In this Dear Melissa segment, Melissa answers subscribers’ questions about transforming IT departments and legacy businesses into agile frameworks, reframing leaderships’ “May I take your order” approach towards their product teams, and making your case for strong product management practices within an IT-minded organization.
Show Notes
Q: Our President and VP of IT want to switch the entire company from project management to product management. What advice do you have for a prospective lead product manager with no prior PM experience?
Q: How can line workers and IC’s help our management see the value of iterative product development?
Q: How do you approach arguing to an IT-minded legacy media company to introduce product discovery when they actually have only one product team to work with and multiple media assets or websites? How do we start building trust so that they are willing to hire more teams?
Resources Melissa Perri on LinkedIn | Twitter MelissaPerri.com
Episode Transcript
If you passionately care about this, and you want to get more teams, and you want to show that you're not just a call center, you're not just IT, you are actually a way for them to make more money and further their business, you've got to carve out the time. You have to find the time to run the experiments, to show them the proof, to show them what you could possibly do. And it's not until they see it that they're gonna change.
They have to see it. I rarely see words change organizations. You can argue with somebody night and day, you can hammer home all the books that you could possibly read, and look at this company, look at that company, and until they see it work for them, it's not gonna change your minds. But as soon as they have that insight that it works for them, man, is that a game changer.
Hello, and welcome to an episode of Dear Melissa from the Product Thinking Podcast. The lines are now open, and we're ready to answer your most pressing product questions.
Which prioritization framework would you recommend and why? Hi, Melissa, do you have any suggestions on developing a product strategy? I'm struggling to get started. I'm struggling to get started. I'm struggling to get started. I'm struggling to get started. I'm struggling to get started. I'm struggling to get started.
Whoa, whoa, whoa, whoa, whoa. That's a lot of questions. All right, let's dive in. Hello, and welcome to another episode of Dear Melissa. Today, we're talking all about taking IT departments and legacy businesses and moving them more into agile frameworks, winning over the hearts and minds of IT heads and leaders in different organizations, and really becoming better product managers, trying to get out of that old way of working where we see IT just as a cost center, but not really the profit center.
So we've got three great questions, but I also want to remind you that if you have a question for me, you can submit it at any time to dearmelissa.com. All these questions are submissions by our wonderful audience out there, and I love answering them. So please, if you have a question for me, some of you will DM me on Twitter, send it over here.
Send it to dearmelissa.com.
I'll answer it on the podcast for you, and then we'll also ping you and let you know when I answer it. I love hearing what you're thinking about. So please go there and do that. All right, let's dive in. First question. I'm currently an IT development supervisor for an insurance agency where I wear many hats from coaching developers, maintaining our commercial lines, underwriting systems, and running projects.
I recently spearheaded a push to start using agile principles, and now the majority of our projects are run that way. The president and VP of IT now want to switch the entire company over from project management to product management and are looking for someone to be the lead product manager. I applied for the position even though I have no PM experience.
The VP and I have worked together for most of my career, and he's excited about what I've been learning from places like your book and believes I would do great in the role once it's established. But the concern, rightfully so, is that I have no prior experience. What advice do you have? While I would love to get the position, I also don't want to be set up to fail if I'm not going to get the support.
Our VP of IT and myself are completely aligned in our thinking on this, so if I can convince myself of a way forward that will work, then he would be convinced as well. If we do truly need to hire someone to help us, I am fine with that knowing I will still end up as a product manager and likely be promoted if the new hire decides to move on. Very good question. I have a lot of thoughts on this, and we're going to answer it right after these words from our sponsor. All right, so we're back and we're talking about somebody with no prior product management position applying for the lead product manager role.
I frequently see this in companies, and I have to say that I don't think this is the right role for you, and I do think you're going to be set up for sale. I do think you're going to be set up to fail if you do take this role as a lead product manager. Here's what I observed in a lot of companies that I've worked with.
As we go through these transformations, we kind of go into the IT department, we look at the project managers and we say, oh, we can just set up everybody to be product managers. We'll train them, we'll have them learn stuff, and then they can lead it. But the type of change that you're actually asking for, which is a whole transformation in an insurance agency of taking a legacy IT department and turning it more into a product department, is not just a functional change, it's also a cultural change.
And that's incredibly hard to lead if you've never done that before. So here's the thing about that type of change. It's not just about becoming the lead product manager.
You have to actually convince everybody else to work that way. You have to convince them that the products that you're going to build are going to further the insurance agency and actually change your business model. Like a good product management system in what you're talking about should be giving more value, more business value into the insurance agency.
