Overcoming Organizational Inertia with Architect Tyler Lynch

Watch this interview on YouTube

In this interview with Tyler Lynch, we discuss methods for overcoming organizational inertia to move your team forwards. Tyler is a Solutions Architect at AWS and mentor with Justice Through Code.

Try to identify what's in it for somebody that we need to pitch this idea to. What do they care about? What's their motivation? Is it incentive-based? Is it fear? Is it, "I need to just keep doing what I'm doing"? ... Start with what's in it for [them]. What are you worried about, and how can we make your life easier? And how do you tell that story effectively? 

Hosted by John Long & Drew Freakley.

John: Welcome everybody. Thank you for joining us today. My name is John Long. I work with Launchable, and I do product design. I'm joined here by Andrew Freakley and Tyler Lynch who we're interviewing today.

Today our topic is really about understanding and breaking through organizational inertia.

Tyler is at AWS, and he is a solutions architect working in the ed tech space.

So Tyler, let's just kick this off. You've been in technology a long time now. How did you get started? How did you get to where you are today?

Tyler: It started with a 386 that my parents bought. Editing autoexec.bat, the contents of it. And I had been trying to figure out how do I get my computer to boot once I messed it up, like the first night I had it. From there, I started working at a local computer store, building computers and selling computers.

And that quickly moved into HTML. Back in the day it was DHTML, and I started local websites, ended up getting a job at a mortgage company, building their websites. Lots of rainbow GIFs, everywhere you look I had rainbow GIF at the time. This is when GIFs first came out online.

That quickly morphed into "what's next?" So e-commerce, enterprise application space, enterprise architecture, and that's been my trajectory until now where I'm at AWS supporting ed tech customers globally, especially through COVID through the pandemic.

It's been a lot. 

John: Wow. Those are those bring back some memories. I remember those days. Tiling backgrounds, rotating email GIFs, there's things that I still miss about the web. During those times it was a simpler, purer place, I think. 

Tyler: So archive.org has many of your favorite websites, archives that you can go back and look at, like, 1996 on archive.org and it looks the same.

The rainbow GIFs are still there. The bad fonts, the marquee scrollers. It's a great nostalgic walk down the history lane.

John: It's actually fun to do. This is a side tangent, for sure. But look at old movie websites on archive.org because some of them are just completely off the wall. Batshit crazy kind of thing. Like how are they promoting this movie with this website?

Tyler: I don't think we knew what we were doing back then. We were just throwing it all up online to see what stuck and what drove traffic. 

John: Okay, so AWS, you're a solutions architect there. What do solutions architects actually do?

Tyler: Yeah. So solution architects work with customers. Pre-sales, implementations, post-sales, through that customer life cycle journey. So we work with that same customer throughout their journey and continue on to help grow. It's a lot of education. We work with customers to get unblocked. Maybe they're trying to do something where there's nothing published yet on either the AWS blog or on Stack Overflow. So we'll work with the customer to put together the building blocks of what they want to do to achieve the desired outcome.

We also work with their C-level executives for strategic alignment. Where do they want to go with right now. With COVID we're seeing a lot of cost pressures. So state and local governments have a lot of cost pressures due to taxes. But online learning is up. And so delivering that same level of reliability and availability while reducing costs is something we've been focused on a lot.

Drew: I know it's been, I think, about a year since you joined AWS, is that correct? So I think, obviously during the time we'd been under sort of quarantine and COVID guidelines, so what's it been like for you coming up to speed in a new job, fully remote.

Tyler: So that was a consideration before taking this job, right? There's a lot of fear. Taking a new job, especially for me at AWS, imposter syndrome, just, you know, abounds, and then thinking I have to onboard virtually - how is this going to work? But luckily AWS had really locked down virtual onboarding. They had a great onboarding plan for physical onboarding, and they tweaked that for virtual.

So what would be one week together in a class, they did it online virtually through Chime. So it was actually fairly frictionless. My laptop came a day late, small things happen, but all to be expected. A lot of my coworkers reached out to make sure that I had what I needed. So I really felt like super supported and connected, even though I hadn't met anybody. I still have not met anybody actually in person that I work with. So it's been interesting, but I think that everybody is doing this, right. I think everybody is finally getting, how do we make people feel connected, productive, sense of accomplishment and do that remotely. It's been an interesting journey. 

