The Transition from Finance Director to CFO: First 100 Days

Megan - 0:23: Today, I'm delighted to be joined by Kevin Appleby, head of partnerships at Grow CFO, mentor to finance leaders, and host of the Grow CFO Show podcast. Kevin has spent years at the heart of the CFO community, supporting new and aspiring CFOs as they step into one of the most demanding roles in the business. Through mentoring, coaching, and peer networks, he has a front row seat to the real challenge of CFOs face, particularly as they move beyond the numbers and into the operational, strategic, and leadership core of their organizations. Grow CFO empowers finance professionals who want to know how to become a CFO to lead with confidence through expert led training, career development, and community. Today's conversation is about what it really feels like to step into the CFO seat for the first time. The pressure, the self doubt, the steep learning curve, and the moments that quietly define whether a new CFO sinks or grows into the role. Kevin has spent years working alongside CFOs at this exact inflection point, coaching and mentoring leaders as they navigate the shift from senior finance leader to true enterprise executive. Today, we'll explore those early months, the challenges new CFOs don't always talk about, and why grounding yourself in operations and peer connection can be one of the fastest paths to confidence and credibility. Welcome, Kevin. Thank you so much for being here with us today.

Kevin - 2:23: Megan, thank you. It's a pleasure to be here. And, certainly, that's a topic that I've got to know a lot about across the last five or six years since we formed Grow CFO.

Megan - 2:34: And this is the first time we're talking about this on our show.

Kevin - 2:38: Yeah. And, really, it's a big area to talk about because that move from being financial controller or head of finance or even have that title finance director moving to CFO, I think is a big, big leap. And the biggest problem is that none of the things you need to do in that role were you ever taught to you to pass your accountancy exams.

Megan - 3:01: So when you think back to the CFOs that you've worked with stepping into their very first CFO role, is there a moment or a story that really captures what those first few months feel like?

Kevin - 3:12: Gosh. And the best place to go, maybe this is a start to a bit about our future CFO program. We see in Grow CFO two communities effectively. We see the community of people who want to become a CFO and the community of people who have become one and need some help. Our Future CFO program is designed at the first set. Now often, we'll end up getting some people who get promoted into their first CFO role during the program. It's a twelve month program to help people. I run two or three modules on there, but the final module, module nine, is titled Your First Hundred Days as CFO, How to Make an Impact. And, certainly, by the time we get to module nine, we've got a divided audience, the people that are still out there looking to get the role and the people that have already landed it. So I know we have some fun in there as we start talking about the things to do and start asking the folk that got the role, how are they getting on, How's it landed? What are the issues? And then start talking to the folk that are still looking to start telling them about what to do when they get that first role, right from the point that you hand your notice in an old job and accept new job right through to being a hundred days into the new job. And nearly everybody is talking about how do I get to grips and get to know this new organization and really understand it when I've been thrust into the kind of front line of the day to day of what's going on right from day one? How do I balance that one, Kevin, and actually start planning for the future as well as being the tactical person I've got to be. And they're certainly seeing a lot of challenges there.

Megan - 5:02: And let's take a step back. So let's talk about Grow CFO and how it came to be.

Kevin - 5:07: Dan Wells, who is the CEO, and myself is Kevin, the COO, we're both doing different things as the as COVID approached. Dan had been an equity partner in KPMG and wants to get out. I'd been working in management consultancy for quite a while, but increasingly spending time in the classroom. Mostly wanted to give back, give finance directors, CFOs, and their teams knowledge into some of the things that we do as consultants that they could easily do themselves, helping them with cost reduction, better budgeting, understanding their cost base, all of those things, things that we regularly came up with in consulting projects. Dan was talking to clients who were fast scaling companies and found that CFOs were all asking the same questions. So Dan had the idea that it would be good to get these CFOs talking to each other while I wanted to bring my courses helping these folk online. So Grow CFO grew out of that. And we launched, really, at a very opportune time, just as we locked down going into COVID. So we had lots of CFOs actually wanting to talk to each other and wanted to find out what each other were doing and how they were approaching, not being able to go into the office, how to use their accounting systems from home as opposed to, again, in the office, how to deal with furloughed staff, all those issues that came up. So we got a community together fairly quickly. As time went on, the problems of COVID that were immediate went away, and we started realizing what the two real main problems were. We found that we had a group of people who really, really wanted to find out how to land that first CFO job. How to get the right skills, how did they approach the market, and so on. Then we found the community of people who were recently appointed CFOs and were frankly struggling with all the demands of the job. So Grow CFOs move forward to support both of those communities.

