Don’t leave your moral compass at home with Natasha Jaffe
What do you do when a leader tells you, "You have integrity. That's rare in this profession"? For my guest Natasha Jaffe, it was the signal she needed to leave.
In this episode of Executives Unplugged, I talk with Natasha, an experienced engineering leader and coach who has guided teams at both Fortune 100 companies and startups through multi-billion dollar acquisitions.
We have a raw and honest conversation about the critical mistake leaders make when they chase productivity gains but accidentally "squash the magic" that makes their teams special. Natasha shares a powerful playbook for leading through disruptive changes—like reorgs or the push for AI—by protecting your team's "flow state" and listening to your own moral compass.
This episode is a masterclass in leading with empathy and principle, offering practical advice on how to navigate immense change without losing your team, or yourself, in the process.
Guest:
Natasha Jaffe: Experienced Engineering Leader and Coach.
Find Natasha's writing at her blog: Nuts and Bolts on Substack
Listen on your favorite platform:
Youtube, Apple Podcasts, Spotify
In this episode, we discuss:
(1:13) What is "Flow State"? Natasha explains why long, uninterrupted blocks of time are the source of an engineer's most creative and deep work.
(2:11) How Leaders Destroy Flow: Forcing teams to prioritize the "important" over the "interesting" for too long erodes curiosity and squashes the magic.
(3:40) The Human Reaction to AI: Why engineering teams often react to top-down AI mandates with trepidation, seeing it as "dystopian" and a threat to their craft.
(4:35) Fear Kills Innovation: When your team is afraid, they won't engage in the productive risk-taking required to innovate.
(5:11) A Case Study in Leading a Reorg: How Natasha turned a messy, demoralizing situation into a success by bringing the team into the decision-making process, listening to their fears, and even choosing a team mascot.
(8:33) The Real Path to Moving Faster: Stop telling your engineers to "run harder." Instead, reduce toil and remove friction to "widen the mouth of the funnel."
(9:16) The Collapsing Talent Stack: Are we moving away from hyper-specialists and back toward multi-skilled teams who can move with lightning speed?
(12:49) The Bell Curve of Team Size: The trade-off between having more minds on a problem and the rapid degradation of velocity and quality when "too many cooks are in the kitchen."
(15:01) Your Moral Compass: Why you can't leave your values at home and how the biggest career regrets come from not listening to your gut.
(16:35) "They Said the Quiet Part Out Loud": The powerful story of how a single comment about integrity was the signal Natasha needed to make a pivotal career change.
(18:41) Key Questions to Ask Yourself: How to get clarity when your job is in conflict with your values, and how to know when it's time to explore a change.
(22:08) On Burnout and Recovery: Natasha shares her personal journey of recovering from massive burnout and rediscovering creativity.
Full Transcript
Natasha Jaffe: 0:00
The leader said something to me like, you have integrity. That's really rare in this profession. A couple months later I was gone. Like, that was it. you know, they said the quiet part out loud, basically. And that was enough signal to lead and it was the best decision, you know, career wise that I've, made.
Keith Cowing: 0:19
This is Executives unplugged, raw and honest conversations with CEOs and senior leaders about how to lead through change. I'm Keith Cowing, your host and executive coach. My guest today is Natasha Jaffe. Natasha is an experienced engineering leader and now a coach for other engineers and engineering leads, and she has led teams at large public companies as well as startups, all the way from. Early days through multi-billion dollar acquisitions. In this conversation, we explore how to make decisions for ourselves using our moral compass and independent thinking, and how to make changes to our teams or our companies while still considering the team on the ground and making sure that you don't go looking for productivity gains and accidentally squash the magic in the process. Let's jump in. Natasha, welcome.
Natasha Jaffe: 1:11
Hi Keith. Thank you for having me.
Keith Cowing: 1:13
Awesome to have you here. Let's jump right into a really core topic for engineers, which is flow state, and you've been an engineer. You've led engineering teams at startups, at Fortune 100 companies, everything in between. Now you coach engineers, and it seems like this is a topic that's really important and maybe sometimes leadership forgets about, especially during times of rapid change. So what does it look like to be in flow as an engineer?
