How Many CTOs?
S1E49 · December 23, 2025 · 12:58

Year In Review: How Many CTOs Does It Take To Finish A Season?

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0:00 12:58
Transcript

In this episode

In this special public service announcement episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub announce that they will be taking a two-week break for the holidays and will return with Season 2 on January 13th. They reflect on their first year, discussing the major themes like the challenges of tech debt, the evolving role of AI in software engineering, and the value of weekly conversations with other tech leaders.

The episode also acknowledges the contributions of their producer, Saffron, and offers a heartfelt thank you to all listeners.

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Transcript: Year In Review: How Many CTOs Does It Take To Finish A Season?

0:00 Brad I think in 2026, the question is going to be, how do we deal with the challenge of the weaker team or the team that's got weaknesses that are then having AI exacerbate those problems?

0:29 Scott Hello, everybody, and welcome to a public service announcement episode of How Many CTOs Does It Take podcast. My name is Scott Porad.

0:39 Brad Brad Hefta-Gaub.

0:41 Scott And it has been a great year.

0:43 Brad It has.

0:43 Scott We've had a lot of fun on this podcast.

0:46 Brad Thanks for everybody that's been listening to the podcast this first year. It's been super fun for Scott and I. But the holidays are upon us. And so this is going to be our last episode of season one of the How Many CTOs podcast. So you're listening to us now. This will be the officially the last episode of season one. We're going to take two weeks off and we will be coming back roaring with season two of How Many CTOs podcast on January 13th. So you guys are hopefully listening to this on or around the 23rd of December and we'll take a couple of weeks off and then we'll be back with lots more How Many CTOs content.

1:33 Scott And don't forget to mark your calendars.

1:35 Brad Mark your calendars for January 13th.

1:40 Scott Okay, let's take a minute, Brad, to reflect upon the year. It has been fun. We've talked about a lot of stuff.

1:44 Brad Yeah.

1:45 Scott What are your highlights? Well, actually, yeah, what are your highlights? And then we should also talk about briefly what are your holiday plans?

1:52 Brad Well, let's see.

1:54 Scott Or what are my holiday plans too? It's not all about you. I mean, it could be all about you if you wanted to go.

1:59 Brad Well, I have a – okay, let's start with – do you want to start with holiday plans or reflecting on

2:05 Scott Sure,

2:05 Brad them?

2:05 Scott let's do it. Let's do it. Holiday

2:06 Brad Yeah,

2:06 Scott plans.

2:07 Brad well, I have – the Hefgab family has had a tradition for several years, a couple decades actually, of doing a big Christmas Day feast dinner. And we recently shifted that from Christmas Day to the winter solstice. So, yeah, I guess if people are listening to this on the 23rd, we will have already had this big feast with 20 family members come. And it's always a big, exciting thing. I always try to do, I love cooking. I love the feast of it. I love the gathering, the community and family. And so that's kind of our big thing. We also do the kind of the traditional Christmas festivities of a Christmas Eve and Christmas morning and stuff like that. That's that's our tradition.

2:55 Brad And then I hope to be doing some skiing. It is snowing up around Washington today, but we've had a really, really wet but warm fall. And so it's a little bit it's a little bit sad, actually. There hasn't already been some great skiing. So. But anyway, those are my holiday plans. How about yourself,

3:16 Scott It

3:17 Brad Scott?

3:17 Scott is. Well, it has a bunch of parks this year to it. First of all, I'm Jewish, so we don't celebrate Christmas, but some of our family does. So we always go to my mother-in-law's house for Christmas Eve. And then we typically go skiing on Christmas Day. We have a celebration we call Jews on snow. But like you said, this year there might not be a Christmas Day. day, ski day. Both because of the snow and the road to the mountain got washed out in a storm. It's unclear if they'll have that fixed in time. So I guess our plan B will be Chinese food in a movie or something.

3:53 Brad There

3:54 Scott I'm not you really

3:54 Brad go.

3:54 Scott sure what's going to happen. And then immediately thereafter, myself and my two kids, neither of my kids live in Seattle or at home any longer, but we're all going to, and my wife, of course, we're all going to New York City for a week.

4:06 Brad Awesome.

4:07 Scott And we're going to do, well, first we're going to visit some family and then we're going to do New York City things, you know, plays and museums and stuff like that.

4:15 Brad That sounds like much fun.

4:16 Scott And then back here, then it's January. We come back in early January, you know, first weekend of the year and we get on with it.

4:25 Brad I love

4:25 Scott Back

4:25 Brad it.

4:26 Scott to recording the podcast, back to doing the work, back to trying to fix tech debt and figure out AI and get people to play nicely with each other and make good software and meet business needs and explain complicated technical things to people who don't understand and try to explain things that immeasurable things to finance people and

4:48 Brad Yeah, totally.

4:49 Scott all of that.

4:50 Brad Well, that's a really nice. That's actually you're kicking right into the question of like, what are your reflections on the past year's episodes? You hit on a couple of topics just now that are like resonated for me, but I'm curious, would you like to what what were the standout? What were the standout topics from your mind?

5:07 Scott I would say there are two things, Brad. The first is I came into this a year ago, and I think you know this, thinking there are these vexing questions in our industry. and maybe we can talk to some people who have answers to them and those are questions like how to deal with tech debt and stuff like that and I don't think we talked to anybody who had answers to them or at least every everybody we talked to was struggling just as much as we were so that was my one takeaway and then I would say the second thing is this became at least for me the year of switching from AI skepticism to, it wasn't AI cheerleading, but it was more like, let's call it AI realism, right? Like, oh, this is going to be a real thing and we're going to have to, you know, figure out how to make this fit into our world.

