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Top Reasons Why It’s Better To Prepare Than Repair (with Iain Montgomery from Now or Never Ventures)

In this episode, Tim is joined by Iain Montgomery, Founder of Now or Never Ventures—an innovation studio for new ventures. Listen as they unpack the idea of preparing rather than repairing when it comes to leading teams, customer insights, and workplace culture.

Interview Highlights

  • Iain spent the last 10 years helping mostly big companies do new things, such as designing and launching new products. He was previously an accountant, found a way to consultancy at a company called Market Gravity. He is originally from the UK, moved to the US eight years ago, then moved to Canada four years later. [1:27]
    For the last couple of years, Iain has been building his own slightly different innovation studio, one where he doesn’t really want to hire any full-time employees. It’s called Now or Never. [2:01]
  • Big companies are designed to do two things: maximize profit and minimize risk, which means anything new and different is inherently risky. [2:46]
  • Iain explains the meaning behind his LinkedIn tagline – ‘agitating stodgy corporate environments for a living’. [3:00]
  • For Iain, leaders should inspire people to go above and beyond where they really are now, go try something new, be a bit brave, learn something, take control or ownership of something. [6:37]

A leader is the person that can inspire other people to go do things that they wouldn’t necessarily be able to do by themselves.”
— Iain Montgomery

  • Iain shares what comes to his mind when he hears the phrase “building a better world of work.” [10:44]
  • Prepare rather than repair is a line that Iain heard on a history podcast. [17:59]
  • Companies know about the change that’s going to come, but they can’t get themselves off this addiction to the way that they currently make money today. They have to be prepared for how the world might change versus by the time they try and repair, though it’s too late, the platform’s already burning. [18:36]
  • There’s a lot of companies that don’t really know where they’re going, or they’re a bit scared to articulate how the world might change. [21:50]
  • People like talking about viability, desirability, feasibility when creating an MVP. But Iain thinks about it from the perspective of lovability, doability and profitability. [25:57]
  • Companies don’t like talking to their customers very often. Actually they do, but they do it through surveys. We put a survey out to customers. Here’s the score that we got and we can quantify this thing, but it never has the context of ‘why’. [30:07]

Everybody in any organization should be out testing what their customers think and talking about it, seeing how it works in the real world.”
— Iain Montgomery

  • If you’re in a mode of constant discovery, when the world changes, you’re more aware to it, you pick up the signals of where the world is going. And it might be that the feature that did not make sense building eight months ago suddenly does. So you go build it. [32:32]
  • Not many organizations have a leader at the top that will actually go out and engage with their customers, engage with their teams. And when they do, those organizations are really successful. [36:04]

If you don’t understand the people who are doing the work for you, then you’re screwed.”
— Iain Montgomery

  • Go talk to customers, go talk to employees, go spend time with normal people. If you do that, then everything you do starts to become based on what people want. [46:35]
  • One of the techniques that Iain uses to really deeply understand their customers was to pretend the company died and write an obituary. That was a great way of getting insight. Something that Iain likes doing with companies that want to go towards their customers is go ask their customers how their brand will die and how they’ll be remembered. [53:55]

Meet Our Guest

Iain has spent the past decade helping established organizations identify, design, and launch the breakthrough new propositions critical for their long-term futures. Iain previously ran Market Gravity in Canada and has helped big companies across Canada, the US, UK, and a few other places along the way to better understand their customers, markets and create bold new ideas to get into market.

He’s helped lotteries across Canada become more relevant to millennials, designed digital banks, launched an instant coffee brand, had a hand in Air Canada’s new loyalty program, and designed a retirement platform back in the day too. Iain’s not afraid to speak his mind and try something different in pursuit of the audacious idea.

With that experience of what has, hasn’t, and might still work, Iain founded Now or Never to do things differently.

iain montgomery headshot

The future of work will be much more driven by how corporate entities drive the changing nature of education.”
— Iain Montgomery

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Read The Transcript:

We’re trying out transcribing our podcasts using a software program. Please forgive any typos as the bot isn’t correct 100% of the time.

Iain Montgomery

I think in terms of, to be a leader, there’s lots of companies that have said, well, everybody’s a leader. We want to make everybody in our organization leaders, big consultancies do this a lot. But I don’t think that I don’t think everybody should be a leader. So you like the leaders of people that inspire you to go above and beyond where you really are now, go try something new, be a bit brave learn something, take control or ownership of something.

Tim Reitsma

Welcome to the People Managing People podcast. We’re on a mission to build a better world of work and to help you build happy and productive workplaces. I’m your host, Tim Reitsma, and today on the show, Ian Montgomery and I will unpack the idea of preparing rather than repairing when it comes to leading teams, gathering customer insights, and of course, workplace culture. So, stay tuned!

Hey, Iain! Welcome to the People Managing People podcast. It’s so good to have you here and I’m excited for our conversation today. We’re going to dive into, I think it’s an interesting conversation about ‘prepare rather than repair’. I mean, that’s, that goes for, I mean, so many different aspects of life, but we’re going to bring it to the place of leadership, workplace culture and use it in that spin.

But before we get going, why don’t you introduce yourself to our audience? Tell us a little bit about yourself, a little bit about what you’re up to right now.

Iain Montgomery

Yeah. So my name’s Iain Montgomery. I’ve spent last 10 years helping mostly big companies do new things. So, designed and launched new product. So it’s this ventures and the like. I was originally an accountant, really not a very good one, found a way to consultancy with a great little company called Market Gravity grew with them. 

Originally from the UK, hence the accent moved to the US eight years ago now. At Canada, four years after that worked for Deloitte for a couple of years after they bought our business. And then for the last couple of years, I’ve been building my own slightly different innovation studio, one where I don’t really want to hire any full-time employees.

So it’s called Now or Never. Worked will all sorts of wonderful businesses, learning about their customers, come up with new ideas, and finding ways for me to grow. 

Tim Reitsma

Well, that’s how we met. We met a couple of companies ago that I worked at and, and you came in to talk us, talk to us about innovation and you know, I think I’d give our audience a disservice if I, if I didn’t talk a little bit about your, your LinkedIn tagline.

