Five Mistakes to Avoid in Your Product Career with Jackie Flake

Matt Paige: Today we’re chatting with Jackie, founder of Option One Partners serving companies through technology and product consulting. And this year she just launched Product X Agile, an on-demand training platform for product managers. And agileists and product and Agile are two of my favorite topics, Jackie, so you already got me one over there. She’s made the list of Atlanta Business Chronicles 40 under 40. So she’s a local Atlantian, which we love here at Hatch Works where we’re founded. And she believes that product management is the key to changing the way the world works, plays and connects. But welcome to the show, Jackie.

Jackie Flake: Hey, Matt. Thank you.

Matt: Yeah, great to have you on and I’m excited for the topic we’re getting into today. So you got a fun one for us. Today we’re gonna get into going deep into the five mistakes to avoid in your product career, as Told by Jackie, who clearly has a lot of experience and a lot to say here. N PS number four is my favorite, so make sure to stick around for that, but without fur further ado. Let’s jump into it. Let’s I feel like we need a drum roll or something. Maybe we’ll add that in, in post production, but what’s number one? Hit us with number one.

Jackie: Okay, sure. Yes. So I created this list because I have made a lot of these mistakes in my own career and I also see a lot of my clients making these mistakes. So very common. Yeah. And things to avoid. So number one is simply believing that you are not strategic. I. And so this is something I really struggled with early in my career as a product manager, and it comes down to three things. The first one is just the simple fact that you don’t know how to be strategic or you think that you don’t know how to be. And I think as product managers, We put this pressure on ourselves. On ourselves. We should be having these light bulb moments that are creating multimillion dollar ideas, right? Like the next Uber, Apple or Amazon. But really it isn’t about that. It’s about understanding how to look at both qualitative and quantitative data to inform product decisions. And while you’re, may not be building the next Apple or Amazon, you’re working on really interesting B2B, B2C, products, and those things can all benefit from just learning how to do discovery work and understand analytics and insights. Okay.

Matt: I love this one cuz when I first saw the list, this one like hurt my heart a little bit cuz I love strategy so much. But the way you’re framing it, it’s not that. You don’t need to be connected to the strategy. Understand the strategy, but don’t be burdened by like the whole company’s strategy on your shoulders, in other words. And it’s like, how do you exactly translate that into product, like you mentioned discovery. Go a little bit deeper there in terms of how you think about discovery.

Jackie: Yeah, so discovery is also something that is a really scary word for product people at times. They know they’re supposed to be doing it, but they don’t know h how to go about it, how often to do it, they know they’re supposed to be talking to customers, but when do you talk to customers? How often and how do you interview them and. And there’s so many different ways to do that. So I always encourage my clients and people that I’m coaching to we learn different discovery techniques and then we just practice using them. Because as an analyst at heart, I believe in experimentation as well. And that absolutely applies to product discovery too. You gain learnings and you iterate on them, and it

Matt: starts with talking to the customer. Any this is off topic, but any fun. Or funny stories talking with customers or doing discovery from your past experience or any my interesting nuggets from, I’m sure there’s too many to even name.

Jackie: Yeah. Yeah. Probably, I can’t think of a thing, anything specific, but probably like coming into a customer interview thinking, I’m gonna nail this. I’ve got all the right questions and just feeling so shut down by all the questions I’m asking and thinking like, I am getting zero insight into this customer’s head right now. Yeah. Things like that.

Matt: Yeah. And I think it’s interesting too I’ve been in discovery calls where, It goes a completely different angle than what you thought it would and that’s why you have the discovery is to actually Yeah. Understand how the customer thinks, how they tick. Yes. Such a big piece of it.

Jackie: Yeah. Okay. So that’s exactly,

Matt: so that’s number one. Let’s jump to number two.

Jackie: Okay, so number two is another huge pressure that I put on myself, and I think this is gonna maybe ruffle some feathers when I say this, but it’s believing that you have to be technical to succeed in product management. Okay. And so what I mean by that is, what is being technical? Like, how technical do you consider yourself to be, Matt?

