How to Stop Overthinking and Start Speaking Up in Meetings

A tactical guide for people who have good ideas but worry they’ll say the wrong thing in meetings, interviews, or high-stakes convos.

Jul 07, 2025

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Welcome to Reframed, where high-achieving professionals come to rethink their careers. Because doing things the “right” way only works if it’s actually right for you.

I'm Ashley Rudolph—a former tech executive turned coach for leaders and next-gen execs in the creative, tech, and lifestyle industries.

Meetings are on my mind this week. If you’ve ever sat in a bad meeting (me!), this post is for you. Enjoy!

INTRO: STORY TIME

There have been many times where I sat obsessing over what to say in a meeting, before a meeting, during a meeting…wondering why I said nothing or the wrong thing after a meeting.

It’s torture.

Meetings are high-stakes.

And I’d take it a step further and assert that for a lot of high-achievers, they’re likely a major source of performance anxiety. They certainly were for former team members, my previous direct reports, and some of my current clients.

It’s the pressure to contribute something smart. To be clear and polished. Strategic. Not too much. Not too little.

It adds up.

I’ve had clients say things like:

“I know I should be speaking up more but I don’t know what to say.”
“What if I say something that makes them realize I’m not as good as they think I am?”

And it makes sense. I’ll go out on a limb and say that many of you feel lost because we’ve outgrown the old rules for how to show up and be taken seriously.

THE SHIFT: LOW-CONTEXT VS. HIGH-CONTEXT AND WHY IT MATTERS IN MEETINGS

And because there’s a huge shift happening right now (cough, cough AI), it’s worth acknowledging that a lot of what used to signal competence in meetings is now low-context work. When I say low-context work, I’m specifically talking about a category of tasks that can be automated, recorded, summarized, or AI-generated. Things like:

Taking notes
Recapping what was said (if you haven’t tried Granola AI for meeting notes, it’s SO good)
Scheduling and organizing

I want to be clear, these aren’t *bad* tasks, but if those types of tasks are the only ways that you demonstrate your value at work, there’s a chance you’ll be outrun by systems.

This isn’t an “AI is taking your jobs” post. You can find many of those on the internet and that angle is a bit too salacious and overplayed for me. What matters more is this: real leadership is moving upstream toward a set of high-context skills that require experience, a POV, and depth of knowledge. It’s the kind of context that requires you to synthesize context, interpret information, and influence people.

So, what does that look like?

Sharing insights based on what you’re noticing across workstreams
Reporting not just on outcomes, but on why something worked (or didn’t)
Facilitating conversations about what to do next, not just what happened
Being tapped into what’s happening in your space (think: your industry, culture, or context)
Having a POV rooted in actual experience, not just regurgitating what’s already in the deck
Storytelling that gets repeated because it clarifies the why. When I’m on (read: engaged in a conversation), storytelling is one of my strong suits. I have also been in many meetings where I might as well have been Casper the Friendly Ghost. My advice is be the former, not the latter.

STORY TIME: A PERSONAL EXAMPLE

I remember being in a room where our leadership team was spinning on drafting our strategic plan, trying to make it fit into a set framework. We were getting lost in the minutiae of what kind of goal to set. After a while I noticed that we were spiraling and I thought it was important to call out that we weren’t trying to define (and therefore, hit) an arbitrary measure of success. What we were actually trying to do is build something that does X better than anything else in the market. We cared about quality, not for the sake of building the absolute best technical solution but because we needed to build a solution that was market beating — that’s what our customers cared about.

That line ended up in the board deck. Not because it was flashy, but because it gave the work a necessary frame. It provided clarity. It was memorable.

None of this means that you should immediately stop doing logistical tasks. My point is that you can’t stop there if you want to continue to grow in your career. If you’re in leadership, your presence in meetings has to do more than inform. It has to add to the conversation.

So how do you show up in a way that makes people stop and listen?

Most people overthink how to sound smart. Few people say the one thing that shifts everyone’s thinking. That’s the difference.

In that meeting I mentioned earlier, the room was spiraling over a framework, trying to force-fit the plan into it. What I offered wasn’t flashy, it just changed the stakes. My contribution gave the team a reason to care. It ended up in board decks and team updates because it named the “why” behind the work.

That’s what I mean by high-context communication. You’re not just summarizing what’s happening. You’re helping people understand why it matters.

Start here →

THE FRAMEWORK: DO THIS AND WIN

6 Strategies for Speaking Up in Meetings

1. Do Prep Work

If you’re someone who struggles to contribute on the fly, I want to be clear: that’s not a flaw. But it is something important to know about yourself. You don’t have to hold yourself to the standard of winging it to offer great insights. The same is true if you tend to overshare, both habits benefit from structure. What you need is a preparation strategy. Great participation starts before you enter the room.

