020: Dave Kashen - Enhance Productivity by Optimizing Regular Meetings
28 Jan 2026 · 25 min
Podcast episode (host Bill Gallagher) interviews Dave Kashen (CEO/co‑founder of Worklife) about improving meeting effectiveness. They present a before/during/after meeting framework: create outcome‑focused agendas before meetings, ensure preparation and shared understanding during meetings, and publish decisions/action items with accountability after meetings. They discuss communication types (information, promises, requests, decisions), cultural handling of promises, and how Worklife's software supports meeting hygiene with calendar sync, collaborative notes, templates, action‑item exports and integrations (Slack, Asana, Trello, Google Drive, Evernote, Office365). Episode includes sponsor mentions for Doxatalent and Align (Scoreboard) and points listeners to worklife.com for trials.
Questions this episode answers
September 7, 2016
Over 3 billion meetings a year in the United States
Doxatalent and Align (Scoreboard)
worklife.com
Chapters
Are you thinking about how to grow your business with near and offshore staffing, but you're also wanting to make sure that it's reliable, cost effective and really well done. I think docsa talent is the way to go. Here's why. They don't just fill your jobs. They bring integrity, top talent, and a people first approach that's hard to find. I've known the people at Doxa talent for over 20 years now and I say that you can count on them. I have talent. Talk to Doxatant and you won't be disappointed. Go to doxatant.com Bill G. Again, that's doxatalent.com Bill G. One more time. Doxatalent.com Bill G. Check it out today. All right. Hello and welcome again to the Scaling Up Business Podcast. I'm your host and Gazelle's business coach, Bill Gallagher. We're talking about meetings today. Having great, fantastic meetings, not soul sucking meetings. And on the show with me today is Dave Cashin. Dave tells me in getting ready for the show that There are over 3 billion meetings a year in the United States and over half of those suck. Those negative words are mine, not Dave's. Dave's the CEO and the co founder of a company called worklife that brings a software solution to help make your meetings awesome. So we're going to talk about how he got into that and what he's learned in the process and what they've tried to bake into this software to make a difference for you and your company. So welcome to the show, Dave.
Thanks so much, Bill. Happy to be here.
Thanks. Tell us, how did you get into this? What was the inspiration? What led you into it? What's the background? You know?
Sure, yeah, I'll kind of go back a bit just so you have a sense of context. I started my career in finance and investing. I studied finance in undergrad and went to work for Goldman Sachs for an investment fund and found that I wasn't as fulfilled as I wanted to be by that work and thought it'd be a lot more exciting and fulfilling to create something in the world that improve people's lives. So I went to business school with that intention and I built my first startup back in 2005, which was an online health and wellness company. And at the time I was particularly passionate about health and wellness because I moved from Manhattan, where I was living a relatively sedentary investment banker lifestyle, out to the Bay Area where I started to become a lot more active and doing triathlons and just Saw the difference that made in my life and wanted to bring that kind of impact other people. So that was my first kind of startup experience and foray into technology. I really loved and appreciated the scale that technology gives you. And then when we sold the company about four years later, it had been a very intense experience, as anyone who goes through a startup knows. So I realized I needed to take a step back and kind of get some reflection space for myself.
So.
