Stefano Grossi: Unlocking Leadership Potential - Tools and Frameworks That Deliver

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Matt

My name's Matt and I will be talking with Stefano Grossi about the strategies for effective R and D investment leadership development and achieving business outcomes through innovation and team growth. I'd like to start with the question about the CPO Summit in Toronto. When we last talked, uh, you mentioned to me like a few interesting topics that you would like to tackle there. And one of them was the framework that caught my interest. It was the framework we use with the board of directors and the team called the Pyramid of Needs. Uh, could you elaborate about it?

Stefano Grossi

Yeah, yeah, yeah. It's, it's a very simple tool that, that we make up, we made up, uh, it's called the R and D Pyramid of need, and it's basically an investment allocation tool and it allows a common language across all levels. So whenever you build a product, you always have to take care of five big, big things. So one is keeping your lights on. So making sure that your system is good, is working well, your SLA are met, etc. You need to take care of quality. You need to make sure you have, you know, the very important bug gets sold and you have that level of quality that you set.

You need to make sure that you enable other teams so you don't keep other team blocked because of something they need on the product or an integration they need in the product. And then you need to make sure that you get what you have at a better level. And so you know that you have your core value and you make your product and its core value even better over time. And then at the last piece at the top there is what we call the roadmap. So this tool I meant to do, because it's in the systems I dealt with if software is older than five years, but in some cases 20 years, it's like the technical debt is there. The Board of Director needs to understand that it's a very big tax you actually have to pay, right? So if 50% of your team allocation is taking care of that, it means that you have half of your team action.

And normally when you look at the board level, when you look with the team level, sometimes you just look at the roadmap and it's just the tip of the iceberg and you don't see all the other very important things. So it's helpful for the board to understand where actually that money goes, right? If you have an R&D department and you spend, I don't know, 1, 20, $100 million, doesn't matter if 50% go somewhere that you don't Expect it, you gotta know. And at the same time it gets the team, it gives the team the autonomy to say, yes, we know we're not going at the speed we should, but if we paid off, we can pay off some of this debt, then the speed increases. So I just build it. And normally it's pretty interesting because when you start tracking for, let's say a couple of months or three months, how your time is spent, you're going to have an actual amazing baseline to do a much better way in understanding your capacity. So yeah, so we call RnD parameter needs.

It's just really to say, hey, we have this investment R and D, this is where actually the money goes for. And then you can play around with the intermediate step that are more discretional, these are more in your power to timebox to give even more or less time to the technical depth of the road. So it's very interesting actually a very dim article on that. But at the CPO summit I got a million questions about it because you know, product folks, they tend to include myself, they tend to really look at the piece at the top, the roadmap and is the shiny object. Right. So very good to get the same language across the board.

Matt

You mentioned a couple of times the technical depth and you have a pretty broad experience working in organization like the FreshBooks is one of them. So a couple hundred people, organization and the technical depth. This is really interesting because when it comes to ROI to the technical depth, it's for developers, it's like clear that they need to, need to improve and at some point get rid of the technical debt. On a business side, it's not always clear that you should work on a technical debt and what kind of ROI you can get out of it. But you mentioned that you got to the point that in your organization that even like all of the people are on board with work and on board on like what is the ROI of the technical depth that you're removing?

Stefano Grossi

Yeah. So I think in the end, at the end of the day, when you look at this, when you look at technical depth, it's very hard to, to believe it a dollar. Right. But when you look at the other side of technical debt, which is the opportunity cost, it's the, the, the speed and the slowness that technical debt forces you to and in some time, even worse downtime or massive problem in the infrastructure, that is all technical debt can create a massive dent on your, on your loyalty, on the loyalty of your customer and on the trust they have on the platform. So when you look from the opportunity cost perspective and you look from the must have today, which is a time, then the calculation of ROI becomes fairly simple like the amount of speed you gain. We used to call it technical debt tax. Right. If you know that everything you build you're paying a 30% tax or a 60% tax and there is a way to get those taxes down to 15 or 20 that you do it right.