Megan - 7:18: And once you see a new CFO in the seat, what's usually the first, oh, wow, this is different, realization that they share with you?

Kevin - 7:27: I think the main thing is that they're away from the knows any spreadsheet all the time. They're away from producing the financial results, and they're much more talking to investors, customers, suppliers, and co piloting the CEO and the rest of the board. That's a major culture shock. And you're becoming the external face of finance as opposed to the internal face. You're dealing with people largely outside of your organization rather than inside. It's a whole new set of relationships. You're operating on a strategic level much more rather than a day to day level. And that's a major, major shift in what you're doing from probably what you've been used to doing.

Megan - 8:14: And I'm sure that also comes with a shift in accountability where decisions that once felt shared now feel very personal. So

Kevin - 8:23: Yes.

Megan - 8:24: Many new CFOs describe an immediate weight of responsibility once it becomes clear that nearly every major decision ultimately lands back on them. How have you seen that pressure show up in real situations?

Kevin - 8:36: Yeah. Yeah. And that pressure shows up because when you're the head of finance or part of a finance team, you have peers who you could share things with, you could talk things through with. Now you're the number one in finance. You don't have that other person that you can talk to, so it shows up as a mate on you. And one of the other issues that would be around in the new CFO is feeling fairly overwhelmed with lots and lots of tasks passing your desk. So one of the things that we counsel people into in this situation is you've got to free some time up so that it's thinking time. That is really, really precious as a CFO, being able to take the time to think about what it is that's coming across your desk, to be able to give a considered view to any of the decisions that you need to partake in. So it really is getting out of being task orientated into being a strategic thinker.

Megan - 9:38: And I'm just curious. As you think about the CFOs that you see becoming CFOs, is it still, like, a traditional route that people are taking, or is it different these days when it used to be?

Kevin - 9:53: I'm seeing some variation, to be honest, Megan. There's still the accountant that comes through and does the required jobs in the finance function, but I'm also seeing folks that possibly haven't come out of that traditional accounting background. Seeing much more the people that have come through of maybe a financial services background, an investment banking background, that kind of person. And you can understand why, because quite often the CFO role is about supporting the company through a major transaction, major fundraising. So you're looking for those skills of understanding the financial markets, understanding what investors want. So I'm seeing quite a lot of folks that are coming from through that route. There are one or two that are oddballs still that are coming through the marketing sort of route, the sales route, but there there are still rarities, I think. I think, though, is useful is where the person with a finance background has spent some time outside of finance on their route to CFO, which might be in marketing, might be in sales, might be in technology. I think that gives them a much broader view of the organization, and you can understand things from a bigger perspective than just a finance hat.

Megan - 11:15: Great advice. And let's talk about imposter syndrome. It's something we hear about a lot, but it's often invisible to everyone except the person experiencing it. So can you share an example of how it quietly affects a new CFO's confidence or behavior early on?

