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Episode 48: Lead Your Team In Your First 100 Days
21 Plays21 days ago
Stepping into a new pricing leadership role comes with expectations, pressure, and very little room to get it wrong. In this episode of the PriceWriters Podcast, Jeremy and Catrin explore Lead Your Team in Your First 100 Days by Neve O’Keeffe and walk through what actually holds up in an insurance context.
They get into where pricing leaders tend to fall short early on, especially the habit of relying on technical strength instead of actually leading, and the areas that are often left too late, like dealing with performance issues or setting clear direction for the team. They also question how realistic the whole “100 days” idea really is in insurance, and why making early decisions based on gut feel or second-hand opinions about your team can set you off on the wrong path. If you’re stepping into a new role or taking on a new team, this is the kind of conversation that helps you think more clearly about what actually matters.
PriceWriters transforms pricing capability find out more at Pricewriters.com
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Transcript
00:00:00
Speaker
You're just a you You're mostly good at... you would fight once Once we pry something away from you, you're okay with that.
Introduction to PriceWrite Podcast
00:00:17
Speaker
Hello and welcome to the PriceWrite podcast with Katrin Townsend and me, Jeremy Keating. Join us as we explore and discuss the world of insurance-related books offering our insight and recommendation.
Discussion on 'Lead Your Team in Your First 100 Days'
00:00:29
Speaker
It's April, so a lot of people will be starting new roles or looking for a new job. So today we're talking about how to start strong with Lead Your Team in Your First 100 Days by Niamh O'Keefe.
00:00:41
Speaker
Katrin, tell us what it's all about. It does what it says on the tin, which is give a practical guide for team leaders who are starting a new role.
00:00:52
Speaker
And the book is split into different sections based on time. So it's all one big timeline. The beginning section obviously is what to do before you start your role. Then it talks about your first 30 days, first 60 days
00:01:12
Speaker
60 days. The next check-in is 90 days. And then it's the final sprint to the 100 days. And she works on this 12... no She works on this seven-part success formula.
00:01:27
Speaker
And when she's talking about being a leader, what she's really talking about is being a role model, being a mission setter, being a recruiter.
00:01:39
Speaker
a communicator, a motivator, a skills builder and a target maker.
Seven-Part Success Formula for Leaders
00:01:48
Speaker
And particularly in the first 30 days, she says, you really need to be thinking about all of these different areas and then pulling out the ones in the 60, 90 and 100 days that need a little bit more focus for your exact team situation.
00:02:05
Speaker
So she uses these seven as a holistic view of what a leader is. And I thought this was really good. i thought it was really good to break down leadership into that way because so often we think of it as just soft skills. And I think she's really put names to what soft skills we're trying to build here.
00:02:25
Speaker
And this isn't all of them. She doesn't talk about stakeholder management, for example. She doesn't give you lots of presentation tips, but...
00:02:37
Speaker
I think what she's done really well is try to distill what you need to lead your team. And of course, everyone is both a team leader and they're also a team member. And they're also a peer of other team leaders.
00:02:52
Speaker
So we all have all these different roles. But I think just by focusing on the what do you need as a leader, she gives a really nice focus and a good way of working out what's missing and what you're not quite doing as much of.
00:03:07
Speaker
It made me reflect on which ones I find easiest, but I'm really interested in your views. Which do you think most pricing leaders naturally gravitate to and which one do we tend to overlook?
00:03:27
Speaker
Yeah, it's a bit recruiter, isn't it? And a bit target maker. Wouldn't you say? The things we tend to overlook. Um, yeah, yeah, well, what, what, what do you, yeah, maybe mission set is the one we actually do.
00:03:46
Speaker
Yeah, what would you say? I think recruiter is sometimes the hardest one because it involves having difficult conversations.
Recruitment Challenges and Team Dynamics
00:03:54
Speaker
Yeah. So when she talks about being a recruiter, she means not just working with HR to secure the resource you need, but also looking at the resource you currently have and doing any performance management, and that kind of thing. And I know from my experience that that first 30, 60 days really the time deal with those issues. If people have got a bad attitude or they're so evidently underperforming so early on, then that kind of...
