How to build resilience in product - Lindsey Jayne (Product Advisor)

Lindsey Jayne is an independent product adviser and coach, and former chief product officer at the Financial Times. She began her career at the Government Digital Service, where she stumbled into product management by chasing someone down a corridor holding a MacBook that actually worked. What followed was 15 years moving through startups, scaleups, and ultimately one of Britain's most storied media institutions.

Chapters
00:00 — Introduction
01:08 — Lindsey's origin story: from a broken government laptop to product management
02:48 — Why product managers burn out: accountability without authority
05:34 — Influencing stakeholders using discovery skills
07:19 — What leaders can do to clear the way for their product teams
08:44 — Stakeholder mapping: the influence and interest framework
09:41 — Recognising burnout signals in your team at scale
11:16 — Balancing passion and sustainability: when enthusiasm becomes a pattern
14:16 — When to transition from individual contributor to product leader
16:24 — Product reviews and cross-team knowledge sharing
18:42 — How to communicate effectively with senior stakeholders
20:40 — Career-defining advice: you don't have to die on every hill
21:43 — Half your job is landing the product, not just building it
22:25 — The most common mistake junior product managers make
24:05 — How to tell your story after a difficult or toxic company exit

Our Hosts
Lily Smith enjoys working as a consultant product manager with early-stage and growing startups and as a mentor to other product managers. She’s currently Chief Product Officer at BBC Maestro, and has spent 13 years in the tech industry working with startups in the SaaS and mobile space. She’s worked on a diverse range of products – leading the product teams through discovery, prototyping, testing and delivery. Lily also founded ProductTank Bristol and runs ProductCamp in Bristol and Bath.

Randy Silver is a Leadership & Product Coach and Consultant. He gets teams unstuck, helping you to supercharge your results. Randy's held interim CPO and Leadership roles at scale-ups and SMEs, advised start-ups, and been Head of Product at HSBC and Sainsbury’s. He participated in Silicon Valley Product Group’s Coaching the Coaches forum, and speaks frequently at conferences and events. You can join one of communities he runs for CPOs (CPO Circles), Product Managers (Product In the {A}ether) and Product Coaches. He’s the author of What Do We Do Now? A Product Manager’s Guide to Strategy in the Time of COVID-19. A recovering music journalist and editor, Randy also launched Amazon’s music stores in the US & UK.

Transcript

SPEAKER_02 0:00

Half your job is building the product and shipping it, the other half is landing it, and that's all about communication.

SPEAKER_01 0:06

Hello and welcome back to the product experience. This week we've dug into the archives and pulled out a conversation with Lindsay Jane, independent product advisor and coach, and ex-CPO at the Financial Times. This conversation happened two years ago, and so many things have changed that the topic is still relevant today. We talked all about how to build resilient product teams and how to cope with the stresses and strains of everyday product life.

SPEAKER_02 0:32

Product management in three words, making valuable stuff.

SPEAKER_00 0:35

What's the most common mistake you're seeing them make in this space?

SPEAKER_02 0:39

When I first joined the Financial Times, product never went and updated the board. You have consistently demonstrated results. I said we will, we have done this. Until you get bored of it. I think as humans, we're bad at a couple of things. Understanding orders of magnitude and scaling, and understanding that life is cyclical and a rhythm and not more, more, more, more, more, more, more. Even in a company that shut down or sold or whatever, you can still tell a really compelling story.

SPEAKER_01 1:08

Hi, Lindsay. Welcome to the Product Experience Podcast. How are you? Hi, Lily. Thank you so much. I'm really well, thanks. Great. And it's so nice to be with you here in person. And it would be great if you could give our listeners and watchers a quick intro to who you are and what you do in product. And also a little bit of your origin story of how you got into this world.