It's not really just picking up projects and turning them into products and growing it that way. Like we have to change the hearts and minds of the business heads that we work with and get out of IT mode, where IT is a cost center, and get product into a profit center mode as well. And that's really what this digital disruption is about when we look at these legacy systems and we look at legacy IT departments.
It's not just about setting up a cool product management organization and saying, hey, now we have product managers, we're new and cool, we can do all those things. It's really about digital transformation. And when we say the words digital transformation, it is a transformation of the entire business, not just the development center.
So having not had any experience working in a company that really operates like that, there's going to be so many things that you don't know yet, right? And if you don't have anybody to learn those from inside the company, it's going to be hard for you to level up and create a career in that and see these things and recognize them for what you don't know, what these gaps in knowledge are going to be. But what you're talking about, putting somebody into that role, you were the one who studied it, you have read everything you possibly can about product management, here's what happens if you take that lead product management role.
You may be able to build up the product managers, talk the good talk about what you've been learning, execute on a few small products. But where you're going to get stuck is trying to rally the team, right? And by team, I mean the business departments and the leadership and everyone else that works with IT around this different way of working.
And that gets really, really hard.
So what happens in these organizations is we need to rather make a role, first of all, it shouldn't just be lead product manager. Like you're talking about, we have a VP of IT, right? That you're reporting to and you're working together with us. Now, you need a VP of product role, you need a chief product officer role.
So many of these organizations that are switching from IT over to more modern development practices, don't do that. They don't actually put a product leader role on the top. And it can't be just lead product manager, that's implying that you don't have the same scope as a senior stakeholder C-suite person.
And if you want to execute on this correctly, like you need that, you need that gravitas and you need that authority built into this role to complete the transformation and to bring everyone on board. I have seen this a million times where we don't do that and organizations don't do that. And they just take somebody who has a lot of potential and I'm sure you have a ton of potential and they throw them into these pseudo leadership roles, but they don't spec out the role well.
They don't have the authority to actually do what you need to do. And they don't have the experience to know like what good looks like or what bad looks like as you start going. And that becomes really, really tricky. So I'd say this is not the role for you right now, but that doesn't mean that you can't lead this in the future after watching somebody else help set this up.
And that also doesn't mean that you are not an invaluable asset to the person who would come in to lead this. But my suggestion for your company is to hire a senior product leader who has done this before. Somebody who is going, first of all too, I will say this, hiring that person, this person is going to want the chief product officer title.
They're gonna want a VP of product title. They're not gonna want the lead product manager. Like lead product manager in the industry assumes like you've got maybe five to seven years experience. You need somebody who's senior and who has done this and can navigate the complexities of working with the C-suite.
That is actually critical to making this happen. So you're gonna wanna hire somebody and you're gonna wanna create the role for that. And it can't be a coach. It can't be a consultant. I have been in that position before where I've been brought in as a consultant to lead a transformation and it does not work, right?
And I've been brought in under chief product officers or lead product managers, exactly like the role that you've been talking about where they don't have the experience. They've never done it before. So they bring me in to help. And it is incredibly hard to affect change when you don't have authority, especially as a consultant.
Like I can advise that lead product manager as much as possible, but they also don't have the authority to put in the changes that need to happen. So this is where I'm really getting at. Like you need to have a senior leader who sits with the C-suite and helps move this forward, helps actually enact that cultural change as well.
Because that's the only way this is actually going to be successful.
And that's the only way you can get out of IT mode. Somebody who's seen it, somebody who can bring their stories, somebody who can change their hearts and minds. A coach or a consultant is only gonna get you partway there if you are leading it. But having somebody to work for who can go do that on a daily basis, right?
Who can be the peer to the C-suite, who can actually enact this change. Working for them, you're gonna learn so much if this is the thing that you wanna do in the future. And you're right. You may get promoted in the future and decide to move up. But in that case, you've just learned from this person so much that you're gonna be well more suited for that role.
You're gonna feel way more confident getting in there. And I'm worried if you don't take that time to learn, you're gonna be set up to fail. And nobody wants to be in that position. That's just an awful position to be in. So that's my advice. Try to get somebody in there who's done this before, work for them, learn as much as you possibly can.
And then in the future, you can stay there, you can go somewhere else, and you can do that yourself too.
But you gotta learn from somebody first. All right, next question. A decade ago, our legacy business moved to a more agile framework on the digital side. We had digital visionaries and management and some technologists in leadership who understood the value of design, engineering, and product teams working together.
So we had the organizational foundations for delivering customer value iteratively, but notice business value is missing here. Hmm, in the last few years, management has changed so much that we no longer have folks with digital or technical acumen in leadership. Leadership treats the digital team like restaurant servers.