Matt: Yeah. Not as technical as the developers on the team, or as much as I think I should. It’s like that imposter syndrome. If I’m working on a Yeah. Technology product, I feel like I should know how to like code and get in there. So I, I love this one. I totally

Jackie: get this. Yeah, exactly. But it’s that. Being technical is such a range and you hit the nail on the head. As product managers, our job is not to be doing the coding, right? Yeah. Our job is to understand what our customers want and need and build products that delight customers under the constraints of our business. And so I think this is an industry debate and I really despise when I see job. Job descriptions that are titled, or roles that are titled Technical Product Manager. Because now you’re eliminating a really big part of the market who are just gonna assume that they can’t apply for that role because they’re not technical enough. And unless you’re building, a heavy backend or API or database product, then I think as long as you’re a PM that. Knows enough to be dangerous. Our jobs are to understand what the technical constraints and abilities are of our product is, and then be able to translate those in layman’s terms to our business partners and our customers. And that is the skill that a product manager needs. Not necessarily being technical. And as you and I both know, as we’ve gone throughout our careers you pick up tech jargon and lingo and you learn as you go. So being, knowing enough to be dangerous is important.

Matt: Yeah, and I think you hit on the big point there. It’s being able to connect it to the business outcome. I feel like that’s such a big critical role of the product manager is understanding the business outcomes that they want to achieve and helping drive the roadmap, translate that for the team delivering. Cuz everybody has a role on the team. And as product manager, it’s not getting into the code per se.

Jackie: Exactly. And here’s my little tip about Yeah. How to get through that as a product manager is, I always like to say, this is what really helped me in my career. I would find a developer on the team or someone who’s extremely technical on the team, and I would, they would become my buddy and they would not make me feel stupid for asking questions. And so I always knew that when I was with that person, it was a safe space. And if I didn’t understand something, technically I could ask them to break it down for me because we’ve all worked with, more technical people that make us feel small for not knowing things that we shouldn’t know in the first place. So finding the developer that doesn’t make you feel stupid is a really good trick.

Matt: Okay, I want everybody to pause if you’re like listening passively, that is such a big point there. Find the buddy on the team, know how to network and find that person that’s like your your what’s the word? Your co-pilot or something Exactly. Within the team. Exactly. I love that. Cuz they can help translate stuff. And maybe now it’s generative AI as like the next evolution of it. That’s a whole other topic. But I’m curious though, what’s, what is the line? Because I’ve like you, I’ve seen some product managers that have no technical expertise and I’ve seen those that can actually be dangerous. They understand how, APIs work, how they can view the code. They’re not gonna get in there and write it, but they can start to understand the logic behind how things are developed.

Jackie: Sure. Yeah. And a lot of times the more technically you are, that can serve you very well, but then there’s times where it can hold you back. You do have a handful of product managers who came from an engineering background and wanted to transition into product management so that naturally they are gonna be pulled to wanna look at code and maybe even write code. But not to say you need to stay in your lane, but you need to be able to do your job and do it well. And with that comes focus. And so if you’re trying to be everything to everyone, then you’re not gonna serve anyone well or your product

Matt: well. Yep. You just hit one of the core elements of strategy right there. You can’t be, your product can’t be everything to everyone, and you yourself cannot be everything to everyone. That’s great. All right, then we’ve hit the first two. What is number three? Give us number three.

Jackie: Okay. So number three is only playing the role of pm. So I know we just talked about being focused in your role, but at the same time when When you are just a PM and you don’t understand how any of the other roles work, then you aren’t able to be a more effective and well-rounded product manager. So what I mean by that is we always talk about in product that we need to have empathy for our customers. However, we rarely discuss how we need to have empathy for our teammates because we cannot build a product in a silo as an individual. Yeah. Taking on other hats allows you to learn tactical skills to be more effective and well-rounded in addition to driving empathy for your teammates. And so the roles I always encourage my clients to learn how to do is QA because. First and foremost, you have to know how your product works and the only way to do that is to QA it up inside and out. And then, wearing your scrum master hat. I grew up in the Atlanta startup scene, so I didn’t always have the luxury of having a well-balanced product team. And so a lot of times I had to run the agile ceremonies and I had to report on the team performance data and product performance data. And so that forced me to learn how to facilitate effectively, how to block out for my teammate. And I think that’s a really core skill that you can take into any role in your career. I say, learn how to wear the dev hat, but what I mean by that is just to try to put yourself in a developer’s shoes because the way that they have to learn how to solve problems through technology and coding is a very different way of problem solving than how you and I approach problem solving. Yeah. Understanding dev and the challenges they undergo in their jobs is important and drives empathy. Other bonus roles would be learning the product design role because again, I didn’t have the luxury of having a fully balanced product team, so a lot of times I’m the one creating the wire frames and drawing out the wire framing. Yep. Yep. Totally. Scary if I look back on the ones I’ve built. And then just also just understanding how customer success and sales work together, and those are the frontline people. In your organization a lot of times, and when you don’t have access to customers, they do. So making sure you’re building those relationships with those people is really important. And then another bonus role would be product marketing. Because if you’re not involved in the go-to-market strategy of your product, then you can’t influence that function either.

