168: Ready Already, with Allister Frost

Your boss doesn’t know what’s coming next. Neither do you. 

That’s not a crisis; it’s the new starting point for modern leadership, where real agency can finally show up.

We sit down with Allister Frost, former Microsoft leader, speaker, and author of Ready Already, to talk about what to do when you have an idea, and you’re not sure it’s ready. He shares what changed when he moved from traditional manufacturing into fast-moving tech, and why the old model of do the job, keep your head down, earn security breaks in a world shaped by AI, constant reinvention, and relentless pace. 

We explore a future-ready mindset built on human superpowers: curiosity, creativity, and collaboration.

We also get specific about the people-first culture leaders say they want but often accidentally block. Allister explains the HIPPO problem (the highest paid person’s opinion) and how one comment from a leader can flatten experimentation. You’ll hear concrete ways to protect early-stage thinking, pilot ideas safely, and use yes-and collaboration so ideas get better rather than die in a rushed meeting. If you’re worried about AI replacing work, this conversation brings it back to what humans do best and how to lead with humility and honesty.

• LinkedIn: https://www.linkedin.com/in/allisterspeaks/
• YouTube: https://www.youtube.com/@allisterfrost
• Substack: https://substack.com/@allisterspeaks

Allister Frost is a business transformation and growth expert, former Microsoft leader, author of ReadyAlready, and an award-winning speaker and marketer. His mission is to save ONE MILLION WORKING LIVES by rescuing busy people from the deadly complacency of their comfort zone. He does this by sharing the new skills and positive mindset needed to stay future-ready for life.

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Transcript

Humility As A Leadership Reset

Allister Frost 0:01

So leaders should accept this as a real invitation to start to get back to being themselves, to get back to having some humility and honesty, and to say, look, I don't have all the answers.

Manya Chylinski 0:16

Hello and welcome to Notes on Resilience. I'm your host, Manya Chylinski. My guest today is Allister Frost. He's a speaker, a business transformation expert, a former leader at Microsoft, and author of the book Ready Already. Today we talked about what to do when you have an idea, how to be future ready and people-first cultures in organizations. It was a wonderful conversation. I think you're really going to enjoy it.

Allister Frost 0:50

Oh, it's nice, isn't it? And you're in the afternoon, I'm in the morning. Everything's crazy when we're doing this transatlantic stuff.

Copycats And Egos In Speaking

Manya Chylinski 0:55

I know. I love it. I love it. So to get us started, what would the title of a book about you be if it was written by your worst enemy?

Allister Frost 1:07

Oh my days. That's a great question. My worst enemy. Um, it would be it would be something like, Who's my worst? I don't have a worst enemy. The only do you know what? I do, I do have a worst enemy, but I don't know who they are. I will, I'm a speaker and I speak on stages, and there's a lot of you know, there's a lot of egos in that world. And I do think there are there are some people who I look at their stuff and I think, hang on a minute, that's just my stuff. You've just rebranded it. So they're sort of my worst enemy, but that might also be my paranoia. What would the book be called? It would be called if they were honest, it would be something like he had all the best ideas first. Because I think it just drives me crazy. There's so much copycat behavior that goes on. And uh yeah, I'd I'd hope they'd have the humility to accept that yeah, they were some of my ideas in the end.

Manya Chylinski 1:57

That is a great title. I love it. Um, thank you for sharing. And you're right, it's hard, I think, for a lot of us to think who is my enemy.

Allister Frost 2:07

Yeah, yeah. I try not, I don't I don't want to have enemies. I'm a nice guy. I like to I like to have friends, but um, so yeah, truly I don't I don't have enemies, but there's some there is sometimes professional um uh anxiety that you build up when you're sort of looking at other people's work and you think, oh, they're doing that really well, or you look at others and oh, they're not very good. And you know, I I you have to kind of just be yourself and and and detach yourself from those feelings as much as possible. Then you don't need to have enemies.

Manufacturing Versus Microsoft Pace

Manya Chylinski 2:34

Exactly. Exactly. You do need to pay attention to what's going on around you and what other people are doing, but not take it too personally and just be yourself, as you say. All right, as we dive into our topic here, I'd like to get started. So everyone has had a moment in their life that changes how they think about leadership or how they think about taking care of other people. What is one of those moments for you?