So that's more or less what what we, what we try to, how we try to explain it but yes, it's not, it's not very straightforward but it can get to a dollar amount and normally dollar amount are a very easy way to cross all levels to, to understand really well the importance of that type of work.

Matt

I love the comparison with the tax. I think therefore it's so, so easy to understand for the business people in our organization. If you call it stacks and you know how to optimize it, everybody wants to.

Stefano Grossi

So the fresh boost was like 200, 250 engineers in an organization, it was like 800. But if you look at, you know, you know very well that the money you spend in R and D are like normally 85 to 90% is BMO, right? So that tax is the time of people. It's the most important commodity you have inside the organization, especially if you develop. So you know that really well.

Matt

It's a valid point. And we've spoken about the roadmaps and the concept of delivering the roadmap versus delivering the outcome. Maybe could you tell and talk about the difference here and how do you see it?

Stefano Grossi

Yeah, yeah, yeah. I really like the concept of, you know, it's called outcome over output which is when you are like you need to deliver the roadmap. If you're a product engineer, if you're a pm, if you're a design, you're going to need deliver the Roma.

That's our job. That's, that's, it's a well known fact. However, there is always the question about so what? Right. There is a stat that says 80% of what you build is basically useless. 20% of what you build gives you 90% of the value. So nailing that 20% is very, very important.

And I think when you think about outcome over output is when you look at the roadmap, you see the steps you're taking to get to an outcome. But when you think about the outcome itself is actually a very clear business value of providing. So to give you an example, increasing revenue or conversion by 20%, that's an outcome. I don't care how you do it. I don't. And the team that is the closest to that should be the one that actually comes back and tell you hey, those are the step we should do, then you can have the discussion. But the reality is if you go down and you tell them already which output you want.

So I want you to remove three question from the onboarding quiz. You're not explaining them why they're doing that work. Instead if you tell them I want to increase 3% conversion and I want the time to value to be reduced by three hours, well then they start thinking about well maybe it's in the boarding, maybe it's in the anti state, maybe it's in the marketing website and we don't have to write one line of code. Right? So for me the concept of outcome pushes team to work together to be more collaborative, more collaboratively operating across organization. And also it gets very clear on the why this is why we are doing this and then gives the team some freedom to go off and decide how to get that, how to get to that outcome through a series of hopefully experiments and output that along the way gives a signal that we are going the right direction. So that's, that's the concept and again it forces people to align on, on a very important thing that you want the business to, to achieve.

I know you're going to ask me about some books at the end so I have one about this so I'll just pick it up.

Matt

I'm waiting for it. I'm waiting for it. We still have some questions to go and you mentioned, I think you are very on such a level of the company and I mean with a couple hundreds of FTEs working for the company, usually the processes are something that you would like to happen side to minimize the risk, to minimize the problems or the issues. But you said you dislike the processes which is not really common to be honest. Like on the size of the company.

Maybe you can talk about this a bit.

Stefano Grossi

Yeah, that's a good one. Now you're getting me in trouble. But I used actually to say I'm going to use it again. But I used to say the process is something you build when you couldn't figure it out otherwise. And it sounds, it sounds like it doesn't sound that nice. But I think that processes are very good when you have a very deterministic something. Deterministic, something that you know has a solution and you just need to get your, your ducks in a line and get it done.

But for me what, what works best for product teams and I'm talking specifically on product teams that I know that there are like areas in the world where we're like unique processes. But for product engineering team I like much more providing guidelines and frameworks so they can build the way that fits the team best in execution instead of creating very rigid processes. Also because they like to get you a great product is not a line with some dots on top. It's like it looks like a five year old's scribble on a piece of paper, right? It's a series of failure experiment tweaks, pivots and go back and go back with what you were doing before and doing it just tweak it a little bit different and it changes the result completely. So that's why I'm like processes are good for some part of the organization, good for something but not really for building product or having product team operating at the best level. I'm like.