Drew: So how about the external elements though?

As I understand it, solutions architects do a lot of, customer onsite visits and customer handholding to work them through sort of project life cycles. Has that been an adjustment for you? Not being able to really get that face time with your end customers? 

Tyler: We do a lot of face time virtually, so just like this, right?

So I'm also on my customer Slack instances and we talk on Slack for short things. We trade emails for important things. But we still do have our structured immersion days. So we have different ways that we can interact with customers for hands-on learning or presentation. And those have actually translated pretty well virtually. What I find most though, is a lot of people in the customer sites or the customer side don't often feel comfortable speaking up verbally but will type in the chat. And so what we've done to augment that as we have additional people reading chat and reading it back to whoever's presenting cause people don't feel like speaking up.

That's been a little bit of adjustment. And I can't see body language; not everybody's on camera. So how do you see and engage with body language? Are you keeping up with the content or are you not keeping up with the content? It requires us to do a little bit more probing. Throughout the life cycle, whatever kind of engagement we're running.

Drew: My last question on this is from a personal perspective, I've seen some people really prefer to engage over the web. Maybe to your point about some people aren't so comfortable speaking up and more face to face, but from your perspective, would you like to go back to seeing customers on site or are you like, Hey, this is the way we work now, and I like remote. 

Tyler: I like onsite; I like remote. My last job, having traveled all over the country all the time to inside teams, working with teams inside the company and I haven't had to travel and it's been really nice, honestly. So not hopping on planes multiple times a week has been really nice.

I'm happy to do it. I think that there's something that's missing when you don't get that face to face. So we can't go for a walk and just talk about some of the struggles you're having in a casual environment. It's always more formal when it's like this virtually. So I definitely miss that camaraderie.

Just going out and like grabbing a quick bite for lunch. You can learn a lot about what somebody is going through and the challenges they're facing just over food.

Drew: Totally. 

John: Yeah, definitely. This is funny. We were talking about your new job at AWS, but you've actually made several sort of career transitions.

How, like how do you get up to speed as you're doing this? What's been the, what are the themes there? 

Tyler: So let's talk my most recent experience. So getting a job at AWS was full of imposter syndrome, but I thought I knew AWS. Until I worked at AWS and then I realized, I really don't know AWS or the depth of the services catalog that exists.

And so that was humbling. So throughout my career, I've been willing to learn. It was really like, I know I don't know everything. That's perfectly fine. I hire people much smarter than I am, but I'm also willing to learn and dive in and just block calendar time to come up to speed on something that I'm not familiar with.

There are things that I don't know that I really, that's not my area of depth and I don't really want it to be. So like networking. It's not something I'm passionate about. I just don't care about your CIDR ranges and your IP ranges. That's not fun for me. But those are the things I forced myself to go learn.

So I at least have fundamental knowledge, even if I'm not going to be an expert. 

John: So when you think about developing kind of that love of learning, we've talked about this before. What are some tips for our listeners here? As it relates to tech. 

Tyler: So I work with a lot of mentees right now and their first exposure to technology is recent, right? So they have never had a technology job, never done any programming, networking, or anything. And we often have this conversation. How do you find what you're interested in? Technology isn't just one size fits all. We have lots of specialties. We have lots of other kinds of technology.

There's programming, there's DevOps, there's SysOps. And so what I ask people to do is maybe take Coursera or A Cloud Guru or any of these online trainings. Take a short, I don't know, one week course. And see if you have an affinity for it. Is it fun? Do you find it challenging? And you just play with other ones, you might try data, try DevOps, try software programming. Experiment until you find something not only that resonates naturally, but that you really enjoy and then pursue that.

The last thing you want to do is be working at a job for something that you just don't care about. You don't really click with. So I think experimentation in that is super important early on in your career. 

Drew: As John mentions about your own love of learning, I'm curious to hear where you go to keep yourself up to date on like new and emerging trends in technology. So are there like groups or forums you would recommend for developers out there who are looking into trends in the industry?

Tyler: Yeah. So in the last couple years I steered away from forums or anything with comments, I feel like anytime that personality gets into it, it erodes from some of the messaging and the things that I'm looking for with like technical depth and clarity.