May I take your order? Rather than the customer and business value focused teams that we are. How can we line workers and ICs help our management see the value of iterative product development? Do we send them to a class, have a respected leader come in to speak, pummel leadership with plaintive cries from the IC?
Right now, the message is being sent by people leaving the company, which puts us at even greater risk for disruption and for our current leadership to see the digital folks as an underperforming quagmire. Help!
I really love the enthusiasm around this question, especially the part about pummeling leadership with your plaintiff case. I love that. So the biggest thing that we have to do here, this is what I would advise to do, is take a step back and start to figure out who the profiles of leadership is. In order to change hearts and minds and start to convince people, you first have to figure out what their agendas are.
I'm sure they have an agenda. So let's take a couple steps back. Let's look at our new leadership, figure out how did they get into the positions they got into? What happened to all of our old leadership and why did they go away? And then what are the expectations put on this new leadership for success?
How are they being measured for success? What are they expected to actually do? Once we understand that and we understand their goals, now we can start putting our case about iteratively working together as product teams into their framework for how that helps them reach their goals. This is one of the things that I see a lot of people who want to enact change don't do.
They don't stop to think about who do I actually have in the room and whose hearts and minds am I supposed to change? Who are those people and how are they being measured for success? If you don't understand that, it's gonna be really, really, really hard to change their minds. You have to put this in some kind of form that they'll understand in some kind of way that will get them excited about it.
So let's say they are business leaders. This is something that I see a lot. Legacy Business works with a bunch of banks, insurance agencies. We've taken those people out of the business and then put them into leadership over the digital sides. And now we've got no technologists, nobody understands the power of technology.
Usually what these people are lacking is like, how can products actually further the business, right? It's that type of thinking together. So it may not just be iteratively working together in the team of engineering, design, and product. It's probably also they don't understand the value of digital or technology when it comes to furthering their business.
So that's actually where I would start because every leadership team has some kind of business goal, right? They've got something they've been expected to deliver. You have to figure out what that is. And then you need to work backwards and help them see that the product team and the technology teams that you're working on, it's not just about building product development stuff, right?
It's not just about executing, may I take your order. It's about furthering it. And there's also something I don't like about these two. When it comes to the may I take your order part, right? Rather than the customer and business value focused teams, it prevents you from scaling. It actually makes you move slower.
You don't deliver as much value because you're not pushing strategy down into the teams. It's gonna be really, really hard to build up a team around that. So that might be an angle to play as well. Like how do we enable people to make decisions on a daily basis through good strategy so that the leadership team doesn't become micromanagers, they become leaders and they think about more of the visionary area of where to go.
That's really where we want them. So you gotta start with the goals. You gotta start with how product can actually help them. And then I think there's a couple of tactical things to get them there, right? Once you understand that, that's where we can start to think about, all right, maybe what I need, and I've seen this work pretty successfully in legacy businesses.
Maybe what we need is somebody who's worked in a adjacent function or a similar company, maybe one of our competitors in the past, but a leader who's gone through this transformation, sees the value on the other side and can talk to them in their own language about what that value is. That's where I would bring in somebody else. Like for me, I can tell them stories about, you know, other companies I've seen do this, but where I see a lot of change is when that leader from that company comes and tells a story about how they did it and how it really changed their lives.
That's a very powerful story. So maybe you wanna bring somebody in who's done this before, who sees the value and could talk to them on their level.
I do think it's good to talk to them about this stuff, but you gotta put the message in the right way. I wanna understand your goals so that I can help you achieve them with our product development team. Oh, these are your goals. Wow, if we actually worked this way, we'd be better off achieving them.
And then some of this too, is you just kind of have to act in a certain way. I've realized that like when organizations get into this, may I take your order mode, a lot of times we're just not pushing back. And then when we do push back, they're like, no, you have to do it our way. Maybe just do it your way, right?
Like maybe take that order and be like, I'm gonna test it. And they'll tell them, just test it, right? And then come back with data and be like, this is a good way to do it or not. That's powerful. A lot of times you have to ask for forgiveness rather than permission to start changing organizations.
And one of the biggest cries I hear from people in these types of businesses is, oh, we're not allowed to work that way.
But when teams just go out and do it, a lot of people are like, oh, okay, well, cool. That worked, right? Like I have nothing to add. Let's just keep going that way. So it's another story and I can't really tell with this. If you have leaders who are breathing down your neck every day and they just don't give you the space to do that.
But if you got a little space, maybe work with them. Maybe just start working on the agile side. Maybe take all of the orders and just question them. And don't question them right back to the leadership. Say, hey, that's a fantastic idea. I'm gonna run it through the pipeline, right? Take the idea and then just go test it and then come back with data and present it in a way that helps them achieve their goals.
