The Momentum Problem: Why Your Team Drifts Apart After Every On-Site
Future Of Work Mastery (ex Enterprise Agility Mastery) · 2026-01-26 · 26 min
Substance score
31 / 100
Five dimensions, 20 points each
What our scoring noted
Our reviewer’s read on each dimension, with quotes from the episode.
Insight Density
A few practical techniques (chat storm, Tuesday Twilight, 2-minute async videos, AI training quizzes) are mentioned, but they're buried in repetitive platitudes about friendship and play, with low novel-claim density per minute.
take something physical, work out how you can do it digitally is a key thing
the best way of duplicating when you want to get together is book a slot and keep that slot there all the time
Originality
Mostly recycled remote-work and agile tropes (psychological safety, water cooler moments, cameras on, builder mindset) with little contrarian or first-principles thinking beyond the 'duplicate physical with digital' framing.
You don't want to work with colleagues, you want to work with friends
just because you're virtual doesn't mean you have to lose the playtime
Guest Caliber
Guests are colleagues/practitioners working together on real teams, but no evidence of senior scale operating; they are described loosely as 'good friends' rather than leaders with demonstrable scaled accomplishments.
someone new to the podcast audience
Jeff Ecker, good friend. We've been working together for a year
Specificity & Evidence
Heavy on vague references and named tools (Miro, Slido, Claude Code, Lovable) but almost no real numbers, named companies, or concrete outcomes; the few figures ('6 or 7 prototypes') are unverifiable and vague.
I think we saw 6 or 7 prototypes come out of just one week working together
One of them is an absolute drop-dead change
Conversational Craft
Host poses some genuine operational questions (the Friday call problem, async attention) but largely uses softball prompts and self-answers; no real pushback or disagreement, mostly mutual affirmation.
So what's your thoughts?
How do we address that sort of situation?
Conversation analysis
Computed from the transcript - who did the talking, and the verbal tics along the way.
Filler words
Episode notes
Episode Description You just spent six figures flying everyone in. The energy was electric. Six prototypes emerged in five days. Now everyone’s back home and the drift begins. In this episode, Ian is joined by friends Shaun Phillips and Jeff Ecker to unpack how to maintain momentum after the magic of being together - including why trust is built through play, not work, the tools that actually replicate in-person connection, and the one daily habit that keeps global teams from drifting apart. Extended Show Notes The Big Idea: Off-sites create extraordinary momentum. Then everyone flies home and the system flips - instead of pulling people together, remote work pushes them apart. The question isn’t whether to do off-sites. It’s how to bottle what works and replicate it when you’re 5,000 miles apart.
Full transcript
26 minTranscribed and scored by The B2B Podcast Index.
This is The Future of Work. Welcome along to another podcast from Ian and the crew on The Future of Work. Let's join them now for the new episode. Well, good morning, good afternoon, good evening, good grief. It's another podcast on Future of Work Mastery. And today I've got a returning friend and someone new to the podcast audience. So I'm Ian Banner. I've got my friend Sean Phillips, who you heard last week talk about genetic AI and things like that. Sean, welcome back. Hi everyone, very glad to be back. And also with us is, from America, you'll tell that very clearly from the accent, Jeff Ecker, good friend. We've been working together for a year in the companies we work in. Jeff, great to have you with us. Wherever you are in the world, it's great to meet you too. Yeah, cool. So what I thought we'd do is this idea, and it's something live for us as a group of people working together, which is we've just had a fabulous week Flew loads of people from various parts of the world to get together, to get a lot of problems nutted well, lots of multi-language people from Poland, people from all sorts of places. We've finished all of that work and the general question everyone is asking is, how can we keep this momentum going? How can we take what we've learned and move forward with it as we move forward? It's another listicle. We're going to go through a few things that are on our mind. Um, I want to just start by saying how you— if you've got this lovely— now trust, the trust level's gone up, people are intent, they've met each other, they've suddenly realized this face on a Zoom call is now a brainy person that's worth listening to. Uh, they've suddenly encountered, uh, uh, you know, clumsiness, uh, happening where people have bumped into each other, glasses have been spilled. Where do— where's this new place we've got to go tonight? Oh no, the lights are Hello. All these fun things that happen and they're all sort of leaving, flights, handshakes, new places