‘Cause it, it gave me a good laugh and also got me super curious. It’s ‘agitating stodgy corporate environments for a living’ — what does that mean?

Iain Montgomery

That’s a great question. So big companies are designed to do two things: maximize profit, minimize risk, which means anything new and different is inherently risky.

And it doesn’t necessarily like generate profit right away. So I found that like a lot of the places where it gets the bone work and like what were great clients is, just the people are lovely, but the culture that sits around it has just become kind of stodgy and stale. And I get to go in and do my thing and go talk to their customers, go be a bit provocative.

Hopefully, build up some like confidence behind new ideas and where they might take them. And 9 times out of 10, it goes really well and we get to do something great together, meet awesome people, and I enjoy working with them. I like to think they enjoy working with me. Maybe the agitating thing is, I don’t know what I’d like to be. 

It definitely upsets a few people and there’s, there’s certain sometimes when I say things I’m like, Tim, I’m very nerd to speaking my mind that I, I don’t tend to bite my tongue very well and sometimes my mouth definitely works faster than my brain. Maybe that’s where the agitating side of it came from because not everybody likes it.

So, yeah. Well, corporate environments can be quite comfortable and safe. And the only way you get them to sort of stay fresh for going into the future is a bit of an agitator. 

Tim Reitsma

Yeah. I, I see that. And I’m just recalling so many moments of my career being involved in large organizations from healthcare to manufacturing and, you know, trying to drive change. 

Great innovation ideas come about, but there, at least from my experience, are often put on the back burner because of the change. People are afraid of the change. People are afraid to lose their budgets. People are afraid, you know, to experience something that’s different. That’s out of their comfort zone. 

Iain Montgomery

It’s kind of like this idea where everyone feels, I like to play with idea that people feel is, and like the UK, if you want to go and do something new and different, it’s often easier in a big company because you’re not going to get fired for trying something new. You might get put into a slightly more boring position, but that’s okay.

You can still pay the mortgage. Most people when they’re in that position to drive change, they tend to have a partner. They might have young children. They’ve probably got an expensive mortgage. Whereas in the US, it’s really easy to get fired. I celebrate failure a bit differently there, but still make people a bit slower and a bit more stale.

And then Canada, it’s like the worst of both worlds where you get, it’s easy to get fired, but if you do fail, you’re sort of known as a failure, which is never a nice thing. But I think that’s what makes sometimes those organizations find it hard to change is that there’s a lot of people who have been good at something, they’ve gotten to where they’ve got to, but it just got a bit too comfortable.

Tim Reitsma

Yeah. So, so you’re in that unique position as an external who gets to come in and, like you agitate, stir it, you know, mix it up, ask questions that maybe are on people’s minds, but people are afraid to ask. And you’re kind of coming in as that neutral party and just getting curious and, but calling it for what it is. I love it. 

Iain Montgomery

I had to have a real job. It’s probably the best way to put it. I have a really good job as an accountant for a year and I really hate it, so. 

Tim Reitsma

I love it. So, you know what you don’t like and then you thought, Hey, I’m just going to go and design my own career. And I love that. 

So, the next couple of questions, again, for those who listened to the People Managing People podcast, I’ve been asking these as kind of standard questions, because I’m always curious about people’s opinions and people’s thoughts.

But what does it mean to be a leader in the eyes of Iain?

Iain Montgomery

It’s a very good question. I think in terms of, to be a leader, there’s lots of companies that have said, well, everybody’s a leader. We want to make everybody in our organization leaders. Big consultancies do this a lot. 

But I don’t think that, I don’t think everybody should be a leader. So you like the leaders of people that inspire you to go above and beyond where you really are now, go try something new, be a bit brave learn something, take control or ownership of something. 

I always look back to one of the guys that he was one of the co-founders of the business that I used to work at Market Gravity. And when I joined that business, I had no idea what I was doing. I blacked my way through an interview process, but I got myself into this company where the two guys who’ve run it with very different individuals. They clearly have a really great working relationship, but there was very different people. But their leadership styles were, go in and figure it out.

We’re not going to stop you. Don’t ask permission, go get on with it. And when you need help, tell me the help you need and I’ll help you. And I sort of, I admire people who are leaders like that, because they give people, they give people the space to go and learn, but they also like there to be the helping hand to pick you up or help you cross something when you, when you get stuck.

So to me, like I think a, a leader is the person that can inspire that in other people to go do things that they wouldn’t necessarily be able to do by themselves.

Tim Reitsma

Yeah. Somebody who’s not just giving you a list of tasks to go and do. Which often in my past, looking at job descriptions, it’s just, oh, here’s the tasks that you’re going to be doing.

It’s like, oh, I don’t think I’m going to be inspired by a leader or inspired by an organization. But if somebody gives you that permission and permission to go and fail, and permission to go and explore, and be here to help from that mentor and that coach perspective, I love that. 

Iain Montgomery

I definitely caused that headache over the years where it was like me going off and doing something, but more often than not, I think I have like better returns than like close, like complete chaos. And when I, when I did make a mess, they look pretty good at teaching me how to clean up as well. That’s kind of important in a leader as well. 

Tim Reitsma

Yeah. It’s not just a, yeah, just go off in your own world and figure things out and that, oh, it’s like, I’m going to create a whole new business line of merchandise.

It’s like, no, that’s not our business, so let’s not do that. And, but, you know, that’s just a made-up example, but, but I think, yeah, a leader is somebody who, who kind of shows you where the goalposts are and allows you to run the place to get to, you know, get to that end line, to get to that goal. Absolutely.

Iain Montgomery

Everybody good at the time it’s like, I want to go open a business in Canada. They just want you to call us when you need help. Go do it. Oh, crap. I don’t know what I’m doing. I didn’t know how to incorporate businessmen none of the dates to be honest, but like all the, all the basic things that my, my head was like, well, I’ll just go wins some work done.

That’s, that’s the first step to building a business. And they gave me the help that I need to go do that. And then when it comes to work I was like, oh, you need some people to deliver this now? Can I hire this guy? And they were like, yeah, sure, okay. Can I get an office? Yeah. Can I have your bank details to pay the landlord? Yeah. 

