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Episode 21: Splitting time and tech strategy with Anna Shipman

    Guest Biography

    Anna Shipman is Chief Technology Officer at Kooth, pioneering great digital mental healthcare for everyone.

    With over two decades of software engineering experience, Anna has led teams both large and small. Before joining Kooth, she served as the Technical Director for Customer Products at the Financial Times, overseeing the award-winning website and FT iPhone and Android apps. She also played a crucial role in launching the GOV.UK website during her time at the Government Digital Service.

    She speaks at conferences, blogs on her personal website, has a mailing list and is always up for a game of pool.

    Social media links:

    Links and mentions


    Patrick Kua: Hi everyone. Welcome to the Managing Managers podcast. Today I’m delighted to be joined by Anna Shipman. Anna Shipman is the Chief Technology Officer at Kooth, pioneering great digital mental healthcare for everyone. With over two decades of software engineering experience, Anna has led teams both large and small. Before joining Kooth, she served as the Technical Director for Customer Products at the Financial Times, overseeing the award-winning website and FT iPhone and Android apps. She also played a crucial role in launching the GOV.UK website during her time at the Government Digital Service. She speaks at conferences, blogs on her personal website, and is always up for a game of pool. Welcome to the podcast Anna.

    Anna Shipman: Thanks Pat! Glad to be here.

    Patrick Kua: It’s wonderful to have you here. You’ve got such an extensive background, both in technology and in leadership and management. So maybe you can give us a quick overview of your leadership journey and how you found yourself in the management track?

    Anna Shipman: Yeah, sure. So when I joined the Government Digital Service, which was about probably about eleven years ago, I was definitely engineering focused. The first few years I was there I did a lot of engineering. Frontend. Backend. Spent time on the infrastructure team. But I did two things while I was there that moved me into the more management track. One was I became a technical architect, which takes you into that influence, delivering through other people thing. And the other separately was that I took on line management. The way we did it at the Government Digital Service was if you wanted to do line management, you did line management. so engineers would line manage. Some would and some wouldn’t. That was actually quite difficult. sSo it wasn’t the management track. It was the individual contributor track with some management. That was actually quite tricky.

    Patrick Kua: That’s a very strange situation. Very unusual, right?

    Anna Shipman: Yeah. I don’t think they do it like that anymore. It didn’t work amazingly well. I found it quite challenging because I didn’t have the opportunity to impact the outcomes of the people I was managing. So I did it for about a year and then I stopped line management, which was also fine in that way of doing it and just focused on the technical. As being a technical architect that grew to like leading teams. So when I moved to the Financial Times and became technical director, that’s leading a team and that’s the management track.

    Patrick Kua: Great. At what point did you start managing other managers?Was that as soon as you joined the FT or was that a while?

    Anna Shipman: Yes. It was straight away. When I was leading teams at GDS, from a technical perspective, there were people who were line managing on my team. But it wasn’t exactly the direct managing managers. But when I joined the FT I was managing some Principal Engineers and they were managing engineers.

    Patrick Kua: Got it. When you joined the FT, what did your team look like at that time? How many people did you have? Or how many managers did you have to manage at that time?

    Anna Shipman: That’s interesting. There were about 50 or 60 engineers on the team. During my whole time there I had between 4 and 6 principal engineers reporting to me. We didn’t have engineering managers at the Financial Times. So principal engineers were both. It was interesting. I think the technical director and CTO are both on the management and the technical track.

    Patrick Kua: Interesting.

    Anna Shipman: You’re not an IC. But you’re still on that track. So principal engineers at the Financial Times were also on that same track where they were both leading technical projects but also managing people. It’s quite tricky though.

    Patrick Kua: It sounds like it’s the amped up version of the Tech Lead Manager where probably your scope gets bigger but you’re sitting both technical and management hats in the same place.