to go, people flying back out to India, to America, people flying in to help. How do you maintain the momentum that this cherished event has happened? The first thing I wanna say is all teams are different. And when I was asked this earlier today by some of my colleagues, I said, you've gotta think about each team as a unique thing. So generic advice, doesn't help. But let's start with Jeff. When we were talking this through, you actually made a really nice point at the start about do you actually need to go on site at all? So what's your thoughts? I mean, I think at the end of the day, we're all coming from different places in the world, different functions, different perspectives. You mentioned spilling glasses, right? You can't have the moment of creating friendships through things like a dropped glass and creating funny memes as a result of that at the happy hour, right? Even though this team has been working together for the better part of 6 months, we probably accomplished in a week what we would have in a month. And I think that a lot of Scrum theory actually ties back to that. More than just the work that we accomplished, it is the friendships that we built. Sean had actually mentioned before that it is building friendships, building— it is the friendships that ultimately build the trust that allows to accelerate. You want to be able to do work with your friends. You don't want to work with colleagues, you want to work with friends. And you build friendships through these types of onsites, right? So yes, it can be expensive. Yes, it can pull you away from other work, but there is nothing like the magic of being in person. As we create those moments like the dropped glass at the happy hour, otherwise that help with those friendships. One of the things that we wrapped with was it's about the moments in work and in life that you can capture to keep us together as a team as well. Uh, we reflect on the moment of a large customer that we had won right at the end of the year. I think we'll reflect on many moments from this on-site, but also remembering that together Even when we're not in the same room, we can continue to build those types of moments, whether it's a big release or deploying to that big customer. It's operating with an entrepreneurial mindset as friends that help keep that friendship going and the trust and the momentum with iterative deliveries. I mean, I always say trust is earned not through when people work together, but when they play together. Yeah. And I guess the challenge for remote working situations, 3 sites around the world, different time zones, is How do you get those playing moments? The broken glass, the stupid lights, the, you know, we've decided to go and see this particular building, but it's closed and we've all just arrived at the wrong time. Me taking one of our colleagues to the world's best stationery shop. It is known as that. All those moments come out unless we let play together. So onsite's useful. I think an idea that came to me when I was talking this through earlier with someone is, oh, when we're doing this thing together, certain events happen, like the broken glass thing, like, oh, we're all in the wrong place, like, oh, we can't have this room anymore, like, let's all grab quickly 10 minutes over there to solve this problem. And I was saying to them, a good thing to do is think for your team, how can you duplicate that with the tools that we have these days? With the tools we have these days, because I mean, 20 years ago, the mantra on these kind of things was a team that works together has to be together, but that's not really true now. So let's run through the tools we have for a few minutes that are really useful in these things. What tools do we have that help us with these collaborations? I mean, Miro or Mural or Jamboard, they're all doing that sort of whiteboard function, aren't they? What else do we have? Definitely those online whiteboards. And I think the fact we can video call now as well, which has been around for a few years and we take it for granted, but actually being able to see the expressions on people's faces and making sure that teams encourage a culture where we have cameras on. There's a lot of teams who still operate with cameras off and you lose a lot of expression out of those interactions. You've also got tools like Slido or other live polling solutions. You can even do this in Miro, right? One of the powerful things that you do on site is the fist five, right? From a 0 to a 5, everybody hold up your hand. Continuing to use those types of interactive tools that you can be in the moment and have everybody speak up and have their voice heard digitally in those types of interactive sessions is also a really powerful way to stay connected. I said think of something you do physically and how you might do it. So Fist of Five, which is you in a room go, on a scale of 1 to 5, where are we all on this subject now? 0 is bad, 5 is good. The equivalent of that is called a chat storm. Now what you do in that, you say in the chat