And suddenly before we knew that there was a certain thing emerging, we had sales coming in. We had people fly over from the UK. And then in hindsight, when I look back at it like I could not have done that all alone, but it would never have happened without me. And to me that was like showed how good their leadership was is that they just let me go on with that.

They gave me the help when I needed it and didn’t interfere.

Tim Reitsma

I love it. Yeah. I could think of a few warm places I’d love to go and set up an office right now, you know, sitting in a rainy day here in Vancouver, British Columbia. 

And so, I love that and I think it plays well into the next question, which is, you know, when you hear the phrase — how are we going to build a better world of work or what does it mean to build a better world of work? You know, what comes to mind?

Iain Montgomery

That’s a really good question. So my work has always been, even today, let me talk about coming out of the pandemic. And people say back to work because they still associate work, but being in office nine to five behind the desk.

But I think that building that future world of work is, but there’s people out there changing what work really means, is less people doing nine to five jobs. There’s more people moving towards these different systems. I don’t know what work will really be into the future, because I don’t know if that’s what, I think we’re still reframing what that really means.

Like I know a lot of people have just got, I do not want to do this corporate job anymore. But they were really good in their corporate job. They had a lot of money in that corporate job. They will respect in that corporate job. And now they’re going, Well, I’m still really good at that, but like, that’s not the only thing I want to do.

I want to have more variety. I want to work on my own terms. I don’t want to have a boss. So I think that I think that the world of work is like changing faster now than it has for the past 50, 60 years. Just because we don’t, I don’t really know what work is anymore. 

It’s not very helpful answer, is it? 

Tim Reitsma

Well, I think it’s, yeah. There’s a lot of questions packed in there, right? When we think about building a better world of work. Yeah, there is a lot packed in there because we just don’t know what it’s going to take. Like you said, there’s people who are in great, you know, positions whether it’s a corporate or small business who are thinking, Oh, maybe I do want some variety.

Maybe I want to go freelance. How do I do that? And, and I think the world of work right now, just so open to lots of different opportunities. 

Iain Montgomery

So much of work was just like, go do your, go do your job, tick the boxes, fill out your balance scorecard at the end of the year. We’ll work out how you performed and then we’ll give you a bonus. I’m already being biased and putting like, placing like think of world of work, is there an office job? 

Like this is the trap we fall into. We think of work as a job at an office and not all the other jobs that people actually do. But I think the idea of what I do for a living, how I do it, how I trained for it is like changing.

I am really interested in this sort of how people will learn for their careers, change what they do through their careers, because it’s no longer about going to school, finishing at 16, 18, 21, whatever age you go through. Go to school through, through the different levels of education and then preparing for a job in the workforce.

Like you used to be that you went to school, you did well at Maths. Okay, you go do it. You go study business at university, become an accountant, spent 40 years in accounts, and hopefully make partner at the end of the retire quite nicely, and then they have a happy life. But it’s like, people don’t do that in the same way anymore.

Tim Reitsma

No, no. It’s, it’s changing dramatically. It’s shifting. There’s a lot more opportunity for, for people to just even jump out of high school and into a career, or, you know, find a online program or online course and study something to become an expert in that one thing, instead of devoting another, you know, two to four to six years of your life into a, into an aspect of business. 

Sure, you know, if you want to become a doctor, you can’t just take a online course and become a doctor. I’m sure some people have tried, but it’s, you know, I, I found a game I found against that, but yeah, when we think about building a better world to work is, is how do we build those organizations that allow for learning opportunities?

Hey, I’m interested in, I don’t know, pick whatever subject you’re, you’re interested in. Okay. Cool. Go learn that, ’cause I think, you know, it’ll benefit you. It will benefit the organization. So, you know, it’s moving away from, oh, here’s your budget. Here’s, you know, what are the three objectives you want to learn out of this course?

And, you know, at the end of the course, submit your grades so we can see if it’s actually adding value to our organization. Instead, it’s going, sure. No, I think, you know, taking that a obscure writing course would probably benefit you in how you communicate. So, go for it. 

Iain Montgomery

And I know the future of work will be much more driven by how corporate entities drive the changing nature of education. 

Thought about this a lot lately, so I’ve been working on that education, not-for-profit project, but like how much of what you learned in school has been relevant to what you do today? Probably not very much. I don’t remember a lot, like I’m just sitting in a chemistry lab and playing with the Bunsen burner and I don’t remember a lot of that. 

But like, I think the most, the things I really remember learning from role and I was sort of left myself, like go to university in the English university is a joke. You do six hours, well, if you do a business studies course in English universities, it’s six hours of lectures a week. Maybe the old tutorial here and there, go read some books and write some papers.

Like you don’t learn how it went to the world of business from that, that can maybe you’ll learn how to be a consultant, but the less said about that, the better. Like the whole way that we teach kids is a bit broken, but it’s like, you sort of look back at it when you hit your mid-thirties. Oh, I wish I’d learned that at school.

And some, there’s some times when it’s, I was not paying attention and someone was trying to teach me that and I, I was not an engaged student, but there’s other times where it’s like, How do we teach people to go do things that are relevant for the modern world? We don’t do, it’s all based, still based in the sort of 1940s and fifties. And that’s going to change. 

Tim Reitsma

It’s going to change. I, I think it is changing. I think you know, I’m enrolled in this online program called “Business Made Simple” put on by Donald Miller and this crew at StoryBrand. And I love it. It’s super practical. It’s heck of a lot cheaper than a bachelor’s degree or master’s degree and it’s, it’s practical. 

It’s things that I’m bringing into my business here at People Managing People and it’s so it’s a little, you know, a little plug for Business Made Simple, but it’s, it’s a, it’s changing, right? The world of work, how we work, how we build a better world of work is changing. And yeah, I think it’s either the corporates are going to change, corporate organizations or there’s going to be a groundswell of small, medium businesses that are doing extremely well, you know, maybe privately owned.