    Anna Shipman: Yeah and it’s tricky. One thing we talked a lot about at the Financial Times was having engineering managers. Like splitting into that track because some people just don’t want to manage people. Some people want to focus more on the management side and less on the technical side and there wasn’t as much room for that.

    Patrick Kua: Yeah, definitely understand that. I’e heard that many times as well. And yeah, see that in some companies where they do split that out. But let’s talk about that journey as you stepped into managing other managers. I understand you were probably doing a lot of leadership activities at GDS or Government Digital Service and then as you moved into managing other managers, did you have any support as you made that transition or what did your support look like at that time?

    Anna Shipman: That’s interesting. So the support I got when I joined the FT was that my fellow tech directors were very supportive. We worked together on a lot of things like calibrating promotions processes and that thing to make sure we were all managing people in the same way. But I don’t know that there was explicit management support. Something explicit to take you to that step. I think it was because I had a background of managing teams to deliver technically and line managing people, the assumption was I would be able to do both at the same time and luckily it turned out that I could.

    Patrick Kua: Good results. Good results. When you did actually start managing other managers were there any surprises for you or contrasts as to what’s different from managing just individual contributors?

    Anna Shipman: That’s an interesting question. What’s very interesting about it is I never thought about it so much as going into managing managers. My experience of managing people without having any impact on their outcomes made me feel that it is really important that you are managing people where you’re also managing the work. To a certain extent. It felt like a big picture thing, right? We’re together. We are running this piece of work. We’re running customer products. We’re delivering the website. We’re delivering the apps. Part of that is thinking about… I mean the way we thought about it was to split it into 3 types of work. Technical strategy, technical oversight and people leadership. So those parts all need to work together in order to help you deliver. So it wasn’t a separate thinking about the managing managers. It was what are other things we need to do so that we, as a group, are delivering what we need to deliver?

    Patrick Kua: Great, excellent. I’d love to delve into what I just heard you say with those 3 areas. So I heard technical strategy. Technical oversight and I think it was people management or leadership. So what do you mean by particularly the first two because I think those two sound a little bit different for managers perhaps? So what do you mean by technical strategy and what do you mean by technical oversight?

    Anna Shipman: Yeah, I’ll do technical oversight first because that’s easier to explain. For example, if you want to change your testing. How you do testing. tTesting strategy. You might lead a piece of work to change that. Or if you know that a few teams are thinking about their deployment pipelines or they’re thinking about working together on a feature or something like that then supporting that from a technical perspective. So making sure the right people are having conversations. Making sure you’re producing artefacts. Making sure you’re leading and directing where necessary and supporting.

    Anna Shipman: Technical strategy is about thinking where you… like working out what the overarching story of where you’re going is. So where are you going? The thing about strategy is you start with a diagnosis of where you are. You have a vision of where you want to get to. Then you have the coherent action which is getting from where you are to where you want to get to. So technical strategy is about understanding where you are technically. It’s like where do you want to be? Where do you want your tech to be? What are you aiming for and then what are the things you do to get there? When I was working out with my team how we should split our work up that was how we thought about it. We should try and be spending a third of our time because as you know managing people can take over all of your time if you let it.

    Patrick Kua: Yes, absolutely.

    Anna Shipman: Because people are very complex. People are a complex adaptive system right? It’s like that’s the hardest thing you’ll have to do. So we were like let’s think about how we should allocate our time. Let’s allocate a third of it to people management. A third technical oversight and a third technical strategy. Strategy will get pushed out if you don’t make time for it.

    Patrick Kua: This is absolutely very true. It’s one of those things where nobody’s asking for it typically and I can see how that ends up being pushed aside.

    Anna Shipman: Yep. One of my colleagues said that exactly. She was like the technical strategy doesn’t send you an email saying you need to get the midyear review done by the end of this week, so it’s quite easy to leave it.

    Patrick Kua: Absolutely. When you talked about having that time, how did that translate into your calendar? Or what practically did that mean? Was it on a weekly basis or did you literally have like third blockers in your calendar? What does that look like for you?

