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Episode 1

Always take accountability

Guest
Ryan McMinn
Ryan McMinn
Head of product for Microsoft OneNote & Sticky Notes

Episode Notes

Taking Important Leadership Notes

Did you know that many historical impactful figures had some form of notetaking habit actively reflecting on their experiences? Research shows you forget 60% of the information that comes into you daily. It also shows that notetakers retain 95% of that information.

In this episode of Dreams with Deadlines, Jenny speaks with Ryan McMinn, the head of product for Microsoft OneNote and Sticky Notes. Ryan who has been with Microsoft for 13 years insists on being a good leader for his team and offering customers product value. He shares how OneNote has developed and grown as a product putting into consideration the target customer over the years.

Listen in to learn why you need to become a notetaker as it helps with reflecting on experiences which is what creates knowledge and wisdom. You will also hear the importance of learning by going through things first hand and gaining experience while finding ways to get over them fast enough.

“It’s very hard to do large things and if you don’t know exactly know where you want to end up, you can end up chasing small things instead of going after big things.” – Ryan McMinn (24:05)

What You Will Learn in this Episode

  • (0:12) Intro
  • (1:37) Learning to be a good leader that sets an example for your successor
  • (3:16) Ryan describes OneNote’s target customers as organized individuals and the set of organized people that exist
  • (9:42) The importance of taking accountability and serving others as a leader without imposing your will
  • (14:53) The principles of trust and product depth that contributes to OneNote’s value
  • (16:47) The strategy and paths to taking OneNote to the people as things continue to change
  • (21:45) Ryan explains how they measure Objectives and Key Results (OKRs) by building on small things to make big things that fulfill customers’ wants
  • (26:33) How and why they created the seven big things to look at as a team that helped them breakdown and actualize the OKRs
  • (32:00) Understanding people’s motivation and tapping into it through trial and error
  • (36:14) Learning to be what the team needs- becoming what is expected of the rule and not what you as a leader is comfortable with
  • (39:26) The best thing that ever happened to Microsoft- being humbled and finding a balance
  • (41:30) How Ryan has learned not to beat himself up when things don’t work out and not comparing himself and the products he creates

Relevant Links

The Full Transcript

Ryan McMinn (00:00):
There's some interesting research that we came across that showed you know, 60% of information that comes into you on a daily basis you forget within 24 hours. It's lost.

Jenny Herald (00:13):
Hi and welcome to Dreams with Deadlines, a podcast where you’ll hear real stories of trials and victories in business. I’m Jenny Herald, Chief Product Officer of Gtmhub. Gtmhub is the world’s most powerful platform for Objectives and Key Results or OKRs. In concept, OKRs are easy to understand but challenging to execute. Until now. Check us out at gtmhub.com to learn more. This is Episode 1. Joining me today is Ryan McMinn. He’s currently the Head of Product for Microsoft OneNote & Sticky Notes. Today, you’ll hear Ryan’s thoughts on steward leadership, how OneNote started with existence OKRs and evolved their OKRs process, why all of us should be note-takers, what is was like to revert a major decision—spoiler alert—it involved getting hit in the face with a pie and more. Let’s jump in. Welcome Ryan. I'm super excited to have you on the show.

Ryan McMinn (01:13):
Thank you. I'm very excited to be here.

Jenny Herald (01:16):
So the first topic I think we're covering today or I wanted to ask you about was the leadership mindset. So you've been at Microsoft now for 12 years, right?

Ryan McMinn (01:25):
12 years. Yeah. It'll be 13 years in June.

Jenny Herald (01:27):
Based on what I've, I've read from an article you posted recently, you've described yourself as the steward of Microsoft, OneNote and Sticky Notes. What has that journey been like for you?

Ryan McMinn (01:38):
I think it's one of those things I started my career in more consulting and in that way you're, you sort of learn in consulting that you're in service to somebody else. And so everything you're doing is to kind of make sure that someone else is successful and you often are not on projects for 15 years. You are in and you're out, you know, sort of doing those things. But my old business partner, Marcus, he had a bunch of really interesting philosophies around how to work and the output of those philosophies is some of the systems that he designed that I worked on when I worked with him back in, you know, 2002/2003 are still running company stuff today, same code, same system and it's a lot of that mentality I learned from my experiences with him of you know, you really want to take the long view and make sure where possible you're doing things that the next person that comes after you is going to appreciate you for.

Ryan McMinn (02:34):
I think that that was such an interesting experience for me coming to Microsoft where if you look at startups and I worked with a lot of startups when I was doing consulting, you're really doing something completely brand new and you have no idea whether or not it's going to work. And so there's a mentality you have around that. I think sometimes if you take that same mentality and apply it to something that's been in market for a long time, that people rely on and they care about and have an opinion about already, it can be a little dangerous. And so I found really taking the approach of it's a gift to be able to work on something that has such love and volume but it's also our responsibility.