So we’re not just focused on shareholder value and able to flex in and devote time to our people. And I think that’s a great kind of jumping-off point, you know, at the beginning of the podcast, I mentioned that we’re going to prepare rather than repair. And I think that we were in this state in our cultures and our workforces, you know, like you said, it’s, our workplaces have evolved so fast over the last couple of years. 

And I think we’re in this state of, in some cases, just repairing. Like, oh shoot, we, we thought we had a great workplace culture, but our attrition rate is as high as it’s ever been. What do I do? So, maybe let’s define that. What does it mean? 

I know when we were in a pre-call we were talking about prepare rather than repair. So, so in your, in your world, what does that mean?

Iain Montgomery

It’s a line that I heard on a history podcast. I’ve forgotten the name of the history professor. I must look this up. But he was talking about how in the mini ice age, in the 17th century, some countries came out of it better than others. And it wasn’t necessarily they deliberately prepared, but certain conditions made them more resilient to deal with that many isolation. They came out of it in a better, in a better place. And then he used the line of ‘it’s better to prepare than repair’. 

So, we’ve all had the stories of how Kodak invented digital photography and Blockbuster knew about streaming. And I know the companies know about the change that’s going to come, but they can’t get themselves off this addiction to the way that they currently make money today.

But the band minimum, they have to be prepared for how the world might change versus by the time they try and repair, though it’s too late, the platform’s already burning. Someone else though is much more well-capitalized is going and building something, building something that you can’t compete with. I was thinking about this the other day.

It was like, there’s a lot of people who are heads of innovation and big companies and their innovation budget is less than a seed round that some, some of the startups that are coming. So we bend on through being funded with. You haven’t got a hope at that point. 

I don’t want to be pessimistic, but like, lot like big companies are generating a lot of cash should be going and looking at, well, how is the world going to change? What might impact is and where do we go from here? The irony is the companies that are really good about that, this are probably the most stodgy old-fashioned organizations in the world, but they’re insurance companies.

The way they work today is, that their ways of working in their corporate plans of their business is still very stodgy, traditional, paper-based, and old-fashioned. But their job is literally to be out there thinking about how the world might change and how they don’t get caught short when it does. I think that’s the sort of mentality that most organizations have to take.

It doesn’t mean they have to act, but at least if they’re better prepared for how the world might change when it does, they’re prepared for it. 

Tim Reitsma

Yeah. And that’s just one aspect of an organization from, from prepare rather than repair, is that the innovation side. I worked for a, quite a large company, and the innovation budget was just a small percentage of, of total revenue, like just a tiny, less than a percent. 

It was just, so it was just let’s maintain the current product offering. And let’s not add anything into not, not, not too much into that budget, and out of hundreds and hundreds of employees, the innovation team was I think, three people. Just really small. 

And, but even thinking about from just the innovation side, but also from a culture and a corporate culture side, and you think of that corporate culture, that environment organization that aren’t prepared for that future of work are really just repairing. I mean, you just got to go to LinkedIn and spend 10 minutes on LinkedIn and there’s still so much talk about the great resignation and people leaving and, you know, there’s a lot right now. 

was reading about, you know, financial wellness of people. And so there’s, there’s a lot of turmoil even in the job market. And, you know, a friend of mine I had lunch with recently, he was, I can’t repeat exactly what he said, but he was saying it’s just, the workforce is, is a mess right now.

There’s so much changeover going on and, and, you know, they’re having trouble finding people and they’re finding great people and they’re getting offer letters every other day. And, and yeah, if you get caught in that, just kind of sitting back you’re going to be in trouble. 

Iain Montgomery

I think there’s a lot of companies that don’t really know where they’re going, or they’re a bit scared to articulate how the world might change. A few years ago it was always really trendy. This is a good moneymaker for big consultancies, but it was the X of the future. What’s the grocery store of the future? What’s the airport of the future? What’s the yada yada yada of the future? 

There’s a load of really good thinking done in those projects, like the workplace of the future. But a lot of it was driven by technology, not people. So it was like, here’s the tech that could come along and how would we apply this technology to a workplace or to a thing to make it the thing of the future. 

No one at the thought about the psychology of it. Like actually, how do people feel about where the world is going? Where that work is going?

I’m working on a thing now, like the subway station at the future. It’s fascinating because a big part of public transit systems has been the nine-to-five commute. Rush hour in the morning, rush hour in the evening. It is what it is. That makes the money. Turn over like turn over some people during the course of the day and that’s public transit. 

In a world where we’re not always going to work remotely. Still going to be timed in physical spaces, but the time you use the system has changed. So you need to though that those pieces of infrastructure have changed. Not a lot of people have thought about that. So if you don’t think about it, you then just keep building similar versions of the same thing that you’ve always had. And then when the problem does come, it’s pretty expensive. 

I think that’s the whole sort of idea behind why it’s better to prepare than repair. 

Tim Reitsma

Yeah, you either quickly pivot and adjust really quick, but you’ve got to have a deep budgets and a lot of, lot of resources behind you to do that. Or take that moment and, and think like really, you know, lots of companies that I’ve been a part of have strategic planning days or weeks. 

And it’s, Okay, where are we going today, and tomorrow, and that next month and then a month after? But let’s actually think about that vision statement for the organization and think about, is this still makes sense? What are we doing to make sure that we, you know, if, if we’re not on, if we have a crazy vision to, I don’t know, make sure everyone feels connected even while they’re working remote, what are we doing?

Like technology sure is one aspect, but there’s other aspects to it as well. But I think so often we get caught in this, in this place of like, okay, we need to MVP. We need to get something out quick and then we just push it forward and fix it later. Like I’ve, I’ve heard that and I’ve seen it and I’ve been part of it.

And whether that’s just internal systems and, and you name it, it’s just, oh, we’ll just get it out and then fix it later. But then you got a higher, a team of people to go and fix it later. So, you know, have you come across this in your work? Is this still a common nomenclature? I think this is probably a good part of your business, but, you know, what are some examples that if you can share?

Iain Montgomery

So I was reading an old HBR article the other day. And it was to be 2013 and it said don’t ever use the term proof of concept experiment. I think he might have said, could’ve say MVP either. It was like say, if you want to do innovation properly, you should use this phrase, many tests. 