Natasha Jaffe: 1:38
Flow is being in the zone, you know, with your work, whatever that work may be, or a hobby or whatever, right? You sit down, you put your head up and it's been three hours and you had no idea because you were just so into what you were doing. And so for most of the engineers that I know, like it's a really. Enjoyable and stimulating thing. And that is when you know their most creative and their most deep work comes out.
Keith Cowing: 2:02
What kind of leadership decisions can enable engineers to be in flow more of the time, and what kinds of decisions can get in the way of it?
Natasha Jaffe: 2:11
Some obvious ones that most people are probably familiar with. You know, just protecting your people's time. Engineers need long, uninterrupted blocks of heads down time, so not lots of meetings. Some people, you know, other functions like they need meetings. That's basically what their work is. Um, engineers know they, they need that quiet heads down time. So that's a big one. Protecting your engineer's time. Another one is being very careful about pushing. A particular focus on your teams. It's easy to say, we have this product roadmap and you are not going to work on anything else that is not directly tied to the product roadmap and doesn't move the needle on the product roadmap. And over time, if you do this for long enough, your engineers are going to lose their flow because they're gonna be prioritizing important over interesting. Flow happens when it aligns with an engineer's natural curiosity, you don't wanna lose out on that. You will see the negative impact over time.
Keith Cowing: 3:08
The story in the market is, well, you can do more with less people now, so you should be, on the ground level, people doing the work are thinking about their jobs and are afraid of that. And then at the CEO level, they're afraid about the future of the company and how do I pivot according to that? We'd love to dig in a little bit about how leaders can make sure that we're making. The rapid changes that maybe need to happen, but at the same point, realizing that there's humans that have to bring you along for the ride and you have to bring those humans along for the ride, and you can't just crush all the flow state, or you're never gonna get that magic that you had.
Natasha Jaffe: 3:40
What I'm seeing in some of the conversations that I have when it does come up it's a lot of trepidation. At best, you know, I'll see sort of a neutral reception. But in other conversations, you know, I've heard the term like dystopian. I've heard a lot of resistance, you know, this feeling that, you know, they're, they're losing something special actually by being pushed to use AI and, and having their tools. Dictated to them by senior leadership, someone who might not even be writing code themselves. It hasn't been for quite some time. Just quickly, you know, one other theme that, you know, you remind me of here that's not specifically related to flow but is related to risk and productive risk taking. I think that's part of what we're talking about here, right? You know, like if it's time to innovate, that, that means productive risk taking. When your people are afraid they're not gonna be taking those risks. And so I think that's something I would like leaders to keep in mind as well.
Keith Cowing: 4:35
And you, in your leadership and in your coaching, you think about empathy a lot. You think about listening to people deeply listening, really paying attention to what's working for them, what's not working for them. What are you seeing? And how people can navigate these crazy changes that need to happen. But doing so while listening to the team, and it could be a recent example, it could be an old example of a big change that a team went through and how you listen to people or how you sound engineer and leader listen to people. How can we listen to people and still make the changes we need to make?