That is where I would start. Sending them to a class, you asked those types of things. If they are not ready to change, if they don't see the need to change, they're not gonna care about the class. Leaders hate taking classes when they see no point into them. And if they think your way of working right now is good, they're not gonna wanna change.
So you have to create the impetus for change.
Like you have to get them to see how it could be more amazing to work this way and they have to want to change. Then all of your tactics will start to work. But I see companies just not want to change and a lot of leadership think everything's fine. We're fluent and like everything's cool. We're not getting disrupted.
And they wait too long to do that. So you have to create some kind of urgency around that first. Otherwise I can't see these people wanting to change. So that's what I would do. Take a step back, understand their goals, try to figure out how I can communicate our way of working in how it's gonna help them achieve their goals.
And then I would also do a little bit of asking for forgiveness rather than permission. Just don't tell them what you're doing. Just go test stuff, come back, give the results again in their way of reaching their goals. And then maybe seek out some people who've done this before who could talk to them on their level and about how this business value gets created from this customer value and how working in an agile iterative way actually helps that.
That's where I would kind of start. But again, it all really comes down to understanding people's agendas and goals. And that's the first thing you need to do with any type of leadership team like this. All right, we've got our last question. Dear Melissa, love your show. Thanks very much. How would you approach arguing to an IT-minded legacy media company?
I already love that it says arguing. To an IT-minded legacy media company to introduce product discovery when they actually have only one product team to work with on multiple media assets or websites. Maintaining the sites take up most of our time while there are lost opportunities in pursuing sales, content, traffic, UX outcomes.
How do we start building trust so that they are willing to hire more teams? Basically, the question is around scarce resources. No multiple product teams, just me and three developers. All right, so you are the solo product manager hanging out basically doing everything. So one of these things it sounds like is they see you as the team that just kind of takes care of the IT, which is kind of what you're saying in here, IT-minded legacy media company.
They probably haven't seen digital as a channel that can help bring their goals out there. And a little similar to what I was just talking about in the last question, you got to go find out what the goals are of this media company and also create some urgency. So how do you take something that they've given you, test it, present new ideas on like how you can get into more sales, content, traffic, UX outcomes?
Like you have to create the space in your team to do that. Now, maintaining the site, I'm sure, does take up a lot of your time, but can you do something where you pull out like five hours a week and just say, this five hours we're going to spend on some experimentation to show them the value of what we do? In order to do that, I would first go to the media teams, try to figure out what's happening.
Like how are they comparing to their competitors? How do they compare to the way that other people run their media businesses and where are they lacking? And where are the opportunities that help meet the goals of the leadership team?
So again, just like the last question, figure out what the goals of the leadership team are, try to find those opportunities and maybe just carve out yourself some time, maybe like five hours a week to start testing that, see if you can get a win, and then come back and present it as, hey, we helped you achieve your goals. We could do a lot more of this if we had more teams. The biggest thing is you have to show people, and I know you're sitting there going, man, but we have so much work, I can't possibly find time to do this, which is a big argument that I get all the time from product managers.
I'm too overwhelmed, I can't do that, I can't focus on strategy, blah, blah, blah. You have to find the time. There's no way around it. And I'm sorry, it's like, maybe working a little bit of overtime, I don't want to tell you to do that because I don't think we should ever like give up our work-life balance like that, but if you passionately care about this and you want to get more teams and you want to show that you're not just a cost center, you're not just IT, you are actually a way for them to make more money and further their business, you've got to carve out the time.
You have to find the time to run the experiments, to show them the proof, to show them what you could possibly do. And it's not until they see it that they're going to change. They have to see it. I rarely see words change organizations. You can argue with somebody night and day, you can hammer home all the books that you could possibly read and look at this company, look at that company.
And until they see it work for them, it's not going to change your minds. But as soon as they have that insight that it works for them, man, is that a game changer. So that's what I would really focus on. How can you run the small experiments? How can you do the things that are going to change your hearts and minds through data and real life?
Like you have to find the time to do those things. And I think you're going to get a whole new organization once they see what you can do. And that's it for our Dear Melissa episode this week. Tune in next week for another guest on our show. We're very excited to have all these product leaders with us telling us all about their stories.
And then if you have any questions that you would like me to answer on the show, please don't forget to submit them to dearmelissa.com. We would love to talk more about your questions and answer them. This makes me really excited every week. Also, if you're loving the Product Thinking Podcast, remember to subscribe so that you get the new episode every single Wednesday. We'll come right to your Spotify or Apple Podcasts or wherever you're listening to us. So thank you so much and we'll see you next time.