And I have an example that always comes to me that is like the Agile Manifesto. Like the Agile Manifesto and what happened to Agile after that? You go back to the Agile Manifesto, individual interaction over process and tools and you say working software, all the documentation, customer collaboration over contracts and responding to change over following a plan and then all framework they came after they tried to build this structure and then on top of them because we couldn't get it done really well, we started creating processes and safe and story points and all of that. Which is super funny because in the actual manifesto there is like just get the people together and give them an objective instead of giving them processing to. So it's, it's actually fascinating the divergence when you see that onion what happens in real life. And I think that if you go back to the beginning and say hey, the philosophy behind the way we are doing this thing was actually to for speed and it should not require all these processes and tools. So yeah, I am, I'm not, not a huge fan but I know that there's some in some areas of organization they have huge merit.

So yeah, don't get me trouble on that.

Matt

I see that clearly after our recent talk because we remove a lot of my questions that I wanted to ask but I see clearly that you are passionate about the people growth, performance people performance, performance reviews and you even like planning to do the next step around it and to build something that, that should, that should work and like cover the, the, your assumptions that you had. So I'm just wondering like what do you do differently based on your experience and what do you see maybe that works for you. Regarding those topics.

Stefano Grossi

You, you mean about that like how do I, what, what do I use to grow leaders? What. What are my best practices? Is what I like your.

Matt

Exactly, exactly. Yes, yes.

Stefano Grossi

Yeah. So I, I think that there are, there are a couple of things. I think that the most important part in that is like for me in hiring leaders, you, you want to look into, you want to look in their ability to grow and change job and in their ability to grow.

They have teams. Any leader I hire and you can ask them, when they ask me how can I be successful in my role, my answer will always be you get to grow your team members and then you can screw up more or less everything else. And that is actually doesn't happen in reality because if they take care of the growth or their teams then their team have their back and so they don't end up screwing up anything else if they keep that one in front. And again, this might be very R and D specific approach but I think it travels very well all the other areas of the organizations. So for me I look at people, I look at how much they can grow their teams and when I said how can they change job is because I truly believe that every time you grow in an organization you are actually getting a new job. So what, what the job of a CE versus the job of a VP and the job of a VP versus job of direct are actually different job. They're not the same job with more people or with more money.

They are very, very different jobs. And so I think that is very important, that level of flexibility and the level of humbleness to really be able to move across this layer and not get tripped by, you know what I did yesterday is works well also today and normally it does not.

Matt

Yes, but I want to get to the nitty gritty details to the concept that you have mentioned. And I mean the concept which is the tool that is pretty useful for you on the career growth side. You mentioned the live promo package. What is that and how do you use it?

Stefano Grossi

Yeah, yeah, that's a good one. By the way, I'm going to give you a shameless thing there. I am actually since I left Freshbook I am building a product. And that product is exactly what I'm trying to build is the solution to me spending 20 years of my life inventing tools to do this job. So I'm trying to get something to market that can actually support the flat organization and startup or scale up to do this job much better out of the box. And one other thing I'm going to put in the product. By the way, the name is Branco. Branco. AI so one of the things I'm going to put in the product is exactly what you're talking about.

A light promo package is something I used, I used like for every person in my organization. And I'm trying to push every individual contributor to really have one. So imagine when you want to get promoted, you get to the point where you are creating your case, you are building your case. In some companies you have to do interviews in some companies to set yourself, it's not coming. You have to build a document or a presentation. Now I'm asking people, put it in writing. Even if you just got promoted, start the next one, it doesn't matter.

You're going to want to be promoted. And the best thing you can do for yourself is analyzing the gap from where you are to when you need to be, analyzing what is missing, analyzing what are your superpowers and what's holding you back. And so I build the structure of a live promo package, which means you always work on this promotion package every month and you gather all the information as you go. When it comes a time to have a promotion to, to put up yourself or a promotion or work with your manager to, for them to put you up for a promotion, you have already the work done and normally test five areas. The first one is why you should be promoted. And probably when you start this document, that area is empty. The second one is why not?

And probably when you start promoting its fault and slowly you start scratching stuff and it's like, okay, I got this done, I got this done. And then it becomes a reason to promote. I overcount that thing. And then how well you fit your current role. So you normally would add in your company some kind of skill matrix or competency metrics and you want to know, where do you.

Where are you at? And then you want to know how well do you fit your next role? So what's the delta? What is what you're doing? Well today that's going to be different tomorrow. And then you want to have an error that has the feedback from others. Okay? And so very, very important.