Kevin - 11:33: Gosh. Yeah. Imposter syndrome. In Grow CFO, we did quite a bit of work on looking at what are the top 10 challenges that hit the new CFO. And actually up there at number one is imposter syndrome, closely followed number two by lack of confidence. And you could argue that they're the same thing. But it's all about this change again from being the internal face of finance to the external face. The shift is so big that nobody is ever 100% prepared for it. I think the individual tends to have a view that they should have all of the skills and competencies that are necessary to be a CFO. And in practice, that's never going to happen. There are so many different skills that you need to have that you're never going to be a master of all of them. And, I think that's where part of the issue comes from, that people think that, oh, suddenly I've got to be a master of business strategy. What? No. You don't. Because, look, you're a master of governance, you might be a master of change management, you might bring other skills to the table. So imposter syndrome comes in there, that you feel as though you're expected to know everything. You feel as though you're expected to have the right answer at your fingertips, which a lot of the time you don't. I think one of the things that bothers new CFOs is when asked an opinion on something, they're asked a quick direct question. They've got to give a definitive answer straight away. There's nothing wrong with saying, Well, not sure about that. I'll come back to you with an answer. Or, Let's have some time and think about that and consider the alternatives, or whatever it might be. That imposter syndrome certainly hits folk. Oh, somebody's going to find me out because I don't know about this Inside Out. Well, what would my advice be? Well, first of all, somebody thought that you were the right person to be CFO. Chances are, more than one person did, because it's very rarely a decision of just one person to appoint a CFO. It's likely that the CEO and other members of the board were part of that decision. So they'll have looked at your resume, they'll have looked at your experience, they'll have seen how you've reacted through the whole recruitment process, they'll possibly have taken references, they'll know a lot more about you. And these days, with social presence and so on, folk know a lot about the incoming CFO before that person gets there, and reasonably confident that that person is going to do a good job. And, therefore, if the CFO has got imposter syndrome, I'd look to them and look to say, well, hang on. These people thought you were good for the job. I'd also say to that CFO, well, wait a minute, what is it that you're doing at the moment? Why don't you think you've got the right skills or confidence to do it? Because in nearly every case, what you're feeling uncertain about, you've done in some way before. You're not being asked to do anything radically new. Yes, you'd be asked to be doing the things with different people, a different seniority. But if you look back on your career, well, we can probably find loads of examples of why you've done similar things, where you've achieved. So why should you have imposter syndrome? One of the best analogies that I've heard is, you've been out on a walk, you've been up on the hills, you've been doing a pretty big hike. You get on the top of the hill as you're going up one step at a time and so on, and you don't really notice the progress. You get to the top of the hill and you look back and you think, wow. I've climbed all the way up here. And if you turn around and look at what it is that you've been doing on this journey, Now it's a similar thing. You look at where you've got to in your CFO career, look backwards. Look at all of the experience you've got, look at all the things you've achieved, and it will be quite considerable. And there's no reason, 99% of the time, why you should have impostor syndrome.

Megan - 16:01: Great answer. You mentioned giving decisive answers, and I just want to dig into that for a second. So CFOs are expected to project calm, confidence, and certainty, especially in front of boards and executive teams. So do you feel like it's okay for a CFO in front of those two audiences to say they don't know and I get back to you? Or is that a no no in front of boards or in leadership meetings?

Kevin - 16:31: It all depends. I think you're going to the leadership meeting. You'll have a responsibility to present the results, to present the financial state of the organization, and I think you need to have a pretty good story prepared. And if the results are off track, I think you're expected to know why they're off track. And that's not simply saying, oh, we've got a variance of budget because blah, blah, blah, blah. No. It's the real why behind it. And a good CFO will know the real why, and I would say that a CFO going into a board meeting, a leadership team, and presenting the finances should have before the meeting, if there's anything like that around in the month's results or the quarter's results, should have been asking the question why over and over again to the various people involved. You should, I believe, be able to speak definitively on those sorts of subjects. Where you perhaps may not be speaking quite as definitively is when you're in a discussion about a strategy going forward, and options will be on the table. In that meeting with the board, a new idea might come up. That new idea may well need some reflection, need some analysis, and so on. I don't think in those circumstances it's unreasonable for the CFO to say, Take a look at that, we'll get back to you. No? An instant answer is often the wrong thing to give, and you shouldn't feel pressured into having to give that instant answer in those sorts of circumstances.