Jenny Herald (03:12):
Who is that OneNote customer for you? How have you identified who that is?

Ryan McMinn (03:16):
Yeah, I mean that's been, you know, sort of a journey as well. I think it's very lucky with the product. Like one note that kind of launched in 2003 so it's been around a long time and we're lucky enough that we actually have customers that reach out to us that had been using it since 2003 so they've been putting in all of their thoughts and sort of their entire digital life into this product for such a long time. And so the sort of our path to discovering kind of who the OneNote customer is today, but also who could also be OneNote customers in the future. And it's kind of the balance that we work through a lot. A lot of it was just spending time on the product. You know, I find one of the things that I see with a lot of careers, especially in tech, is this need to move around a lot.

Ryan McMinn (04:04):
And so you see someone who will work at company A for eight months and then company B for a year and then company C for eight months and then company D for a year. For me, time is what really being immersed in something over time is what brings me understanding. OneNote is this amazing product for people who have a need to be organized so they can be organized by nature. That's the hardcore early adopters of OneNote. The people who are out on Twitter telling everyone about it. A lot of them are people who are organized by nature. So, when they open up a tool and they see multiple notebooks and multiple sections and lots of ways to organize, they're very happy and they get in and they enjoy it and they do amazing things with it and they help new people come in. And then you sort of have the next set of customers who are people who are organized by profession.

Ryan McMinn (04:57):
So, there's a lot of professions that are kind of have an organizational structure built in. One of the best examples is lawyers. We hear from a lot of lawyers that love OneNote, again, because they have a very structured, organized way of working that requires really being on top of everything. There's a real cost to not being organized. They open up OneNote, they see all the different capabilities, they're very happy. And then the third kind of group is people who are organized by introduction. And so we've had, you know, an amazing ability to be able to be part of the education experience for a lot of kids and a lot of teachers over the past few years. One of the takeaways that I've had from that experience is, you know, you get a profession like teaching that there's a lot of demands on your time and you're very selflessly doing this for other people.

Ryan McMinn (05:45):
It's one of the rare professions that I've come across where, you know, it's not uncommon for teachers to be spending their own money for school supplies. They're working super late at night to really perfect lesson plans and oftentimes the pay isn't commensurate to the amount of effort that they're putting in, but they're doing it for a larger reason. So if you, if you give a teacher OneNote just without any instructions, it's pretty overwhelming. They don't have a lot of time, they're very busy. They're trying to get the things done they need to get done. But if you give them a class notebook that already is built to map to the way that they work, it's got sections for collaboration, it's got sections for each student, they get it and they're excited and they can get in and get value out of it quickly and so, but they need to be introduced.

Ryan McMinn (06:30):
So, there's that set of customers that need to be introduced. And then the last set that we've seen that are closest to my heart, I think a lot are, are people who are organized by necessity. So they're, they're a bigger group of humans who for the most part are not organized and they've got their own tools. They use the notes app on their phone, they use pen and paper or they use Excel, they've got lots of tools to do things. And then something happens to them that there's a cost to not being organized. Whether that's they got to renovate a house, they have a new baby coming, they've got a new job. Sometimes it can be something like a medical emergency, something happens where they, the tools, they have no longer work and that point, there's enough friction in their life to go looking for something.

Ryan McMinn (07:18):
And when they find OneNote with that kind of problem, they really love it. And you know, we went through a lot of our five star reviews to kind of get a sense of the people who make it through and really like it. What are, what are they doing with it? And it's often those life moments that it helps them get through that moment. And then they associate getting through that moment with the tool. And then what we find is once they know how to use it, when they need a grocery list or they need a place to store recipes, so they need something more simple, they use OneNote because they already know it. And so those kind of four chunks are a lot of where our current customers are. And then what we're really doing now is how do we expand it out? Because you know, I believe that every single person in the world can be served by becoming a note-taker.

Ryan McMinn (08:04):
There's some interesting research that we came across that showed, you know, 60% of information that comes into you on a daily basis. You forget within 24 hours it's lost. And in that same research study, they found that note-takers retain 90 to 95% of that information that's coming in. Take any historical impactful figure, whether it's an actor, an author, a politician, inevitably you will discover they had some form of note taking habits, whether it was journaling there's some, they, they were doing something to actively be reflecting on their experiences. And that reflection is what kind of creates knowledge and wisdom. And so my belief is that the more people we can get to take notes, the wiser the world can become. And that means the product needs to meet everybody where they're at. And it can't just be when they need organization right now.