    Anna Shipman: No. I think it was more of an agreement that this is what we would do. Then we would try and make sure that we were doing pieces of work that fit into that. It didn’t always work perfectly. Definitely there were times when one thing would take over. Often the people management would take a bigger share. But it was more of a kind of guideline for us to keep us honest.

    Patrick Kua: Yeah. I also love the definition of what you talked about with the different components of strategy. One thing you sometimes hear in leadership/management groups is this idea of managers being responsible for strategy and other people maybe for the tactics. What’s your philosophy around that and how do you react when you hear that difference of strategy and tactics?

    Anna Shipman: That is really interesting. So one thing is, what is strategy? What is tactics at your level is strategy for the people below. So you might have a strategy. A technical strategy and as part of that, you have testing strategy and app strategy or whatever. Those are things you do to meet your overarching strategy. But then your reports might take a piece of that and that will be their strategy. So that’s one way of looking at it. That something that’s a smaller piece of work to you is a big and really interesting piece of work to somebody who’s reporting to you.

    Patrick Kua: It’s strategy and tactics all the way down.

    Anna Shipman: Yeah. yeah. Also though, it’s interesting because you said managers think about strategy and everybody else thinks about tactics. But I think there’s a manager leader thing, right? It’s like leadership is also thinking strategically and thinking about strategy. And management is about making sure that that strategy actually happens. You need to do both.

    Patrick Kua: Yeah, yeah. Absolutely and those terms are always a bit fuzzy in terms of how do you delineate these things? What people perceive by that? But I really appreciate that perspective of what you might call strategy or tactics really depends on perhaps your scope or current role and how you’re looking at that. What’s an example of how you think about organisational strategy and make sure it’s aligned throughout perhaps all the way down to an individual contributor? Can you think of an example?

    Anna Shipman: Yeah, it’s interesting because while you were saying that I was also thinking about the other. Can I say something else about strategy and tactics? Because it’s not quite that straightforward, right? That your tactics are somebody’s strategy because also you might do something tactically which is not on strategy.

    Anna Shipman: The point there is… You don’t want to… Sometimes it’s better to make a quick decision that it takes you in the wrong direction. Because that actually gets you to where you need to go. But that certainly might be a tactical decision. The really important thing is to make sure that you are tying it back up into an overarching strategy. So if you are making a tactical decision that takes you in the wrong direction you’re doing it on purpose. You’re doing it advisedly. You’ve decided that that’s the way to go. You don’t then move in that tactical direction and carry on in that tactical direction because you’ve already done it. You’re aware that you’ve made that decision that’s off your strategic track.

    Anna Shipman: So back to your question you just asked me, part of the role of leading on strategies is to make sure that everybody understands what the strategy is and how what they’re doing is either part of it. Or if they’re doing something that is tactical, not on strategy, they know that it’s off. That they go in different directions and that’s fine just for now. But it’s not a long term thing. So that might be the difference between doing something really well and just getting it done because it’s just a tactical thing and we’re going to go in a different direction later.

    Patrick Kua: Maybe just following that sidestep into you might do something tactical, what would be a good reason to do that that isn’t aligned with the overall strategy?

    Anna Shipman: I mean if there’s like an urgent need to deliver something. To meet an agreement with a customer or something and you know you could do it quickly by continuing with a supplier that strategically you’ve decided to move away from. That kind of thing. Or you could build it quickly but actually your strategy is to engage a supplier in the long term or outsource that part of it. That kind of thing. So your question was an example of leading strategy within a team and keeping people.

    Patrick Kua: Exactly and then keeping it aligned throughout the organisation or how people can contribute to that.