00:04:28
Speaker
is an indication that you might have to deal with it. And I think that a lot of managers think, well, maybe they'll get better under a new leader. So I'm just going to leave that a little bit, particularly as I'm leaving. So i I think that's a common attitude. And that means that new leaders come in and sometimes have people concerns or people performance issues that they need to resolve fairly early on. and And so I think that's, I think that's the first one that we overlook.
00:05:00
Speaker
When she talks about the section on recruiting, she also talks about not being pushed by HR. into long timelines and she will just wait and see or, you know, well, we need to go through a long process of securing the budget and blah, blah, blah, yeah this process, internal first, all this kind of thing.
00:05:21
Speaker
yeah She is quite, I think quite assertive on if I need people, I actually want them to be in role within the first hundred days as well so that we're not always in this place of having to build and onboard a team her idea is that by the end of your 100 days you have a functioning team that is galvanized that is well bonded not just between the leader and the existing people but that is going to be your team for the medium term if not the long term so I think that's pretty tricky for people in big organizations where there's often the cogs of governance and HR sometimes run slow
00:06:03
Speaker
Yeah, I mean, I would say we're probably more in we're probably stronger in the role model space actually. And I think maybe that's a mistake some of us make in like when modeling how to be a good analyst when we actually should be leading.
00:06:17
Speaker
So I think often probably we probably a lot of us fall into this role model space where it's like,
Common Misconceptions in Leadership
00:06:22
Speaker
if I'm the most technical, if I'm really brilliant at being technical, people will think I'm a great manager.
00:06:28
Speaker
And that's just not true. It's patently not true actually. But I think a lot of people fall into that trap. I feel like I have to know the most. I have to be the best with the tools. i have to be the best at Python, be taken seriously as someone that can lead other people doing that work.
00:06:45
Speaker
And that is a mistake that I think an awful lot of us make, certainly when we're new into it, but actually I'd say even two, three or plus years in, there's still people who are heads of teams who think they ought to be the most technical and they're making a mistake. They're going down right the wrong path. They're going to cap their careers off and get stuck at a bit in a level.
00:07:06
Speaker
So I would say that I would say we probably have this habit being role model. I would agree with you. I think recruiter, target maker are all things that we find quite harsh. Some of us like sharing our skills. So skills building might be sort of in between in the middle where sometimes kind of okay.
00:07:22
Speaker
I think motivation, we can find a bit hard actually. We're kind of lucky in a way that a lot of us really love what we do So our analysts are already quite highly motivated and often really into solving the problems.
00:07:37
Speaker
So when we do have a motivation problem, it can really hit us in the face actually. And we're just like, oh, how do I deal with this person? They're not working. They're not working hard. They're not engaged in the role.
00:07:48
Speaker
I've never had this problem before. What do I do? And can be actually a real shock to us because it's and something that probably doesn't happen early on in our careers. So it can be quite a surprise when we suddenly have had to deal with motivating.
00:08:02
Speaker
Communicating we aren't always the best at, though some of us do build relationships, but certainly the first one hundred days, it's probably quite hard to be good in that box.
00:08:13
Speaker
I'm feeling like i i can think of a particular time when I could have done with a book like this. So I moved to France and took over a relatively small team over there. but had to build it out quite it quickly and deal with a different culture at the same time.
00:08:28
Speaker
And I would say... that there are places where I, I couldn't, everyone could do this assessment after the fact there are lots of places where I think I made mistakes or I could have been better and I'll do it differently now. So I think that's what I would say. I'd say we tend to be doing the role model, the skills builder and maybe we fall down on the other ones.
00:08:54
Speaker
Yeah, I agree. i think that's definitely, they're definitely the ones that we don't get as much help and guidance on. What is really good about this book is that she tells you exactly how to do these things, exactly what to say.
00:09:08
Speaker
She gives lots of examples of missions that you can use. Although actually, if you want some more insurance pricing specific examples of that, check out my podcast with Julia Lessing. So when i went on Julia Lessing's podcast in March 2025, we talked a lot about missions. So I gave you my Pricing manager, a mission statement in that podcast.