Here’s what thoughtful prep can look like:

Understanding who will be in the room. What do you know about what they care about right now?
Look at the topic. Even if the full agenda isn’t shared, what’s the likely focus? Are there decisions that might need to be made? If so, can you share any relevant insights?
And most importantly, what types of things do you want to contribute? What have you seen, noticed, questioned, or tested that others might benefit from hearing?

Take 10 minutes to write it down. Don’t write a script, that will make you come across as rehearsed and unnatural. Jot down a few anchors. Prep is the bridge between staying silent (or taking up too much space) and speaking with confidence.

2. Think Beyond Tactics

In my experience, most people know how to start a meeting. Fewer know how to steer one.

For example, there’s no shortage of advice on how to kick off a meeting: start with an icebreaker, kick things off with a check-in question, use polls.

Tactics like that can be useful in the right context. But they’re not strategy.

Your job, whether you're leading a meeting or just a contributor, is to help focus the conversation. That means reading the room, knowing what needs to get done, and helping people actually get there (navigating tangents along the way!).

Sometimes this means finding opportunities to create connection. Sometimes it means cutting through the noise. Sometimes it means getting straight to the point.

Try something like:
“Here’s what I’m seeing from the customer side, I believe it adds helpful context to the conversation.”

This strategy is about helping the group get to the point. That’s how you build trust.

3. Share a Noticing

High-context contributions can be as simple as offering up a noticing. Observations like these have the capability to reframe a conversation.

Try this:
“One thing I’ve been noticing is…”
“This has come up in a few places now and I think it’s worth looking at differently.”

Noticings are typically not fully baked ideas. The value you offer when you share a noticing is your ability to recognize patterns. It says: I’m paying attention. I see something forming.

That’s exactly what I did in my storytelling example above, you’re signaling your capacity for leadership. You don’t always have to be the one that offers up a perfect solution. Sometimes being the person who surfaces a meaningful insight is one of the most valuable things you can do.

How to work with me

You’re in higher-stakes meetings. People are looking to you for insight. And you’re trying to figure out how to meet their expectations. That’s what I coach on.

If this post hit home, take it as a nudge. We can make sure your voice matches your value. My Elevate program is 1:1 coaching for high-performing leaders in transition or growth mode.

Explore ELEVATE

4. Ask a Smart, Strategic Question

Some high achievers fear being the person that says things just to say them. Sure, you technically can ask a low quality question just to appear engaged. But some of the most respected leaders ask questions that help people in the room (1) think better or (2) make better decisions.

The best questions:

Surface a blind spot
Clarify a trade-off
Connect execution back to the why

Try this:
“Are we okay with the cost of doing this? Making this decision means it will cost us x.”
“If we move forward with this, what are we saying no to?”
“What does success look like to our stakeholders/clients/customers?”

Strategic questions change the quality of the meeting. They increase alignment across teams.

5. Reference a Relevant Trend

Most people come to meetings prepared to talk about their work. Few people show they understand the context surrounding their work.

This is where you shine.

Bring in what you’re seeing out in the world. It could be an industry shift, a cultural signal, or even a pattern across departments.

Try this:
“We’re seeing more teams moving toward [X], and I think there’s something we can learn from that.”
“This mirrors a broader shift in how customers are responding to [Y]. Are we accounting for that?”

It doesn’t need to be complex. You’re not writing a research paper. You just need a sharp headline and relevant context. You are helping people zoom out and that’s a differentiator.

6. Follow Up with Intention

This tip is about showing you’re listening for alignment and acting on it.

You can even do this in meetings where there’s no explicit action item assigned to you (like an all-hands or senior leadership update).

Try this:
“One thing I took from this discussion is [X], and here’s how I’m thinking about applying that in my work.”
“That shift in strategy you named makes me think we need to revisit [Y] — I’ll take a first pass.”

This is especially effective when there’s a message from leadership that needs to cascade. You don’t wait for instructions — you find the thread and move it forward. That’s what high-context communication looks like.

CLOSING THOUGHTS: THE WRAP UP

Here’s what I want you to remember. The most impressive leaders notice what’s unsaid.

They draw connections.

They say something that lingers in the room long after everyone leaves or signs off Zoom.

They leave behind a POV, a story, an insight, or a question that’s exactly what their team needed to hear. And later, those insights become what actually moves the needle on things that matter.

That’s what people remember. That’s what builds trust and credibility.

Good luck! See you next week.

Ashley

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