If you keep doing this one for a year, it becomes so straightforward. And if you share this one also with your manager, with others, it becomes really, you know, clear and under the sun. And you know that you have an action plan that is working for you. And yeah, so this is one of the tool I use and it's lightweight, but we basically try to build it in a product that works with continuous feedback. Because the most difficult part is really to have good feedback that is timely and that helps you to build an action item and it helps you to build action items that are great in the type of work and the stuff you have to get done. So, basically, what Branko has has four pillars, which is hard skill, soft skill. It has what you have to get done and then it has your individual plans and it has a loop inside that keeps gathering feedback on top of all these four axes.

And it keeps providing you a even better action plan suggestion so that you can get even better at what you do. And it builds this action plan based on what you're going to do next, so that instead of having the very weird conversation about math, you need to improve your communication skills. And that's it. And we all leave the room and you stay there like, you know, a cow looking at the train and saying, what just happened? Instead of telling you that, I'm telling you, Matt, since we need to improve your communication, I need you to present to the team in two weeks your technical approach in the solution of the particular problem you're working on today. And you're going to do a video and you're going to do, and that is going to create so much more actionable item for you that are like, okay, I know what to do, I know my plan, I know what I need to get done and I know I can do it during my job. So it's not an abstract.

Go take a training and then come back in six months. Never apply it, and then we are good. It's not like that. It needs to be really is exactly the way executive coaches work with executive. They will go around, get feedback from everyone, they will synthesize it, they will look at your strength, look at what you need to get done, look at where you want to go, and then build the plan to get it done and in the job during the day.

Matt

So that's what I try to build. Amazing concept.

Stefano Grossi

Amazing concept.

Matt

Yeah. Yeah, amazing concept. Stefano, when do you plan to release a beta?

Stefano Grossi

I'm releasing actually the first bit. I didn't have the login until like 3 days ago. So we just built the core of the product to test that the integration with the AI and LLM works properly, to gather this. Like, I want it to be super lightweight. I want people to spend no more than like three to five minutes a week in giving feedback so that in the end of the year you actually have a hundred pieces of feedback that creates a trend, et CETERA So we tried really to do that core part. So to not have the drop off of people and not having really the power behind. So debate I think is going to be in about three, three, three, four weeks.

We are working on it for the last five weeks. So I think that yeah, two, three months to have actually people to be able to sign up would be good. And yeah, if you go to Branko AI, you're going to find either a waitlist or they're going to already add the sign up page. And it matters. It's a matter of days now. So I could wait for people to come on the board, but the waitlist is there. So you can go in and get, and get a waitlist.

Matt

Nice, nice. And taking like a step back. So the thing is like we discuss like how to grow the people. Right. But I think to grow the people you need to hire the right people. And I'm wondering in your case, do you have your own best practices? How do you, how do you look for those great leaders?

Stefano Grossi

Yeah, and I was, I was, I think that during, during an interview you can see it very well how much people are talking about their team. I think that that's, that for me, for a leader, that's the key. Like how many times I see the, I hear the word we. It's, it's really important even in stuff that they invent that they come up with like hearing the word we and during the fact that they, how they talk about their team. And when you ask them about the best, like the most, the most impactful thing they've done, for me, a great answer is I actually got every single person in my organization to the next level. I really think that the organization I left, it's much stronger than the organization was like two months before and three months before and six months before. And so for me it's like what I'm looking to leaders is how well can they get their team to grow.

And that's, you know, I cannot tell you exactly what are the theme, but the flags are. Yeah. How many times do you we. And when you ask them biggest accomplishment, they talk about outcome, they talk about what did they change in the business and they talk about how their people do that and they don't have to be the one doing all the work. So that's normally what I look for. Those are the signals.

Matt

And how about your own growth? Like do you have any tips and tricks or best practices? How do you grow yourself? How do you approach yourself?

Stefano Grossi

Yeah, so I always have, I always have my Own my own, my own promo package really. I have an action plan. I always try to keep my action plan with hey, those are the things I need to work on.