Matt: Yeah. And for anybody in product they probably get this or somebody thinking about getting into product. That, that sounds scary because you’re talking about almost every area of the organization. But it’s true though. Like that product manager, I’m sure you’ve heard it before, they’re kinda like the CEO of their product, so they have to have tentacles into these different areas. And I love the way you put it, empathy. In two of the roles you mentioned, the developer side and the design side. One thing that I’ve. Notice painfully through my own experiences, again, make friends with them and get them in the process early on. Because if you’re defining things up front and then handing it over to design to do something and then handing it over to Dev to go build it, you’re in this kind of like transactional output focus. But engineers are super smart for a reason, and if you can bring them early on, They may have a different way of solving the problem that you have. Knowing how the thing is architects, I love getting them upfront in the process.

Jackie: Yeah, absolutely. Product idle, Marty Kagan says, if you’re not bringing your developers Yeah. Early into the discovery process, you’re only getting 50% of their value. Yeah. Yeah.

Matt: Marty Kagan’s like a one of the main people we love here at Hatch works. Anybody that has not same, read some of his books, like just, stop what you’re doing. Go to Amazon. Go purchase both of his, I think he’s got two books right now. They have a couple others through Silicon Valley Product

Jackie: Group, but yes. He’s great. Yeah. I have the opportunity to meet him and work with him. No way. December. Yeah. Really it was awesome. It was good. Good.

Matt: Deeper on that. I’d love to, I’d love to hear more about that.

Jackie: Yeah. Marty Marty and I agree on the same thing, that there’s not enough product co management coaches in our industry. And so he invited 50 product coaches from around the world to New York City in December for a two day workshop. Wow. Okay. Just to network with other product coaches so that he could then recommend them to his client. And but it was also work shopping, learning from the best. He brought the entire Silicon Valley product group team and I was fortunate enough to be selected to go as a product coach and meet him and work with his team. And I’m still on Cloud nine, and that was five months ago.

Matt: Wow. Jackie, why was that? You should have gave me that as part of your bio. That would’ve been the ultimate should have book like I’m best friends with Marty Kagan, that, that should have been the intro. I would’ve

Jackie: been that far. I don’t know if Marty would agree with that, but I still. I still look up to him so much.

Matt: Nice. That’s great. Okay, so we’ve hit the first three. Let’s do number four.

Jackie: Okay. Number four. This is very tactical in nature, but this is the inability to write really great user stories. And I say this is a mistake I see in people’s careers because if you as a PM are not able to write great user stories, or your team, if you’re a leader is not writing great user stories, then you are. Doing a lot of wasteful work upfront if we take all of that time to do amazing discovery and understand what our customers want and need, and then we don’t take the time to distill that down into the smallest unit of work to translate our product strategy and vision to our team, then the downstream effects of that are devastating to your delivery function.

Matt: Yeah, that, that’s your main mechanism of not your main mechanism of communication, but it’s your artifact in a lot of ways and having structure and I’d love to hear how you structure it, but it’s not just the as I want to do so I can X. There’s the acceptance criteria element. There’s all these different pieces that are critical in helping your developers, your designers. QA folks, you know everybody across the board, but I’d love to hear your thought on user stories and if you have a framing that you, you use in the process.