Allister Frost 3:01

I started in a traditional manufacturing company, and then I went to the tech sector at Microsoft. And the contrast between those two was just so extraordinary. I think that's we're uh many of us who have not experienced those two sides of things are starting to witness it now when we see AI and all of this radical change coming upon us. And I think that's that totally affected the way that I look at my entire life because I'd I'd gone through my university years thinking that what I have to do is get a job, I do well, that will give me security, and then you know, you that that there's that sort of model in my mind. And of course, none of that's real. Um, you can work well, but there is no security because the world is moving so quickly. And I realized when I went to Microsoft that everything we know and do can be improved, it can be done differently, it can be better. That's not just because I was a Microsoft and some of our products are a bit shonky. Uh, but it's genuinely true that the world is moving so quickly, everything is obsolete. And I didn't have that at all when I was in the traditional manufacturing sector. It was very much a if it ain't broke, don't fix it mindset. So that was the big shift for me was realizing oh, actually, my job, if I want to be an active player right now through this extraordinary time of living in, is to be somebody who brings improvements, who looks at something and says, That could be done better, that could be done better, and I want to make that happen. And that's where I got a lot of my energy from uh in my corporate working life, and I do today as a speaker.

Manya Chylinski 4:29

Oh wow. Interesting. I started my work essentially in corporate, so I don't really I've I never had that aha moment. What's one of the things, I guess, that was the biggest surprise when you started in corporate after moving on from manufacturing?

Reclaiming Agency Through Improvement

Allister Frost 4:48

Uh when I went to the so I yeah, so it's traditional manufacturing to the technology sector. I think that's the that's the thing. It was just the sheer pace of it, the the sheer ambition, the idea that if something works, it can be made better, let's have a go, let's have a try. Um, and what we're seeing now is that um, and this is what I I tell the the audiences that I work with, you've got to look at your job. Whatever your job is, if you've been doing anything for more than a week, it can probably be done better. And I know that's kind of a daft expression, but it it's kind of a I would set your framework like that because that's the truth. Someone somewhere somehow has figured out a better, smarter, cheaper, sexier, whatever way of doing it. They just have. Um, and that doesn't mean you have to improve everything right now, but it does mean you could. If that's your priority, if that's the thing you want to get made better, it can probably be done better. And with a bit of uh effort, a bit of research, you can find that thing and maybe introduce it. And that's really the mantra I try to get people to embrace is that your job is not to keep things the same, is not to protect your comfort zone, it's to constantly stretch it and try to find a way to do things in the best way possible. Not because you know you want to be more efficient so you can go home early or anything, but because you want to do more of the good stuff that you do in your job. You want to have a bigger impact on your customers or or their families or whoever it is that you work in the service of.

Manya Chylinski 6:19

It's so interesting. You use the word comfort zone, and I flashed back to my own corporate experience, and I never thought about work that way. It was this is what I come in, I know what to do, this is what I do, I go home. And there wasn't a lot of thought on my part of how can we make this more efficient? How can we make this better? How can we improve? It was just this is what I was hired to do, and this is what I'm doing. And exactly.

Allister Frost 6:52

And that was that was my experience as well. That's what I thought, right? I I was brought up to think, as many of us were, that if you do well at school, university, whatever, you'll be able to get a good job, and then you your company, you a company will employ you to do a job, and your boss will tell you what the job is, you do the job well, you'll rise up the ranks and so on. It was only when I flipped that agenda completely in my mind that I realized how much agency I had. It's not that a company, or the way I think you have to look at things is a company employs you to do a job, but actually the real power is with you because you employ that company so that you can do incredible things in the world. Now, if if I you know I worked at Microsoft and I had some big responsibilities there. I launched operating systems, I I did um amazing things by bringing in new products and stuff like that, not single-handedly, of course, but I couldn't launch an operating system or be the spokesperson for a you know big company unless I was working at Microsoft. I could not do that amazing stuff. So I very much started viewing as I'm employing my company so that I can do this amazing stuff. Can't do it on my own, but with their name over the door, with all of the resources it gives me, with the power you know that brings, I can affect the world in incredible ways. And that's so much more empowering than just thinking, oh, well, I'll do this job, I'm a cog in the machine, and then I'll go home and I'll do it for the rest of my life until I retire. That's not enough.

Manya Chylinski 8:21

I am so pleased that you brought this up because you said the word agency. And I think that is something that is missing for a lot of people in the workplace. And when I, you know, I think about the the people side of the organization and how are we supporting people in their real lives and what they're dealing with. And I think often in the workplace, we don't think we have the agency. In some workplaces, we might not, depending on the way it's it's run, if it's not a people-first organization. But I think we don't think about that agency that we have, and we don't think about we are employing them and what are we getting from the relationship beside a paycheck.