    Anna Shipman: So the way we did it on was we had a quarterly meeting. Initially we started with our diagnosis and our vision. At that time. This has now changed. But when I was working there, at that time, we’d launched It was great. Really exciting. The exciting hot new thing in the company and then the company had moved its attention elsewhere and we’d started to drift. So the diagnosis was that the tech was drifting because we didn’t have a direction anymore. We’d launched. We’d met that milestone. We weren’t necessarily aiming for anything next. Our strategy was to not do that. To get it back on track. To make it really focused and something that was sustainable. So that we were building new staff, swapping pieces out in flight and making it continuously better. What we did was, having set out where we were and where we wanted to get to, we then had a quarterly meeting in which we talked about what are the top three things that we could do that would get us closer to that? To where we want to be.

    Anna Shipman: So I like three. It’s always good to have three things to work on. It’s really clear. It’s easy to remember. We started by picking three things. Then the next quarter if one was done, we’d then pick another one. So we’d always have three things on the go. That conversation involved Principal Engineers, Senior Engineers, Tech leads and people from product and delivery. Not everyone in the whole organisation. But the senior people were working together and contributing to how we did that. Then you just have to make sure you communicate it to a lot of people. Know what you’re working on. People know how they can contribute if they’re not in that meeting, etc.

    Patrick Kua: Great. Yeah, it’s a fantastic example of walking us through that process. I can see how as you’re doing the diagnosis, building that approach about how you’re going to do that and how that gets involvement as well and buy-in from people who were part of that. And then they can probably drive that into their own teams or their people that they’re working with as well. What happens if you feel that as people are working on things that it’s maybe the wrong direction? Has that ever happened to you? Or how do you get feedback that you’re working towards it and that your overall direction is the right one?

    Anna Shipman: Do you mean like if I’m leading a team and we’re working on strategy and I think actually that group of people who’s working on that particular thing have gone off in the wrong direction?

    Patrick Kua: Yeah, perhaps. Or maybe that as you’re discussing where you’re going for your strategy that you maybe feel, okay, falling into groupthink and maybe we’re getting to an okay outcome that you’re unsatisfied with but maybe not really moving us forward.

    Anna Shipman: Yeah, yeah, that’s a great question. There’s a few things. I think the one thing that I didn’t mention about how to lead people in strategy is the same as any leadership thing. It’s all about communication. So you have to be constantly communicating. Communicating where you’re heading. What you’re doing. Why are you doing it. Also communication is also about listening. So hearing how people feel about that. Having an open forum for people to ask questions. So every quarter we also had a talk where we’d talk about that and we’d invite open questions. So there’s a couple of things there like if you’re… one thing is that people will, if you give people the opportunity to contribute, people will say we’ll give you great contributions. So the engineers who weren’t involved in defining the strategy would ask incredibly good questions. That really helps keep you honest on the are you really heading in the right direction. I can’t remember what, but I do remember times went on when somebody asked, “Have you made the tough decision here?” or, “Is this just the middle ground?” People ask really good questions. So that’s one way to make sure you’re keeping it.

    Anna Shipman: Because if it’s a good strategy people will feel motivated by it. They’ll be excited by it. If it’s a woolly strategy an engineer will point that out to you. So that’s incredibly important. Just keeping that open communication is really important. If you are not making tough decisions, then you definitely haven’t got a good strategy. So if you’ve said something and everybody agrees you haven’t got a strategy because part of a strategy is what you’re not doing. What you’re not doing will be something that somebody thinks is important. The way we addressed this on was by prioritising. So it’s not saying this is not important. But saying it’s not the most important thing right now. That does involve some tough decisions. But I think we could definitely have made some tougher decisions.

    Anna Shipman: Reflecting back on that one of the… I didn’t tell you the we had a title which has a little bit of a backstory but the tech strategy, while I was on The new site was called next. It was drifting and next cost to £10M and it took the business, it’s 2 years where the business couldn’t have what they needed. To take us to build next. It was drifting and we didn’t want it to drift so far off track that we had to throw away and rebuild it. So our strategy was no next next. It’s great. It’s amusing. But it’s also, looking back at the reflection, it’s defining something that you don’t want to be, but it’s not really giving you a focus of where you want to get to. So I think we could have made some earlier tougher decisions.