But like many tests doesn’t, if I said I’m doing many tests, it would make me sound like a bit of an idiot. It’s not very like clever-sounding language, but the idea was like, you’re just continuously testing things as you go through. And like, if you say many tests, failures, or is almost a better option, because you’ve learned what doesn’t work versus trying to prove what does.

So the thing that, MVP still gives me shivers, because I think about it and like old-world consulting would be design thing. Show the potential of this beautiful and amazing thing or this is what the business would go. And then strip out all the interesting things out of it to make it viable. The people like talking about like viability, desirability, feasibility.

I was getting viability and feasibility confused. So I think about lovability, doability, and profitability. What ended up happening was we went on something could be really lovable to a customer, but because it’s quite hard to do, we wouldn’t do it. So you could score something 10 for lovability, but two for doability and it ends up in the bed.

If something’s like, 5 in lovability, but 10 for doability. I still think we can give really easy, but nobody really wants it. That gets prioritized. So, so many minimum viable products where like, it’s the minimal thing you can build, but nobody wants it. But the problem was everything we built went over budget because we could build it like a thing, spend a load of money.

I’m thinking of one that there’s an example is, it’s still out there as a product today, but it’s like, and I’m sure that team who was behind it, none of it there anyway. But working with an insurance investment pensions company called Avon in the UK, and the whole idea was building a digital platform for them. 

Because the problem was people who were aged 50-yish did not have enough money to be ready for it. So we went out and designed this like amazing product. A certain big consulting company, won’t mention names, but they came in and we went to do the build for it and basically stripped out all the interesting features. Somehow we all agree that well, that’s the MVP, we’ll go build this thing. 

The build took months and months and months, it might be two years to actually build something and get it out. By the time it was out in market was outdate. Nobody really wanted it. The CMO moved on to another job, the CEO of the business changed, and he didn’t really want to be associated with this old thing that it wasn’t his legacy.

It was somebody else’s and it wasn’t working. The right answer would have been plowed a bit more money into it and keep going. But because it wasn’t there they just killed it and went back to square one again. I’ve seen that so many times where like the minimum viable products was never viable. It was never minimal.

It was barely a product. It took so long with so much money that the world changed and then they just started again. So I think that that’s where my, most of my excel goes. We have to get better at this mini-test mentality, which is like, go test lots of little things, but then when you find the thing that you want, put the chips in. Rather than like taking this approach, which ends up being in the middle ground, or if we build things that people have one that half work that don’t make any money.

And by the time we’ve got them out that somebody has got bored and moved done. 

Tim Reitsma

Well, I can imagine being on that project team rolling out something new and, and yeah, it’s like, Great, look at what we’ve built. And it’s something that nobody wants, it’s out of date. And, you know, for, for those who, even who are listening despite resonate with you, but whether you’re in a leadership position, in product or in HR, you know, we’re thinking about new processes and new ideas like this, this mindset of many tests. 

I like it. I haven’t heard it. I’m going to go on now research this because that’s what I like to do, but it’s, it’s something that that I think we need to be doing instead of just gathering some requirements and disappearing for three months and then coming up with something that actually isn’t what people want.

So how do we shift our workplace cultures into this more in this preparation phase? So out of this idea of, oh, we’ll just repair it later. But into this preparation phase, you know. I think back in my career, I studied business operations and when we were looking at improving a process, 80% of our time was spent in that design phase.

Gathering requirements, asking questions, interviews, root cause before we even attempt to design something new. But so often it’s, we don’t have time for that. Just go and implement something. So how do we, how do we shift our organizations?

Iain Montgomery

I think one example of that is companies don’t like talking to their customers very often. Actually, they do, but they do it through like surveys. There’s a guy called John Sills whose newsletter on it was great last week with all these examples of like, companies who are addicted to surveys because you notice a research manager that it’s going like we asked 11 customers. We put a survey out to customers.

We, here’s the score that we got and we can quantify this thing, but it never has the context of why. This one is the exam so you get like a survey for that sort of format Canada day, the day it’s like, do this survey, let me take you 14 minutes to complete and I’m like, do I get anything for this? 

Like totally, I haven’t been on an air Canada flight since August. It’s totally out of context of anything. I’m not even thinking about flying Air Canada at the moment. So I think like there’s companies that have done that and they’ve got a bit to, to it when they start to realize there is other ways and they swing back towards qualitative research.

I do a lot of that. Pretty good for my business for disclosure. I love talking to your customers, pick up the phone, pay me some money. I’ll happily go do it and come back with a lot of ideas. But at one of my clients at the moment is, I can bring you in and we can go talk to customers, I mean, you can go talk to my customers for me, but I really want my team talking to customers.

So this idea of going and getting, encouraging companies to go talk to their customers, rewarding employees for doing so. And actually doing something with the information that they get. So I think one way of agree, shifting that is everybody in any organization should be out testing what their customer’s think and talking about it, seeing how it works in the real world.

And how’s that for drinks for the guy who works for a drinks company last week, from what he was making his drinks order, he was like, and what do you make that cocktail with? And they explain it’s not his company’s products. It’s like, why would you not use my company’s product for that? And they gave a bit of an explanation behind it, perfectly reasonable.

It’s been actually, is that cool? Can you make my drink with my company’s product? I think that the lots and that interaction with a server, nobody rewards and incentivizes that. I think that that’s a really good way to shift mentality in any, actually doesn’t have to be a large business, any business. Go and spending time talking to customers because once you start doing that, it’s addictive.

You don’t stop. And that’s what you sort of shift from being like, here’s the requirements, go build it. If you’re in a mode of constant discovery when the world changes, you’re more aware to it, or you, you pick up the signals of where the world is going. And it might be that the feature that did not make sense building eight months ago suddenly does.

So you go build it. So I think that that’s a really interesting way for companies to combat that. 

Tim Reitsma

Yeah, I love it. It’s picking up the phone. Man, it’s I was reminiscing. I’ve got a young son and I was reminiscing and chatting with him about the phone back in my day and how we actually used a phone to talk to people, not just use our fingers to talk to people. And you know, something that my eight-year-old just doesn’t understand, but there’s power in it.