00:09:31
Speaker
ah But yeah, she gives you exact wording on what to do, on how to run the review workshop after the first 30 days, that kind of thing. She is very practical and gives a lot of really helpful application of what she's saying. I'm sure I really like this, but she also tells you what not to do, which is often helpful as well.
00:09:53
Speaker
The downside of this book is that it's not very introspective and as
Pre-Start Suggestions and Industry Practices
00:09:59
Speaker
pricing people we probably are quite introspective in a lot of ways. She doesn't talk about using your natural strengths particularly.
00:10:08
Speaker
She kind of briefly mentions what kind of leader are you, what kind of leader do you want to be, but it's very early on and it's have like a paragraph.
00:10:23
Speaker
people who were kind of mid to to later on in their careers do have a wealth of experience from, you different products, different projects, even maybe different parts of the industry we've worked in and thinking about how we can bring those skills to this role and what new role you're doing.
00:10:41
Speaker
She doesn't really talk about that a lot. So i think that's kind of missing. i think the other thing that's, not missing, but it's just not very realistic for insurance at least, is that the first couple of chapters are about what to do before your first hundred days.
00:11:01
Speaker
So the time between you've got the job, you've signed the contract and your first day. And she talks a lot about things to email your team and introduce yourself.
00:11:14
Speaker
Things you should request from your team. So you should tell them before you even join that you want them to do this presentation about themselves and their skills and their ideas and things like that. So you can listen to those on the first or second day.
00:11:28
Speaker
Things you should request from your company about company targets, financials. It's not realistic for insurance companies because...
00:11:39
Speaker
We have garden leave or we have notice periods where you are still locked into your previous company. And to be honest, even if you're not in those positions, insurance companies just won't want to share that with you on an unsecured email address. So there's quite a lot in there that for me feels like,
00:12:02
Speaker
you just wouldn't be able to do. So you'd have to end up doing like 110 days or something, I don't know, to try and fit that part of the work in from when you start your role as well.
00:12:15
Speaker
The premise is all about your first 100 days. And so I think that's kind of for me where it becomes a bit of a pressure point if you aren't able to do the pre-work before you join role.
00:12:29
Speaker
What is interesting is that actually 100 calendar days, not 100 work days. Oh, really? Okay. Okay. So it's three actual months and a bit.
00:12:40
Speaker
Yeah, three months, basically. why Okay. One quarter come in. would say that's probably quite tricky because there's so much. And you're right for exactly the reasons you've just mentioned. So you're simultaneously learning the ropes. Yeah.
00:12:56
Speaker
and you're meant to be running a team, it can be pretty difficult to slot in. And it gets harder the higher up you go, actually. And the, yeah, if you slot in as a direct, like a director, even a head of, you're very much expected to start answering questions before you've even really got your feet under the table.
00:13:16
Speaker
Yeah, it felt a lot to me, even if you were able to do the pre-work, to get in, to get to know your team, to galvanize your team, to set an initial target and then achieve that target. She says in her in your first 100 days, you should set a team target and actually achieve that. So whatever target is has to be realistic within that 100 days. But yeah, it feels a lot to do particularly if there are existing projects on the go or existing BAU to be done, it did feel bold target. Do you think that is realistic? Even with a great team already in place, well-resourced and in a role that isn't too new to someone in terms of project experience and things. Do you think it's realistic?
00:14:14
Speaker
I think one those times where the book probably works for a lot of people in a lot of their types of roles, but it doesn't necessarily match us. but So I can see if you run a call center or if you're a manager in a call center or a sales team and so on it's more often more clear from day one what you need to achieve. And I don't mean this as a criticism, but it can be quite hard to even discern objectives in a very big organization with a pricing team when you've just arrived.
00:14:44
Speaker
Because for a time, a lot work would have been done by other people or other teams and so on. There's often lot of rejigging when you come in and you are personally responsible for your delivery. But oddly enough, as numbers people, we often struggle to set very clear, like smart targets on people for their delivery, which is an interesting catch 22 in itself as to why we don't do that.
00:15:10
Speaker
So I would probably say no, i don't see that as being that realistic for someone coming into a sort of manager, head off or director role in a pricing team.