    Patrick Kua: Right. So we know what we don’t want to do but the absence might mean that people fill in that with different interpretations as well as a risk. Interesting

    Anna Shipman: It was fine. we muddled along. I mean we didn’t even muddle along. We did really well and people took it to mean make it sustainable. Improving things and we did really get focus there. But we could have done better as well.

    Patrick Kua: Yeah, yeah. I appreciate reflecting on those situations. Obviously things always seem better in hindsight. Well there’s always some element you can improve from that. What I take away from what you said is that there’s a lot of, as you talked about, communication. That focus on listening as part of communication. And also what I’m sensing is a sense of inclusiveness. So bringing people as part of that conversation. So it’s not just you as a leader talking at people and then testing for responses but actually creating opportunities for people to contribute. One thing I heard you say is that engineers will call things out. One thing that often happens with somebody in your role like a manager of managers is perhaps title or perception of authority. Do you think consciously about processes that perhaps make it more inclusive for people who are maybe more anxious to talk to somebody in a more senior role?

    Anna Shipman: Yes I do. You’re absolutely right. The more senior you get the more people will say what they think you want to hear or not say what they don’t think you want to hear. Yeah, that is something that I think a lot about. A couple of things I found helpful is… 1) is something I’m going through right now in my new role is meeting everybody on the team and making it clear that I do want to hear those things. First of all, meeting them to ask them, What’s going well? What’s going badly? Then the last question I ask is there anything I should know? When I was an engineer I would like… there’s really obvious stuff happening and I think leadership has obviously made a decision to let this happen. Why is that? The reason is they have no idea. Now I’m in leadership position I see that there’s so much going on that you just don’t see. You have no idea about. So I say to people, is there anything I should know? It might be that the only way I find out about it is if you tell me. So please do and we’ve met now. So if something else comes up later that you want to tell me then please do. That’s one thing.

    Anna Shipman: I had feedback that I did that at the FT as well and a few people said that they felt able to raise things with me that they wouldn’t otherwise had because we had that initial conversation. That initial connection. Then the other thing that I think is really helpful is staff surveys with comments. Because if it’s anonymous people will make comments. Sometimes it’ll be quite hard reading. Sometimes you’re reading the comments like I’m doing my best. I’m working really hard here but it’s extremely extremely valuable because people are saying stuff that you just won’t hear otherwise. It’s worth paying attention to what those comments are.

    Patrick Kua: Yeah, yeah, great. Have you run a staff survey in your current role or in your previous role? How often would you run staff surveys?

    Anna Shipman: So in my previous role we did a Peakon survey quarterly. In this role we use OfficeVibe and it’s weekly. But it’s not the full set. So every week you get a smaller number of questions. I think I prefer that actually. The weekly of the two. Because quarterly it’s a big commitment. Then going through it’s a big commitment. Whereas weekly it’s an ongoing pulse of how things are going.

    Patrick Kua: Yeah. I can definitely relate to that. Where you get the results of the survey. Then the discussion of what you do with these things. It’s a bit like the big batch releases and moving to a bit more continuous delivery of constant feedback.

    Anna Shipman: Absolutely. Yeah.

    Patrick Kua: Love it. Let’s talk about your current role then. I understand you’re relatively new. Can you describe what your onboarding has been like in your CTO role?

    Anna Shipman: Yes, yes. It’s been really great. So they put it together… the person who joined before me put together an onboarding plan because we didn’t have one. She had been onboarded and was slightly more haphazard, so she put together this really comprehensive… It was quite intense. I had to put in a few breaks of what a new CTO needs to know. It’s meeting my peers in the exec team, who’ve all been really very generous with their time and very happy to talk to me about what’s going on. Then I was lucky enough that I had a one week overlap with the previous CTO. So just like downloading information from him. Technical architecture. Stakeholder mapping. What the team’s like. I joined in the middle of a promotions round. So that was good. That wasn’t planned but that was quite… just after midyear review. The other thing was introducing myself at various meetings. I think somebody said to me, you will be welcomed at least 5 or 6 times in your first week and it was true and it’s very nice.