So I'm seeking out like ThoughtWorks, their technology radar. I think that's the gold standard. That's what you should, everybody should be keeping an eye on that. There's some great, like the AWS open source blog, it's published weekly on Monday, that is a great place to find out what's happening in open source. You can see - it's not just open source for AWS. It's open source that could be used on or around AWS. So I find that's a great place to go. I read the Netflix engineering blog regularly. I think that's a great engineering blog. You can go super deep on what they're doing at Netflix and just amazing engineers there. Same thing for the LinkedIn engineering blog, Twitter engineering blog.

That's where I go. So it's content that has been filtered, revised, it's it is high quality content to deliver a single or maybe two learning objectives. And you just like spin through that catalog. I find that's the best way for me to learn.

John: So obviously at this point in your career, you have gotten quite good at the technology side of things.

What about the non-tech side of things? What are some of those challenges that you've faced and, you know, what kind of advice can you give us on facing the non-tech challenges in the tech career? 

Tyler: I think the non-tech challenges are actually the hardest and they're the most interwoven and complicated things you have to deal with, especially in a corporate environment.

I learned early on in my career that different cultures have different ways of interacting and reacting. I was doing some work out of Asia through a parent company. The developers said, everything's fine. Everything's fine. Everything's great. And it wasn't great. So we got time to go to a demo and there was nothing to demo, but culturally, that group of people did not feel it was okay to say no or challenge the superior.

It was a big learning lesson for me. I'm like, Oh wow. There's these cultural differences I'm just unaware of. I'm completely ignorant to it. And so since then, I've done a lot of learning about how do people react and interact and what motivates people? And that kind of drives into organizational inertia.

We started looking at organizations, you start to say how do we know what's motivating somebody? How do we know what's causing fear in somebody? And those are the things I look for and I try to analyze to help people block down that inertia.

John: Let's dive in a little bit more into organizational inertia. What do you mean by that? 

Tyler: So I often would say, anybody at Amazon will tell you, like it's always Day One. More importantly, no company ever became number one or stayed number one by staying the same.

And I worked at a lot of large companies, billion dollar companies where the status quo is perfectly fine. It is not expected that you're going to have evolutionary jumps in either your software life cycle or your price performance profile, nothing. It's perfectly okay to stay doing what you're doing.

And that's inertia. So when somebody's new, or somebody has a new idea or new technologies out. And they try to introduce that into a system that is working, right, if you like this is our format and it's totally working, sustaining success. There's nothing wrong with it. There's inertia to take on any change.

And I don't see this in small companies or startups as often as I do in medium size and large enterprises. It's something we have to all overcome. As an example, one company I worked at there was a, an architecture rule that you were only allowed to use one certain type of database, a wide column store, period.

So you're building a new application, you have to use that type of database. Wow. That's just really not what that database is meant for. And there was inertia to take on new types of databases. They'd only approved this one type of wide column store for use in new applications. And it was driven by fear, right?

They didn't want to have to learn how to support something else. They knew how to scale this thing, even if it was a screwdriver to try to put in a nail. It was okay. And that was the inertia that I had to work through at all levels of the organization. 

John: So I was just going to continue that thought.

So here I am, I'm working in a new organization and they've always done CSS the vanilla way, and I want to get them to try SASS, giving you a softball here. What do you do? 

Tyler: Ah, so there's a sales technique called WIFM: "What's in it for me?" And so you turn that around and you try to identify what's in it for somebody that we need to pitch this idea to. What do they care about? What's their motivation? Is it incentive-based? Is it fear? Is it, I need to just keep doing what I'm doing. Maybe there's not capacity to learn. Maybe the roadmap is really full and management is worried about introducing new technologies and the learning curve and not being able to hit whatever roadmap they decided or, and, or committed to.

So I start with what's in it for me. What are you worried about, and how can we make your life easier? If you're worried about committing and making a commitment to other parts of the organization or external parties, would something like SASS be able to speed up that delivery. And how do you tell that story effectively?

So WIFM is where I start, what's in it for me. And I build on that, whether it's fear-based or success based metrics. 

John: Gotcha. Give us an example of where this has worked for you.

Tyler: Let's talk about identity. So I think identity is often undervalued, especially in big enterprises. We think it's usernames and passwords, but it's so much more than that. So I worked at a company that was based primarily off acquisition, billion dollar company, multiple different identity stores.