SPEAKER_02 1:31

Yeah, that that would be wonderful. So I'm currently the chief product officer at the Financial Times. That's a bit of a pace shift for me. I came out of a world of scale-ups and startups, but it actually harkens back to how I got into product. My very first job was early in the days of gov.uk. And I've always been quite civically minded. And so I joined the civil service to make a difference. And someone gave me a laptop that took literally 11 minutes to boot up. And a few months into this horrible hierarchical, this isn't going to go down well, somebody walked past me holding a MacBook. And I was like, why does that person have a computer that works? And so I chased them and found out about the government digital service and convinced them that they needed a translator between the world of government and the world of tech. And as somebody who grew up with a computer in their bedroom, very fortunately, and sewing machine alongside it, so that creative and science bit coming together, it I just like I just happened on this world I didn't know existed. And so for a year or so I was the translator. And then I felt I knew enough that they let me loose on the product itself. So that was oh gosh, 15 years ago, 10 years ago, something like that. And here we are today, still at it.

SPEAKER_00 2:48

Great. And one of the things we want to talk about today is why so many product people experience burnout. Why it's so hard for us still? And we know we've been doing this for a long time. We're well established as a function in most businesses, in theory. In theory. But why? Why are we still having this experience where people are finding it so hard to just do the job that they thought they were hired for?

SPEAKER_02 3:12

Yeah, I mean, I sometimes I'm like, is it causational correlation? Are we drawing in a bunch of people who really care and really want to try and therefore are passionate and are just pushing because it's such a rewarding job when you put something out there and you see someone using it and it goes well. But that seemed like it might be too blunt an idea. And like you say, the the craft has been around a while and organizations might have different interpretations of it. But I think this there's two main problems I've observed. The first one is in large organizations, there isn't really still an understanding. When I say large, I mean non-tech organizations. There isn't necessarily an understanding of what the role is. There's quite a lot of accountability to give to what can sometimes be a junior role. So you see people sort of reading the textbooks and then raging against the machine because it's not like the textbooks. Conversely, if I look at the world of tech companies and tech scale-ups, in one stage there was so much venture capital money being pumped in. There, the burnout was ship it faster, grow faster, hire. I mean, when I was at Monzo, 50% of my time was hiring just to keep up with the demand of all the ideas and the capital we could deploy. And since that money is trickled away with sort of difficult economic circumstances, then it's like we have no runway, you better be making money, go, go, go. All of that wrapped up in the fact that you are accountable for the success of something that you don't have direct authority over. You can't make an engineer do that, you can't make product marketing do that, you can't make sales behave in that way, and nor should you. But it means that a lot of your job is about influencing everybody around you.

SPEAKER_01 4:59

So, as we like to say, all the responsibility with none of the power. That's the one.

SPEAKER_02 5:06

And interestingly, if there is conflict or tension or a bit that doesn't actually work in the flow, that can go hidden in an organization for a really long time. But it will get surfaced in the moment where you try to launch a product because you will need legal to talk to this department in order to do it. So you're quite often the person going, hey, there's a difficult issue we need to get through here. And I think that can be quite challenging too.

SPEAKER_01 5:29

I think it's interesting because that dynamic of all of the responsibility with none of the power, it really makes product managers have to operate in a very particular way. What are some of the ways in which you coach product managers through where they are having to convince or persuade people, hopefully they're to get on board with their ideas, and hopefully their ideas are the right ideas.

SPEAKER_02 5:55

Yeah, and and this is something I'm still learning myself. And I feel like never mind A-B testing 101. We all need how to have difficult conversation training 101. And in fact, I'm actually developing that for my team right now, how to deal with you know difficult situations and how to influence. But the number one thing for me is you've got to meet people where they are. Go find that stakeholder, go find that person and get really curious about what they care about and what's going on in their brain, and don't try solve it in one go with, but here's my idea. You know, you're not in this, it's a marathon, not a sprint. So you might go make sure they really know you care about their concerns, you understand their world, and just be really curious. Don't assume they don't know what they're talking about. Really? Uh don't go in with that conflict. And and that might mean the first time you ship their crazy idea. But you've got to kind of slowly be bringing them into understanding that you can be trusted and that data is a really important part of what you do, and that delivery is an important part of what you do. But I think that that can take a bit of time.

SPEAKER_00 7:06

Yeah, I love telling people, you know, you've got these skills that you've learned about discovery. They don't just work on customers. You can use them internally on your stakeholders and your partners as well.

SPEAKER_02 7:16

That's such a great metaphor. Yeah, yeah.