now, put your number between 1 and 5. And you watch them all come in very quickly and you say, so overall that's a 4. Anyone who gave that a 2, do you feel you can come on mic and tell us why that was right? So you're not over, you know, you're not oversensitive, but you get the idea of take something physical, work out how you can do it digitally is a key thing, I think. And I am on record as soon as COVID started saying to anyone I knew, buy shares in Zoom. Buy shares in Zoom today, get them bought because I knew it was going to take off. Sorry, Tim. Well, just because you're virtual doesn't mean you have to lose the play either. There are plenty of opportunities to come together. I mentioned Slido before. You can use Slido to do a fun quiz with random questions and fun facts about the team. There are tools out there to guess where an image is on Google Maps and see whoever was closest. Just because you're virtual doesn't mean that you have to lose the playtime. So it's important to build in that space, especially in a virtual setting when you're pulled in various directions? Yeah. So I mean, another one is treasure hunt. So as a fun item, you're on a call and you say, okay, we just take a minute. Can everyone go and find something from their childhood that's blue and just bring it to the screen and tell us what it is? And special award for the best of those will be, I don't know, a voucher or something. Just people rush off, Come back. I've done one for most outrageous hat before, which has been a crowd pleaser. By the way, I must say kudos for the hat video. I do hope that makes it. I can't explain to the audience why that matters. It will forever be a mystery. Yeah. So loads of tools around, find more. I mean, there's some great retrospective tools that work. I bought early shares in something that does essentially what we'll call Lean Coffee. If you know what Lean Coffee is, Lean Coffee is, came outta Seattle. The idea is people would get together for a coffee, They'd talk through whatever they want to talk about. And someone said, well, maybe we could do this without the coffee, Lean Coffee. So the idea is if you know that technique, you sort of start with, let's write all the things we want to talk about. Okay, now let's vote for all those and each one gets 5 minutes. And at the end of 5 minutes, you stop and say, should we stop or shall we do another 2 minutes on this? And people thumbs up, thumbs down, Lean Coffee. I mean, you can just do that with Zoom and Mural, but actually there is software around that does that specifically now. I think Coffee Table is one that does that. There's loads. So loads of these techniques, we have discovered ways of doing them, I would say virtually. And some of the big training understandings, training from the back of the room is one of the real understandings of how to do training well. Even that now has an entire virtual track, which I happen to be one of the supervisors for how that's done for anyone who gets TBR training in the world now. So that's. And you do, you find interesting ways to do it. So another facilitation technique you use in the room, 1, 2, 4, All, really well known. 1 minute on your own, write an idea down. 2 minutes, talk to someone else. 4 minutes, 4 seconds, sorry, I confused that a bit. Let me say it again. 1, do it on your own. 2, find someone and talk to each other. 4, find a group of tutus, talk to them. And at that point you can sort of call out all the answers, or if it's a big, you go to 8. If it's a really big, you could go to 16. That converts quite well into Zoom, although my experience of that is you go 1, 4, all, because breaking out into 2s and then breaking out into 4s is just a ministry. So I guess what I'm saying about that is, if you could think of something you did that was so good, we are brainy people. The people we work with are geniuses. They can find ways to do it. It's the intent, I think. I think ultimately we talk a lot about tools and process as well. So it's about creating that space, uh, making sure that you're in daily contact, right? But it is about creating that framework, especially for a larger team like ours. We've got multiple tracks working towards a big problem. At the end of the day, it's, it's all about empowering teams with the psychological safety to know they're heard. They will be heard. They should be heard. And we've created tools and processes for them to operate independently towards big problems. As friends with an entrepreneurial mindset, having that owner-builder mindset, constantly iterating. And so in an onsite like this, you have the opportunity to create that space and set the foundation and have people have that aha moment where they all click together and fall into that groove. I think we saw 6 or 7 prototypes come out of just one week working together. One of them is an absolute drop-dead change how we— Foundationally leapfrog us into the future. Absolute game changer. And you think, Fabulous. Fabulous. But we created that space and now they have the opportunity to continue