And there was this cultural fear and company-wide cultural fear of the identity system, having outages or going down or making evolutionary changes, you can make incremental changes all day long. But if you wanted to change anything about the persistent store, change the standards that are supported... Hard no. And so I started diving in, I'm like, what is this?

What is this I kept hearing about this "day of darkness." And so there was a term culturally inside the company of "the day of darkness." And what had happened is they'd upgraded the system , a major upgrade, changed the persistent store, and it caused multiple day outages where people could not log in. Consumers could not log into the software, any of the software.

And so there had been a lot of corrections and blocks put in place. You couldn't make any types of changes that could have that kind of outage. But we were reaching the end of life on what we could do with that scale of the system that it was today. It was very clear. And we had some strategic objectives coming down that we were working with from the CEO that we had, we knew we were going to start to see 20, 30, 40% more usage currently and the system wouldn't support it. And so working with them across different directors, what's in it for you? What are you afraid of? What's hurt you in the past? And building out literally a two by two metrics for every person that had a stakeholder relationship in identity and working through how do I get past this with each one of these people?

It's very systematic and it's, it's unique to each person and what they're responsible for, what they're worried about. 

John: Yeah. That makes sense. So at Launchable we, for a lot of our decision-making we use something called DACI. Are you familiar with that?

Tyler: Yeah. 

John: Yeah. So it's just a decision-making framework where you're identifying like who is driving the decision. A lot of times, we ended up making pros and cons lists on different decisions, things like that, but we have a kind of uniform way of approaching it and making sure that the important people are involved in the decision, I guess you could say, and what their roles are in making that decision. It's been super useful for us working through these things.

Tyler: Yeah. So I think when I was fighting cultural fear and like the historical nature of the day of darkness - you can imagine that, like the voice that you hear it in: "the day of darkness!" - you can't do this.

I didn't realize that there were things called one way and two way doors. I didn't know how to pitch this. And so Amazon talks a lot about one way and two way doors for decision-making and a two way door is something that we can walk back through. It is low barrier to change and those decisions get made all day throughout all the organization.There's no review.

The one way doors, we base on risk and cost, right? What's it gonna look like? Can we reverse this or not? If it's non-reversible we need to put more scrutiny on it. I didn't have that same lens and visibility to be able to tell that story in that way, which I think would have really helped.

We were, of course we were building in redundancy. We're building in eject buttons and other things to change out a persistent store to a full identity system. But I didn't have that same knowledge to tell the story. So I worked the individuals, each stakeholder. And we got it done. We ended up buying a third-party solution from Okta.

It was a wonderful engagement but you're talking multi-year engagement to get that done. But yeah, and it was fine. It was fine. It was something we needed to do as an organization to not have identity be so core. Core competency is education technology, not identity. But it took a lot to get there,

John: So obviously there's, there are these techniques for breaking through, but what do you do when you get to that really difficult person? 

Tyler: Yeah. I think the first thing you need to do is to challenge your own biases, unconscious or not , and hear them. Listen to them. What is their objection?

Why are they objecting? And really try to understand why are they objecting to something? If you can't bring yourself to fully understand their position, you'll never be able to overcome it. I think that's super important, right? I know I can be a little bit stubborn sometimes and strong headed and I want to do this because X, but taking a step back and just listening and saying why does this bother you? What are you worried about? What history told you or what precedent have you seen that makes you object to whatever it is we're talking about?

And that's been super helpful. So number one, you might find out you're wrong. And you just need to be willing and able to like, okay, this is a bad decision. It's not the way we should go down, but you have to be willing to end up at that conclusion. 

John: Put yourself in their shoes.

Tyler: Not just with lip service, we need to empathize with them and their position, what they're responsible for, what they've seen and been through. 

John: For you, how do you find that you do this best? Like just getting time alone or do you write things down? How do you get in that mindset?

Tyler: Honestly, I find that you can get to motivation, but you can't get to fear in a group setting. To understand or really empathize somebody's fear. Like, what are they fearful of?