Ryan McMinn (08:59):
We need to find a way to, when they don't know they need to get to get them into that habit. And the wonderful challenge, which is what I love about working on an existing product versus a brand new product, is how do you expand the user base of a product to a new kind of use while still keeping the people who love it and depend on it for over a decade happy and content. It's a, it's a really interesting design and product challenge to navigate that. And that's what I find really fun to do because it's, it's hard. And it's, there's no pattern to follow. And that's what makes it exciting for me.

Jenny Herald (09:38):
Yeah, so to that point can you share with our listeners what your answer is to that question—Are PM's the CEO of the product?

Ryan McMinn (09:44):
Yeah. To me, I don't think so because I think if you look at most products, especially if you're a large company, there already is a CEO or there is an equivalent of a CEO and it's not you.

Ryan McMinn (09:55):
I think there is a way you can approach acting like a CEO that's from a service perspective, which is positive. You know, you are taking accountability because the CEO has full accountability. So if you read it and go, Oh, that means I should be fully accountable for everything. But oftentimes I've found people read it as I get to make the decisions. I'm the boss. And I think as soon as you voice those words that have that feeling you've lost because what you're really doing is everything you do is in service to others. If you really want to be a leader, the only thing that you own is accountability. Everything else should be going to other people. And anything that makes you think that you are somehow in charge or the decider and get to make all the decisions and it just is not, it doesn't create good behavior.

Ryan McMinn (10:46):
I found it creates a lot of people running around thinking, trying to make their own little kingdoms inside of other things versus trying to have the bigger picture. And I think if you look at a large company, one of the biggest challenges, and I've seen this improve tremendously in Microsoft, but still not where it needs to be by any stretch, is the ability for someone to lift their thinking outside of the box that they're in. And that box can be the product they're working on. It can be the organizational division they happen to be in. It can even be the company they're a part of. You know the best people that I've worked with have the ability to take a problem and and then really raise it up to not just how will this affect me or my team, not just how it would this affect my division or my company, but how would this affect the marketplace, the world like the, the higher you can lift that you're going to make better decisions and that really becomes along with you doing things in service for others versus just for your own benefit or your own product's benefit or your own company's benefit.

Ryan McMinn (11:53):
I recently read a book I really enjoyed called Extreme Leadership, which is written by a Navy Seal and it's an awesome book that you can get through really quickly because they break each lesson into three chunks, the Navy seal story, the principle itself, and then a business story. And you can just skip the Navy Seal story and the principle and just read the business stories and you'll get through the book in like 20 minutes. And when you read, when you read the business stories, it is for me anyways, it was like, the same feeling I get watching Silicon Valley. I'm like, ah, I know. Yeah, that's happened. Yep. That's happened. And a lot of what I talks about is sort of the underlying principles that are, that are part of that kind of military mindset around, you know, as the leader, you're accountable.

Ryan McMinn (12:40):
You know, I think they have a quote in there that says, "There are no bad teams, there are only bad leaders." And I really love that. I think the more you can take accountability, always take accountability. If something goes wrong, it's your fault. It doesn't matter whether you're an IC on a team that's giant or whether you're the boss, you know, the ability of, of a human being to go don't care who created that problem. It's my problem. I'm going to go, I'm going to go help. I'm going to go be a part of fixing it. I'm going to have that mindset of there's no, there's no them. There's just us. We're going to go figure this out, the best people always do that. And those are the people you want to work with. That's my experience with a product like OneNote too, because when you start, you are, you are not the first person.

Ryan McMinn (13:27):
You are the 15th person and you will not be the last person. And so it's very easy when you start to go, all of these previous decisions were terrible. What were they thinking? Why would they have done this? Why would they have done that? I didn't do that. Why am I paying the price for all of their bad decisions? And that's like a very human reaction when you come into the middle of something. And the work for me has really been, that's all my fault. It's all my problem. It doesn't matter who did it when it happened. I'm here now. I have an ability to make it better. So I have to take accountability for it. And I have to say it's mine. And you get that when you talk to customers, you know, you'll have a customer call you and make a complaint about something that's nothing to do with your product. It's to do with some other product at some other far part of the company. And I think as leaders it doesn't matter. You represent the company and so you have to take accountability for it too and, and jump in and help. There's, there's no place in my, my feeling there's a place for finger pointers. You're either part of the solution or get out of the way.

Jenny Herald (14:34):
Yeah. I think something that you and I have both talked about before are our personal core values. And I remember you saying to me that one of yours is to lead from the front. And oftentimes we also have a set of values or principles for the products that we build. What are some of the core product principles you have for OneNote?

