Long Story Short
Most meetings fail because the leader is doing all the talking — and therefore all the thinking. We built you Libby’s Good Meetings Toolkit to help you design meetings your team will actually want to attend.
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Jess here!
I have sat in a lot of meetings. I have run a lot of meetings. And if I’m being honest, for most of my career I thought I was pretty good at it. Clear agenda, check. Came prepared, check. Kept things moving, check.
What I didn’t realize until embarrassingly recently: I was doing most of the talking. Which meant I was doing most of the thinking. Which meant everyone else in the room was essentially along for the ride — following my train of thought, reacting to my ideas, waiting for me to land on a conclusion they could agree with.
I thought I was running a good meeting. I was actually just thinking out loud at a group of people who were too polite to check their email.
AND here’s the thing that makes this feel even worse: it isn’t malicious behavior. It comes from caring. From wanting to be helpful. From feeling responsible for the outcome. When you’re the leader, stepping in and solving things feels like the job. But it’s not. Not in a meeting, anyway.
A leader’s job in a meeting is to facilitate — to ask the questions, hold the space, and let your team do the thinking. And when you get that right, something shifts: meetings stop being the place where work goes to die and start being where your problems get solved and culture gets built.
If meetings become a place where issues get resolved, you prove to people that meetings can be useful.
The Person Who Transformed Her Meetings
Libby Fischer Connell (now Helia’s COO) spent 7 years leading Whetstone, an EdTech company, before eventually guiding it through an acquisition. Somewhere in there — through a lot of trial and error and at least one recurring meeting that was basically just “people reciting their calendars to each other” — she figured out how to design meetings her team actually wanted to attend.
Libby comes from a teaching background, which turns out to matter more than you’d think. In teaching, there’s a concept called Teacher Talk vs. Student Talk. Whoever is talking is doing the thinking. And the whole point of good instruction is to make sure the students are doing the thinking, not the teacher.
She brought that same lens to every meeting she ran. If she was doing most of the talking, she was doing most of the thinking. No wonder her team was bored! She realized her job was to facilitate. To ask the questions that drove the conversation forward. To hold the space. And to trust her team to do the cognitive work to get to solutions.
“If meetings become a place where issues get resolved, you prove to people that meetings can be useful. In doing so, you build their trust that their time is being well-spent, AND you build the practice of solving issues as a team.”
She also figured out something that doesn’t get said enough: the purpose of a meeting has to evolve with your organization. What works when you’re a team of two stops working when you’re a team of twelve. The meeting that made sense last year might be the meeting that’s killing your culture this year.
That’s not a failure. That’s just growth — and it means someone (cough…the leader…cough) has to keep paying attention.
The Key Takeaway
Most meetings fail because the leader is doing all the talking — and therefore all the thinking. Everyone else is along for the ride, reacting to your ideas instead of generating their own. Good meetings are the ones where the leader is facilitating and everyone else is doing the talking and thinking.
Libby’s Meeting Agenda
If you’re a “just give me the meeting agenda and I’ll figure it out” kind of person (aka Helia’s COO, Libby), we built you Libby’s Good Meetings Toolkit to get started.
If you’re a “tell me why this works first” kind of person (aka our Founder, Jess), read on. Here’s what we’re going to cover:
- Step 1: Build an agenda that does the work for you — the structure that surfaces real issues before they become fires
- Step 2: Give people a reason to meet — how a simple Scorecard gives your team something worth showing up for
- Step 3: Facilitate, don’t solve — how to shift the cognitive load to your team (and why it matters)
- Step 4: Redirect tangents without losing the room — scripts and norms that keep things on track
- Step 5: Use meetings to build culture, not just get through work — the piece most leaders skip entirely
How Libby’s Meeting Agenda Makes Meetings Stick
Step 1: Build an agenda – ideally one that surfaces what actually matters
If you can only do one thing to improve your meetings, Libby is clear: make an agenda.
But not just any agenda — one designed to uncover the issues worth talking about, not just review what’s already happened.
There are four items on Libby’s 1:1 agenda:
- What’s keeping you up at night?
- Issues / Strategic Discussion
- Tactical Items
- Next Steps
She opens every 1:1 meeting with one question: “What’s keeping you up at night?” It works across personalities, roles, and departments. “It cuts through the noise of the day-to-day and puts the biggest problem at the top of the agenda.” And it builds trust — because people feel heard before the work even starts.