And I know this from even recent experience at to our organization, we’ve got an online community and we’re thinking about next product and product ideas and, and just engagement ideas. So at first, the idea was, that came to me was, Hey, we’ll send out a survey. Like we’ve done that and I think I was, yeah, we, we garnered some great insight out of the survey.

I think we asked some really good questions, but why don’t we get on the phone? And sure, we’ll buy people some virtual coffees and I know we do this at one of our sister sites as well. And so far we’ve only had two conversations, but I’ve learned more in those two conversations about our product that, and it actually challenged some of my assumptions.

That I was quite surprised about, and it’s just two conversations and somebody might be listening going, oh, that’s not enough data. Well, it takes time. Right? You got to carve out time to have these conversations, but I even think about internally. You know, I, I was in I, I’ve had an opportunity to run numerous teams and we think, oh, we’re going to introduce a new process.

Well, I’ve, no, I’m guilty of this. I don’t ask, which is due. And then it just throws everybody off. But what if we crowdsource an idea? What if we just ask, Hey, you know, I’m exploring how we track our time. What works, what’s, what doesn’t work for you. Let’s understand that. 

Iain Montgomery

I still haven’t thought that working with one client is a financial institution in Alberta called ATV.

I don’t know, probably been in their office like about a week and a half as a consultant, but this guy just like comes down to sits in their little space where we were borrowing a debt. He goes, what do you do? I’m like Jose and I’ve worked with designing on. Well, like in a research phase of this project, is that tell me what you’ve learned.

Let’s put 22 a bit longer about workload, really engaging guide, and asking questions. And when I got to live a break, I was like, what do you do? He’s like “Oh, I’m the CEO.” What keeps you busy? He’s like this and he just wanders right. And keep wanting. I’m sure he did lots of other CEO-type stuff, but you’ve dedicated chunks of his day to go and engage with the staff and the vendors and the customers.

I learned that when they had a big technology implementation that went wrong and it meant a lot of customers struggled to access their online banking. If you went on the radio and said, here’s my phone number. And so customers were calling him, probably giving all sorts of shit that they couldn’t access their money and how much of a terrible bank they were. 

I’m sure he couldn’t solve all of it, but like the man at the top was listening to the people that ultimately trusted him with their money. That’s infectious. Not many organizations have a leader at the top like that, that will actually go out and engage with their customers, engage with their teams.

And when, when they do, those organizations are really successful. I think if I actually, brands like Richard Branson, he, the man isn’t a great entrepreneurial visionary. And it probably was in the seventies when he did record stores and was trying to like compete with British airways with planes. But like what he’s, what the Virgin brand became was like this rebellious brand that one stood out to a generation of customers.

I don’t think it stands out to young people anymore, but people who work for Virgin went above and beyond to care for and engage with and understand their customer. And it showed them their products like Virgin Atlantic is a morning, is a better airline to fly on as a passenger than British airways. Virgin money has way more personality as a bank than points like that trains were fun. 

Like even how they get everything from the announcements to what they put on the side of the train, to the food they have. They went above and beyond and they all came from understanding like if they understand that customer’s personalities, the brand could then have personality.

I think that’s a good way of like staying, staying on-trend, staying ahead of things. Most big businesses aren’t good at that. So maybe that’s how we bring it back to leadership. If the leader at the top is going away and doing those things, it’s the sign that everybody else should be doing it too.

Tim Reitsma

I think that’s how we truly empower our teams and our people, and just carving out that time in our weeks, in our days of not just saving it for you know, a monthly sync up or whatever it is or review. But it is asking, you know, what’s keeping you up at night? Asking our teams that. I know a great leader always asks us team that, asks, Hey, you know, what’s going on?

Not, how are you? But, what’s, what’s keeping you up at night? And when we even ask our customers, it’s not necessarily asking what’s keeping them up at night, but just getting rich insights and having those conversations and allowing time for that. When I led a, a sales team many years ago, I wanted everyone on our sales team to know what our customers loved about us and hated about us.

And so part of there, we didn’t script out sales calls. We tried that, but it was, we, I, I’m not the biggest fan of that. So, we personalized it and sure, we’d send out surveys to everybody, but the team was empowered to go and ask questions. Hey, what could we be doing better? And we found some rich insights like we’re packaging products, individual products, and cardboard.

And they’re like, oh, we ordered a thousand at a time and we ended up with these thousand boxes. It’s like, okay, let’s bring that to product management, product development. Let’s try to redesign something. And it worked, but you know, your internal teams have so many rich insights just about your customers, whether it’s an internal customer or external customer.

Iain Montgomery

Let’s bring it back to the work thing. I think like the, I think about this earlier. The CEO said that this really well where the CEOs who engage with like said that Dave guy at ATB, it wasn’t the CEO during the pandemic, but like the organizations that are really good at understanding what the world of work looks like into the future, they spend their time with, they’d been on video calls with junior employees, or like not even junior, but like, not senior execs. 

And they’ve seen that they’re working from beds, or like they’ve seen that they’re working from sofas. They’ve got kids in the background, there’s pets getting into vehicles. And I think that those executive have lots of income. Hang on. My world’s a bit different here. Whereas if you have the people that only like don’t engage with their teams so much and spend more time that they have a lot of money, they live in a bigger house.

They spend time with their colleagues who had a lot of money to live in a bigger house. Who don’t like they can go to the office before, like up the rest of the teams back in the office because they have a corner office and they can spend their time in that all day. The ones who engage with the people that have seen what the real world of work look like for the last couple of years, I think they’ve done an amazing like they’ll build great cultures that are preparing for the future because they recognize working from home can be quite nice.

Can be a bit stressful. Balance those two worlds out, you build a good culture for the future. There’s quite a bit of correlation between the ones that over in their ivory towers in the physical world and the ivory towers in a virtual world and everybody leaving because they don’t want to go back to an office nine to five.

I’ll be told what days they have to go in or whatever it might be. So I think that that’s a really interesting thing to think about. 