SPEAKER_00 7:19

So that's what uh a little bit of what people can do on an individual level. But you're in a leadership role. What is the responsibility or what can you do in a leadership role to help create an environment where the people have a better chance of succeeding and a better chance of, you know, you're easing the way of engagement for everybody else?

SPEAKER_02 7:40

Yeah, I I think that there's a lot of things that you could and should do to clear the way. The first thing you need to do is make sure if you're looking up and out at your own peers and at the the if there's leadership above you in the organization, that they understand the value of what you're doing. You've communicated it in plain language, you're not the weird tech people in the corner who speak a different language, and that you have consistently demonstrated results. I said we will, we have done this. I said we will, we have done this until you get bored of it. When I first joined the Financial Times product never went and updated the board. And I was like, okay, ask number one. I want to go in there at least every six months and say, this is what we said we would do, this is what we did. What do you need? And then I think it's it's also just I find stakeholder maps a really useful thing for teams who are trying to figure out how to update people, what they're doing. And yeah, just helping teams navigate what the incentives might be and who they should talk to. But I think you've got to have those relationships right at your level as well, so that they can work uh to the whole team.

SPEAKER_00 8:44

I've seen different versions of stakeholder maps. What does a good one look like for you?

SPEAKER_02 8:48

Oh, don't ask me this because I this there's one that like it is, it sounds terrible, but it's where my brain always remembers it, which is the two by two. And on one dimension, it's I don't like it's like power. But it's not power, right?

SPEAKER_00 9:02

No, influence. Influence. I mean, I think it is originally power, but I like it influence and interest is the two, is a much nicer way of saying it.

SPEAKER_02 9:11

It is, yeah. You know, how disruptive could this person be? How much will they shape the future? What could happen? And then you're giving yourself the opportunity of someone super high influence, maybe particularly low interest, and isn't that invested in understanding what you're doing, they could just sideswipe your whole thing and make it go away. So it's important to make sure your communication and what those people know about is specific to their user need. Um but like you were saying about discovery, what are the user needs of the various people around you?

SPEAKER_01 9:41

And just coming back to another topic that we touched on at the beginning around burnout. So obviously, if you're managing groups of product managers, how do you ensure that you are aware of sort of any signals that this could be happening within your own teams and taking any action there?

SPEAKER_02 9:59

I guess nothing that revolutionary. Um, I have a hundred folks in my team, so I concentrate quite closely on the people I speak to regularly uh kind of every day. For but at the sort of scale of a hundred folks, we do use like PCON, which is a tool that surveys people regularly, that helps us understand how they're feeling and what they're doing. So we get like that kind of raw data out of it. I think there's just also knowing people well enough to know when their resilience is low and they're not being themselves and helping them be proactive. And some of that can just be making sure they take holidays or taking them to one side after a difficult meeting and let them scream into the void before you go back in again. And I think I'm really lucky. I work in an organization that very much prides itself on creating work-life balance and on being flexible about when people can do things. But at the same time, the job is very challenging. So I think it's just the people you see every day keeping knowing them well, making sure you have authentic communication so they can kind of go or you recognize where they're in a bit of a pattern, and then at scale, just making sure that you're you're getting enough data out of people.

SPEAKER_01 11:09

I think it's really interesting that you know, quite often when people talk about burnout, it can almost be attributed to the the company culture and like pressures of the company. But I also see people who are so just excited and passionate about what they're working on that they want to work on it more than they should. More than they should be, and more than is healthy for them. Yeah. And I was having a conversation with my product team the other day about you know what work was so exciting or so filling that you could just lose yourself in it and you wanted, you know, you might want to open your laptop after dinner again and just be like, oh, just look at this again and look at do a bit more. What do you do with you know, with people like that where you know you want to harness that excitement and their kind of self-motivation, but also look after them?