    Patrick Kua: Yeah, that’s lovely. I mean it sounds like a really good onboarding process. I hear stories, particularly, with executive roles where it’s like you have to work it out for yourself. You don’t really get that polished onboarding plan. So it sounds like a really good process.

    Anna Shipman: So the person who set it up she did a really good job there. She thought about it. She also asked ChatCPT what a good onboarding process for a CTO would look like and that was very helpful.

    Patrick Kua: Good bit of AI. Nice. Can you describe a little bit about your current organisation then? What’s the size? Shape? How many leaders or managers do you have?

    Anna Shipman: Yeah, yeah, sure. So we are about 500 people. The majority are practitioners. So we do mental health. Digital mental health. It’s mostly in the UK for children and young people though we do have adults as well. You interact either with our content or with a community or you can also speak to a counsellor through chat. That’s all message-based. The majority of the staff are practitioners. Counsellors. In the exec team, we are, I think 7 or 8. I should get this right.

    Patrick Kua: It’s normal.

    Anna Shipman: It’s a normal size. Of whom 3 are board members. Then we have three non-execs on the board. Then the rest of us, we’re peers but three are on the board. The engineering team. There’s a Chief Product Officer. So engineering and product work very closely together. But we’re separate organisations. Product is about, maybe, 10 people in product, and then some others. There’s design. User research. Insights. Then in engineering we are about 40 people of whom about 20 are in the UK. Permanent stuff in the UK and then we have some contractors working with us in the UK. We’re also working on a big project in California as well at the moment so we have some people working out in California. I’ll be building a team out in the US. So in fact I should make a pitch now. If you’re in the US and you are interested in working at Kooth then watch this space because I’ll be advertising for roles soon.

    Patrick Kua: Yeah. yeah. Fantastic. Sounds like a good growth opportunity and the West Coast could be a little bit challenging UK time zone wise it sounds like a good opportunity.

    Anna Shipman: We’re actually building out in the states. We’ve set up a hub in Chicago because we also have customers in Pennsylvania and potentially some others. So we’re going to locate in Chicago so at least there’s some overlap on the time zone.

    Patrick Kua: Yeah, a better number of hours overlap at least.

    Anna Shipman: Yeah yeah.

    Patrick Kua: Excellent. Then in terms of your engineering leadership team. What does that look like at the moment?

    Anna Shipman: At the moment, I have two engineering managers and two principal engineers. So unlike at the FT, there is that split and that actually works quite well. The principal engineers are overseeing from a technical perspective and architecture. Sorry, one is a principal architect. One is a principal engineer. The principal architect is overseeing architecture and the principal engineer is overseeing engineering of the teams. Then the two engineering managers line manage all of the UK staff between them. So they each have 10 reports, which is quite a lot. They’re doing great. But I think that’s outside of how many people you can manage comfortably.

    Patrick Kua: And do you expect them to also be or are your engineering managers also individual contributors or are they just a purely management role?

    Anna Shipman: No. Yeah, but it’s not just people management they are doing engineering management as well. So delivery and leading on pieces of work around security and data management.

    Patrick Kua: Got it. Excellent and then how do you run your engineering leadership team? Can you talk about us through maybe some of the rituals of how you keep in touch with what’s going on?

    Anna Shipman: Yes, so at the moment we have a weekly meeting. Global engineering leadership. So that’s the four people I mentioned and then also the person who’s leading on the California project, who is, he’s a contractor. But we’re working very closely together. We meet weekly and discuss topics on an agenda. We have a fortnightly. This is a process that was already in place when I joined. So there is a fortnightly tech strategy meeting, which we have now changed to be monthly in person. Because we’re remote but people can come in with notice. We’ve got a monthly tech strategy meeting in person which is an hour and a half. Then we’ve got a shorter check in every other week on tech strategy. Then I have 1-1s with everybody. So at the moment it’s relatively light. But one thing I really like is that they already had that space carved out. That time carved out for working on tech strategy.