with that entrepreneurial mindset rolling even virtually when they're not all together. So a phrase we use here that is not as common as entrepreneurial is builder mindset. So let's talk on what that means for a few minutes for our audience. When you say builder mindset, what are we really talking about? Well, it's especially relevant in the age of AI, right? If you think about a builder mindset, it's not just talking about it, right? It goes beyond admiring the problem to actually trying to solve it. We've always talked about that in the past, but more than ever, we're now empowered with tools to go 1, 2, 3 steps forward and start with something like a vibe coding tool, a V0, Figma Make, a Lovable to kind of give the impression of, hey, I built this thing to capture the story that I'm trying to tell. Um, or, uh, we've been empowering folks to go one level deeper into the Claude Codes of the world to actually bring it to life in a coded fashion that, um, our, our engineering partners can actually implement. I think Sean, you can probably speak to, even before we got together, some folks on the product team actually coded up the ability to do timeline milestones, passed it off, and I don't think it needed too much extra work. Yeah. And we've spoken in a previous episode about how the bar for entry into software development has never been lower. Now is the easiest time to get hold of a tool and just give it a go and try something. And That point about you, it's not work, it's play. And you're playing with your friends. The time when people are feeling most psychologically safe is when they're just playing with their friends and they're not being judged on something at work. There's no targets or performance reviews related to it. They're just having fun. And that's when we really see the inspiration start to come out. It's all about when do you cross that unwritten threshold of having fun? I think we had a chance to do that today, and hopefully we've created a space where people will continue to do that with their teams going forward. Absolutely. The number of people who said goodbye, thanked me, and said they had great fun. It's just, it's very, very nice. I feel like I've had a party all week. A party all week. Yeah, I know. And like many other geeks, I now need to lie down somewhere. I'm very tired. For a few days, detox my brain of everything that's gone into it. But that's just life. Yeah. So here's a question. So my team, or one of my teams, has a great sort of touchpoint, like we've just sort of said, on a Friday evening. Well, not Friday evening, but a Friday afternoon. And they will have just an open call. They can go and join and teach something they can't do in the week. And that works brilliant when things aren't too busy. But as soon as things start to get stupidly busy, that's when they start skipping that call. When they're working remotely, and especially with teams around the world. So if you've got a global footprint, say US, Europe, and India, it becomes very difficult to get that contact time. How do we address that sort of situation? Yeah, I think there's some podcasts on this called Stupidly Busy is the New Stupid. You don't actually get work done if you're that busy. But I do have some thoughts on this, which is, first of all, Just practically, end of the week is not a good time to do those kind of calls. They're far easier at the start of the week. They're far easier Mondays, Tuesdays than Thursdays, Fridays. Timing it so that the time zones work is important. Now, if we're all together and we're all in the same time zone and we want to go off for 5 minutes to have a quick chat, we can do that. And I think the best way of duplicating that, I mean, we haven't got into Teams yet and talking about that, we will, but the best way of duplicating when you want to get together is book a slot and keep that slot there all the time. So, uh, the company we worked at, we used to call it the Tuesday Twilight because in that case it was in the mid-afternoon point and we would, everyone had to keep it free and everyone had it in their diaries. And the good news was if there wasn't any use of it, then, you know, you got your time back, you could do something else, but it was always there. And so we could go, oh, um, this is, um, uh, let's, let's do that on the Twilight tomorrow. Can George, Cyril, and Philip make sure you come to the twilight? And we used to do them on Tuesdays and Thursdays. We didn't do them Fridays because, you know, in the end, if you're really serious about it, you're either exhausted or maybe you've gone home already or you've got things to do that have got to finish. So it's less likely that you can use that for like fun slots. But still this idea, I think, of leaving a twilight in the diaries. So I have a team meeting now, which is 8:30 every morning. Um, and then we, we duplicate that at 2 in the afternoon for different time zones as well. They're always there every day. Every day we talk. Every day we talk. My job is to make sure we don't keep talking and