SPEAKER_02 12:02

Yeah. I I think as humans, we're bad at a couple of things. Understanding orders of magnitude and scaling, and understanding that light is cyclical in a rhythm and not more, more, more, more, more, more, more all the time. And I think it's absolutely fine to be so excited about a piece of work that you cannot put your laptop down. But it's not okay for that to be a pattern that is consistent. So I would be very chilled if someone was really enthusiastic for a while. I'd be very worried if I was seeing Slack messages at this time, or it was clear that they were all scheduled for the morning, or that sort of thing. And that I think is just a conversation about it being a marathon rather than a sprint. There's there's like two things, right? If you think about it like gardening, there's a plant that will grow really, really fast and high but might not be that strong. And then you can put that plant in the sun or in the shade, and that will help it do one or the other. So I always try to think about people as plants, apparently. Um I always try to think about what's the environment doing and keep an eye on it. But then also what's the individual sort of tended towards. Uh, and I'm married to somebody who will who I tease and say you are like there's a I don't know if it's true, but they say horses will literally walk work until they drop dead. Um, he does, so you have to stage interventions. So I I have a lot of the signs to watch out for.

SPEAKER_00 13:21

I had uh uh an an aspiring product manager on a team at one place who was going through a breakthrough. She was totally leveling up in her skills, and she was so excited, and the ideas were bursting out of her head, and she was working nights and weekends, not because anyone expected her to, but because the ideas were just flowing and she was learning and she was really enjoying it. And I had a friend coaching her, and he was telling me he was a little bit worried about her burning out, so I had that conversation with her, and I said, It's okay to do this so long as you never feel like you're expected to do this. The minute you feel pressured to do it, you need to stop and you need to be watching out and you need know that we're watching out for you, but we're not gonna tell you to stop if you really want to. It's okay.

SPEAKER_02 14:04

It's creating the condition and the knowing there's no expectation, but then also and giving people context, but also trusting them to to sort of know when they're in the zone versus know when they're feeling a bit frazzled.

SPEAKER_00 14:16

Aaron Powell I see a lot of people uh, you know, product managers, it's in the name. We're managers, but we don't necessarily control the team. So we're really more individual contributors at the the base level. Then we get to the next level up, and you're usually expected to start managing other product managers, but you're still managing your own dev teams and your own stuff as well. At a certain point, that doesn't scale anymore. So in your organization, and I'm curious about your attitude towards this, when is the right time? What's the right balance at uh as you start to go up to you know group and head and things like that? When do you stop doing the day-to-day stuff? And what's the right balance of being able to manage other people, give them the time and create the environment for them that they need versus actually running things on your own?

SPEAKER_02 15:04

Typically we don't have, I don't set the world up so that group product managers are running, you know, have a team and a product that they're working on as well. Sometimes uh we nearly just hired our first principal product manager who you might say, you know, this is a big, impactful project. We want someone, you know, who's really got amazing skills on it, who's a master of their craft. But it is a real shift to, you know, you've always delivered through others, but a lot of the fun is in the delivery, and now you're up here having to do that. But we've been having some really interesting conversations about the difference between knowing what is going on and being able to coach on the specifics of the work versus stepping back and thinking your job is just to help the development of those individuals. And my personal preference, I think if all I'm doing is helping you be a manager, but I don't know what's happening in your product, for me that means you're not getting the benefit of the years I spent doing product work. So I think that there's a way for managers who are shifting out of having a team themselves to still understand work in progress, to still understand what's going on and help their team ask questions of their team rather than just suddenly become a human manager, which is a very different job to what you first signed up for.

SPEAKER_01 16:24

Are there specific things that product managers who are kind of moving into more of a leadership role? And I guess even if they're not and they just want to support their other, you know, product mates, where you know there's a really good format for sharing that product work. Because I I appreciate you know, you've got so much going on in your own function or your own kind of squad or whatever that it might be hard to take in. Yeah, exactly. To kind of step back and take in everything that's going on in another team and be able to offer helpful advice.

SPEAKER_02 17:00

Yeah. I there's two things actually. The first one, I think our design uh design have the most beautiful ritual, which is the design critique, you know, done well, where you come in and go, I'm at this stage of problem solving. I have tried these solutions, and I'm looking for feedback on this thing over here. You know, colleagues from different, you know, product lines across help me solve this problem. I think it's absolutely beautiful because you, A, you're seeding knowledge everywhere, but B, you're getting the benefit of those people's brains without it being massive overhead. All you have to do is show up, answer some questions, and disappear again. When I'm looking at product group product managers, I think that the magic of a multidisciplinary team sometimes disappears at leadership. And I love to get them to model that by uh setting up product reviews. And what they are is a meeting which, you know, no presentations, but it requires a team to bring a problem and a work that work that's in progress. It's not reviewing what you've done, it's helping you work through stuff. And the team will present that to the leadership team of product, design, research, data, whoever the right leadership team is, and use that connective experience for the the group PM to go, what options have you rejected in favor of this one? How, what are the other ways in why you might test this? Have you had a conversation with this person over here? And I think that's a really great way to just keep consistent context. Also, if you have amazing analytics and also a dashboard node in the mornings, you might be busy, but the first 15 minutes looking at all of the product data will will give you um like like an ongoing context that's almost effortless to maintain. It's going in and getting familiar that takes a lot of energy, I think.