So I hired a coach for myself for the first time and through that experience went through different personal development programs and essentially realized that I had had a story about myself not being good enough in some way. And I kept doing things that were very impressive on the outside, but weren't particularly fulfilling on the inside. And if I could let go of that story, what occurred to me as most authentic and my deepest passion would be to just help people be fulfilled and live their best lives as individuals, together in teams and organizations. I realize that people spend the majority of their waking hours at work, so it's a really powerful channel through which to make a difference in people's lives. So I got trained as a coach and in leadership development and organizational and team dynamics and spent about seven years really rolling up my sleeves and working as a consultant and coach with hundreds of fast growing technology companies, helping them to perform at their best and create the kind of conditions that bring out the best in everyone. So that was very soulful, very fulfilling work and I loved doing it. And at the same time, a couple of years ago, I started to feel a pull to have more scale of impact and I missed the way that technology allows you to do that. So with actually a former client of mine who became my co founder, we both shared this passion for helping people be their best in particular at work. We started brainstorming so what are the biggest problems we could solve, the solving of which will help people be more fulfilled and effective at work? It felt like an aha moment when it came to us. We were like, oh gosh, meetings. As you quoted earlier, there's so many 3 billion meetings a year, it's estimated that half the time spent on them is wasted. So the way we saw this, it's one of the biggest wastes of human potential that there is. And most people who work in the corporate world or even startup world have experienced this. It's a fabric of our working lives. It's inherent to collaboration, which is hugely powerful force for good. Yet when groups of people get together and meet, most of the time that's a relatively ineffective experience. So we set out to understand, first of all, why does that happen? And what's the difference between those kind of meetings and the ones where people leave feeling satisfied and fulfilled, that they really effectively use their time?
Yes. And so what did you distill? What are the key things that matter? What makes a difference?
So my friend Brian Franklin has a quote. He says, in most meetings, the future escapes unscathed.
I love that group.
I think it really highlights why it's so frustrating for us to be in meeting because we know that it's not actually impacting the future. So from that vantage point, we looked at really the whole process of running an effective meeting. And our goal in building the software was to automate the process of running effective meetings. So I'll kind of break that down. If you think about, it's useful to break it into three stages. Before the meeting, during the meeting, and after the meeting. So what we found is before the meeting, the highest leverage move you can do is create an agenda. And the reason that it makes such a difference, like almost anything in life, when you go in with clear intentions, you're more likely to have an effective conversation. But the other thing that having an agenda does is allows people to prepare so people understand what's happening in the meeting. It allows people to collaborate even before the meeting, starting on deciding what you're even going to talk about when that's appropriate. And it also allows people to make an informed choice about whether or not they are needed at the meeting. So many times we don't know what the meeting's about, so we just show up and then find out halfway through or at the end of the meeting why I didn't really need to be there. So that's kind of the basics, just having an agenda. And then the other thing we've seen at the sort of 201 level is a lot of people, when they create an agenda, it's essentially a list of topics. And while that's way, way, way more useful than not having a list of topics, what's even more useful than that is if you can actually form each agenda item into a specific outcome that you're trying to achieve from the meeting. Because what happens is when you have a list of topics, a few things happen. One, people have a different understanding of what's going to happen in the meeting around that topic. So if somebody thinks that, for example, let's say you're discussing your China strategy, if someone thinks the point of the meeting is to fully flush out your strategy and you leave the meeting Having just created a committee to flush out strategy, they're going to be really dissatisfied, even though that was your point of the meeting. So just kind of scoping it and having a clear objective can make a huge difference. So that's all kind of the before the meeting and then during the meeting. Of course, if there's preparation to do, actually doing it is the other thing that can make a big difference. And so having some kind of accountability, where you assign work and have a way that you check in whether people did the work before or at the beginning of the meeting and then during the meeting. The biggest thing we've seen is you have six people in a meeting and those six people leave the meeting with six different ideas of what just happened. So during the meeting, the really key piece is to come to a shared agreement and a shared understanding of what is being decided and what the next steps are. And too many times you have a nice discussion, but you leave the meeting without clear action items, clearly agreed upon action items. So that's what we found is critical in the meeting. Having shared understanding of the decisions and action items. And then after the meeting, communicating those out, communicating whatever information or decisions are relevant to people who are not in the meeting, and then finding some way to close the loop so that you create accountability for what got agreed upon in the meeting to actually happen. Brilliant.
And I'm guessing your software does all this?
That's right. That's exactly what worklife does.
Yeah.