    Patrick Kua: That’s great and sounds like it’s already been part of that habit. Not something that you have to bring into the organisation and educate people around. It’s really just about refining the time about how you’re using that and getting the most out of that.

    Anna Shipman: Yeah, exactly.

    Patrick Kua: One interesting thing I heard you say is it’s relatively light. I can imagine the current team size and you’ve got some senior people in there. One thing I hear about people who are in managing manager roles is that breadth of having to work across the business a lot more. Probably as well you being now on the executive team how much time would you say you split between say just engineering versus other teams or departments? What does your calendar look like effectively?

    Anna Shipman: That is a very interesting question and something I was thinking about this morning. At the moment, and what I was thinking about this morning was that it’s too much focused on engineering, because my coach said to me before I joined, don’t just focus on your own area. Make sure you pick things up elsewhere in the business. I was like, yes, I definitely will. But of course there’s so much in your own area, it’s very easy to. So at the moment we have some group work as an executive. We have some meetings and some strategy work. I have 1-1s with all of the other execs but on a maybe three-weekly cadence. I do pick up… like if somebody asks for some help with something then I’ll definitely prioritise that. But I was thinking this morning that I should be doing more cross-company work and less focus on engineering. So I would say that I haven’t got the balance quite right yet. But in my defence I’ve only just started.

    Patrick Kua: Exactly. You’re in the onboarding phase. Absolutely. We’ll chat again. But I could imagine one thing that is probably quite important is that coupling or connection to product and the importance of alignment there.

    Anna Shipman: We meet twice a week.

    Patrick Kua: Okay, great. Have you got any tips on how to build a strong product and tech relationship that work for you?

    Anna Shipman: Initially I think it’s just about spending a lot of time together. So at the FT, the product director and I met twice a week as well. I mean 1-1 twice a week. We meet in other contexts. We’re in meetings together much more frequently than that. But because I’m just building this relationship, we meet twice a week for longer. We probably spend an hour and a half at least every week together. Over the week and then we talk a lot. I think to begin with it’s really about just trying to get to know somebody and share your thinking on things. It’s quite an interesting one because, to me, the relationship with product is obviously, not obviously, but to me it seems very clear that it’s the most important. Product and engineering have to be working incredibly close together. That comes from the top. If the product manager, the product director, or the CPO and the CTO aren’t getting along or aren’t aligned then the teams have no chance of…

    Patrick Kua: It definitely cascades in. Causes chaos.

    Anna Shipman: Just a little misalignment turns into a big difference in the team. So yes, so I’m basically prioritising. I’m not sure I’ve got tips apart from just trying wholeheartedly to really work on that.

    Patrick Kua: Great. Yeah, no. I mean it’s really important as you talked about, of keeping that relationship there. It’s great to hear that you’re investing so much time early on. I think that makes a huge difference as well. As you said, just getting to know each other as people. Trying to find those common things that you can align on and to help and support each other to build that relationship. So we’ve talked a little bit about strategy and if you were to help people learn more about that, what are your favourite resources on helping people understand how to think strategically or how to act strategically?

    Anna Shipman: I mean I have a book that I recommend to absolutely everybody which is, Good strategy, Bad strategy.

    Patrick Kua: Great book.

    Anna Shipman: by Richard Rumelt. That is excellent. I mean I think that probably is the main resource that you need for thinking for how to think strategically.