Allister Frost 9:06

No mind. This is this has changed though in recent times. And a lot of it is because of technology and the fact that the world moves so quickly means that no one knows what the next stage is going to be because it's it's coming at us fast as ever before. In the past, things moved relatively slowly. So the bosses who are empowered with knowledge and wisdom about the direction of travel, they could to some extent predict what was going to happen next. However, now it's moving so quickly, they have no better idea of what the future will be than the per the lowliest person in the organization. We're all figuring it out literally as it happens to us. So this is where your agency comes from, I think, because you have a job, you know your job, whatever that job is. It might be just writing the weekly report, or I'm not saying that to denigrate it, it might be a very lowly job or it might be a very senior job. Doesn't matter. You know your job, the responsibilities and the output that that can generate better than anybody else in the organization. No one can argue with that. So who is best placed to look at that thing and figure out how it can be done better? It's you. You have absolute agency to improve everything you do. You don't have to sit back and wait for the boss to say, oh, yeah, it's okay, we can change the way you do that. You can have ideas. You can have, you can look at a new piece of technology or a new way of thinking or a new idea that's coming out of anywhere in the world and bring that into your work and say, I think this could be a better way of doing it. Everyone can. So you can have agency, but you've got to accept that responsibility to create something that's for your future and for the organization's benefit.

Future-Ready Mindset For Stuck Cultures

Manya Chylinski 10:40

Yes. And you have to be working in an organization that accepts that you have that agency. I can imagine people thinking, well, I could never say that to my boss, or I could say that, but my boss would never listen, or I could say it to my boss and they would take that idea as their own. And I think your experiences in a workplace where that was celebrated and that was the culture, but that's not the culture in every workplace. So, what do you do if you're if you're in one of those and you're wanting to show that agency?

Allister Frost 11:14

I I hear this complaint all the time, and it's entirely valid. Many people feel like they're in an organization where they can't have an idea or they can't speak up. And we've tried that before, and and they're kind of stuck. Um, and and it is true, I will accept there are some places that you you you're not going to change it. That's the way it is, that's that's the culture, that's the boss's uh overburdensome way of running things. That I do accept. But in my experience, in the vast majority of cases, the boss feels an incredible lightness when they feel the responsibility for identifying what they need to do next is lifted from their shoulders. When they accept that actually it's no longer on them to have all the answers and to control everything, the best people to figure out how to do the small things and the big things better are the people who do them. And so that's where I came up with this concept of a future ready mindset, and I call it ready already in my book of the same name. How can you be ready already? And it's an individual model to help each person figure out what is it within my remit that I could improve, and then to apply some, I call them human superpowers, to think about them differently with curiosity, creativity, and then to collaborate with their colleagues so that it doesn't land as a threatening idea, which is what a lot of people would feel it would be cold, but it actually lands on the right ears to gain the support that you need so that together you can make that change happen, even if you have that overburdensome boss who's who's really difficult and slow. And most of the time when you go through the when I go through this with clients, they actually quickly realize oh, the boss, the boss didn't want to behave that way in the past, they just thought that's what their job was. And suddenly there's like, oh, I'm released from responsibility to have all the ideas, and I can ask you to have ideas, and and the people who want to have ideas are expressing them. It's a joyful place to get to, it's where we need to be.

Manya Chylinski 13:11

It does sound joyful and kind of work that you're talking about. So individuals do to have that agency and identify who who and what and where they can express that, then that's gonna change the culture of the organization.

Allister Frost 14:03

Yeah, for the better. It's um it's it's not an overnight fix by any means. Um, but yeah, I I say to leaders, their responsibility is to create an environment where people can come to work, be themselves. You can revel in the diversity of ideas and the spirit and the passion that people bring when they truly believe in what they're doing. Um, and and there it's just create that environment where people can be their wholesal, where they're where they want to be there. And then for the employees, if you know it's not like there's a linear divide down the two, but for the employees, it's to step up and say, okay, my job is not just to go through the motions, to keep things the same, to protect my comfort zone at all cost. My job actually is to identify what the next thing is that we could be doing, the next way I could be fulfilling my responsibilities and bring ideas to the table. Um, and actually to create the future, which is such an empowering place to be. And it's so different to this sort of feeling of victimhood that a lot of people are feeling right now with all of this change, all this worry, things like AI is oh, is it gonna take my job? What is that? What's my role? Oh, where am I gonna go? Well, you know what? Lock into the human value that you bring, express yourself and your your brilliant, diverse ideas, and then you'll find that there's you've got something, you bring something that AI simply cannot do.