It takes one-on-one, it takes a coffee date, virtually whatever it's going to be. I feel like there's a little less formality to that: Here's what happened, Ty. We tried to do this once before in XYZ, or maybe they'll say, I'm worried about my engineering staff doesn't have that experience. And how are we going to upskill them and make these deadlines? And so you start to peel back that onion a little bit. It really empathized with somebody one-on-one I find that's the best forum. 

John: And then if you do decide to move forward that you're not wrong. You're creating a targeted plan to address the concerns, the fears, that type of thing.

Tyler: Yeah. I think you're responsible to address every stakeholder's fears and concerns. If you're driving a project or you're trying to do something new, you need to account for those and have some sort of risk mitigation plan.

And it could simply be we identify this as a risk, but we're not going to do anything. But specifically calling that out, I think is super important and provides a level of comfort and visibility to all stakeholders. 

John: Do you have an example of where this went wrong for you? Not to put you on the spot!

Tyler: Not to put me on the spot! Not at all. Wow. I usually don't go to bat severely unless I firmly believe something. And it's either going to be based on like a moral compass is telling me we have to do this, or it's something from a compliance reason. But I have certainly done and made some bad decisions in hindsight, thought, man, I really shouldn't have, but what I'm interfacing with somebody else as a, another part of your stakeholder?

I typically won't like toe a line. I certainly have my position changed quite a bit.

John: Did this way of approaching stakeholders and things that you're describing, did it come naturally for you or was, how did you learn this?

Tyler: I learned it from realizing that going into conversations in an adversarial manner wasn't providing any value for anybody. Walking into conversations, collaboratively, and like asking for compromise from the start seemed to be making progress. And oftentimes progress is better than no progress. Not always, sometimes you just need to make that evolutionary jump, and I'll decide that before a conversation.

But, I can be adversarial in nature and that's a pattern of behavior I don't want to exhibit in my professional life. And so I work very hard to make sure that I approach each interaction as a collaborator, as a coworker with empathy. But it did not come natural. Absolutely not. 

John: How do you, how did you become aware of that about yourself and you say adversarial by nature?

Tyler: Oh, so this can go into a full rabbit hole we'll get into. So I am in a recovery program from drugs and alcohol. I've been sober for eight years and three days. And through that program I've learned to do a lot of introspection about how I react to things and how people perceive my reactions and how they react to me. So it was through that program I had a lot of introspection and self judgment and really understanding how I'm perceived in the world.

That led me to: I really shouldn't be such an adversarial jerk, especially at work!

John: That makes sense. I think a lot of us have had those kinds of detours in life. And they change you hopefully for the better. 

Tyler: Yeah, I think a lot, I'm pretty open about my recovery. I'm always designated driver in any work function, which is kinda nice for everybody else. So I'm very open about it. I speak openly about it on like LinkedIn. It doesn't bother me, but that's really where I had the genesis of introspection and reaction and how I'm engaging my own reaction. And it's not, I don't know. I don't so much care about how you interpret me. I care about how I feel like I am being presented and how I'm presenting myself.

And I want to be a better person. My character defects are strong and they run deep and it's on me. It's not anybody else's responsibility to fix those or do justice. 

Drew: That's excellent. 

John: I guess the contrast that's with just shooting from the hip and just being yourself kind of thing. You may not actually know how you're being perceived. You may think it's one way and it's completely different the way that you're being perceived. Learning how other people perceive that can help you present yourself better.

Tyler: It's funny you say that. At work recently, my manager was like, Hey, I want to give you some critical feedback. There was a Slack message and you came out and you're pretty fiery. That's not like you, you didn't end with the solution. You normally like when you do dress something a problem, you always follow up with the solution. Here's how we're going to tackle this. 

And I said that was intentional; that wasn't unintentional. And I exhibited that behavior because I wanted it to be so out of character, people took notice of what I was talking about.

She was like, Oh, that's interesting. But yeah, no, I was intentionally fiery because it's so out of character, I want people to look at it and say, maybe this thing he's worried about is something we should be worried about too.

So I do use that strategically, honestly. 

John: Yeah. That makes sense. That makes sense. 

As we're wrapping up here thinking about careers in tech. Is there any other kind of advice that you would go people who are either starting out or maybe they've been doing this for a while? 

Tyler: My first advice, I want to address people that have been doing this for a long time that are either individual contributors and have a hand or influence in hiring or hiring managers directly there.