repeat and repeat and repeat. And I do that. So, you know, we say we get together and, you know, usual rules, stay on time. We have a lovely technique here of starting 5 minutes late so you can rotate breaks and have a pee, but we start on time and if we can, we finish very quickly. And I think those kind of things help with the calendar side. But the thing we haven't talked about, the big tool that can help with this is if you use Slack, WhatsApp groups, or probably Teams is the big one, isn't it? It's starting to get better. I think if you're very good at using Teams for what is async, i.e., out of sync communications and getting them done, you know, things like let's all look at this document and I want all the results in by end of play tomorrow. Teams decided to add a feature to do short videos recently, and that's a game changer, right? So you always want to show up to a call with options so that the team can make a decision. One of the best ways to share your perspectives is now in a Teams chat with a 2-minute video. Don't go to 10, don't go to 15. Just here's some context, here's my proposal, here's the options and why I propose this one. If everybody has a chance to watch that 2-minute video, you show up and you have a very productive conversation. So we have Zoom, we have these short videos that you can use, it's all async. I I guess all these tools let me say, you still have to be intentional about what you discovered when system together was around. So let's say there's two systems here. One is we're all together. That's a system that provokes us to interact, to communicate. When we're apart, the system is the opposite. It's drifting us away from that. So we have to be intentional about forcing those back in. Is that fair? Yeah, absolutely. You don't get those sort of water cooler conversations. When it's remote and you've actually actively got to go and make those happen. So one of the best things about this week has been people walk past each other in the corridor, someone they're not expecting to see, but they have a really interactive chat or spot a collaboration opportunity that they wouldn't get online. And you've sort of got to organically go and hunt those out when you're working remote. Tools can be a trap in that you can get into a mode where you're tossing something in a Teams chat and you're done. It's not always the case. You've gotta follow up. You've gotta make sure that people actually had a chance to grok it. They have a chance to talk about it. You also run into the end of the meeting and then you're done. It's not always the case, right? Whereas you have to have, well, hopefully not the meetings always go over, but appropriate follow-up or just a roundup at the end of a meeting to say, did we really accomplish our goal? Do we need a follow-up here? While also trying to respect everybody's time. So there's, there's a balance there to make sure that you are maintaining that actual connectedness even in a virtual setting. Yeah, if you think of this, one of my big things I want to say to everyone is what you can do together, think about how you can copy that when you're not together. One of the things that happens when you're together is you get in a room and you know everyone's got your attention. You're looking at eye language, people are calm. So I haven't solved this, but how do you make sure on async chat, you've still got the idea that everyone has seen and looked at this. Well, you just ask them their perspective first thing when you get together in the next meeting. So one of the things I've developed with my AI sort of hat on recently is a training system whereby if I say to people on training, here's a video to watch, the training system tells me whether they've watched it or not. And if they say they have, I can look immediately to see that they haven't watched it yet. Also, the system does, little sort of AI quizzes. So you would feed the training URL in and you would ask for a 10 mix and match or 20 multiple choice, really easy ones to do, but you post that and people have to get 30% on that. You know they've watched the video. So that gives me, the point I'm making here is if it was a live training event, I know people are paying attention. If it's a video training event, I can't guarantee that even with cameras on, but if I give them a quiz, afterwards. I can do it. You see my point? My point there is essentially you can— if you think about how to solve what is great about being together, you can solve it when you're apart with some thought, I think. Okay, uh, final point on this before we finish is, um, you made a point earlier, Jeff, which I liked about there's— there is a fear of being on-site. Now when you said it, I thought, yeah, geeky people like me do not want 8 hours a day in front of 500 people. That's not me. But That is a case. I'm not saying it's not a case, but that's not what you really meant, was it? Well, fast forward 6 months from now. Do you want anybody to be able to poke holes and say, oh, that team got together and spent, you know, X