So it creates in the cloud, shared record for every meeting automatically. So it syncs with your calendar. It prompts the people in the meeting to create and contribute agenda items. It shares those automatically with people so they know what the agenda is coming in. It invites everyone into this shared space to take notes together in real time. Sort of like a Google Doc in that way, where you can see everyone typing. And then it has a template, you know, a basic kind of default template for agenda notes and action items. And then we also allow people to create their own templates and modify the templates and then again it automatically sends out the action items, makes it easy to export and share the summary into different systems. You can even create action items during the meeting in other systems. So if your team's on a system like Asana or Trello, you could actually create the action items during the meeting in those systems so that they're actually going to get done, because those are the systems that people use.
Yeah, we have cut quite a few people into both of those platforms and using them quite well for a lot of Project management. I'm curious what evolved in the process of developing this? I know you had some initial inspiration so things. But I'm sure as you rolled out the first few testers, that kind of thing, that you discovered some things you hadn't expected. Can you share any of that with us?
Sure, yeah. One thing that we discovered was that people like to take notes in all different ways. So in our original platform, it was fairly rigid in its structure. And what we found is that that really worked for some people. People for whom that was the structure that they were already using or that that really resonated for them. They loved it. And then there was this whole other group of people for whom it was too restrictive. So we had to make it more flexible. And that's when we came up with the idea of templates where we could allow the people that wanted a particular structure to have it, but also allow other people to have more flexibility or different kinds of structures. So that was a big evolution. The other was around integrations. So we didn't consider as fully as we now do the degree to which the system needed to seamlessly integrate into the existing tools that people use. So many people we talk to are just overwhelmed with the number of different tools that they have to use that don't actually communicate with one another. So way too much of their time is spent copying and pasting from one system to another. So we started to build out all these different integrations into Evernote and Google Drive and Office365. And I mentioned Asana, Trello, Slack, and those really made a difference for people. So for example, if you're Slack user, you can get your. Before the meeting, you'll see a message in Slack announcing the meeting, showing who's there. And you can even add agenda items. We built a Slack bot that lets you even add agenda items right from inside Slack, so you don't have to leave Slack to go add the agenda. So things like that, where you're meeting people where they already are in the systems they're currently using to make. Make it frictionless for them to go through the process.
Yeah, I like that we get a call for that. Of course, we have a core platform that we use for planning that goes into two of the typical meetings that companies have, but don't encompass all the other meetings. And they're really great. But the integrations, there's a lot of call for integrations that aren't all there today. And some have done their own. But that's a really powerful thing to be able to do is to tie into the other things that you're doing. If you've got task manage, if you've got calendar management, if you've got project management, what's the tie in and how can you work with that?
Yeah, the other thing I was going to share that's sort of a little beyond the basics of meetings. But one thing that we've found in talking to a lot of people is one of the core frustrations with meetings specifically, but even just communication in general is there's generally way too much information sharing. And what can often happen, communication is a sort of hot button issue. And across companies, employees often cite communication as one of the big challenges or one of the things they're most frustrated by or that's not working is communication. And the trick is that when managers hear that what they tend to think of as communication is information sharing, so then what they do is they schedule more meetings, they create newsletters, they create all hands, you know, town halls to share more information.
Yes.
And most of the time what we found is what employees really mean by that, by this communication issue is either they're having to make promises that they don't believe they can keep, or they're not able to make the request that they need to get their job done. And so if you think about it, at the framework level, there's four key types of communications. One is information sharing, as we discussed. But the other three that are often way more powerful than sharing information are promises, decisions, and requests. The way we typically think about it is you can't have information sharing go away. You need to be able to share context, but you want to share just enough information that provides the context necessary to make whatever decision you're trying to make or for whatever request you're making to be answered in a valid way. And so just that shift from spending time in information sharing to spending time making decisions, requests, and typically there's responses to requests or promises or commitments makes a huge difference in the effectiveness and the quality of communication in general and meeting specifically.