We all need to acknowledge that the talent pool is never going to keep up with the amount that we are hiring in technology, specifically the senior and principal level talent. The only way we're going to get those people is by stealing them from other companies and paying more and more.

And that's just not a sustainable model, especially the growth that we're seeing. And so as hiring managers it's on us. To really start looking out and building that bench. And it's about empowering entry-level candidates, bringing them in and really investing in them, not just hiring as an intern, investing in their education, making sure that they are mentored, making sure that they're gonna be successful for their first year, maybe two years by some sort of like formal apprenticeship program.

This also aligns with diversity and inclusion, but we need to start building the next, the next generation of leaders and it starts with entry-level jobs. We can't just keep hiring senior people from other companies, it's not sustainable. So that's where I would start.

I would also say for managers, it's on you to make a commitment, if you're taking resumes, that two of every five resumes you get from a recruiter or sourcer should be female. Period. Don't accept resumes, unless you're getting some female resumes in there. It's on us to do better.

If you're just starting out, find your passion, explore a little bit. Technology is really wide swath. There's many places that you can go and do things. And there's actually technology jobs that you might not think as technology jobs. Principal product designer, product engineers, product managers, these are technology jobs, and they're amazing and they're needed and they're necessary, but maybe they're not writing software.

Maybe you, your affinity is developing and designing a program and seeing how people interact with that program or system. Those are much needed. A lot of people think that software engineering is where they'd have to go or cloud. I don't think that's the case. So I hope people realize that there are many different avenues you can walk down in high-tech jobs.

John: That's really good advice. I've been thinking recently that it's very easy to get locked into your identity when you're in tech. You're a developer, my case here, a designer, whatnot, but the truth is a lot of people make transitions like in and out of these roles. And sometimes it's fun just to experiment, learn a little more about yourself, that kind of thing.

Tyler: Let me give an example. So I'm working with Columbia University on a program called Justice Through Code and where they work with previously incarcerated individuals in a bootcamp like setting to learn Python, cloud... There's mentoring, there's resume writing. It's all done through Columbia and this program is scaling and the goal is to get them hired into high tech jobs.

And some of the folks that I'm working with in this program, previously incarcerated individuals and mentees, have a great affinity for software engineering. Sure. They get it. It's natural to them, but some not so much. And they get really frustrated. Like I'm trying to learn Python, they can't learn it. And so I talked to them say, you don't have to be in Python to be in high tech.

You did sales, why can't you be in enterprise sales? What about designing a product? Talking to users, focus groups, UX design. One person did Photoshop, but like maybe you would want to look at the design field, that's high tech. Absolutely.

So find what works for you. Don't shoehorn yourself into what your idea of what tech is because tech is many things, and there's wonderful jobs out there to be had. And there's lots of them. 

John: So Justice Through Code. That sounds like a very interesting, you've been doing this for a while. 

Tyler: About six or eight months now. Started doing a pilot with AWS.

We announced it officially at Re:invent that we were doing this program with Columbia. And we were having mentors, but you'll also see Google, Box, Netflix, lots of companies are having mentors work with folks that are in this program called Justice Through Code. AWS is going on the record and saying that we're hiring directly out of there.

As a matter of fact, my mentee Kevin just got a job at AWS. Pretty amazing. So he'll be working in fiber optics and data center stuff. And so it's wonderful to see somebody that had zero technical experience land a job at AWS and what's arguably the most sophisticated data center and fiber optic network in the world.

John: Where should people go to learn more about Justice Through Code? 

Tyler: If you just Google "Justice Through Code" you'll end up on Columbia University's website. There's a great program dossier there. Aiden is the program coordinator and the founder. You can read about it. You can also see our article recently released in TechCrunch that talks about it.

And then the AWS blog is also, mentioning again, some videos. And so what we're finding is enterprises, medium, small companies that want to focus on diversity and hiring, but don't know how to start. This is a good avenue. So they're having their employees mentor and they can start to understand what the caliber of people that we're seeing.

They're super high quality learners, and then potentially work them into either internships or full-time positions that are entry-level, supported with an apprenticeship type program. And we work with those companies to build those programs out. 

John: Wow. Tyler, it's been really great talking with you today. I appreciate you joining us. Thanks so much.

Drew: Thanks Tyler. 

Tyler: Thanks guys.