Natasha Jaffe: 5:11
One of those sort of classic sources of change is reorgs. People just got used to their team the way it was, and then the team was split in half and then recombined, you know, with half of another team. and maybe their product mandate was changed. And all of a sudden they have no idea, you know, what are they working on? Like, what is the value they drive? How can they demonstrate that value? And more often than not, it makes them disengaged. And demoralized. You can end up with like all this negativity on the team and it's not good. and so as a manager, at least, you know where you start is the one-on-ones I. you, you listen and you pick up on the themes, um, and you try to figure out like, no, what is it that they're actually concerned about? What's important to them? Like what are they worried they're about to miss or lose? And then you speak to those things. You can't always tell them, Hey, the thing you're worried about is not actually a concern. You're fine. is more like I hear what you're saying, this is how we're mitigating that risk for you, for example. Or This is what you can do to make that scary outcome less likely. So at the end of the day, it is about empowering and giving them the right information, making sure they know they're not alone, and also getting buy-in, you know, and, and the alignment. So in one of my last roles as an engineering leader I took on a small organization that was very much in flux. They had. Been through a reorg and had just been through another reorg like a few months later, and they'd lost a couple managers and it was, you know, it was a mess. and I was looking at what we had and I realized, look, we have three teams right now, but it makes no sense because we lost like half our people. That means like one IC and one manager, and then the second team is like two ics and one manager. And we're, we're gonna have to condense here. We're gonna have to. I had go from three to two. And there was a lot of apprehension about that. And so how I went about it and what I think worked well, is that I brought everyone into the decision making process and I structured the exercise. We thought about what are the themes between our teams, what makes most organic sense for our structuring? Um, and then little things too, like. Choosing a team name and a team mascot, like that feels very kind of like band aidy, but it, it, it still helps. And if nothing else, it gets people, you know, to loosen up a little bit and to create, get into the creative thinking. so the big ones, I guess, are making the hard decision, you know, despite the fear, bringing people into how they actually get there so they, they feel like I, I was part of this. Maybe they didn't take my suggestion, but I was part of the discussion and they listened to my, the risks I brought up, and then they mitigated the risks that I brought up. And then also like the creative play piece, you know, play is so important, especially when we're going through stressful things.
Keith Cowing: 8:06
And when you think about burnout and you think about big changes and you think about. Pushes to move faster, and right now there's a big push of we better move faster, we better move faster, we better move faster. What do you think right now, given the tools that are out there, where teams are or the changes in the air, what are you seeing actually helps engineering teams move faster on the ground in reality?
Natasha Jaffe: 8:33
You know, the toil and the process. so that's why to encourage leaders to look to in general, you know, especially if they're thinking to themselves, oh, I want people to use AI to do X, Y, Z. No. Like say, actually, how can we use AI and other tools to reduce toil? If I, if you think about it, like say you have a funnel, right? And you're trying to get more things through the funnel, so you could just push really hard at the top of the funnel and you can tell your engineers run harder, you know, at the goal, or you can widen the mouth at the bottom, right? Um, and so you do that by removing friction. You do that by reducing toil. You reexamine processes that don't need to be there.
Keith Cowing: 9:16
I'd love to hear your take on. Something I'm seeing and feeling in the market, which is we went through an era of generalists in the nineties, you'd have a bunch of engineers, you'd have a team lead it. Like they may not have even had a specific title. It was just the person that was the manager is the boss and, and then the people doing the work and, and everybody was hands-on and. I think full stack was just assumed, like if you just built, did whatever you had to do. And then we got into specialties where we had front end engineers and backend engineers and product managers and designers and data scientists. And they all had their functional Exactly. And they all their functional realms. And one at a time we'd grow a new one and product managers became experts and only growth products for B2B two C. And it seems like maybe it got a little outta hand and now. It's, I wouldn't say rotating back to generalists, but I see a focus particularly on bias towards the early stage. But in small companies having multiple specialties where people are wearing multiple hats and maybe in the past they couldn't because you couldn't do two jobs anyway, so it didn't really matter if you had multiple skillsets,'cause you had to choose one. And it may have been fun, but unless you're the CEO and the founder, you really didn't have that bandwidth. And now I see people that are filling in and maybe there's 1:00 PM that's also doing some design work or an engineer that's also doing PM work or Yeah, data scientists and an engineer sort of really acting as one with ai, helping with some of the trivial work so that they can do the meat on each side. And when you say toil. I am fearful of that collapsing of the talent stack, meaning that there's just less roles in some situations. But on the flip side, I think you can move lightning speed because if you have one person doing multiple jobs, there's one less negotiation point. And a lot of toil in my experience, is driven by like everybody trying to get on the same page and. And there's just less people to get on the same page. You can move so much faster, and there's a tension there because you want intellectual debate to make the process better, but at a certain point there's, that turns on its head real quick and just turns into getting gummed up. And so how do you think about specialties and moving fast and sort of more voices in the room versus fewer voices in the room?