The second bullet, “Issues,” gets populated between meetings with, well, issues — these are the problems or roadblocks that your team truly need your help to solve. Once her team got into the rhythm of sharing what they needed help with, this section started populating itself. “We stopped using “What’s Keeping You Up at Night” because everyone just started putting those things in the “Issues” section.
Always discuss more complicated topics at the top of the meeting when you have the most brainpower.
Tactical Items are the simple decisions that don’t need a ton of brain power or discussion. Libby found that creating space for these non-urgent decisions in her weekly 1:1s cut down on the number of one-off decisions she’d receive via email and Slack, which ultimately made her more productive. Half the time, folks answered their own questions before the meeting. “If people ask you a question the second it pops into their head and you immediately answer, they’re going to keep asking. If there’s a little time and space built in, usually the can handle it on their own.”
And the order matters. Libby insists that Issues/Strategic Items come before Tactical Items: “Always discuss more complicated topics at the top of the meeting when you have the most brainpower.”
Step 2: Give teams a reason to meet — start with a Scorecard
When it comes to team meetings, Libby’s agenda is slightly modified:
- Company Scorecard
- Issues / Strategic Discussion
- Tactical Items
- Next Steps
The Company Scorecard is the group version of “What’s Keeping You Up at Night.”
Each department tracked one to three leading indicators — data points that showed how things were going early, before small problems became big ones. “We were sick of fire-fighting and being reactive. We wanted to catch things before they started keeping people up at night.”
For Sales, leading indicators might be the number of new qualified leads added that week, or outreach-to-meeting conversion rate. For Customer Success, it might be support tickets opened by new customers in their first 30 days. For Engineering, the percentage of critical bugs still open.
Before the Scorecard, leadership team meetings tended to devolve into status updates. People went around the room and recited their to-do lists which, Libby says, “was an absolute waste of time.” Once the Company Scorecard was in place, the conversation shifted. The team started looking for patterns.
- Where was something off?
- Where was momentum building?
- Where did someone need backup?
- Where was one department slowing another one down?
Solving issues together not only led to better outcomes for the organization, it built trust across the team and the entire company. “We started catching issues while they were still small — not just when they got so big that we couldn’t ignore them. That radically improves everyone’s day to day.”
Step 3: Facilitate, don’t solve — shift the cognitive load
This is the hardest shift for most leaders. And it’s the one that transforms most meetings from something people dread to a place where actual work gets done.
As a former teacher, Libby was trained to always be aware of “cognitive load” — a fancy term for who is doing the thinking. Typically, whoever is talking is doing the thinking, and at a certain point Libby realized it was her voice that was taking up most of the meeting. To increase the amount of time her team was talking during the meeting, Libby started with small shifts.
- She added a “Good News” section to the top of the agenda where everyone shared something good in their lives. This set a tone that everyone’s voice mattered.
- Rather than reading out Scorecard data herself, she asked each team member to give a summary of their data points. Naturally this led to folks identifying issues Libby hadn’t even thought of.
- Then, instead of going through the bullet points in the order they were added, Libby put 2 minutes on the clock and asked her team to prioritize the items for discussion. She admits it was hard to stay quiet when she had her own priority list, but over time the team improved their prioritization skills precisely because they practiced it every meeting, not because they did it perfectly the first time.
The big shift was shifting from always jumping in to answer questions to instead ask questions. “I was at Whetstone so long I had enough context to answer most questions well. BUT, if I was the one that had to answer every question, that meant I became the bottleneck. I wanted my team to be able to think through and answer things for themselves, and that was motivating enough for me to shut up,” she laughs.
Libby’s favorite phrases for getting people thinking instead of just listening:
- “Can you say more about that?”
- “Why do you think that’s the case?”
- “What will happen if we don’t do this?”
- “What will happen if we do?”
- “[Name], what do you think of [other person’s] idea?” — (for when one person is dominating)
The purpose of a meeting has to evolve with your organization. What works when you’re a team of two stops working when you’re a team of twelve.
Step 4: Redirect tangents before they lose the room
“Tangents are the scourge of a good meeting.” Libby says this with what she admits is a little too much intensity. And she’s right — tangents don’t just waste time, they signal to everyone else that their time isn’t being protected.
Her favorite norm: Tangent Alert. She gives her team cards with “Tangent” written on them and full permission to hold one up whenever the group wanders off track — even if it’s Libby leading the tangent. (Beyoncé, apparently, is a recurring tangent topic.)