Ryan McMinn (14:54):
For me, one of the biggest ones that we spent a lot of time focused on and thinking about with OneNote as far as the product value is trust especially because it contains a lot of unfinished things. It's a very lightweight kind of scratch-paddy product in some capacities and that of course it gets used sometimes within more formal kind of knowledge based scenarios as well, but that's probably the biggest one I think about is trust because people are putting, you know, their life's work, their team's work in there and they have to have the trust that that data is going to be safe and it's going to be reliable and when they need it they can get it. It doesn't matter whether they're on a phone or on someone else's computer, they know they can get to what they need when they need to get to it.

Ryan McMinn (15:39):
I think that's a big product principle. And I think the other one, which is kind of a, you know, a life's work for me anyways in terms of all of the products I've been on is how do you create something that's simple and complex? The depth of a product like OneNote has a lot of value except the challenge is exposing that depth makes it hard to get started. But if you don't expose enough of it, it's not going to be used for really important things. And so this is the eternal balance. And I experienced this when I worked on Microsoft Access, a little bit when I worked on Skype. It's that challenge of how do you thread that needle of making it easy to get started and approachable, but also deep enough to be able to solve real problems and use [it] for real important things. And so those are sort of the two big ones that I think about a lot with, with OneNote.

Jenny Herald (16:36):
So, if we were to zoom back for a little bit, right, 'cause we've been talking about the legacy and trying to think ahead of what the future might hold in those future customers, how are you defining your product strategy?

Ryan McMinn (16:49):
Really having a base understanding about who our current customers are and how do we continue to incrementally add value to them. And then on the flip side, how do we go introduce the rest of the world to note-taking and get them into this system. So there's sort of those two parallel paths that you have to be very careful don't stomp on each other 'cause they can, they can be in conflict sometimes. It's one of my favorite kind of military quotes that a friend of mine shared with me a long time ago, which is, you know, you have to learn how to live in multiple truths. And that's I think a case for a product as you try to transition it to a broader audience too is you have to live in those multiple truths where they have different needs. But you have to figure out how to serve both of them.

Ryan McMinn (17:33):
And hold both of those concepts in your mind. So a lot of what we've thought recently with OneNote is we've got a good core base product and we've got a lot of customers who love it, depend on it. You know, I'm consistently blown away with stories that come through of customers that have used OneNote and have gotten value out of it. It makes me very grateful to work on it. And then it also makes me realize, wow, how many more people out there are facing the same kinds of issues that we're not getting to, that no one's getting to and how do, how do I become part of that? And that's where a lot of our current strategy is thinking is Hey, the world's different today than it was in 2003 one one who came out and people are taking notes and their expectation of how they take notes and how they get started, you know, has been changing every year. And so how do we really make OneNote work great in those environments? Mobile is a big part of that. The way that you take notes on a phone and the ability for you to take notes on the phone is so different now than than it was seven years ago, two years ago.

Jenny Herald (18:40):
To that point, right. Part of our jobs is to create and keep up after a system of shipping, like we have this obsession with shipping because we need to make sure that that maintains itself, but we also have to balance that with delivering that customer value like you said. What does your system look like at OneNote in balancing these things?

Ryan McMinn (19:01):
It's hard. I mean I don't think like, I don't have like a, we've got an amazing system and it all works great. I think you sort of go back and forth because one of, I think one of the challenges I found is, especially with a larger group, you know, we've got a decent amount of people on the team over over a hundred people on the team and so, it's very hard to sort of map a very structured system, which was this is how we're going to measure it. This is what success looks like with also the nuance of, you know, irrationality of human beings and how things change all the time. And so what I spend a lot of time trying to do, and I, I don't know how successful I am, some days I feel like it's good. Some days I feel like it's not good trying to take the place you want to end up.

Ryan McMinn (19:48):
Right? And so you look at sort of two timescales, one much further, which is really helping the team and everyone you interact with understand why this product exists and what value it's supposed to bring. And that goes back to what I talked earlier about trying to, you know, make the world a wiser place. Trying to get as many people in the world, taking notes because we believe that taking notes will make your life and the people's lives around you better. So trying to take that part. And then also where do we think we could be in three years? Where do we think the landscape is? Where do we think the product needs to be three years? And then trying to connect the both of those things back to, Hey, I've been asked to go move this particular number or I've been asked to figure out how this particular part of the puzzle will be measured against, you know, where we want to go.

Ryan McMinn (20:39):
And what I've found is if the team doesn't see the endpoint, it's very hard, to have really good conversations about the tactical stuff and if they see the end point, then you can let some of the tactical stuff go a little left, a little right, a little left as they learn how to rethink, how to do things from being very much like, Hey, I like this idea, let's build it and send it out to, Hmm, I like this idea. Is it a good idea? How can I test it in the smallest possible way? How do I measure whether it's moving towards that vision or not toward that vision. And those are all things that I would say we're very much still in a learning phase about.