Natasha Jaffe: 11:28
Yeah. No, these are great questions too. First though, just to point out the toilet reduction piece, it's interesting. I actually don't see the toilet reduction piece, at least within software engineering, eliminating roles per se, so much as allowing those same people to move faster. So just that sort of one thing to point out there, but that might not be true in other roles, in another function when it comes to three people now becoming one. Yeah that's really interesting. And so the, like, just split tracking here, like the fear that you're pointing out, the risk that you're pointing out rather is everything we lose by not having sort of the. The group mind there to help test ideas more thoroughly. You know, one answer is potentially ai, right? Like more ai, use your AI as a thought partner, make them poke holes in what you're doing. And some, we were just talking before this, right? Like some AI chat bots are better at that than others, right? I don't know. But I do think that the answer has to be you, you, you do need somehow to retain rather, that human connection. You should be having conversations with another human about your ideas no matter what.
Keith Cowing: 12:34
Oh yeah, for sure. And and I would say, you know, I think going from one person to two is an exponential growth in the quality of the thought and the decision making. Then going from two to three is probably incremental growth. And then when you get to eight, you've squashed it
Natasha Jaffe: 12:49
too much like you've lost, you've fallen off the other side of the fitness curve.
Keith Cowing: 12:53
Right, and there is a bell curve, I think, where the X axis is the number of people involved and the Y axis is like the quality and velocity and it sort of peaks and then it just degrades really rapidly.
Natasha Jaffe: 13:04
right? Like you kind of go like this and then
Keith Cowing: 13:06
Falls off, right? And so I, I am actually optimistic in some situations that instead of having eight seats at the table, maybe it's three. I don't think it's one. I don't like one, but having two, having three, then all of a sudden you can get aligned really quickly. And even if quality is less. Even if the decision making accuracy is less, if the speed is twice as fast, then maybe moving twice as fast because of decision making, not getting gummed up and causing its own version of toil, that that's actually a better model long term
Natasha Jaffe: 13:42
that reminds me of, you know, a lot of the trade-offs between small teams versus big teams, right? So there's not just what we were just talking about, which is, you know, the decision making when you have too many cooks in the kitchen. There's also just focus. If your team does Scrum, for example, stand up on an eight person team is a misery. And no one gets much of any value of it in any way. But a three person stand up. That's great and you also don't have to do it every day. you do it twice a week and that's terrific. And you have like sort of these focused, you know, project, you know, sinks.
Keith Cowing: 14:15
You spent a lot of time. Talking to people about where they wanna go in their career, what they want to do, where they get their flow state, where they get their joy, where they're productive and successful. I would love to hear a little bit about advice you're giving people today on how to follow their moral compass and how to engage in an environment where no matter what everybody's. Gonna have uncertainty in the air, but you can have uncertainty in the air just because we don't all know the future and still have an environment that is honest and open and really productive and has other things like clarity and support and psychological safety and appropriate risk taking. And so how are you talking to people right now about navigating the career landscape of where do they want to be?
Natasha Jaffe: 15:01
Yeah, sure. Like, so for what it's worth, like the moral compass thing, it's, it's more of an internal reflection. And it also feels a little odd or, or maybe that much more timely to talk about it right now when so many people are impacted by layoffs and they have to make, you know, very practical decisions with respect to their employment. Right. you know, the thing that's been on my mind is. Don't leave your moral compass at home no matter where you are. If you're actively searching for a job, if you're in your role and you find yourself in a place where you've been told to do something right, told to pick up some task, implement something in some way, cut a corner and your moral compass is making noise, listen to it. so, you know, in my own career, I think all the biggest regrets I've had have, have come to not listening to my moral compass or not doing it enough. And the times where it's paid off the most, you know, the decisions that I make are, are when they are in line with my moral compass. Um, so if you wanna talk about specifics, you can, but it's just the general advice, like don't discount it. Money is important. Yes. Status. You know what? That is important. These things are important. You might, might be more important for one person than for another, but don't discount the moral compass.
Keith Cowing: 16:18
I think that's really powerful. What are some of the things in your experience that have put that at risk in your decision making or caused you to accidentally sway into a direction that later on you realized you needed to change?