This is the business value they produce. Those are the steps I want to take, those are the dates I want to hit those steps and those are the small win I have along the line. So I always keep a live document of that until I have a product that can help me doing this. So that's going to be soon. But. But now I do it documents and I think other people Tip of tricks. If you want to go like more less specific about career growth but what I do to optimize my time, I have two massive tips that I give to everyone.

The first one is ditch all your lists and to do and stuff like that. Just use calendar, right?

Like a list. UA is like a backlog of 400 items, right. It's like you're never gonna get to the bottom 10%.

Just ditch it. I'm like whatever you do, whatever it's important. Put in your calendar. Now you have how much time are you going to spend on it? You have when you're going to do it and you're actually going to show you're going to follow through. And when and when you start moving stuff in your calendar out, it's so painful because it's going to allocate more time in your calendar. So very, very important digital to do list use calendar only. That's it.

And then empty inbox for me is a kind of a religion. So. So every item I have in my inbox is item that is waiting on me. So I know I'm holding someone back. Why I have stuff in the inbox and so my inbox is always really, really clean and that is really just to optimize my my time and my flow and just to make sure that I don't hold people back too. Yeah, those would be two tools. I don't know if that's helpful, but they work very well for me.

Matt

It's really helpful. But you know the one thing that interests me the most what is your, you know, the things that you are working on this year on your own growth. What is on this list?

Stefano Grossi

Oh wow, I have an inference list. No, the most important part I think it's for me it's about learning in this new world of the startup. It's really how much faster is the pivot and how much more difficult is to maintain something very stable for a longer period of time. So my communication towards the team and how do I approach the infinite seemingly change of direction that are actually not change of direction, but they are like just refinement of the information. So and the other pieces, for me the stable item is really about making sure that I can provide the why behind the thing. And the communication of the outcome that we want to achieve is crystallized and then very specific. I tend to really give a visual level thing and assume that everyone has the same level of understanding that I have.

And so removing assumption is really something I need to apply all the time. And so every time, every time I come off like when I come off this, I'm going to be like, did I make an assumption when I was. I have to do that. Right? So yeah, those are the things. Very, very important.

Matt

And the last but not least, the question that I'm asking all of my guests, and this is related to the book that you wanted to share with the listeners and me here is, you know, any books or conferences, podcasts that have been like, you know, influential on yourself.

Stefano Grossi

So I, I have, I, I have many. I would say I'm going to go from the most important to, to the, to the, to the one probably that is, that are kind of must and everyone knows. I think that a. One of the best book I've seen about product is escaping the build Trap. Melissa Perry that book is fantastic. It's all about outcome. It's all about.

I actually bought it for my entire executive team. I bought it for everyone in leadership position in my organization. And then every PM I actually ordered, I think I did the biggest order of that book to date.

But it's a great, great. Another person that I can't stop, I have a huge brain crush on is Simon Sinek. Everything writes, everything that kind of turns into both for me is like, you know, obviously start with Y is kind of the first piece. But very, very influential person and I think he brings everything back to a very first degrees and philosophical level. I like that. Another one, I would say what got you here won't get you there. Which is kind of a mantra that you need to live through, especially if you are in leadership position.

Yeah, I would say that's it. There are other two books that for me are very exciting because they have the same name and they're both good. They're called Accelerate. There's one from Jess Humble and the other one is from I can't remember, but One is about DevOps and the outcome of the DevOps movement. I think that for engineering leaders that's a must have. And then the Accelerate XLR8, I think, is written. It's more on the organizational structure and the fluidity on the organization's platform.

So I would say this one, this one out of five. Five is good. Good number. And many of these are podcasts, too. So I would say, I would say follow both.

Matt

Awesome. Thank you. Stefano, thank you so much for a lot of insight. Really meaty, gritty content, I would say. So a lot of tools here. I have finger crossed for your startup. And yeah, thank you for today.

Stefano Grossi

You're going to be a customer, right?

Matt

Yeah. Number one.

Stefano Grossi

That's it. He's already taken. That's taken. All right, Matt, it was great to see you.

And thank you so much for having me.

Matt

Thank you. Follow Matt and Leshek on link.

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