Jenny Herald (21:21):
Yeah. So to that point, like trying to look at a longer term view, like in your case three years, and then pull back to let's say this quarter because we're now Q1 2020, I know that you all use OKR, or at least have adopted them. How do you make sure that the things that you're tracking kind of makes sense with time, right? Because sometimes what we want to see happen, these outcomes lag of it.

Ryan McMinn (21:50):
Oh, for sure. I think that there's that aspect of it. There's also the fact that you know, a lot of the metrics that you track in terms of how you run the business, things like, you know, monthly active users, daily active users engagement, retention, those are things that, you know, oftentimes an a small, you know, five or six person engineering crew feature are not going to have a measurable impact on it at the scale of the entire product. And so you're sort of, you're, you're sort of trying to figure out how to, you get indicators for, for things like that. I think there are parts of our product where we're good at this and there are parts of product where we're really learning. And I think it, it maps perfectly in my mind to sort of the, the scale between art and science.

Ryan McMinn (22:38):
And I think this is the fascinating thing about the transition of the way software is being built to be more data informed. You know, whenever you have transitions, you generally swing from one end of the pendulum to the other end of the pendulum. You, you rarely ever go from one end of the pendulum to the perfect middle. It's always this kind of back and forth that happens. And so I've sort of watched going from the idea is king, whoever has the best, boldest idea is what we'll build a ship and now we'll see if people like it. You know, I think I would, you know, my analogy for that is like, like a late seventies double album concept record. You know, like we're going to go into the studio and we're going to just make this amazing thing and three years later we hope people are going to buy it all.

Ryan McMinn (23:23):
And then on the far end of the other spectrum you have this really fast iterative, let's just try a bunch of things and measure it and figure it out thing, which has really taken over in a lot of places and I have a lot of issues with that side of things too because to me that feels a lot more like touring a record. You know, you make this record and then you go tour and touring is amazing, feels great because you're out in front of a crowd every night, you're getting instant impact. You can try tweaks to a song, you can see if the crowd reacts like the same way that a comedian will build up a standup specials. They sort of just keep going out and trying and trying and trying and sort of iteratively built this thing up. What I find in that that method in its purity over on the far end of the pendulum is it's very hard to do large things and if you don't know exactly where you want to end up, you can end up chasing small things instead of really going after big things.

Ryan McMinn (24:20):
So I've lived through both of those ends of the company from when I first joined in 2007 that's the way we built office. It was the concept album, you know you would work on it for two and a half, sometimes three and a half years. You would release it. You wouldn't really know whether it was working or not because of how long it took to deploy for another year and a half. And then by the time you, by the time you found out if that feature you made was working or not, you were already halfway through building the next one. And so it was very disconnected. But then I see what, how a lot of teams have adjusted to this more data informed way. And then they're just doing a bunch of small things, trying to go as best they can. And it's not adding to anything.

Ryan McMinn (25:03):
And it also burns people out. Like, you know, that's one of the things that you can't go tour a record for four years, you know, you're out on the road, it's too intense. And so you have to try to find that balance. And, and that's what I'm spending a lot of my time thinking about now is how can you create the outline and frame of an amazing concept double album. Because what customers want is an awesome concept, double album. They just don't want to wait three and a half years for it and they don't want it to be wrong, you know, but, but they want it. So how do you take that? How do you do just enough of the framing of that album so that the team can see it, but then build it in a, in a track by track song, by song, iterative learning way. So that you might not end up with the exact outline at the end, but you are building towards something that's bigger than, than just the pieces. And that's sort of where I, I think a lot about now is how to do that. Cause that seems like a very fun challenge and I haven't seen a lot of people doing that successfully. And so that makes me interested in trying to see how to do it.

Jenny Herald (26:10):
Trying to figure out what that concept album should sound like whilst cutting it back song by song really means just taking this really big thing and breaking it down into sizable bits that are consumable. Right. And it also means then you need to be tracking and monitoring as you go. Then how are you as you're thinking through this now, keeping track on what matters most if we're talking from a data informed perspective?

Ryan McMinn (26:39):
So, what we ended up doing, you know, was we have a set of OKR sort of at that, at the team level. But they're very broad cause it's a large team. And we're learning. And so some of them are very clear like, Hey, we need to move our, you know, cost per user on the service from this number to this number because that's our target. So some of them are very straightforward. You can go run at it. Some of them, because we're entering, you know, are writing brand new songs. We don't know. They're more existence OKRs, like we sort of are picking a date and a time and saying we need to have something by this date and time. So they're, they're more a forcing function to get working code and iterative stuff happening. And I think those are my least favorite.