Jackie: Yeah, for sure. I love user stories. I love teaching people how to write them. And I actually have built, I’ve done several client trainings on user stories, and I’ve built a an on-demand course on user stories because it is so important to get a right. Yeah. But really what it comes down to is your job as a PM is to create a shared understanding of what the work is and equally as important, what the work isn’t. And so getting user stories right. Is re about removing assumptions and ensuring everyone is on the same page. Otherwise, we’re doing a lot of rework. We’re rolling back releases. We have unhappy customers. Downstream effects are just, very negative. And you’re not serving your team or your customers

Matt: yeah, everybody hates rework, or at least they should if they don’t. Yeah. And you hit on one piece there. It’s that shared understanding and. Knowing what to do and what not to do. It’s back to that empathy element for your team, because if there’s ambiguity, you’re leaving it in the developer’s hands to interpret, how they think. It should be interpreted. So having that clarity is important. And I’m sure like this is discussed in ceremonies, like your sprint planning or your refinement sessions where you get to have that discussion around the actual user stories and clarify as well, right?

Jackie: Yeah, absolutely. And what I hammer home to all of my clients is that I want you to share the user stories with your team at least twice, if not. Three times before they start working on them. Because you can’t just take a user story, run into sprint planning, throw it over the fence to your team, and expect them to hit the ground running, right? Like they need time to think through how they’re gonna approach it again as a developer, how they’re gonna problem solve it. They need to see it several times so they can iterate on it. And also, we’re humans, so we’re not gonna bring a perfect user story to the team for the first time. So we need time. For once the team pokes holes in it to go back and fix it and iterate on it and just work it and get it to a good place.

Matt: No, that’s a key lesson and I’ve been at fault of this. Your team should not be seeing the user story in sprint planning for the first time. That’s great. Especially with exactly different personalities on the team. Some people may prefer to, take time to understand something, think through it versus on the fly, so you’re not getting as much collaboration if you go that route. That’s great. Yeah, exactly. All right, last one, number five.

Jackie: All right. Number five applies to anyone in any career. This is just simply not meeting people where they’re at. And this one is really important as a PM because. Product management is, I like to say, is one of the hardest jobs because you have to get people to work for you that don’t report to you. And so that is a huge challenge. And I’ve seen people do it. Horribly, and I’ve seen people do it really well. And building those relationships with my team has really served me well in my product career. And just understanding that everyone has something to offer no matter if they have years of experience on you or, they’re much older than you or much younger than you. Just not making assumptions that you know more than them. And so I also like to say that, we assume that we need to find commonalities to connect with people. Like I have to, go play Dungeons and Dragons with a dev on my team in order to connect with that person. And that’s not necessarily true if I don’t enjoy that as well. Yeah. But it really is about developing micro connections and shared experiences and I have an example from From a job long ago. So I was working at a local Atlanta startup called since been acquired by Oracle and nice. We had a huge deadline. We were building a product for one of our clients, which was Sports Illustrated. And we were really running into Just this deadline with two weeks to go and we were not as far as we needed to be. And we did an estimation and the devs were saying, this is definitely gonna take us longer than two weeks. And so leadership had asked the team to work overnight until they could get the product launched. And so that was really hard pill to swallow for the devs, but they were agreeable to it. And so they were gonna stay. They stayed till three and four in the morning. We’d go home and sleep for a couple hours, come back around eight or nine. Get back on the horn and start coding again. Everyone else in the office left and would just leave these guys. To their loan summit. I was like, I’m the PM at the time, and I couldn’t leave my team. It was just I wasn’t, I couldn’t contribute to the quality of the code. I couldn’t contribute to the actual speed of the code, but I could be there to order them food, get them coffee, give them pep talks, answer their questions around the tickets and things and be there to review their work and. That time was really critical for us. And it really just, that created such a safe space for our team. And that’s an extreme example. We were up many nights in a row. And I lost years of my life not sleeping then. But that’s until you have kids and then everything and then,

Matt: yeah. I know we were just chatting right before this. Yeah. We both had some fun child, had a sick one last night and Yeah. A whole nother Exactly. But I love this though. And that story is such a great example. It’s, meeting people where they are, and I know you’ve experienced this, those teams that have that level of connection. It’s intangible. You can’t really put your finger on it, but they just perform so much better. Their, their velocity is so much higher the ability to get things done. It’s that connection and it’s intangible. But I’ve felt it on teams that had it and didn’t have it, and I’m sure you have too.