5:58 Brad Yeah.

5:58 Scott And so that I think were the two themes for me of this podcast for the year. And when I think ahead to 2026, gosh, I don't know.

6:09 Brad Yeah.

6:10 Scott what the themes for next year will be. Well, I guess we'll have to see what happens. How about you? What were the themes for you this year?

6:14 Brad Yeah. So before I touch on the themes, I thought I would also say that. The ritual of getting together with you every week and talking about these complex topics has been really rewarding for me. You know, you and I kind of we we started the podcast because we would kind of regularly chat with each other and just kind of talk through these types of themes. And you used to jokingly call it like CTO therapy that we would have each other's as a support team. And I feel like that's. something that I look forward to every week just to be able to pick your brain about topics. And when we've had guests come on, it's been really, you know, really a joy to like hear these other perspectives.

7:02 Brad And I think that your point about the challenges that we face as CTOs, nobody has perfect answers to these questions. And so there's a little bit of a maybe a misery loves company. aspect to this when we are facing these complex things so I guess you know I want to say thank you to you for getting together with me every week and sharing this time and sharing these thoughts and sharing this these challenging questions

7:30 Scott 100% agree. It is the highlight of the week for sure. I've got meetings all week long and this is the one I look forward to. I don't think I look forward to, well, I shouldn't say that my boss might be listening, but I don't think I look forward to a lot of them, but I look forward to this call every week for sure.

7:45 Brad As far as themes go, you know, I do, I guess I would say just that the first theme, it's great to just connect with other leaders and to. bounce ideas off of them. And so there's been so many times when either I have felt I've learned something a little bit new or a different, a slightly different way of looking at things or felt validated by, you know, their approaches to the problems that I've encountered as a CTO.

8:18 Scott Mm

8:18 Brad You know,

8:18 Scott -hmm. Agreed.

8:19 Brad the guests that we've had, that's been really enjoyable and I hope we're going to do more of that in 2026. And then there's no doubt that 2025 has been really, I think, a turning point for the way that we use AI in software development. I think that I just. Look at it in all the teams that I work with, the ones that have really, really embraced those tools as power tools that make good engineers even better engineers has been really amazing. I think I sent you this text yesterday. I got one of the one of the engineers on.

9:05 Brad one of the teams that I work with as a fractional CTO messaged me saying, oh my God, this AI stuff, I'm really embracing it. It's like I got done in an hour what would have taken me two days to get done in the past. And I see that with all my teams. So yeah, there's no doubt about it. It's been really quite. compelling, I

9:31 Scott Mm

9:31 Brad would say.

9:31 Scott -hmm, yeah.

9:34 Brad And so there's no doubt that there's no doubt that that will still be a topic that's constantly coming up. But I think that what's been what's been fun is and I think there's a lot of of fertile ground to explore in. OK, but, you know, when we like the couple couple episodes back, we did that. We looked at that door report on how has AI affected Dora metrics and, you know, it is I do think that. It is not a magic potion that makes all engineering teams better. In fact, I think that it's AI, generative AI for software engineering is a magic potion that reveals the character of the team. uh exponentially

10:15 Scott Hmm.

10:16 Brad and so if it's already a strong team they get much much stronger if it's a team that has weaknesses the generative ai i think exposes those weaknesses and um so that's why i think we're going to see more of that i think in 2026 the question is going to be how do we deal with that how do we deal with the challenge of the weaker team or the team that's got weaknesses that are then and having AI exacerbate those problems.

10:44 Scott Yeah, that is a great theme. I don't have thoughts on the solution, but I got a lot of questions I want to ask.

10:51 Brad Not now. We'll wait until the next year,

10:52 Scott Not now.

10:53 Brad the new year for that.

10:55 Scott There's one other thank you I feel like we should put out there, which

10:58 Brad Yeah.

10:59 Scott is that we have a producer named Saffron who keeps us on track and makes really makes all this stuff happen.

11:08 Brad Yes.

11:08 Scott And so thank you to Saffron.

11:10 Brad Thank you to Saffron. Saffron Heftagab. No relation. No actual relation. She is my daughter, but she's a fantastic producer of this podcast. award-winning producer in her various podcast production roles that she has. But

11:27 Scott Oh,

11:27 Brad yeah,

11:28 Scott that's great.

11:29 Brad it's interesting. I agree. Thank you, Saffron, for everything you do. This wasn't exactly her cup of tea, so it's been fun to watch her bring her talents to a topic that's not necessarily her. Her forte, but she's a fantastic producer, so we're lucky to have her.

11:51 Scott All right. Well, with that, are we calling it a wrap? I mean, the thing is we could end up talking forever. That's how this whole

11:56 Brad We thing will.

11:56 Scott got started.

11:57 Brad We do. That's the thing. I said we got to cut it off. So all right, everybody. So the news of the day is thank you very much. This is our last episode of season one of the How Many CTOs podcast. And we will see you all again in two weeks time when we come back on January 13th of 2026.

12:16 Scott Just pray for snow.

12:17 Brad Pray for snow, everybody. Pray for snow.

12:20 Scott All right, see you,

12:21 Brad Brad. See ya. This episode of How Many CTOs Does It Take Podcast was edited by Saffron Epigow. Our theme song was AI Generated by Brad. Please follow us on all the social media platforms at at how many CTOs pods. You can find us on YouTube, LinkedIn, Instagram, Facebook, Threads, X, TikTok, and Patreon or at our website at howmanyctospod.com. And remember to rate, review, and subscribe on the podcast platform of your choice. Thanks for listening.