00:15:23
Speaker
And we've talked about targets before in this podcast where if you set numerical targets, it's very easy to show that you have or have not hit those targets. With pricing teams, you're only responsible for the price if you are very senior in the organization and you control the risk pricing, the street pricing, the optimization, the portfolio management.
00:15:46
Speaker
If you can control all of those things, relationships with your aggregators or pricing personal websites, your brokers, maybe if you're in that role, you're sufficiently high up, you do control all those things, you can be responsible for the price. But otherwise, it's very difficult to prove that you've hit your pricing target.
00:16:07
Speaker
And that's even before we get to questions about if the target is profitable gross, then What does that even mean? And that today's results are actually from last year's pricing.
00:16:23
Speaker
And so you could make the best pricing in this 100 days, but you're actually not going to start feeling the benefit of that properly. for quite some time. I think those things do, I think particularly with targets, it does feel really difficult. And I actually think that's why the mission statement part of the role is so important because if your mission is about building statistically strong models, meeting your stakeholder needs,
00:16:53
Speaker
And it might also be something like research or automate research or automation or process improvement, something in that realm as well. There aren't necessarily targets of if you automate your process, you yeah, you might save a day a week or something like that, but it's quite hard to know what you're going to save before you've actually come you've actually started that project. So I think that's some of the issues.
00:17:18
Speaker
I agree with you that. And I would say as well, it it links in interest with the things we talked about with the 12 week year, a lot of objectives in an insurer in our annual.
00:17:29
Speaker
So i would say it just doesn't line up very well with how we operate in our companies. And I'm not saying we couldn't operate better, but I'm just saying it's not going to really work in how most organizations actually operate.
00:17:43
Speaker
I do still think it's a good idea though. You know, you only get one chance to make a first impression. true And a lot of her point is around if you can really nail this first 100 days,
00:17:54
Speaker
your team is on board with what you're doing and they clear with what they're doing and they feel motivated and a bit of a morale boost from having achieved a smaller target you're going to be a lot better placed to deliver whatever comes after that hundred days equally your boss your stakeholders whatever level you're at, they're also going to see, okay, well, they've come in they've got good control over their team already.
00:18:22
Speaker
They're receptive to what other people in the business need. And I can see that they get stuff done. And that's a really good start, I guess. So we don't think the hundred days is realistic, is only a minor flaw in a book called lead your team in the first hundred days.
Objective Skills Assessment
00:18:40
Speaker
But is there anything we can do to make this more realistic or to help people who are being put in these situations, they're parachuted in to a new team. They're under a lot of pressure to actually deliver, to turn something around real, really quickly. What can be done?
00:18:58
Speaker
Yeah, I think whether it's right or wrong, insurance companies just naturally do move quite slowly. I know that can be frustrating to people, but the reality is it's not like selling e-commerce. We're selling what is effectively a relationship that typically lasts a year or could be longer with a customer.
00:19:16
Speaker
And then settling claims can take years after that. So we naturally move slowly because of the nature of our business. It not because we're big lumbering oil tanker organizations. It's a failure to understand our business often causes people to think we move slowly.
00:19:32
Speaker
So I'll just defend us in that way for once. It can actually be really difficult when you first arrive in a role to even assess your team. So you might well get told some handover information about who's good at this and who's good at that and so on, but it's often not very structured.
00:19:49
Speaker
It's often quite subjective what people tell you. And sometimes I've known people who perhaps haven't had the best of...
00:19:59
Speaker
I've not told been told the best things about, but I've actually found to be really good at their roles and vice versa. Actually, I've sometimes found people that are rated quite highly who I felt haven't actually delivered.
00:20:10
Speaker
So it can be quite difficult coming in even in a couple of months to actually get used to what people are and are good at. I think for that reason, it's really important that there is some objective way of assessing skills.