Jackie: Exactly. Yeah, you’re absolutely right. It’s about building that trust and just, like I’ve seen PMs that take that complete dictator approach where they just, hand tickets over build this devs can’t even ask why. Devs can’t even look at a roadmap or understand the big picture. And they’re not there to sit in a basement and code with a hoodie on, like they are there to do strategic problem solvers. That’s great. And so building that trust and building those safe spaces with your team will only serve your product better. Yeah.

Matt: It’s that servant leader approach. And yeah I love those that are not on video, can’t see this, but you actually have a. Kanban board, I mentioned this earlier. Yes. That you have a Kanban board behind you. And this is the Kanban board for, is it for your life or your work? You actually have a physical that just goes how far, you are a practitioner of agile and the product way of thinking.

Jackie: Yeah, for sure. I run my business on Kanban. I wanna be authentic to what I’m teaching my clients. All day long. And I know it works. Yeah. No, perfect. No, that’s the reason to use it. Yep.

Matt: So there’s the five. And just to recap, let me see if I can hit ’em all. Don’t put pressure on yourself to be strategic and let me know if I’m butchering any of these. Don’t put pressure on yourself to be too technical. Understand how to write a really solid user story, meeting people where they’re at, and the ability to wear multiple hats. And I think I got ’em a bit out of order, but did I nailed it? Did I sum ’em up there? Perfect.

Jackie: Nailed it. Yeah.

Matt: That’s great. It’s all right. So I want to try something new. We have not done this on an episode yet, but I wanna do a bit of a rapid fire round. We’re gonna test this out in the practice of iterate to improve. It’s one of that core values we have at Hatch Works. So let’s test something new out. So Rapid fire, I’m gonna ask a few questions and just give us your first thing that comes to mind. All right. First one, what company is doing product management right?

Jackie: This is a shout out to a local company here in Atlanta. The Home Depot is actually Oh, okay. I’m very impressed by their product transformation. I was I. Brought in to help them support their product transformation back in 2016. And they, just to see their growth since then has been amazing. They really focus a lot on discovery. They are very good at talking to customers and getting those quick feedback loops. They’ll go into stores, talk to customers, talk to associates who they’re building tools and products for. And I’m just so impressed by them. And you wouldn’t think that of a, a. A hundred year old retailer, but their tech Yeah. Tech team is doing awesome. That’s

Matt: great. That’s an Atlanta staple right there, home Depot. Yeah. And to your point, it’s like you, you think of those kind of older, large enterprises as not doing this well. So that’s great that’s an example of one that is, I feel like I’ve been living at Home Depot lately. We just laid out mulch across our whole house and Yeah. Hey,

Jackie: I almost over the

Matt: weekend still hurting from it. Yep. Exactly. That time of year. All right, number two. Who is inspiring you right now in terms of the product management community? An individual. I think I may know the answer to this one.

Jackie: Yes. All right. So my first, we talked about Marty already love him. I always will or gimme somebody else. Honestly, it is probably the career changer. I, like people who I work with a lot of career changers that are coming from other disciplines or industries moving into product management. And I really, I’m really passionate about coaching them into product. I work with a lot of former teachers, former nurses who are making that transition Oh, cool. Into technology. Cool. And when you think about it, those type, those people that are coming from those types of industries, they have all the soft skills they need to be successful in product or in an agile role, right? They care about people, they’re compassionate, they want people to succeed and do well. They’re used to moving things outta people’s way so they can succeed. They, they know how to talk to people and make them feel good. They know how to teach and educate. And I would say career changers who are, they’re just so brave to take that leap. And to learn something new. And, I find that so inspiring.

Matt: I love that. Okay. So you took the angle of a persona, a group of people. That’s really cool. I like that. Yeah. All right, next one. This is one I’m really interested in with everything going on right now, but what’s your take on how generative ai, G P T all, everything LLM will shape the discipline of product management.

Jackie: I’m really excited about it, just like any other new technology. I think learning how to use it to your advantage is what you have to do in order to succeed and, yeah. Have growth in your career. And I, what I would say is for product managers to figure out how to leverage it and use it for the things that anyone can do. And then, Still focus on the things that only you can do and not try to, fit it into a mold of something where you’re thinking through strategy or your ability to do discovery or your ability, like to connect with your customers and stakeholders. Like AI’s not gonna replace the ability to do that.