Leading Without The Hippo Opinion

Manya Chylinski 15:26

Right. I like that term human value, because I think there is a lot of fear right now. And I think AI is a is a great tool. I don't think it's gonna do all the things that we're afraid it's going to do. But I want to actually go back for a moment. You talked about leaders, and and I know there's not necessarily a divide between because um leaders are also employees, and but if if someone is in a leadership role or a managerial role, what are some things they can do to show that they are open and interested in someone's ideas and wanting to make these kind of changes?

Allister Frost 16:07

I I think is accept that your your position, you probably worked extraordinarily hard to get there. You probably deserve it. Well done. Um, but you are now the highest paid person in the room. Congratulations. But that doesn't mean you have the best ideas in the room. A leader has to accept with all humility that they are no better at identifying the next thing for the organization or the next way to do that job, whatever, than anybody else. They really aren't. I my abilities to anticipate what was right for the next step did not improve as I gained more experience and I rose through the ranks. In fact, I think I'm honestly got worse because I became less attached to reality and more stuck in this weird cocoon of leadership where I sort of had visibility of lots of things and was sort of expected to work in a certain way. I was less me and I was more it. And I think there's so leaders should accept this as a real invitation to start to get back to being themselves, to get back to having some humility and honesty, and to say, look, I don't have all the answers. I know that you guys are brilliant at finding the answers, and I'm here to support you and I will listen. Um, and I I you know I jokingly say they're the highest paid person in the room, and they are, but I refer to their opinions as the hippo, the highest paid person's opinion. And the hippo is often the least welcome thing in an exploratory meeting or a discussion that's going on when you're thinking about could we do this? What if we tried that? How about this? I've learned about this. The hippo has an extraordinary weight, literally and figuratively, because they're they're as soon as they say, Oh, I'm not sure about that, it can kill an idea, it can destroy the energy in the room, or it can lift it up. So I actually try to get leaders to excuse themselves from a lot of those thinking processes and discussions, and to let more junior people get on with the thinking until they're ready to bring that idea to the hippo and say, okay, we're all sort of on board with this. We think there's something here. We think we might want to try this, then be absolutely supportive and try to try to make that idea as good as it can be. Don't just default to the no, because there's never but no budget, that won't work. You've got to give people space to pilot stuff to test to learn and make their own mistakes. Um, because some of those mistakes will turn into the greatest success you ever had.

Manya Chylinski 18:36

Okay, I love that acronym, hippo. Um, because right, hippos, you think they're kind of cute, but they are the most dangerous.

Collaboration Using Yes-And To Sell Ideas

Allister Frost 18:48

Exactly. Exactly. So uh the the whole process I have is the the the uh the frost framework, as many people call it, because they're five steps and they spell the let the the word frost, which is my surname. Um, but I called it the ready already growth cycle in my book, ready already, because that it's all about individuals, and it's only in the fifth step, the final step, that's where you get a few people together to sort of say, to talk about what you've been doing. It's very much an individual process. And that final step, don't invite the hippo along. Don't expose your thinking to the hippo until you're absolutely ready to say, okay, we we kind of feel like this is right. That there's a mistake I made, and I don't know about you, I made this too often in my career. I'd see, oh, there's something that I can needs improving. Oh, I can just fix that. It might be a simple thing, you know, I'll just I'll just sort that out, I'll I'll make sure that's all sorted. And I had many brilliant ideas and I did many amazing things, and no one in the organization knew about it because I just got on and did it. I was that sort of person, right? And I've never in my life had an idea that has not been improved in some way by being exposed to other people on the journey, right? And and it even if it's just that they say, Yeah, that's a good idea, you should do that. Or they might say, Oh, that's interesting. I think I know somebody who's done something similar. Maybe you could talk to them. It's always better to bring people with you. So stop trying to do the hero thing I think I was guilty of for a lot of my hit career of just, oh, I just saw that out. I'm oh no, don't worry, boss, I've sorted that out. No, find somebody else to talk about it with, bounce it around, get the recognition you deserve, but also you'll do better work with other people. It's collaboration that's so important. And again, it's uh a magical thing that technology and AI can never do as well as us humans. So lean into those skills because that's the stuff we need in organizations.

Manya Chylinski 20:41

Right, right. The things that can be automated, let them be automated, and we need to do the things that we're good at. That's so, you know, you talk about kind of keeping the idea to yourself. I've done the thing where I have this idea and it's not fully formed, and then I take it to the boss, but it's not, it's not fleshed out enough. We don't know what to do with it, and they don't know what to do with the information. And um, that's also not a great, that's not the next step when you have an idea.