00:20:23
Speaker
And, you know, at PriceWriters, we have a capability audit where we can objectively assess skills that are relevant for you you and your team. And for multiple teams, if you want to see a more holistic view,
00:20:37
Speaker
Because I think the danger is if you don't do that objectively or you just take that subjective information as the truth is that people who fairly or unfairly had a poor relationship with the previous manager,
00:20:54
Speaker
Or people who have improved a lot. Maybe they've only been enrolled for a fairly short amount of time. So people still see them as the newbie, even if they have grown lot since then. But the other place I see this is in senior analysts a lot, where they started in the company as graduates. Everyone still thinks of them as the graduate, the person who can crank the handle.
00:21:18
Speaker
Even though they have really good leadership or management potential, they're still thought of as the graduate. And so that people don't give them a chance for more leadership or more of a step up. So I think there are some real risks if you only go on that subjective assessment or if you make snap judgment. Things like the person who wears a suit is the most qualified, or the best at that role, or that person is the management potential.
00:21:48
Speaker
That's not true. i mean, that's so patently not true, but it still is something that I hear and that I genuinely do see people have that perception in insurers right now. We've got all had situations where the quietest person in the team's been the most productive and the best at promoting themselves has not been the best at the actual work.
00:22:15
Speaker
I think that's probably something that that occurs to people. So it is important to have an objective view of people's skills as well, because Somebody at arm's reach might only see how they present and they might be very good at presenting, but actually that might not mean they and they're very good at doing the work. So often getting under the hood of this and working out who's right for which roles and who's right for promotion, what their gaps are, so what they really ought to be learning about.
00:22:44
Speaker
And sometimes that can differ to what people even themselves think is the areas they want to learn about. So we alluded to it earlier, but there comes a level where learning more Python is not going to help you advance in the organization. Sad as that is, because we all love learning Python, but we need to learn more about people in order to, to advance and how to, and management and organization, which sometimes doesn't come naturally to a lot of us.
00:23:10
Speaker
So actually I would say coming in, being able to outsource and get some objective views on the capabilities in the team and also get that training, get those, that get plugging those gaps and working out where we need to help people in a system and actually developing further and then provide that help.
00:23:30
Speaker
So I think we can all probably relate to times where we've been given a PDP that says something like, I think you need to improve your... impact analysis skills. It's like, okay.
00:23:42
Speaker
Great. But there's no, there's nothing to actually do that with other than doing some more impact analysis. If you don't get anyone telling you how to do it better, it's not going to make you better at doing it. It's just going involve you doing it again and again and again. And actually, there does tend to be an attitude of if you just do it more, you'll get better at it.
00:24:02
Speaker
And that there's some element of truth in that, but I would say it's a bit like a line like that, whereas getting some education in it could be a line like like that or or more. So i think that's important to realize when you actually have people in your team, you assess their abilities and you need them to improve and you want them to do it quickly. So you're doing better in the role.
00:24:22
Speaker
Getting that outside training is essential. Yeah. And the one thing that I think with the seven part success formula she uses is how interconnected they are. you are not going to be able to recruit effectively if you haven't got a good assessment of what people's skills currently are and what skills you're missing by definition, but you're not going to be able to do that skills assessment very helpfully. If you personally, as a leader, don't have a very clear mission for your team evening and that mission is also going to inform your targets.
00:25:01
Speaker
But also if you can't communicate why that mission is important to people that they're not going to want to learn. So i I think that those are all interconnected. But the other thing is, like you say about role modeling this, if you say to people, you should go and learn something, but you as the leader aren't investing in your growth as well.
00:25:23
Speaker
Um, Because, you know, getting to know your team and bonding with your team is a two-way experience for sure. Then they're not going to believe that. Then you're not going to be credible as a role model if you're yourself not applying those same standards. so Yeah, if I can be a bit
Modeling Growth and Learning
00:25:41
Speaker
blunt there. How many of us have been told that we need to work on our influencing skills by people who are pretty bad at that, actually? So I think that's quite interesting. I think we can all relate to times where we've been...
00:25:53
Speaker
where things that we've been told we need to improve, if we're perhaps being told by, and that's often the person we're meant to learn from. yeah Okay. All right. So although we could probably share some more stories on that. We best not. We best not. What is the best thing you recall a new leader coming in and doing in their initial three months that just really impressed
Richard Breton's Transition Success
00:26:18
Speaker
you?