Megan - 18:16: And in your mentoring work, do you see a common mistake that new CFOs make over and over again?

Kevin - 18:23: I defer that question, actually, Megan. I don't do a huge amount of mentoring with that community. We've actually got in Grow CFO a team of professional mentors who have been CFOs in various organizations, have been there, done that, got the t shirt. And, generally, those folk will act as one on one mentors to some of these new CFOs, as well as would be a part of our CFO program. We'll offer one on one mentoring to those folks. So, really, I would be asking that question onto one of our mentors. What mistakes do you make? I don't know that I necessarily know the answer. Certainly, I'll get involved in running modules on a future CFO program. And increasingly these days, I end up talking to a group CFO. I tend to be involved these days much more on the technology side of finance than mentoring.

Megan - 19:22: And when you see someone stepping into the role, how do you guide them to create their first one hundred and eighty day plan? Like, how should they be prioritizing, and what should they be focusing on?

Kevin - 19:37: In module nine, our future CFO program, I kind of split in two sections. There's the first part is the, what are you going to do in order to create an impact or be an impactful CFO? And then the second part is, how are you going to be? So first half, we look at the first hundred days. We split it out into, well, well, the period before you arrive at the organization, which I counsel people to do as much research as possible. You can start getting to know people in your new organization. And the CFO should start thinking about, well, where does this company sit in its industry? What are its can I do a SWOT analysis on this organization? Am I able to put together maybe a Porter's Five Forces? Things like that and really find out about what this company is all about. Then you land in the organization. First ten days is a meet and greet, induction. Meet as many people, say hello to as many people as possible, start conversations. It's the part of the journey where you can ask all the silly questions, because once you've been in for a hundred days, you should know better than to ask a silly question, and you can get away with an awful lot in the first ten days. As you move in to the next ninety, I've split that up into three chunks of thirty days on the course. The first thirty days is all about fact finding. That is, I'd recommend to any CFO, take your team off-site. Get your team to tell you what the issues the problems are and where the systems don't work and where the problems are dealing with other parts of the business and things like that. And start building up a view of what are you inheriting, what needs fixing, what might an action plan look like. And, of course, you're having conversations wider in the business as well and finding out what needs to be done. You've probably been recruited to fix something. You'd be recruited on the company journey, so you should be starting to assess, will the systems and team that I've inherited on day one still be the right systems and team in twenty four months' time when we've just had a series b or we've just done something major expansion wise. And all of that comes together into forming a blueprint for finance, which is, talk about that being the next thirty days' job is to say, fine. This is what we've got. This is the starting point. This is what needs fixing. This is what needs changing. This is what needs beefing up. Put together your blueprint for finance, and go talk to the board about it. Go talk to the leadership team and say, here's what I need to run finance the way it needs to be in accordance with our strategic expansion plans or whatever. Here's what I need, which might be new systems, extra people, so on. So form that blueprint. And once you've got a blueprint and a plan for going forward, your next thirty days is about putting the first steps into action to implement that plan. Getting the rest of the finance team on board, it's likely that CFO these days you're running much more than finance. Lots of CFOs seem to run property, legal, HR sometimes, IT sometimes. It all depends on the organization, so your plans might be a lot wider than just finance. So next part is communicate it to your people and start putting together their plans and starting to implement whatever you'd got in that blueprint. And once you move outside of that first hundred days, it's all about implementation. So hopefully in the first year, you get a lot done, and you make an impact, and that sets you up for the rest of the journey. But very much the doing side of it, The other side of the first hundred days is the being side, which is I'll start that by actually putting a slide on the screen that that's titled This is a blank piece of paper. And the audience is going to say, Kevin, should you really have that slide in the deck? Well, yes, I should, because the culture of the organization, the values of the team, the habits and routines that you want to have in place, the ways of relating to people and so on, all of those softer things, you need to establish those across the first hundred days. And the problem is that blank sheet of paper, if you don't fill it up yourself with what you want, then it'll get filled up for you. So as the new CFO, you really must think about what culture do I want in this team? How do I want to be as a leader? How do I want them to approach me? How do I want us to work for it and work as a team? And we do an exercise, a breakout exercise at that point, where I say, Okay, folks, you've worked for a number of leaders in your career so far. Now go and think about that. There have been good leaders and bad leaders. What makes a good leader from your experience? And then get them to reflect on how are they going to turn themselves into that good leader they've just identified, what things do they need to put in place. So there's a lot to do in that first hundred days. As I said earlier, Megan, the biggest challenges is that you're thrown in at the deep end and business as usual is going on alongside all of this. And possibly and it's an answer to the question I deferred earlier. What's the biggest mistake that people make in the beginning? Well, one of the biggest mistakes is that they get so sucked into business as usual that they never really get time to do that thirty, sixty, ninety day plan, what they should be doing to make an impact. They never really get into filling that blank sheet of paper in around the strategy, the values and so on of the team because they've just been thrown at the deep end into all of the stuff that's going on in the business. The CEO knocks on your door, asks you for an opinion on something, asks you to take part in a dealing with a supplier or an investor, and it takes over the focus of your time, and you don't have time to do the stuff that we teach in the first hundred days.