Ryan McMinn (27:28):
But that's the learning process we're going through. So what we ended up doing was between, the kind of high level OKRs and what people are actually working on every day. We sort of created the, this thing we call core projects, the sort of, you know, the seven big things that we really want to deliver as a team. And, and we created those. And then a lot of the work is driven around those. And what actually sort of happened, not intentionally but pretty naturally was once we started getting those going, those started to feed back into the OKRs. So we started to then break down the OKRs to more granularity based on what we were doing with the core projects. So we started getting better at making the OKRs more actionable, more understandable, higher resolution. But it was hard for us to do that without going through this intermediary step.

Ryan McMinn (28:19):
And I don't know whether or not that is a long term thing or a short term thing. Oftentimes I've found in my career that sometimes you need a certain process or a certain way of thinking to unblock something and then after you've unblocked it, you don't need it anymore. Sometimes you need it over and over, over again. What I love about OKRs is they really feel like an evolution of past ways of thinking versus this completely like new thing. And I think the challenge that I've found with them is how do you accept the fact that they are another lens of looking at the same set of human problems? Like why are you doing what you're doing? How will you know whether it's working or not. There are very long running fundamental human problems about how to build anything. So how do you accept the fact that they're built off of the past?

Ryan McMinn (29:18):
Look at them in a new lens. Cause I think the thing that I've noticed the most and I've been guilty of this for sure is you end up taking the last methodology you used and just mapping it to the current one. Every single team that I've seen do OKRs including myself, the first thing you do is take your old smart goals and you just rewrite them, right? And you go, Oh I got okay ours now. And like I watched this happen all over the place. And then, the second thing I see happen with OKR is a lot is you'll rewrite the ones you already have and then you have like a million of them. And so you'll have some PowerPoint deck that has like 28 items per slide with, with a little 0.8, 0.7, 0.6, 0.8, 0.9, you know, for each how, how people are tracking.

Ryan McMinn (30:04):
And then I'm like, well now I don't even know what's going on anymore. And so that's also this transition period too. I think there's no shortcut to learning. You have to learn by doing and failing, you know. You can learn a little bit from what other people do, but oftentimes you need to experience it. And you know, I feel the same like, like the greatest lesson that I've been learning right now is being a father of a second child. Because if there was some mental shortcut for me to have had the same lower level of anxiety around the second baby sleeping through the night, not being like waking up every 20 minutes and like checking to see if they're still breathing like I did with the first one. If there was some mental way to do that, Oh, it'd be amazing.

Ryan McMinn (30:52):
But there isn't the only, it's just experience. You go through it and then the second time you go, ah, I learned a bunch of stuff and now I don't need to do this and that, but it wouldn't have mattered how many times another father had told me, dude, you don't need to do that. I still would've done it. I needed to go through it. And that's what I watch teams go through. The same kind of thing is that, so what I spent a lot of time thinking about, and I don't know how successful I am in this either, is how can I push through that first time as fast as humanly possible? Like how can we just get something going? Because I know the first time it's going to be rough and I know we're going to learn a lot. And so how do you just get the first time over with, how do I get to number two as fast as I possibly can, but that it's that same thing for work is, is whenever, whenever I'm facing something that's new and I don't understand it and I don't know it, how can I help get me in the team through it the first time as fast as possible.

Jenny Herald (31:49):
Yeah. So I think that's really hard because some people really don't respond well, right. To being pushed or failing quickly. Right. And as time goes on and we start to see that things aren't going as planned, how do you keep people focused and motivated?

Ryan McMinn (32:06):
Yeah. That I would say is the most fun and challenging part of my job. Because, you know, one of the people I used to work for previously, who you know, Laura Butler, wonderful, wonderful human being. She had this great saying that she used to say, which I love and I use the all time now still, which is, you know, if you look at engineering the people that self select into that field tend to be people who want to go into a room, close the door and work on things all day. They actually don't want to be around people. That's why they picked engineering. Yet that is the job. The job is people. And so it's this interesting dynamic of you're trying to motivate a very diverse set of people who all share one thing in common that they don't really want to interact with people if they can help it.

Ryan McMinn (32:53):
And that's just this fascinating thing that everybody wants a system that they can just turn on. It will just work. And I think the thing that I love is trying to understand the motivations, the diverse motivations of a group and then how to navigate those motivations in order to get the best out of people. Because, you know, every team I've worked on has one share thing, that's always the same. Everybody's coming to work, wanting to do their best to be their best. Especially when you're at, you know, companies that are very hard to get into, like Microsoft, people fight to get in. They are coming here to want it. They want to do their best. They want to be driven, do their best, they want to perform. It's about how do you tap into that and if you've got a hundred people, you've got a hundred different ways that they want to be pushed and you've got to figure out how to navigate that.