00:26:18
Speaker
Right, this time I'm going to name check someone. So I remember Richard Breton quite a few years ago now taking over as pricing leader in a newly formed department post reorganisation and he just got a handle on it really quickly. i think it's very impressive how well he did in that actually.
00:26:40
Speaker
Is there anything specifically you recall him doing that you think helped get a handle on it? Yeah, taking the time to get to know the team. That's a really big one. Obviously it was a big change for a lot of people. There was high levels of uncertainty. There were jobs that hadn't been filled. People were moving into new roles.
00:26:58
Speaker
And if you are head of a department, been through a reorganization and you are somebody's boss's boss's boss, it's still worth taking half an hour to talk to the individuals in the team, even when it's a lot of people.
00:27:14
Speaker
that will make a big difference to how the team operates. And so I think, I think it was really that actually getting to know the people in the team quickly and getting a handle on it while something that just really impressed me.
00:27:30
Speaker
The thing also with Richard, he won't mind me saying that he is somebody who very much invests in skills building. And actually remember very particularly, he sent everyone on a training course straight away. And it was a couple of days training. That's a lot of people to send on a training course. It was a lot of money that was invested, but actually.
00:27:51
Speaker
If I can be careful what I say, I'll just say that the previous management, perhaps across the whole organization had maybe not indicated to people enough that investing in your development matters.
00:28:06
Speaker
It was one of these cases where there were some people on the actuarial team who get lots and lots of money spent at them. ah Most people were not on the actuarial team and the actuaries were sucking up all the training budget.
00:28:19
Speaker
And I'm sure few of us can relate to situations like that.
Final Recommendations for New Leaders
00:28:25
Speaker
All right. So we'll finish up by saying that I definitely do recommend this book. I recommend this book if you are in that situation, you're about to move roles. I would ideally try and read it both before you start your role.
00:28:40
Speaker
And she actually says at the beginning, she says the way to read this book is to read it all in one train journey, like all in one go, just whip so through it.
00:28:52
Speaker
And then go back and reread the section you need when you need it. And it honestly, it really was not that long. It took me a return journey to London. So about an hour took me.
00:29:03
Speaker
It's like 150 pages, pretty big font, actually, which is nice. So read it all. And then when you need it read the right section slightly ahead. So I do recommend this if you're in that situation or if you feel like there's one of these seven that you just don't really know how to implement.
00:29:25
Speaker
I think that's also really important if you're not just in your new role, but also if you there has been a restructure and you're left with a new team or a team that is new in the sense of you've got a new mission or you've had a big churn of people.
00:29:41
Speaker
So I actually think that this book is probably one that I would buy, actually, and just keep on my shelf for any future new roles. So I actually do really like this one. I'm worried about the phrase future new roles, but...
00:29:55
Speaker
but back but I think I'll probably get a copy as well. I can literally think of a time in my career where something like this would have been really helpful. would say one of the other downsides with it though, is that she has a consultancy called First 100 Days.
00:30:10
Speaker
And this book mentions a lot of, in a lot of places, or you should get a first 100 days consultant. And yeah while that may or may not be true, yeah and most teams, let's be honest, don't have the budget for a special first 100 days consultant, right?
00:30:26
Speaker
I do think there's a lot of really good stuff in this book that you can use just as it is. You just might want to skip over all the trademarks. Every time she says first 100 days, she it's trademarked and it's just a little bit hard to read.
00:30:38
Speaker
um But apart from that, I really recommend this book. So that's fantastic, Katrin. So a big recommend for us and a book that I'm going to be buying myself. Excellent.
00:30:49
Speaker
Well, join us next time on the Price Writers Podcast when I am going to be talking about a book called Buy Back Your Time by Dan Martell. This is one I've read a couple of times. I'm doing a reread at the moment. and It's all about delegation. And let's be honest, a lot of us in pricing could benefit from learning more about delegation.
00:31:10
Speaker
So I'll look forward to telling you all about that next time. I feel personally called out by that.
00:31:27
Speaker
PriceWriters transforms pricing professionals into the most respected leaders in insurance. Find out more about our capability audits by visiting pricewriters.com.