Tim Reitsma

Yeah, that’s that is, I didn’t make that connection. And I’m glad you brought it back to that, because when we think about the future of work and building a better world of work, yeah, it’s, it’s interesting that the companies who are doing it and doing it well, I’m guessing, and this is totally hypothesis, have paid attention. 

You know, where are you working? Where are you working from? Hey, your background’s always blurred. Unblur that for a minute? It’s like, oh, I’m working beside the sink full of dirty dishes, or, you know, you, you fill in the blank.

And I was having a conversation with somebody who recently started a fully remote job. And one of the most extroverted people I know and is really struggling, been at this job for five weeks and it’s going, like, I need to talk to people. And so she was going to explore, Hey, maybe the company supports a WeWork or you know, a workspace where, sure I’ll be amongst strangers, but at least I’ll, I’ll get the energy from people.

Iain Montgomery

I think we worked things interesting. I can’t decide if I’m going to do really well on after this or not, but like the whole entirely remote thing, I think you can do a lot of work remotely. It kills my brain, but after this point, I’m like okay, I’ve just been at home too much, I have to get out. But it’s like later really interesting companies that going okay, we are fully remote.

You can watch from wherever you want. It’s going to work like this, but every three months, this company is getting together and we’re going to put you on a plane. You’re going to fly to wherever we decide to be, but we are dedicated and we are there for that period of time. And if you can’t do that, you can’t work here.

And I think that’s really interesting. I don’t know if that model is going to work. I don’t know if he’ll fly. Maybe only works with like agencies and consultancies, who knows. But yeah, experimentally, that’s going to be interesting. I can’t mention at TD Bank doing that, but. 

Tim Reitsma

Yeah, it is shutting down a banking system for an entire week, but, but there’s companies, I mean, tech companies have been doing this for, for quite some time.

I think of Zapier and reading a story about what they do and they’re hundreds and hundreds of employees fully remote. I remember hearing the CEO talk once here in Vancouver and he was saying, look, they don’t have an office. I think they have an office for, you know, because they need a, an address, but it’s, but that’s about it.

Or they might meet a investor or a partner or something, but numerous times throughout the year they bring everybody together, hundreds of people and that’s, that’s their culture. And yeah, how would this adapts to the banking industry or the hospital industry, or healthcare? I mean, who knows? But that’s, that’s going to be fun to think about like, how can it actually, and, and what I’m getting out of this conversation Iain is, you know, how do we prepare for this?

Let’s just have some conversations. Let’s have some, let’s, you know, sit down by, by your team member, a coffee, whether they’re a bank teller or a frontline nurse. You know, carve out 15 minutes, ask them what’s working, what’s not working. What would their ideal be? You know, it’s like, oh, we need to do shift work.

It’s gotta be, you know, four days on a couple of days off. And, and then you’re working afternoon shift and then evening shift. And, and is that going to work? Who knows? But I think it’d be fun to have those conversations.

Iain Montgomery

There was a show I used to like when I was pretty on TV when I was a kid. And those go Back To The Floor. So, as they said, it was like a UK show and I’m sure that Undercover Boss, whoever their North American version is, but it was like, it wasn’t actually undercover. The episode I remember is with the Burger King CEO. So Burger King in the UK really struggled for a long period of time. And they hired a French food CEO to become the CEO and they became a UK.

He was really French. He goes on the show and they, he, he’s like manning a fryer. He’s manning the tail like he’s cleaning the floors of a Burger King. But he’s talking to the staff about like what it’s like to work there. And like, I just thought this show, must’ve been like 18 years ago now. I could look up to see how, how when it originally came out.

But that sticks in my head. It was like this guy like did not understand the people who worked in his team at the very shop floor level. And then he spent like two weeks there. And at the end of the two weeks like, well, what are you changing? He changed a ton of stuff. He’s like, I’m changing how we hire. I’m changing how people get paid. I’m changing how we make the burgers. I’m changing how we enforcing different things about cleanliness. 

There’s all sorts of stuff that he did. But like at the end of the day, I think that’s so much of business comes down to that. If you don’t understand the people who are doing the work for you, then you’re screwed.

Tim Reitsma

Absolutely. It’s a, herein, I think the North American version of that is Undercover Boss. Same thing where, you know, the CEO or it’s usually the CEO or founder just, you know, puts on a disguise and goes in and is working in the organization.

And undercover uncovers so much has going on and sure, maybe you’re listening to this going, Oh, I’ve only a company of five people. Yeah. You can’t put on a disguise and go undercover. But what you can do is take, you, take some customers out for lunch, buy them a virtual coffee. Take your team out for lunch and just unpack and. 

You know, as we look to wrap up our conversation, I think about, you know, that one thing somebody can do today and maybe that’s it, or maybe you have something else, Iain, but what’s, somebody who’s listening today, maybe they’re inspired to go in and drive some change. Maybe you’re a leader or an individual contributor somewhere in the organization.

What can you do? Where, where can you start?

Iain Montgomery

I think a lot of it is just that, go talk to customers, go talk to employees, go spend time with like normal people. And it doesn’t all come at once, but rather than trying to force it too hard but just spending time with the observations. If you do that, then everything you do starts to become based on what people want and how do I make it fit the model that exists today versus trying to like, go, what can I do?

And how do I cram that in? I teach a lot of companies on how to do good customer insight. I actually think the best companies in the world have, like, they start by being customer-led. And they eventually become, like, they recognize the product mentality that can come into that. Whereas like a lot of other organizations start with, well, what can we make and how do we make people want it?

And the example I always use, and it’s still a favorite of mine is like the Colgate beef lasagna. If you’ve ever seen this and that, listen, there’s an online museum called the Museum of Failure. They’ll Colgate when our brand and that research showed by doing surveys. That Colgate was a brand that was associated with healthy products.

So their extension became, we’re going to do a line of ready meals with the Colgate brand on it because we’re known for being healthy, and that will be a thing. Yeah, I totally associate Colgate with healthy stuff by and associated with the minty fresh feeling in the morning and at night before I go to bed.