Ryan McMinn (33:43):
And I think you know, a lot of it is trial and error and trying things and also being okay with you know, we went through a thing this past year where we reversed a large product decision that we had previously made. We were in the process of trying to move everyone from one version of OneNote on Windows to another version of OneNote on Windows. And as we got deeper and deeper into it, it became clear that that just wasn't a path that was going to work. And so we reversed it and we're bringing back the other version. We're going to have both versions and support both versions and, but one of the things that we realized the team needed was a bit of a release on that too, because you, you know, you're a human and so when you reverse something, you want to blame somebody.

Ryan McMinn (34:27):
And even if the people who made the original decision are long gone, that doesn't matter, you still have that feeling in you. And so what we ended up doing was as part of our kind of give campaign for charity, we let anyone on the team come hit us in the face with a pie. We called it, we called it a, I told you so. Right? So we were able to like, you know, cause the engineers, a lot of the engineers and the PMs, the for years they've been saying, what do you, what are we doing? And so we thought, okay, let's figure out a way to, you know, even to release that and let them come. And it doesn't matter if I personally was 10% responsible, 100% responsible, it's not interesting. I am in the role now of being the head of product.

Ryan McMinn (35:10):
And that role has a set of responsibilities and accountabilities and the role is constant. Who is in it is temporary. And so a lot of what I think about is what are the responsibilities of the role? And, and that's what I have to try to live up to. And I never live up to it. But, but I try every day to live up to what I think that role needs to do and I try to do my best job to fulfill the duties of that role so that whoever comes after me is hopefully happier with the way things are when they take over than I was when I took over that role.

Jenny Herald (35:48):
Sure. So you mentioned that the team needed a release because there was a, a decision that was made a while ago, whether or not you made it was immaterial, right. But they needed some human element to this. I think similarly when teams are pushed right and they work through all of the learnings and then finally something works out, then the team can take a pause and look at it and feel good about it. How do you capitalize on that moment?

Ryan McMinn (36:20):
That is such a wonderful topic. I think that's an area where I would give myself a very low score for, I think it's one of those things that me personally, I've always had an adverse reaction to over celebration. And what I've sort of discovered in myself over time is I've allowed that to remove opportunities to celebrate on my team because I personally have a very visceral reaction to people celebrating people, celebrating things that I think are nonsense. You know, if you work at a large company, you often will get these reply all things that happen. And so someone sends out an email saying, Hey, we just made this amazing number. And you know, when you read it that underneath that there's a lot of caveats, you know, like yeah, you made that number but you tanked your retention and you ignored this other thing and you know.

Ryan McMinn (37:21):
So you sort of see through the message. But then what ends up happening is all the way up the chain, you start to get the wow, amazing, you did great, you're the best. I love you guys. And there's something about that that just has always rubbed me the wrong way. And so what I've been spending much time on recently is thinking, yeah, but I'm also robbing the team of being able to celebrate the amazing things that they're doing. And so I've been actually thinking a lot recently with, with, you know, my peers on this team is how to really craft milestones and celebrate them and be okay with it being a little uncomfortable for me at first because that is an instinct that I have is to sort of, you know, maybe it's from my Scottish father, you know, you, you don't wanna, you don't want to say you're too good.

Ryan McMinn (38:13):
You don't want to, you know, you don't, don't, don't think you're better than anybody else. You're not better than anybody else. Just stay quiet and keep your head down and do the work. You know? And I think what I'm learning as I, as I try to become a better leader is it's not just about you, it's what the team needs. And so like going back to what I said earlier, it's really trying to take the mindset of what's expected of the role, not me, Ryan McMinn, human being what's expected of the role. Okay. What's expected of the role is a bit of cheerleading, so I'm going to have to find that in myself and maybe something that I wouldn't naturally do in all cases. Although I do like a good cheerlead once in awhile, but that's, that's this journey of figuring out what does the team need and not just what I'm comfortable with.

Jenny Herald (38:59):
Yeah. I think we spend a lot of time thinking through the scenarios where things did not go as planned because that is more often the case, right? We experimented, we tried and it didn't work out and we focus on this process of reflection and learning and sometimes in some organizations I've heard like reprimanding, right? How does that look at OneNote as you're looking through things, you tried something, it didn't work. How do you all handle those situations? What are you looking at?

Ryan McMinn (39:33):
Yeah, I mean I think, I think like one of the things I noticed, this is a Microsoft thing, at least in my experience at Microsoft, and it could be very different in different parts of the company. But when I, when I joined office, you know, 13 years ago, I expected a lot more arrogance and confidence and, and I think, you know, I joined at a time that I feel like the company had been beaten down pretty heavily by the Department of Justice stuff, which is, you know, from my personal opinion, one of the greatest things that ever happened to the company, the only way for a human being to transition from underdog to steward is being humbled. It's incredibly rare for someone to have the self reflective ability to do that without being humbled. So you kinda need to be humbled. And I think that was great.