It's really fascinating the tie into the types of communication and the power around the specific types, the categories of communication. You may be familiar with the work of Fernando Flores, who did some work in communication years ago, and he talked about promises, requests, assertions and declarations as some fairly powerful pieces. And it ties right into what you're talking about there. Promises and requests being very clearly one, and decisions being highly related to declarations. And then assertions are pieces of fact or information shared, right?
Yep, exactly. And I think the one that jumps out at people when they hear the framework is promises.
Yes.
Because it's like it's not a usual word that we use in business. We talk about commitments, goals, agreements. But I think in some way that's the usefulness of the word. It sort of, it highlights the degree of commitment that you make. When someone says I promise something, they're really putting their word behind it. And it creates a much more high integrity level of communication. And sometimes the pushback I've gotten when I've shared this with people as well, do we really want to be making promises? Isn't that dangerous? To which I think the most useful thing to think about there is, well, what happens when the promises are not kept? And that's, I think a lot of what ultimately determines sort of the culture, the dynamics, the level of safety in teams and in organizations is the answer to that specific question, what happens when promises aren't kept? Are they honored in that people name them and talk about them? Are people shamed for missing them? So there's probably a much longer conversation, but just something to point people to. I think it's a really important conversation to be had around what kind of culture we want to build. And it largely hinges on the answer to that question. What happens when we don't keep the promises that we make?
So I think there's two things it's a really fascinating area to add into this and one that I've spent a lot of time working with people on and ongoingly do and not always so explicitly, but there's two sides to it. Right. What happens when a promise isn't kept brings up two things. What happens in the, in the group, the organization or whatever when a promise isn't kept for. In that group's relationship to the individual having made the promise. And then the flip side is what happens for the individual when they can see that they're not going to keep a promise in whatever. And the first thing that I notice is people get very hung up about making explicit, clear promises in an organization because of exactly that. They're worried about what will happen. And, and people are fairly inhibited from making promises that they know they can keep. So there was a great example is President Kennedy who stood in front of the nation and made both a declaration and a promise, said we're going to put a man on the moon and do the other things. And he did that. And it was very powerful, galvanized the whole country and so on. And it was very clear, heard and so on. And yet we'd never done that before. Right. We had not yet been to the moon as a species.
Yes. And didn't even have some of the technology necessary to develop some of the technology necessary to go to the moon. So it was really bold.
Exactly. There were many things that needed to happen in order to make that. And yet in a company, somebody's like, great, what are you promising for next quarter? I'm like, I don't know. So we'll go and we'll promise the same production or delivery or performance or whatever that we promised the last quarter, plus 2%, which is a straight line extrapolation of our growth rate for the last three quarters. There's very, very. Not. No, but very little ability to say, promise something extraordinary and engage in it and then not know if you can succeed at it or not. Not have any idea, like, I'm going to promise something that I'm fully promising and fully going for and I may fail. Right. There's. And not all companies create an environment where people have any room to fail because I think at the same time, when we promise things, we don't necessarily deal with the impact when we can see that we're not going to keep the promise. So, great, I promise something and now I'm starting to fail. I don't often communicate it early enough. I often wait, hoping and dreaming, praying that it's going to go some other way because I've made the promise and not saying, look, I promised this, and now I feel like I'm failing and it looks like I'm going to fail. I just want everybody to know, I don't know what there is to do about this. Let's talk about it. Let's help. That's a very powerful kind of a conversation that doesn't happen an awful lot.
Yes. And when it does, it's so critical how that communication is met. If someone's willing to be that candid and transparent, say, look, I promised this, I realize I'm off track. Are they met with support and help and appreciation, or are they met with shame? And a lot of it, I think, depends on the level of fear of the leadership or the leader of that team or the person's manager or direct boss, because if they're kind of living in this place of fear and they're scared already of failing, and it sort of just. Then it just cascades down because inside of that fear, they can react negatively and end up shaming the person. And then, lo and behold, they create the exact opposite of the behavior they want. So next Time, the person doesn't bring it up till the end, and. And then they wonder, gosh, if you're off by a month, how come you didn't tell me until two days ago?