Colgate lasagna apparently sells really really well in New Hampshire and Maine and nowhere else. But it was a great example of because we can doesn’t mean because we should. And I think that mentality of like, go understand what customers want to go on and go really deep with them. And it doesn’t have to be just be customers, it can be employees. 

And if we understand that, then we’ll design really good things off the back of it. I think we’ve had several years where organizations have not done that. And I think it’s becoming cool again, which helps me because that’s what I do for a living. But I really feel that at the moment, those are the questions I’m being asked.

And, and I, I admire the companies that take that approach because it’s not easy just to go talk to customers. It’s not easy to know what to do with it next, but if you don’t do it, you will not know what to do. 

Tim Reitsma

Yeah. It’s step one, you got to talk to people. Step two is, you’ve got a lot of rich insights, now go and figure, figure out what to do with it. And if you don’t contact Iain. He’s we’ll, we’ll put his email and his company in the, in the show notes. 

Iain Montgomery

Can I throw it in like a thing that I thought, I don’t want to move making a thing out of something that doesn’t quite fit, but like, you know the Ukranian president. I thought the line he gave of, like, I don’t need a ride. I need ammunition. 

But like as a leader, in terms of what does, like, what does leadership look like? That guy is like a former comedian was on dancing with the stars that you created version also learned he was the voice of Paddington in the Ukrainian, dealt with the Paddington movies like that man is not a President.

Like people do not become president based upon that career unless you’re Donald Trump, but what, well, I’ll read it, but we’ll forget that. But it’s say most people in jobs as they work their way up, like the things that, that made them successful at the jobs as they worked their way through the ladder.

And not necessarily the things that you need to be as a senior leader, CEO, politician, et cetera. I think he’s a great example of its traits and ways of thinking about the world and behaviors that make him at the moment. He’s got to be the greatest leader in the world because I wouldn’t know what to do in his situation.

But like, if I was a Ukrainian and you’re praying, I wouldn’t be fleeing, I’d be fighting. Probably because I’m watching what that guy is doing. And I think that that’s the, I don’t know how anybody applies that to their own situation, because I can’t imagine what that man’s going through. But it’s a great example of like, indeed to me that’s leadership.

I don’t necessarily know what I’m doing. It feels like the right thing. And I have to take other people with me if you do that really well, then you’re a great leader. Like wandering around the streets Kyiv on Saturday morning. 

Tim Reitsma

Yeah. I love that. And I love that you brought that up and yeah, when I think of leadership and all the reading that I’m doing right now, just about the world of work and just the world in general.

And, and that line really stood out to me recently is, I don’t need a ride. I need ammunition. And that to me is, it’s a, a servant leader, somebody who is leading by that example. So yeah, if you’re listening today and struggling with, okay, what does it mean to be a leader? There you go. But also what do I do?

What do you do in your organization to, instead of just repairing things? Cause that’s not fun. That gets exhausting, but how do you prepare when you can only prepare as, as much as you can and you can’t foresee what’s going to happen in an hour? I have no idea what’s going to happen in an hour. I look at my calendar and something might come up.

I don’t know what’s going to happen, but how do we, how do we best prepare? And, and one thing is, is, yeah, let’s just get out and talk to people. Have conversation, have some meaningful conversations. What do your customers love about you and hate about you? What what do your employees love about you and hate about you?

How, if your organization’s going through turmoil, how will you stand up as a leader as well?

Iain Montgomery

Can I share one really fun technique that I use? 

Tim Reitsma

Oh, yes, please. 

Iain Montgomery

I’ll share the full story, but like years ago I was doing some work with a lottery corporation and it was all-around sports betting. And so they knew Canada was going to legalize sports betting like a single event betting.

And they knew when that happened and it’s happening right now that they would be in big trouble because Patty Power, that 365 Skype, all those big players could come into the Canadian market. Having done it in Europe and couldn’t do it here. These guys wouldn’t want, okay, we’re going to design what our proposition could be pre-legalization, and this was 2015 or 16.

So six years have gone by, but they’re now in a really good state to do it. We held a co-creation session where we invited eight players that are pro-line. We didn’t have any incentive to pay for it. We just said, Hey, we found eight guys who liked playing pro-line and brought them into the office after hours.

And like, we, they all walked in with their hats. We gave them some Pro Line swag . They all took off their Patriots hats, Leafs hats and put on these like Pro Line hats. And then we said, right in a bitchery to this brand and they wrote the most cutting funny, like sometimes a little bit too painful, like newspaper at British series to a brand that they love.

And then one of the guys was referencing how, like, he, like pro-line was effectively his mistress because he was hiding money away from his wife, because he didn’t know how much he was betting on it. That led to a really great idea around how could these people best play this game by suite built like an app that like mixed with an in-store experience so they could like pick their pro-line, make their picks on their phone.

Go to the store, can’t scan a QR code, and then handle the cash to get the tickets of blending the digital and the physical realms. They were preparing, they knew that the platform wouldn’t burn for five or six years, but they knew it was coming. And one of the techniques that we use to really deeply understand their customers and who used it at the time was we pretended it died and wrote an obituary.

And that was a great way of getting insight. So something that I kind of liked doing with companies that want to go towards their customers, go ask their customers how their brand will die and how they’ll be remembered.

Tim Reitsma

Oh, man. I’d love to hear some of those stories, but there you go. There’s, some free consulting from Iain on getting insights from your customers, whether it’s even internal or external.

It’s I just think of like, translating that to internal, it’s like if you were to get a job offer what would you say in an exit interview? And then that might be a little scary, but Hey, it’s just gathered those insights, because, you know, somebody might be looking for your talent, but, 

Iain, it’s such a, such a pleasure to have you on the podcast. I think we could probably go on for a couple hours and but yeah, I appreciate you coming on. 

And for those who are listening, please check out the show notes. We will put a link into Iain’s LinkedIn, as well as his company if you want to get ahold of him. If you’re looking for help, consulting help, and innovation, whether it’s internal or external Iain’s your person to go and talk to.

So, Iain, thanks again for coming on. And for those, again, who are listening, we’d love to get your feedback. Please let us know your thoughts about this episode and please subscribe. We love it if we can get this episode right into your platform. So, thanks again and hope you have an amazing day.