Her scripts for redirecting with care:
- “That’s important and I don’t want to forget about it — let’s put it on the Issues list and come back to it.”
- “Sounds like something for you two to discuss 1:1 — let’s give you the room after we adjourn.”
“The key role of the facilitator is to ensure the meeting is achieving its purpose. If you lose the thread, you lose the room — and eventually you lose the trust of your team.”
Step 5: Use meetings to build culture, not just get through work
This is the piece most leaders skip. And it’s the one Libby thinks about as much as any of the others.
When she took over as CEO of Whetstone, she inherited a Monday stand-up. At the time — just her and her CTO — asking “what are you working on today?” was actually useful. A few years later, with a full team? “I realized we were just a dozen people standing in a circle reciting our calendars to each other.”
So she scrapped the status updates entirely and turned it into a culture touchpoint. Celebrating wins. Sharing key numbers. AND kicking things off with deeply silly “Would You Rather” questions drawn from her own life. (Would you rather be divebombed by a crow on your morning walk or followed home by a clingy stray cat?)
The magic wasn’t just the ritual. It was the mindset underneath it: every meeting is a chance to remind people they’re doing this work together. All workplaces are built on relationships — and so many of those dynamics play out in how we meet. Getting meetings right isn’t just an efficiency move. It’s a culture move.
Getting meetings right isn’t just an efficiency move. It’s a culture move.
When to do this Yourself vs Bring Someone in
Everything in Libby’s framework is something you can start on your own, and Libby’s Good Meetings Toolkit is a good place to begin. Pick one meeting that isn’t working, try the agenda structure, and see what shifts. You don’t need to overhaul everything at once.
That said, some situations call for a thought partner. Consider reaching out if:
- You’ve tried fixing your meetings and the same dynamics keep showing up — status updates, one person dominating, nobody actually engaging
- You’re stepping into a new leadership role and want to set the right norms from the start
- Your team is going through a growth moment — new hires, a reorg, a shift in strategy — and the meeting cadence that used to work just isn’t anymore
- You want to think through a full meeting operating system for your organization, not just one meeting at a time
If You Want Help
Libby Fischer is Helia’s COO and works with leaders and teams who want to build organizations that actually function well — not just in theory, but week to week. Meetings are one piece of that, and she’s thought deeply about how to make them work at every stage of growth.
She’s a good fit if:
- You’re a founder or CEO who’s realized your meeting culture is costing you more than you thought
- You want to build a leadership team that solves problems together instead of waiting for you to solve them
- You’re ready to think about the full operating cadence — weekly, monthly, quarterly — not just fix one meeting
- You want someone who’s actually done this as a CEO, not just coached others through it
Connect with Libby!
Try This Yourself
Libby’s Good Meetings Toolkit:
- Libby’s 1:1 Agenda Template: A simple, shared agenda structure for 1:1 meetings.
- Libby’s Team Meeting Agenda Template: A team-meeting version of the same structure, built around a Company Scorecard that gives your whole team a reason to show up.
- Team Meeting Scorecard: A scorecard template for tracking one to three leading indicators per department — data points that show how things are going early, before small problems become big ones.
- Light-Hearted Meeting Openers: A running list of Would You Rathers, Something Good prompts, icebreakers, and quick physical resets.
Recommended reading:
- Death by Meeting by Patrick Lencioni — Libby’s go-to for meeting transformation
- The Five Dysfunctions of a Team by Patrick Lencioni — Helia’s favorite leadership fable for building trust and connection
Questions to Sit With
- What’s the real purpose of your recurring meetings — and is that actually what’s happening in the room?
- In your last team meeting, who did most of the talking? What would it look like to shift that?
- What’s one issue that keeps coming up in your organization that has never actually gotten resolved in a meeting — and why?
- Are your agendas designed to uncover what’s keeping people up at night, or just to review what’s already happened?
- What’s one small moment of joy or connection you could bring into your next meeting — and what’s stopping you?
This article comes from a coffee chat with Libby Fischer in June 2025.
As always, take what’s helpful, leave what’s not, and make it your own.
About Libby
Libby Fischer Connell led Whetstone, an EdTech company, through its acquisition by SchoolMint — and somewhere along the way, turned meetings into something her team actually looked forward to. She’s a former teacher and CEO, a current writer and Fractional COO, and someone who brings humor, clarity, and genuine care to every room she’s in. She’s also the kind of person who once got divebombed by a crow on her morning walk and turned it into a team-building ritual. That’s Libby.
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