quickly with the right approach.

ok so what about the skill issues

First, it’s very important to create a learning loop. Simply talking more without getting feedback won't get you anywhere. You need targeted input to improve. Tell a trusted colleague or your manager what you're working on and ask if they'll debrief with you after meetings to discuss how your contributions moved the conversation forward.

If you're serious about improving, block 10 minutes on their calendar after meetings for immediate feedback. And don't just ask vaguely "for feedback" – ask specific, insightful questions like:

• Which of my contributions added the most value, and which could have been skipped without affecting the outcome?

• Do you notice any patterns in when I speak up versus stay silent? Are there particular topics or people that seem to trigger my hesitation?

• If you ranked my contributions today on impact from 1-3, how would you order them and why?

• Did my delivery style—tone, pace, body language—enhance or detract from my message? Did I seem nervous? Was I being pushy?

• At what point did my contribution seem to influence someone's thinking or change the conversation's direction?

[The above questions all came from Claude, BTW. You could feed Claude this newsletter, some context about a recent or upcoming meeting, and your specific insecurities to get more questions tailored to you.]

the three skills I coach people on the most

I've had countless conversations with people trying to improve how they speak and hold the room in meetings. While this is genuinely difficult to master, there are three areas I find myself coaching people on again and again:

1. use “landing words”

This technique is so simple, so impactful, and yet I never hear anyone talk about it. People struggle to “get a word in.” They try to speak up, someone talks over them, they back down. Or worse, they start with rambling: “So, OK, I kind of think, maybe this is what you were saying, but…” Meanwhile the execs are staring them down like, get to the point already, MAN.

This happens because people need to “buzz in” to secure airtime, but they're still organizing their thoughts, so they ramble while figuring out what to say.

The solution is to have "landing words" ready in your back pocket. Landing words are simple and emphatic. They claim conversational space, buying you precious seconds to collect your thoughts before making your point. I say my chosen word decisively, people turn to look at me, I take a beat, and then I start talking.

Landing words I use constantly:

• “WELL . . . my interpretation of the data is more like...”

• “WAIT . . . they don’t love you like I love you here’s what I don't understand…”

• “QUESTION . . . have we ever tried anything like this before?”

• “TO CLARIFY . . . does anyone here think this is a bad idea?”

• “YES . . . I completely agree with Helly.”

Names work brilliantly as landing words too:

• “MARK . . . just so I'm clear, do you disagree with the argument?”

• “IRVING . . . I don't mean to cut you off, but I'm keeping an eye on the time...”

2. prepare things to say ahead of time

This one's straightforward but crucial. If you struggle to come up with things to say “in the moment,” spend 5-10 minutes before important meetings reviewing the agenda and materials, then jot down potential contributions. Prepare a few insights, clarifying questions, or challenges in advance. This takes the pressure off trying to spontaneously conjure brilliant thoughts when you're already nervous.

3. learn how to manage your nerves

I used to get incredibly nervous before speaking in important meetings. Presentations I could do, but…trying to respond compellingly to a point someone just made, in front of a bunch of important people? My face gets red, my heart races, I become convinced everyone thinks I'm full of shit, and my ability to think on my feet vanishes completely.

I ended up working with a professional coach—shout out to Gitta Sivander, she's the best—and we did tons of work to help me feel more in my body: breathwork, visualization exercises, physical grounding techniques. As I got more comfortable, I was able to get more reps in, which helped me improve my skills more and more. Now I rarely need these techniques and feel very at ease thinking and speaking on my feet, even when the stakes are high. But this did not simply happen as a natural byproduct of growing in seniority. I put a lot of work into it!

playing the long game

If you want a seat at the table when important decisions get made, you need to be known for adding value to conversations.

By the time most people realize just how important this skill is, they're already in situations where the stakes are sky-high. The senior leadership meeting where million-dollar decisions are made isn't the time to start figuring out how to speak up effectively.

That's why I believe in the power of deliberate practice when the consequences are manageable. Every team check-in, every project update, every minor cross-functional meeting is actually a perfect training ground. Each one is an opportunity to test a landing word, to practice managing your nerves, to try articulating a half-formed thought and see how it lands.

Also, something I've observed repeatedly: the people who end up with influence aren't necessarily the most brilliant or even the most articulate. In fact, people tend to dislike the person who swoops in with the "well, actually" perspective that makes everyone else feel diminished. The ones who gain real influence are those who build on others’ ideas, ask clarifying questions that untangle confusion, or synthesize disparate viewpoints into a clearer path forward. People value their perspective, not because they're the smartest in the room, but because they make the collective discussion more productive.

No matter who you are, you have a unique vantage point. Your perspective—shaped by your background, your role, your specific experiences—is a resource that nobody else can offer. Don't talk yourself out of sharing it. <3

xoxo, hils

Art by Maurice Sendak, Chicken Soup with Rice