Ryan McMinn (40:21):
But the interesting thing, again back to that sort of pendulum swinging concept is when I joined, I was surprised at how, how people thought the products we worked on were crappy and not good and how hard. Like people were. Like people always were like, it's not good enough. That's not good. Everyone else outside of us are doing things that are better. We're the slowest. There was this real sense of like, be really humble and don't, don't think you're better than anybody else. That I think was the reaction to thinking we were too good. And then getting sort of, you know, told by the government that we had gone too far. And then I think the balance of trying to bring that back and navigate that has been this interesting thing of there are pockets where people are really good at reflecting on what's not working. There are pockets where people are really good on reflecting on what's working. I have not found a, you know, a great system to balance those two things other than just continuing to try to find examples of what's working and spread them, you know.

Jenny Herald (41:25):
You've, you've had an amazing career, a lot of experiences. You've shared a lot of nuggets of wisdom so far. Well, what did you wish you had known when you started out?

Ryan McMinn (41:34):
I think, I think if I could give advice to the younger version of myself, it would be to, to try and increase the lens of time. I think there was this great expression that Steve Ballmer said a long time ago, I can't remember what project it was around, but it was something along the lines of like, hurry, but don't rush. Which is the kinds of expressions I love because they're in conflict with each other. You know, like isn't hurrying and rushing the same thing. But trying to find that balance of, you know, when you're young you want to get a lot of things done and you want to put your name on things and you want to make and show progress. And I, I found as I got older, I understand that things take time. But that doesn't mean you shouldn't be making lots of action in the short term.

Ryan McMinn (42:25):
But it's that balance of those two things of like, Hey, sometimes things take a while to figure out, don't beat yourself up if things don't, aren't perfect right away. And, and I think the other one that I would give to myself as I was younger, and this is something that I try to tell myself every day, it's one of the things I try to repeat to myself is try not to compare yourself with others. And that's a statement as a human being, but also as a product. You know, when you look at other products you can, you can use them as inspiration, but as soon as you start getting into the world of comparing, it's just a very unhealthy place. There's no, there's no benefit from it. And you watch something as simple as the effect of something like Instagram on, on kids who are now comparing their own daily lives with the fake best version of their friends daily lives that aren't actually the truth.

Ryan McMinn (43:20):
And then feeling bad about themselves because they're not doing as cool things that their friends are doing, but their friends are making up the things they're doing anyways. Man, it's, it's a lot of personal work to, to think about, but it's an area where you look back and go every single time I fell into that trap, it was a mistake. It never ended up being good for me. Trying to avoid comparing yourself against other people, other people's success and trying to take the longer view of things. And, and really look at your career as a career, not this week, next week, next month. Like trying to look at it from a larger perspective I've found would be advice I wish I could have taken earlier.

Jenny Herald (44:03):
That's advice that honestly I could tell younger Jenny as well.

Ryan McMinn (44:07):
Yeah. And I think like we recently went through this values training at the company. A really interesting bit of training about sort of just trying to, you know, Microsoft's going through this transition of, of trying to really push a, a culture first approach. How far can we really get in terms of improving the cultural aspect of what we do. And, and I love that. And part of what was in the training that I liked was, you know, they listed out a bunch of these attributes that were good, good examples of culture and then also bad examples. So you sort of get a sense of like, and you know, the, the exercise was when I'm at my best, I do this set of things when I'm at my worst, I do this set of things. And it was just a reflective exercise. And one of the things they said during it, which I really stuck with me was, this isn't a list of values to go put on other people.

Ryan McMinn (44:59):
Like this isn't a tool for you to go, Hey, Johnny's not living up to value X. And Jimmy's not, it's not about that. It's about you reflecting about yourself and how you are living into those values. And I love that concept because what you have complete control over is your actions and your behaviors and your attitude and the way you react to things. And I, I love any exercise that I get to try to live into values and focus on myself. And, and if I can make myself better, maybe I have a shot at making someone else better, but not focusing on what other people are doing. Really just being focusing on what you're doing. How are you improving? How are you getting better? How are you holding yourself accountable? That's for me, the work and it's, I feel it's for me, it's amazing and I'm incredibly grateful that I get to come to work and work on myself and I get paid to work on myself and try to become a better human being and try to improve the lives of the people around me, which hopefully will help improve the lives of the people.

Ryan McMinn (46:02):
The product gets the touch.

Jenny Herald (46:04):
Well, let's hope that that's a thing that happens for all those that are listening today that build products, even if they're not that we're just trying to improve ourselves one step at a time every day.

Ryan McMinn (46:17):
Yeah.