hundred thousand dollars. What did they really accomplish? Right? You want people to be proud of what they accomplished and remember it, not only to build the momentum coming out of the week, but also to make sure that nobody can look back and say, oh, that was a waste of money 6 months later when budgets are tight. Right? Um, we solve this problem by asking the hard questions up front. What do you think you'll be able to solve by the end of this weekend? And sharing your perspective as leaders so that folks have a little bit of something to hit the ground running with. Also the openness to say, feel free to totally throw this out. We want you to act as an entrepreneurial unit. You own this problem set. Come back to us and let us know if you think it's the wrong thing. With a little bit of scary trust in— okay, yeah, we're going to do daily check-ins and Scrum sessions, but at the end of the week, let's see what the teams came up with and how well they actually answered these questions. I think this week we found that they truly delighted us and impressed even themselves with how far they came. They're right there. And I think of this live, I think if we got a sample survey of people and had maybe 10, on a scale of 1 to 5 on a survey, how do you feel on this issue, this issue, this issue, this issue? And then said to them, these are the results. How are you guys gonna make sure you get those scores in 6 months even if you haven't been together? What are you going to be doing? And we can put this out again in 6 months and see where the scores go and see if we have lost this. That might be something useful. Yeah, make it a metric. As soon as you make something a metric, people are going to aim to improve it. So I think that's a really great idea. So we just have to work out, my instinct is 5. You know, I was talking about 3s and 5s 2 days ago. My instinct is 5 things, 5 words on a scale of 1 to 5, where are you now? And then we just play that back every month and say, you know, is it going up or going down? And if it's going down, what can you do about it? Might be an idea. All right, we're probably at end of time. So, um, as, as, as anyone who listens to podcast from now, this point we usually go, what's the big idea that's hit you this bit during this chat? So I'm going to go around the room. I'll do mine first. Actually, that idea of a 5-5 thing, 5, 5 things and fight grading and sampling, I think I might want to pursue that and work out how I could create that within some kind of system. I am now immediately thinking of doing some Google AI Studio coding later tonight on that very subject. So go to the site FISTA5 and tick that link with a code, I won't say anything that might mislead or intend, and go and do the survey. Here are the results. So that's mine. What about you, Sean? What's it you in this one? Yeah, I think the that people work best when they're playing together, when it doesn't even feel like work. And for me, this week hasn't felt like work, and the challenge is to really replicate that in a remote setting. So yeah, just bringing all of those ideas over, and I think we're doing the right thing to look at what went well and find a digital way to replicate that. But yeah, allow people to play together with their friends. I like it. Yeah, I think to me, oftentimes big ideas are just small ones that make a big impact. And so yeah, we're all just trying to have fun with our friends. So I think it's remembering that we're all human and that concept of, if I had to say one thing on how we're gonna maintain momentum after this week, it's about daily contact. As humans, we just wanna be heard. We want to hear from our friends. That one little active, the action of reaching out just to make sure, hey, I touch base with everybody on my immediate cross-functional team today is a great way to pulse check at the end of each day if you've successfully done your job to pull the team forward together. Yeah, I said to someone today, think of 3 people you've met this week that you really enjoyed the company of. That you don't normally meet with and just put half an hour in with them every week on Teams and just say, let's talk, how you doing? I enjoyed it last time, what you up to? 25 minutes, 'cause we start 5 minutes early. 25 minutes, 'cause we all start 5 minutes early. Give you the 5 minutes back, that's how it works. I have those breaks for coffee. All right, well, that's, so how do we maintain momentum? That's the sort of idea. Thanks very much for your time, both of you. Really appreciate you both, honestly. As others will know, I don't invite a lot of people to come and do a podcast, 'cause, don't usually get great insight. So brilliant that you've said yes. Brilliant that you did it. Thanks very much, Sean. Thanks very much, Jack. That's it for this week. Join us next time for more insight on the future of work. There is also a Linktree site, which is at linktree.io/ianbanner. If you like this podcast, please like, subscribe, follow, and tell your friends. Send them a link. It's for free.