Top Reasons Why It’s Better To Prepare Than Repair

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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