Natasha Jaffe: 16:35
I've had times in my career many years ago where I was offered a role that I felt rightfully belonged to another person. I. And the, the leader trying to get me to take the role pushed it pretty hard. Um, and at the end of the day, I refused knowing that they wouldn't give the other person the role. Um, and I remember it stuck in my head so much. The leader said something to me like, you have integrity. That's really rare in this in this profession. A couple months later I was gone. Like, that was it. That was, you know, they said the quiet part out loud, basically. And that was enough signal to lead and it was the best decision, you know, career wise that I've made.
Keith Cowing: 17:16
And how do you uncover that going in? You're digging down deep to say, Hey, from a principal's perspective, and I think this is true in all relationships, if you have the same values, then a lot of the other stuff you can figure out. Different personalities, different styles, different approaches, different skills, different passions, but values are really important, and integrity is a value. That's a core principle as a human. And so how do you test for those principles and values where on the surface, frankly, people are very likely to lie to you when you're interviewing.
Natasha Jaffe: 17:48
With the interviews, like that's hard to uncover. But when it comes to actually working within a role the signals are tend to be clear. The big one, of course, is like your gut. You know, you're gonna, I know about you, I feel a little sick, you know, when my moral compass is trying to tell me something. I feel it. but the other thing to be aware of is, you know, how much time am I. Am I spending on rationalizing things on mental gymnastics? Especially if you have, if you're a leader and you have to turn around and explain to your team like, oh, no, no, you know, this is good. This is actually really great for the client. You know, that, that sort of thing. Or it's great for you. And you feel that, right? Maybe you have to focus a little more. But that's the signal. Like, how much time am I spending on these kinds of activities?
Keith Cowing: 18:30
Or if you're defending decisions that you don't fundamentally believe in.
Natasha Jaffe: 18:34
right, that do not align with your core. And if you realize, oh, it's really hard for me to do that. There's a reason there's a reason it's hard.
Keith Cowing: 18:41
If somebody out there is trying to figure out whether or not the fundamental values and principles are aligned, what questions would you be asking to help them go through that self-discovery process?
Natasha Jaffe: 18:52
so what's bothering you? What, what about this is, is setting off your alarm bells. So I'd ask that to help dig into it to pressure test it a little bit. Could be that, there's some discomfort that's being caused by something else, right? But more importantly, like honestly, date, get clarity. Like what is the thing, what is the problem? And then sort of the next set of questions, you know, would focus on, well is this something that you can change? Can you change this in place? I think that should always be the first option. Like, try to make it better, you know, wherever you are, try to affect that change if you can. Unfortunately, oftentimes that the answer is no. You know, we like to think like every, every person is empowered. I remember at, at like a previous employer, like there's an auditorium. There are like thousands of us there and you know, the leader of that part of the organization held up a penny. He's like, this is your magic wand. You know, if you see something, you know, you write to me. And I remember thinking, like sitting in the back, just being like, he, how? Right. But that all that being said, like, first, what can I do where I am, what can I do to make it better? What needs to be true in order for me to be brave? What needs to be true? What is the worst thing that could happen if I was brave and it didn't work out? Like, what is the worst thing that can happen? How can I prepare for that? but then also, like, can I work here? And still follow my moral compass. That's important too. And if the answer is no, start thinking about that. Start exploring that. That's a luxury, by the way, in this job market as far as I'm concerned. But it doesn't mean that you don't have the thoughts and you don't develop those thoughts. I,
Keith Cowing: 20:25
You can have two ideas at the same time. One is where you stand from a values and principles perspective. And the other one is, what's the reality in the market today? And.