SPEAKER_00 18:40

We had a uh a chat recently with someone who's a specialist in organizational development, and he talked about one of the challenges for product people is at an organizational level, you're being expected to operate a couple levels above your pay grade.

SPEAKER_02 18:55

Yeah.

SPEAKER_00 18:55

You're being expected to negotiate and communicate with people much more senior than you on their level. So, what are the skills, what are the things that we can do and help people with as individual contributors to operate at that at that level?

SPEAKER_02 19:10

It's it really is so true. And I think I was so lucky because that kind of beginning in government meant I had to go brief scary ministers, and then my first translator role meant the people I was working with on a day-to-day basis were the director of finance for the government, and I couldn't read a statement, and all of my stakeholders were really, really senior, and I was really confused by like emails we would get by people who are like, you have to help me with this. I'm like, you have no understanding of the perspective or what constitutes escalation. You just seem very disconnected from the interests and the needs of this group. Why is that? So this weird experience of coming in really understanding the senior perspective and not really understanding the perspective of my peers. And I think for our teams, it goes back exactly to what you said, which is uh what we said about influence, which is about understanding what's on their table, what matters to them. If you, you know, what was on the CEO's desk this morning, and and then go ask someone and see if you're right. What were the three things this person were in this person's diary before I met I went to meet them, and how much context switching did they have? So I I think there is there are practical skills around how you present your voice, your body language, being well prepared for meetings, trying things out, asking for feedback afterwards. But I also think there's a bunch of empathy for your users and understanding where they're coming from as well that will power up those skills of being hella prepared and uh being able to sort of present.

SPEAKER_01 20:42

What's one of the pieces of advice you've had in your product career that has really shifted your perspective or changed the way you operate and has really like made a difference to you?

SPEAKER_02 20:54

There are actually two, but in the context of this situation, I will go with the one that has helped me not to burn out, which was I was working with a founder CTO in one of my roles, and he looked at me and he went, You don't have to die on every hill, Lindsay. And I was like, Oh, oh, you're right. I'm prioritizing what I build, I'm prioritizing in every area of my life, but I really care about quality and I really care about us finding the best way to do stuff. So I was dying on every hill. And so now if I'm feeling frazzled or if I'm catching myself speaking because we're in a meeting, and so you can, I just have a little filter that goes, is this a hill that makes the cut?

SPEAKER_00 21:39

I like that.

SPEAKER_02 21:40

So I want to know what the other piece of advice was. I actually just mentioned this in we would the at the roadshow talk I just gave, which is half your job is building the product and shipping it, the other half is landing it, and that's all about communication, which I guess also speaks to influence and visibility. It's not done until people. Know it's done and they know with context. We sometimes say about strategy, whenever we have a an OKR about strategy, it's a terrible thing to do. I always use the result you can stop a random person, service desk person who's a few weeks into the job, a junior user researcher, and you've asked them what the strategy is, and if they can answer clearly, then you've nailed it. And until then you haven't. So yeah.

SPEAKER_00 22:24

What's the biggest mistake you see? People that uh more junior product people, people on your team's people that you coach people at other companies. What's the most common mistake you're seeing them make in this space? What's the one thing you wish that they all knew and would just start doing differently?