Matt: Yeah I love that kind of co-pilot analogy there. And we’ve started testing it, actually helping write user stories. And it’s, a big part of, it’s the prompt and what background you give it and all of that stuff, but it, yeah, it quickly iterates if you give it the right structure, based on, you mentioned you have, I think, some courses related to this. If you can prompt it, the right structure, it can give you something good to work with. And obviously you gotta fine tune it and all of that. But we’re starting to play around with some of that at Hatch Works now.

Jackie: Yeah, for sure. And I’ve tested it too in user stories and I think it can absolutely, make you more effective, but even you have to understand how to break it down and, cause it really wants to bulk up the acceptance criteria.

Matt: Exactly. Yeah. Yeah. And that’s it’s an art and a science I think with prompting as a, we’re starting to learn and that’s the key. I don’t think the product manager role. Ever goes away. I think it gets enhanced by generative ai, but I think it’s still gonna be one of those core run ones that’s always around there for all the points you mentioned. Yes. What’s okay, what’s one thing you wish you could go back in time and tell your former self before you got started, either in your career or the company you founded gi Give us a nugget of wisdom.

Jackie: Sure. For me it is probably in line with the five mistakes we just discussed, but it really would probably be not putting so much pressure on myself to succeed, I always, in my career, I’m always the one that got in my own way and yeah, it was, by no one else. I always had cheerleaders. I always had mentors telling me that I was gonna do amazing things and, really saw me do growing heavily in my career, and I just never believed in myself. And I’ve, I’m so happy to finally be at a place where I do have confidence in what I do and the value I can bring to my customers and clients. And I wish I had known that just starting out, but, it takes experience and failure and to learn.

Matt: Yeah, that’s the key thing. Iterating as you go. I struggle with that as well, and. At the end of the day, nobody’s paying that much attention to you anyway, so it’s okay if you mess up here and there along the way. Exactly. Exactly. Alright I got let’s see, I got two more for you. What technology are you most excited about or tool, technology, anything that you’re using today?

Jackie: Oh, man. All right. Let’s see. There is a really cool, so speaking of ai there is a, like a headshot tool that you can use. And I’m forgetting the name of it, but you can input your picture and it’ll spit out like 50 different headshots that look really professional and good. So if you’re like, sick of using the same headshot over and over again and it’s got some tweaking it, it needs, it. It kind of messes up here or there, but it’s definitely like making pictures in your likeness and everything, so there you go. You don’t have to go hire a photographer,

Matt: yeah. Has so many use cases. We’ve started playing around with Adobe Firefly. We’re in their early beta testing and playing around with it. Similar to like a mid journey text, two image, and it’s insane. Yeah. The stuff you can do with it, it’s really cool. Cool. All right, last one for you. If you weren’t in product, what would you be doing?

Jackie: Oh, that’s a good one. If I wasn’t in product if I wasn’t in product. Let’s see.

Matt: I stumped you with that one.

Jackie: You did stump me. I wasn’t prepared for this. I don’t know. Can I be a professional traveler for a living? Yes. That’s perfectly accept. I love traveling. Yes. Okay. Okay,

Matt: good. Fa, favorite spot to travel? What’s your favorite spot to go?

Jackie: Oh, I love Hawaii. Oh. Have you been there?

Matt: Never been to Hawaii. I’ve been to Costa Rica recently where we have a big presence down in Latin America. Yes. Costa Rica’s amazing. If you haven’t been there, check that out.

Jackie: I’ve been one. Cool. Amazing. Yeah. Yeah.

Matt: It’s such a cool place. A awesome Jackie. Thank you so much. But please let me know where can people find you maybe a little bit more about Option One partners or this learning platform you’re building.

Jackie: Sure. So yeah, option one partners.com. Find me on LinkedIn. We love to serve companies through consulting and staffing work. And then productxagile.com is where we have on-demand courses to help product managers and agileists upskill in their careers. And we actually have a promo code for you guys. So HatchWorks30. At put that in any on the checkout page at any of our courses at Product X Agile, HatchWorks30, and you’ll get 30% off a course.

Matt: Nice. Hatch works 30. Okay, perfect. And I think we had the user story course, so that one’s out there plus many more. Yes. I can’t wait to check it out. Yeah. Awesome, Jackie. Thanks for being on Built Right. We’ll talk soon.

Jackie: Okay. Thanks Matt. Bye-bye. Bye