Natasha Jaffe: 20:33
do I get through, how do I continue to support my
Keith Cowing: 20:36
Right. You need to make the decisions that are right for you, which don't only involve that, but when you can make a decision based on that, you do. And then other times, you know, and this is one of the reasons why we work so hard, so that we can buy ourselves literally the opportunity to be able to make those decisions more and more on our own in the future. It makes that schlepping worth it. Um, and I love the simplicity of the questions that you are asking of what is bothering you. I am amazed sometimes by the questions that sound simple and obvious are the most revealing. Frequently. A lot of times I'm simply asking somebody, well, hold on. There's all this stuff going on, all these stakeholders, all these people in your ear. What do you want? And more often than not, people are not nearly as clear. You use the word clarity. Clarity is not as sharp as they think it is when they have a moment to sit and reflect and we don't have a lot of moments. You're in the whirlwind every day and all this stuff going on. And so, I love that simple coaching of just really basic questions, but they get the heart of. Okay, where's your moral compass gonna take you now? And what's the reality in the world? And now what do we do about it? And at least you're clear about everything and you don't wanna make things, make decisions by accident, by not being clear,
Natasha Jaffe: 21:51
Or have them made for you.
Keith Cowing: 21:53
Exactly right. And it's amazing how much pressure we get from society, from our friends, from families, from et cetera, et cetera, et cetera. It's like, what do you want? Moral compasses are an independent individual thing.
Natasha Jaffe: 22:06
yeah.
Keith Cowing: 22:07
What are you excited about these days
Natasha Jaffe: 22:08
I love watching what's going on with biotech. I. And drug discovery. I've been following that a lot. AI and drug development, you know, which is a bottleneck right now. I think that's a fascinating space to watch. Um, I love writing. I've been really enjoying that. I have a little blog. Anyone who doesn't know, like I'm a stay at home mom right now. I've been on hiatus for like a year and a half, and it was after like massive burnout from software engineering that never quite got resolved. And so I took a break from software engineering for like a year. I did nothing. I tried, I tried to write code and I couldn't, like, my brain just did not want to do it. and then finally, like several months ago, like it turned into my hobby. Writing about software engineering turned into my hobbies. So I've been enjoying my hobbies. but no, the rest of the time I, I love being with my kids. I have a little toddler. He's really fun. I get to have my 6-year-old when he comes off the bus. It's, it's awesome.
Keith Cowing: 23:04
What clarity did that break bring to you?
Natasha Jaffe: 23:07
I think the clarity that I had been very, very, very burnt out and that I needed the recovery. then, you know, let's call it last August or last September experiencing creativity again for the first time in what must have been multiple years at that point.
Keith Cowing: 23:27
Wow.
Natasha Jaffe: 23:27
retrospect, flow coming back to sort of our original topic and just the clarity of like, oh, that's what that is, what that feels like and what I've been missing. This is really great. I need more of this. So the clarity that I, I need creativity. I, I need to do creative things. It's a thing that I need, in order to sustain myself week to week.
Keith Cowing: 23:51
And where can people find your writing?
Natasha Jaffe: 23:52
They can find my writing@natashajaffe.substack.com. It's called Nuts and Bolts.
Keith Cowing: 23:58
I love it. Well, thank you so much for sharing your insights, your questions, your views. I think it's incredibly important for people to have that moral compass for people to think about listening to their team and having. Thi as we all go through these changes, and if we keep this kind of stuff in mind, I think we can be really successful in navigating that change and do it as humans. So, Natasha, incredibly insightful. Thank you so much for joining me.
Natasha Jaffe: 24:22
This was so much fun. Thank you.
Keith Cowing: 24:23
I took three main things out of that conversation with Natasha. The first one is just to take a moment and reflect her notes about clarity and really figuring out what you wanna do are powerful. The second one was about the moral compass. I love how she pointed out, don't leave your moral compass at home. And for me, I would expand that even more to say, don't leave your independent thinking at home and then the final piece is listen to your people. Don't go making changes to your company and get rid of 20% of the people on a team, hoping that AI can enable you to have the same output or more with less people, and then blow it up so that you get rid of 20% of the people, but 80%. Of the productivity because you squashed the flow state that your people that are creating the great stuff that you sell have to experience in order to have great products. If we can think for ourselves, lead with our moral compass, and then listen to our people on the team so that even when we make hard changes and fast changes, we put in the work to do it right, then we can be successful. I hope you enjoyed. This conversation and this episode. If you did, please leave us a five star review on your favorite platform. It helps the show and it helps other people find the content and benefit from it. Until next time, enjoy the ride.
