--- title: What This Entrepreneur Learned About Better Meetings description: Breaking news and analysis from time.com. Politics, world news, photos, video, tech reviews, health, science, and entertainment news. canonical: https://time.com/partner-content/charter/what-this-entrepreneur-learned-about-better-meetings/ author: Jena McGregor article:opinion: false article:content_tier: free article:published_time: 2026-07-07T10:30:00.000Z article:modified_time: 2026-07-02T21:55:17.069Z og:title: What This Entrepreneur Learned About Better Meetings og:description: Breaking news and analysis from time.com. 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Politics, world news, photos, video, tech reviews, health, science, and entertainment news. twitter:image: https://static.time.com/v3/assets/bltea6093859af6183b/bltaf5f091470444ea1/6a46ddeffdd19624bbb2cf4e/charter-english_(1).jpg?branch=production&width=3840&quality=75&auto=webp&crop=16:9 --- The information presented here is created by Charter, independently from the TIME editorial staff.  Time charter * [meetings](/partner-content/charter/tag/meetings/) ## meetings # What This Entrepreneur Learned About Better Meetings by [Jena McGregor](https://time.com/author/jena-mcgregor/) Editorial director and VP, content strategy, for Modern Executive Solutions Jul 7, 2026 10:30 AM UTC  Art: Charter by [Jena McGregor](https://time.com/author/jena-mcgregor/) Editorial director and VP, content strategy, for Modern Executive Solutions Jul 7, 2026 10:30 AM UTC Boston-based entrepreneur [Paul English](https://www.linkedin.com/in/englishpaulm/) has founded multiple companies and a handful of nonprofits, and is now working with Boston Mayor [Michelle Wu](https://www.boston.gov/departments/mayors-office/michelle-wu) to fund an AI literacy [program](https://bostonpublic.ai/) for all Boston Public School high school students that will launch this fall. He’s also recently written a [book](https://bookshop.org/a/664/9781394391790) about how the best companies run meetings better, which prompted the idea for his [latest startup](https://gumdrop.ai/). Charter spoke with English about his hacks for better meetings and the AI initiative he’s funding in Boston’s high schools. Here are excerpts from our conversation, edited for length and clarity: **What made you write the book?** We spend so much of our time in meetings. The idea of the book is to say, if I can make meetings 10% more effective or 20% more effective, that'll do good for a lot of people. I consider myself a sort of part-time psychologist as an entrepreneur…If you're an observer in meetings, you start noticing things. You'll notice men interrupt women more than women interrupt men, which is obviously terrible. You can coach people and get rid of it. You can also notice if someone rolls their eyes whenever someone else talks. You can figure out, ‘Wait a minute, that relationship's not working.’ Meetings are a sort of theater where I get to watch that stuff. Sign up for Charter's newsletter to get the handbook for the future of work delivered to your inbox. Email Address You can unsubscribe at any time. By signing up you are agreeing to our [Terms of Service](https://www.charterworks.com/terms-of-service/) and [Privacy Policy](https://www.charterworks.com/privacy-policy/). **But you also are the CEO and founder of a company that offers AI-driven pre- and post-meeting summaries.** **Is the book to promote it?** The company came out of the book. I spent a year working on the book and I interviewed leaders and founders of top companies like LinkedIn, Intuit, Airbnb, and OpenTable. I tried to learn from them. I \[also\] surveyed a thousand people on LinkedIn about what they hate about meetings and a big fear was, ‘Oh my God, I have a meeting in a minute. I'm not prepared.’ Then there was \[the problem of\] how there's no agenda and then there's no follow through…those are the big frustrations. What we're doing with [Gumdrop](https://gumdrop.ai/) is trying to address all three of those in a way that is fun and light. **You're a serial entrepreneur—Kayak may be the most well-known company you’ve founded. What are some of the most effective meeting practices you've used?** I try to have an agenda for every meeting. A second thing is I often will end meetings really early. Sometimes we'll schedule an hour meeting, but if we've got the agenda done in 20 minutes, I'll end it. People are surprised by that, but I like giving them that free time. Another thing is I view my role as a meeting organizer and \[facilitator\] a bit like an orchestral conductor. It's like, ‘A little more timpani!’ and ‘A little more violin!’ What you're trying to do is move the energy around the room. You want everyone to participate and hopefully not interrupt each other. Call on people and make sure everyone feels heard. I want to end the meeting at higher energy \[levels\] than it began. \[Finally\], I also like the person running the meeting to be able to succinctly synthesize what was said. At the end of the meeting, I try to say, ‘okay, we made these three decisions and now this is the next big action for us for the week.’ **Is AI having a positive or negative effect on meetings?** It's very, very easy to build a note taker, particularly using the OpenAI platform. I predict in somewhere between one and two years, every meeting's going to be recorded whether you want it to or not. At some point it's going to be built into the operating system. We're going to start realizing the benefits of—if the computer and your phone is an extension of your brain—asking questions about anything that happened. Now, there are downsides of transcribers. \[One is that\] some people won't be as vulnerable. If I think of being transcribed, maybe I won't talk about my [bipolar illness](https://www.businessinsider.com/kayak-founder-paul-english-bipolar-illness-leadership-2025-3) or whatever…It’s often said that people will follow confidence, but they'll be loyal to vulnerability. If \[the person running the meeting\] models the vulnerability… \[people\] get vulnerable back. As leaders we have to acknowledge, ‘I'm confident in certain things…but there's a lot of things I'm terrible at.’ Particularly when there's new people in the room, I just acknowledge the things I'm terrible at. **Any other meeting hacks you use, or that you heard in working on your book?** One of the guys I interview in the book is [Nate Blecharczyk](https://www.linkedin.com/in/blecharczyk/), a co-founder of Airbnb. He has said that if there’s no agenda \[for the meeting\], he doesn't show up. I talked to [Glenn Fogel](https://www.linkedin.com/in/glennfogel/), the CEO of Booking Holdings. He said, ‘If you just randomly cancel 20% of the meetings across the entire company of 30,000 people, I'll pay you whatever you want me to pay.’ Obviously he's joking around. But I think what he realized as a leader of a big company you need to give people time to work. I like the \[idea\] of no meetings on Wednesdays. Get synchronized at the beginning of the week, sum up at the end of the week, and give people time in the middle to stretch their legs and perform. You want less meetings, less people in meetings, and shorter meetings. If you keep those three things in mind, you'll do well. I’ll tell you something funny I did at Kayak. I bought an attendance clicker. I hung it outside every meeting room. It meant, ‘Paul's paying attention to how many people are in this room.’ If you have 10 people in the room, I'm going to stick my head in and say, ‘What are you guys talking about?’ And they'll tell me, and I'll say, ‘There's not three of you smart enough to figure that out?‘ I always pressure people to push decisions down, let new people make decisions, and try them. It's okay if they fail. **Can you tell me about your AI literacy initiative with Boston Public Schools?** Last August, Boston Magazine contacted me and said they were doing a special \[feature that asked\], ‘If you were Mayor for a day, what would you do?’ I thought a lot about it. I \[thought\], ‘I want to be the first major city in the country that equips 100% of our students with AI.’ There's three benefits to doing this. Number one, it's about making better students. It's about personalized learning—how to use AI to quiz yourself, how to use AI to go deeper. Number two, they're going to take it home to their parents and teach their families little things about AI. And number three, they're going to take it into the workforce. Let's say there's an 18-year-old young woman who decides she doesn't want to go to college. She gets a job as a secretary in a two-person real estate startup in Boston. If she's AI-trained by us, she can completely revolutionize that two-person firm and make it look like a 200-person firm. **What else to read:** * **How AI is** [**making meetings**](https://www.charterworks.com/ai-meetings-dysfunctional/) **more dysfunctional** * **Five steps for** [**solving calendar overload**](https://www.charterworks.com/five-steps-for-solving-calendar-overload-and-unnecessary-meetings-for-your-team/) * **The best AI** [**note-taking tools**](https://www.charterworks.com/best-ai-note-taking-tools/) **for meetings** --- ## Read more from Charter [READ MORE](https://time.com/partner-content/charter/) [Open article: How to Improve Meeting Culture](https://time.com/partner-content/charter/7372685/how-to-improve-meeting-culture/)  ### How to Improve Meeting Culture [READ MORE](https://time.com/partner-content/charter/7372685/how-to-improve-meeting-culture/) [Open article: The best AI note-taking tools for meetings](https://time.com/partner-content/charter/6987522/the-best-ai-note-taking-tools-for-meetings/)  ### The best AI note-taking tools for meetings [READ MORE](https://time.com/partner-content/charter/6987522/the-best-ai-note-taking-tools-for-meetings/) [Open article: What to do about poor quality meetings](https://time.com/partner-content/charter/6972744/you-probably-have-too-many-meetings-and-not-enough-are-high-quality-heres-what-to-do/)  ### What to do about poor quality meetings [READ MORE](https://time.com/partner-content/charter/6972744/you-probably-have-too-many-meetings-and-not-enough-are-high-quality-heres-what-to-do/) --- ```json [{"@context":"https://schema.org","@type":"NewsArticle","@id":"https://time.com/partner-content/charter/what-this-entrepreneur-learned-about-better-meetings/","mainEntityOfPage":{"@type":"WebPage","@id":"https://time.com/partner-content/charter/what-this-entrepreneur-learned-about-better-meetings/"},"headline":"What This Entrepreneur Learned About Better Meetings","datePublished":"2026-07-07T10:30:00.000Z","dateModified":"2026-07-02T21:55:17.069Z","description":"","url":"https://time.com/partner-content/charter/what-this-entrepreneur-learned-about-better-meetings/","keywords":[],"thumbnailUrl":"https://static.time.com/v3/assets/bltea6093859af6183b/bltaf5f091470444ea1/6a46ddeffdd19624bbb2cf4e/charter-english_(1).jpg?branch=production&width=1200&quality=75&auto=webp&crop=1200:675&height=675","author":[{"@type":"Person","name":"Jena McGregor","jobTitle":"Editorial director and VP, content strategy, for Modern Executive Solutions","url":"https://time.com/author/jena-mcgregor/"}],"articleSection":"","image":[{"@type":"ImageObject","url":"https://static.time.com/v3/assets/bltea6093859af6183b/bltaf5f091470444ea1/6a46ddeffdd19624bbb2cf4e/charter-english_(1).jpg?branch=production&width=1200&quality=75&auto=webp&crop=1200:675&height=675","width":1200,"height":675,"headline":"charter-english (1).jpg","caption":"","creditText":"Art: Charter","representativeOfPage":true}],"publisher":{"@type":"Organization","name":"Time","url":"https://time.com/","logo":{"@type":"ImageObject","url":"https://time.com/images/logo.png","width":528,"height":156},"foundingDate":"March 3, 1923","sameAs":["https://www.facebook.com/time","https://www.instagram.com/time/?hl=en","https://twitter.com/time","https://www.pinterest.com/timemagazine"]}},{"@context":"https://schema.org","@type":"BreadcrumbList","itemListElement":[{"@type":"ListItem","position":1,"item":{"@id":"https://time.com/partner-content/charter/what-this-entrepreneur-learned-about-better-meetings/","name":"What This Entrepreneur Learned About Better Meetings"}}]}] ```