Megan - 26:13: Yeah. And I'm sure also that a lot of new CFOs are, at some level, expected to start making transformations across the business. So I imagine that makes it even more difficult. I mean, you have to learn the business, and then on top of that, you're expected to start improving it or transforming it.

Kevin - 26:33: I guess that goes into another big mistake category that you dive in and start trying to do that transformation before you actually understand what it is you're trying to transform. I can look at that from the point of view of having done a lot of finance transformation as a management consultant rather than the CFO. And you go in and you start talking to the client about the problem. It's fairly normal, in my experience, in that sit sort of situation, that you find out the problem is actually something suddenly different to the one you were told it was. You learn to spot that as a consultant because you're going into these situations all the time. I'm not sure you spot it quite as easily as a CFO. And you can, I think, because you don't have that experience initially, get sucked into solving the wrong problem?

Megan - 27:20: And we've touched on this a bit, but once you get to the top, it can be pretty lonely. And you've built spaces specifically to address that gap. So can you maybe share an example of how peer conversations or informal benchmarking helped a new CFO gain clarity or confidence?

Kevin - 27:39: I've talked a lot about future CFO program. We've also got the CFO program where, we take a group of new CFOs together on a journey, again in a twelve month program, what you find is that those people within the program form a support network, and that really, really helps on the journey. They're able to bring along issues that they've got in their own business, and they're able to talk about those things with fellow CFOs. And I think having that safe space to have those conversations and support each other really, really helps. It's a little bit of different support to the one on one mentoring that we're probably offering alongside that. But, no, it is, as we said earlier, a lonely place at the top. You don't have naturally in your own organization the peers you can rely on. So finding those peers outside of the organization, I think, something powerful that you can do to really help.

Megan - 28:46: And to close us out, looking across all the CFOs that you've supported over the years, what's the single mindset shift that you see that most often helps a new CFO move from feeling overwhelmed to feeling genuinely in control of the role?

Kevin - 29:01: For a good number of people, it's learning to delegate stuff, learning that they've got to have a good number two that they can pass things off to. But above all, it's about learning how to form really great business partnering relationships. The CFO has got to get very much out of the mindset of where finance, what's the finance result, what's the finance strategy into the mind of the other leadership team members. What's keeping them awake at night? What can I do to help them with those problems? And I think once that shift has been made, and the CFOs genuinely seem to be really contributing by other members of the leadership team, that's the step change.

Megan - 29:53: Kevin, you've offered us some valuable advice, and this has been such an informative session. Thank you so much for being here with us today.

Kevin - 30:00: Thank you. I've really enjoyed it.

Outro - 30:03: To all of our listeners, please tune in next week. And until then, take care.