Allister Frost 21:13

We do we do a lot of weird things as uh uh when we have an idea, don't we? We either rush, you know, I've got to tell someone, I've got to go and tell the boss, I want to get all the credit for this one. Or we worse, more commonly, we think about it and we sort of have a brilliant idea while we're in the bath, and then the next morning we think, oh no, that won't work because and we've you know we've we kill off our own ideas before they've even been aired. Um so my process really says, look, you need to have bigger, bolder ideas without the expectation that you will get the best idea or you will find it a viable idea. It's okay to have ideas that are a bit out there, a bit wacky, but what you must do is share those with a few colleagues, a few trusting colleagues, uh, and invite them to say, yes, and we could try this. Yes, and you should look at this, yes, and and how about we we pair up with these people, whatever. And it's deliberately a yes and response that you will need to get from your colleagues rather than a no because or no but, you know, that we're so used to hearing. Then that idea will take either it will either re you'll either realize, no, actually it's not viable, it's not right, and actually it should be killed off. That's fine. Or you'll realize actually this feels good, this feels right. Now we can take it to the boss. Now we can we can expose this to the hippo and see see if we can get the support that we need to make it happen. Um it's so often the case that we just destroy destroy our ideas. So the medium is the message. The way you tell people about your ideas is as important as the idea that you have. And far too often it it breaks my heart when I think back, not just to my ideas, but other colleagues, people who worked with me, they had ideas. And you have a meeting, and maybe you've got five minutes at the end, you go around and say, anybody got anything? And someone will say something and say, Oh, well, I'm just working on this idea. And because we're all closing our laptops and busy to get off to the next meeting, we don't really stop and listen. And in the signals that that sends them, it destroys that idea. It destroys the energy, the impetus that they had. And we don't realize we're doing it. So if you have something, if you have an idea and you need help from others, put as much effort into how you're going to tell them as you do for the idea itself. And that means, you know, don't just take them to the meeting room. You know, take go somewhere different. Give people an excuse to sort of really stop and think, dress up in a funny hat if it will get their attention. You literally put the energy into how do I communicate this idea and hold their attention so that they want to help me make it better. And when people do that, they get remarkable results.

Manya Chylinski 23:42

Absolutely. And I know there's there can be fear of sharing a new idea or something different. And you can then communicate that as you're talking, oh, I just was thinking about this, or or I don't know if this is a good idea, but insert idea here.

Ready Already And How To Connect

Allister Frost 24:00

We you're off the hook. That's the thing. You're you are literally off the hook. You don't have to have no individual, no individual today should ever be expected to have the perfect idea. It's impossible because it's too complex. You need there are too many variables going on. You need other people's eyes and brains on it. You need to bounce it around and use tools like AI to help you stretch the idea, to test stress test it, and all of these things. You you you can't do it on your own. So the minute you accept, oh, it's okay for me to have the start of an idea, but the only way I'm going to get to the finished solution is with the help of other people. The minute you do that, you you don't need to fear exposing your unthought, unfinished ideas. You don't need to worry about that. It's okay to be vulnerable in that moment, but you shouldn't fear that moment.

Manya Chylinski 24:50

Yeah, absolutely. Allister, I think we could talk for many more hours, but we are at the end of our time. So uh thank you for being here. And and before we go, can you share with our listeners a little bit more about yourself and what you do and how they can reach you?

Allister Frost 25:07

Yes, of course. My name is Allister Frost is a business transformation and growth expert, known for his energy and passion for helping others to embrace positive change. As a former Microsoft leader, his book and highly acclaimed Future-Ready Mindset talks inspire curiosity, imagination, and courageous collaboration to unlock daily improvements, strengthen resiliency, and fuel high-performance teamwork. He is the author of ReadyAlready and an award-winning speaker and marketer. His mission is to save ONE MILLION WORKING LIVES by rescuing busy people from the deadly complacency of their comfort zone. He does this by sharing the new skills and positive mindset needed to stay future-ready for life.tair Frost, and I am the author of Ready Already, a small book designed to help people to think differently about their work and to come up with fresh ideas. And most importantly, just to keep up with the relentless pace of change. Uh, you can uh you can find me online if you can spell my first name, which is not easy because my parents gave me a crazy spelling. So the easiest thing is just to go to ready already.me. And that was where you'll find out about the book, about me, and uh get in touch. I love hearing from people and uh and helping them on their journey through life.

Manya Chylinski 25:43

Excellent. Thank you, Allister. And I will put links in the show notes to make it easier for folks to find you. And um, so I really appreciate this conversation. Thanks for being here. And thank you to all our listeners. We will catch you next time.