For sure, yeah, we can see that happen again and again, that ability. So I noticed that it makes a difference in getting some freedom around making big promises, if there is some room to do that. And part of the way that you do that is by having the initiative and the courage to start to bring any expectation of missing a promise as early as possible. Hey, I realize I'm going to be late. I just wanted to send you a note. I don't know what impact that has on you. So we start to imagine and grapple with the impact on us and the others around us of missing a promise, and you start to look for other ways of doing it. Like, oh, could I get there sooner, or could I reorganize something? All of that seems like it can make a big difference if I'm initiating it, if I'm looking for what breakdowns ensue from that. And that fear that you talk about in a company is often a fear of the impacts of the sort of cascading impacts of a failure to perform in some area, things that are dependent on other things. And then everybody gets very anxious about the impact on the initiative and on themselves personally. Right.
Yeah, exactly.
And yet, of course, the sooner that you bring it up, the bigger it is. There's one of our quarterly objectives that we keep failing at. We've had many conversations about it this quarter. And so each week, as I touch that, I asked myself, great, who else could I ask about? I'm sure this is handleable. Right. And I just haven't figured out how to handle it yet. And so. And then earlier today, I reached out to somebody new and said, hey, this is what we're working on, and we're failing so far. What ideas do you have? For me, it's very liberating to deal with it in that way.
Yeah.
All right, so just some recap then. Right. So work life, and then just good habits in general. What you've distilled and then what you've built into it that anybody could apply, whether they use it or not, is creating this clear agenda. But it's an agenda of objectives, not merely topics. So it's not a list of things to go over, but what to come out with. And so I often start when planning our sessions with clients, like, what do we want to get out of this? What are we aiming to accomplish? In this meeting, what do we want to walk away with that creates objectives and then the agenda clearly builds on accomplishing that to the best of our ability to understand it. And then in the middle of the meeting, if things are going wrong, we can see or feel like they're going wrong or different than expected. We can look at it and say where are we trying to get to? And do we need to adjust our approach based on that? Right. Then that shared set you talked about having some clear understanding and clear items, capturing that stuff before, during and after the meeting. And that got us into this whole aspect of communications. The decisions, the requests and the promises that are made in a meeting, capturing those so that the team can follow through and take advantage of the work that was done in the meeting.
Right, exactly.
It's really beautiful, powerful and simple stuff. So we're going to point to your website in the show notes Work life. You can of course find worklife.com and and trot and software. You probably have some kind of groovy free trial offer, don't you?
We do indeed.
So that's great. So people can get in there and play with it and so on. And I've seen it and I probably haven't paid attention to the latest, but I have seen it and I think there's a lot of fabulous stuff there and it certainly dovetails with all of the work we do as Gazelle's coaches in helping companies to scale up. So I think it'll be of interest to our whole audience and I really appreciate your time taking the time to chat with me, what what you've learned, what's gone into it and how you got here today and what people can do with it. Thanks so much.
My pleasure. Good to be with you, Bill.
Are you ready to turn your goals into daily wins? You should check out our scoreboard software. Powered by Align, it's the official software for scaling up. With Scoreboard, you'll get an AI driven coach for priorities and KPIs and it'll help keep your team focused on what matters most. With Align, you can track your goals in real time and you'll even see results on the go. With their mobile app, you can rest easy knowing that Align has world class onboarding and support to set your team up for success. This is really more than just software. It's what I actually use to manage growth in our scaling up client teams. Unlock clarity and results with Scoreboard by Align. To try it now, go to aligntoday.com Bill G. One more time. Aligntoday.com Bill G. That's aligntoday.com Bill G. Check it out and try it now.