SPEAKER_02 22:41

It honestly is that rage against the machine. I've done a lot of interviewing in my time and a lot of um coaching recently to help people prepare to find new jobs, particularly in the context of difficult exits from jobs or or places where they didn't have a choice from leaving. And you really, from a million miles away, can see someone who's leaving a job versus someone who's going to a job and what baggage they're carrying with them. I think you have to, if you are making that job change, I think you have to get it out of your system, mourn it, get over it, come up with a, you know, explain that job and and why you're moving on in a way that that is authentic and makes sense to you, but has some of the heat taken out. And if you're in an organization, it is what it is. You are one person. And if you go up against a thing that is not human, you probably you might change it, but you probably won't. So pay attention to the environment you're in, accept it as it is. It's this it's the alcoholic, give me the serenity or whatever, to accept the things I cannot change.

SPEAKER_00 23:41

Just serenity prayer, yeah.

SPEAKER_02 23:43

Yeah, the serenity prayer, there we go. That's the piece of advice I'd give to PMs just for sanity. You will ultimately get more shipped on a two, you know, on a two-year horizon than if you just try blast through with the stuff in front of you.

SPEAKER_01 23:54

Yeah, I think that's such good advice. So just thinking about the um what you're saying about, you know, people leaving from potentially quite difficult situations that they're in. And then you have to build a picture of like what you were able to do in the business before. You know, what advice do you give people in that in that space? Because, you know, I'm fortunate enough to have been in some good, really good situations, but yeah, even then it's been tricky if there's, you know, the funding's run out and things like that, then you feel a certain level of shame or embarrassment of we weren't successful and having to explain that. But you when things are even worse and you're in a fairly toxic situation and you just you're not able to operate at the level that you want to. Like, how do you how do you coach people to explain those situations in a way that is still attractive to an another employer?

SPEAKER_02 24:53

There's probably some psychological basis for this, but my observation is that people will tend to extrapolate failure around a company to an individual and be worried about being contaminated with it on some sort of, I don't know, deep psychological level. So, what I often work with people to do is find ways to draw out their personal successes or the bits where they avoided it or you know, where the limits of their influence were, so that even in a company that shut down or sold or whatever, you you can still tell a really compelling story. The other one is if it's been really toxic, I try to use the metaphor like you're either starting at ground level, and if conditions were perfect, you'd have got here, but you started in a in a hole and you worked your way up to ground level. So then the story you're telling might be, okay, so my previous job, I was able to turn this thing around within two weeks. In the company I went into afterwards, there was less familiarity with product ways of working and the technical infrastructure wasn't there. So I embarked on a program of you know change that meant that six months later we were able to do this. So asking people not to discount the work they did to make their job possible. It's not just what you shipped, it's what you did to make that possible, and I think that can be quite powerful. And also just having a place to go, like let that stuff out, get over it, say it, be done with it until it had the heat's taken out, and then you go right to the interview.

SPEAKER_00 26:19

I um I was hiring for a role once, and we were uh hiring people from a particular culture that was not very big on individualism. So every everything, all the stories people were telling us were we did this. Yeah. And we kept pressing, myself and uh the the co-interviewer kept pressing, okay, that's what your team did. What was your role? What was your contribution? It's interesting you're talking about you don't want to get uh contaminated sometimes with the company. So the balance of this is what we did, but this is what I did in that context. Yeah.

SPEAKER_02 26:53

Yeah, yeah. And if I can do this, if I can create this kind of result in this crazy context, imagine what I can do, and I'm sure you're a perfectly functional company. High functioning, you know, wonderful emotional intelligence. Just imagine how I will soar there. I also think that there's something about when you have a match with a company where you have similar values, that they probably are going to recognize your value. They are going to be smart, they're going to want people who've been brave enough to try and fail if it's an environment that will reward that. So I think that you might meet a lot of frogs, but and it's painful, and sometimes there's a financial reality where you've just got to get paid. But I think that those rejections are maybe a good thing.

SPEAKER_01 27:35

Lindsay, thank you so much for all of your advice today. It's been such a pleasure talking to you.

SPEAKER_02 27:40

Thank you very much. I'm definitely stealing some of the ideas you came up and using those elsewhere. Discovery on stakeholders.

SPEAKER_01 27:48

The product experience hosts are me, Lily Smith, host by night, and chief product officer by day.

SPEAKER_00 27:54

And me, Randy Silver, also host by night. And I spend my days working with product and leadership teams, helping their teams to do amazing work.

SPEAKER_01 28:03

Lou Ron Pratt is our producer and Luke Smith is our editor.