    Anna Shipman: When I first started working on strategy, the director of strategy from the Government Digital Service I met him for coffee. I said how do I do this? And he said I’ve bought you this book and he was absolutely right. But what I didn’t quite understand was how to do it. So since then I’ve done some courses. So I did a course at the Institute of Directors on strategy which is really good for telling you what models and things you can use to work with people on strategy. I did a talk last month where I went through some of those models. I did the talk that I would have wanted to hear when I was starting out which goes through some of those models. So that might be a good starting resource.

    Patrick Kua: Is that talk now public?

    Anna Shipman:

    It is and the slides are available. I’ll send you a link.

    Patrick Kua: I’ll make sure it appears in the shownotes. I heard you say the course was from the Institute of Directors. Is that a UK body?

    Anna Shipman: It is, yeah.

    Patrick Kua: Got it.

    Anna Shipman: I would recommend it but it’s very expensive. You definitely want to get your company to pay for it.

    Patrick Kua: Got it. And is it remote friendly as well?

    Anna Shipman: Oh yeah I did it remotely.

    Patrick Kua: Great. Excellent. Love to see all the movement now in the education space with a lot more accessibility for people in different places as well.

    Anna Shipman: Yeah, yeah, it’s good.

    Patrick Kua: And then maybe heading towards the end in terms of wrapping up with the theme of managing managers, if you were to help somebody move into that role for the first time and they had to start managing other managers, what is some advice that you would provide them?

    Anna Shipman: I’m going to say two things. One is when you are managing people you can take each problem and think about how to solve that problem. But when you start managing more people you need to think about how to systematically. If somebody has one issue, likely other people have had similar issues. So how do you find out what the processes are and if they aren’t processes, how do you build them and how do you make sure everyone’s following those? It’s a more systematic way of thinking about it. Then the other is some advice I’m trying to take myself that I haven’t quite gotten as good as I would like at, which is, if you do learn coaching methods, then you help when you’re managing somebody and you coach them, then they grow themselves and then they coach their people as well. Learn coaching. I would say you might have a different view but don’t have to go on a course about coaching but just read some things. Start asking coaching questions. Start learning about it. I’d love to hear your thoughts on that, actually.

    Patrick Kua: Yeah I mean from my perspective I am a big believer in training. But also training is really about getting people to build some skill that they can practise. I think what you said is really the essence of it is can people learn a little bit of coaching skill. You don’t need to go on a course to learn the skill. There’s lots of great resources out there and I think the important part is them being able to actually practise that. The good thing about managers is they always have a lot of opportunities to practise these coaching conversations.

    Anna Shipman: Absolutely.

    Patrick Kua: One other thing that I’ve heard a lot with particularly, probably in your role as well, is it gets lonelier at the top as you manage other managers. So what are your personal strategies for dealing with that?

    Anna Shipman: So I have a coach, who is very good. I think it’s true. It gets lonelier because there are lots of things that come up that it’s not appropriate to discuss with other people. I found it really good to discuss with my peers in the exec team some things that have come up because they’re your first team and they will have similar… but again some of them you don’t necessarily want to discuss with colleagues. I think coaching is very good. Learning how to, and this is again something I am working on improving, but learning how to put it down at the aend of the day as well.

    Patrick Kua: Yeah, so knowing how to close the book. Or to establish that boundary. Yeah. Could definitely appreciate that and I have lots of memories of that too. But my final question for you then is if people wanted to contact you or reach out to you, what would be the best ways?

    Anna Shipman: So I’m on Linkedin. I don’t really use Twitter anymore very much. I also have not exactly a newsletter, but I publish blog posts on my blog and you can sign up to receive those as well.

    Patrick Kua: Fantastic. We’ll make sure all those links appear in the show notes as well.

    Anna Shipman: Thank you.

    Patrick Kua: Then with that I want to really thank you very much for spending the last hour with me. It’s been really fascinating, talking about your experiences. Very exciting to hear about your current journey and where that will bring you and I wish you all the best as well for expanding into the US.

    Anna Shipman: Great. Thank you. It was really nice talking to you.

    Patrick Kua: Great. Thank you.

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