🔗 2 years as a CTO - a follow up

One year ago I wrote this post. I got very interesting feedback and realised I was not the only one having these kind of issues. I received some DMs too and got to chat with a few of you, and it was amazing. I also received some nasty comments, which are not the best thing to read when you are going through a rough patch. If you are not interested in this kind of posts, downvote and move on, no need to be an asshole.

Anyway, things have improved alittle and I am more optimistic, and some people left comments asking for a follow-up, so here it is: year 2 as a CTO.

Let me start summarising how I got here: got hired 2 years ago to lead a team in a non-software company and it was a mess: outsourced team had all the knowledge and their own agenda, hired members knew nothing and the lack of focus and best practices caused lost, frustration and fights. I got promoted to CTO and had the responsability to lead this transformation, and things went south.

Alright, so after i wrote the last post things got worse. And I mean a lot worse. At that point both the asshole Head of Product (former asshole PO) and the lead of the external team focused all their efforts on lobbbying against my decisions. I said we should have more test coverage to avoid mannually testing everything each release, they said testing was a waste of time. I said we should focused on one or two fronts at a time, they would open one front per team member. Anxiety kicked in harder than ever. On top of that, the other PO which I got along with decided to leave the company after only 8 months or so. My only ally in that team had banished.

A few months past by. Every monday I would wake up to an email from the asshole PO asking why everything was advancing so slowly, ignoring the fact that they had a junior guy trying to build an LLM from scratch because AI is the buzzword of the year.

I sat with both of them and asked them to have an honest chat about how things were going. I convinced them to drop most of the ongoing developments and focus on 2: having 2 teams of 3-4 people working on each of them. They agreed until they didn't.

I had to go through a minor surgery procedure and took a sick day (wisdom touth removal, nothing important, thanks for asking). The next couple of days I went to a conference with a coleague of mine, so it was going to be 3 days OOO. I left some guidelines and asked the team to keep focus on wht we had planned for the week. The first day at the conference, my coleague told me the outsourced team lead said my guidelines were shit and decided asked the team to do the opposite. I had been out for one day and this jerk was undermining my decissions.

At that point, during the conference, I noticed something was wrong. talking to my coworker I started feeling anxiety as I never had before. I excused myself, went to the toilet, proceeded to have a panic attack, told my coworker I felt sick after surgery, and went back to the hotel. I barely remember the next day at the conference. I was numb, only thinking about quiting. And so I did.

The next day I called the CEO and told him I was quitting. As I explained, I got offered the job because the CEO and I are friends (kinda). I trusted him enough to tell him how I was feeling and how my mental health was not at it's best and how work was making me sick. He understood and we drafted an exit plan.

And there I was, having an existential crysis thinking how my CV would look and how nobody will hire me and how my wife was going to leave me and die alone. I had the feeling I made a mistake.

Two days later the CEO called me. He asked me to stay. He had decided to fire the Head of Product. He thought whomever took my position would face the same issues, and the goal of the company is to build a robust software product. Still, it was not enough for me to stay, but as I said, I was second-guessing myself. I asked him to fire the outsourced team. As a reminder, last time I asked him to get rid of these guys he said no. the outsourced team company owner and the CEO were partners in other businesses, so he did not want to risk that. This time he agreed, so I stayed knowing if things did not get better after this I would have burnt my last chance. Now I see this was a mistake. I do not like the idea of threatening with my resignation to get what I want, and I feel it came out that way. It's a trump card I was not planning on using, but I lost control of the situation. I wanted to quit for real and I think this made me lose credibility.

I met with the outsourced team and told them their contract would end by the end of the month and that I wanted to have everthing properly documented. Of course they didn't do so, what was I expecting.

I told the team all the upcoming changes and the response was mostly positive. There were a couple of members in the team that did get along with the outsourced team and were not happy about this decission. From my POV, the outsourced team was not what we needed, but they were not assholes nor hard to work with except for their lead. And even him had a great relationship with some of them. Anyway, these decisions are hard and I knew some team members might want to leave after this.

The exit of the outsorced team and the head of product kicked off a transition period. I used the budget from the team to hire a couple of very experienced devs, making it clear one of their goals was to make the more junior members better devs. I also hired a new head of product. I got in touch with a PO I had worked with and offered her the job. She accepted and we hire another PO, one for each of the products we are bulding. We took this hiatus to research what the outsource team left there hanging, document everything and make everyone feel confortable working with it. We messed things up, might have destroyed an environment or two, but nothing we couldn't fix. And now the team is a lot mor confortable with Terraform, which is something the other team handled.

One year after my last post things have gotten better. A lot better actually. Still, we are not a perfect team. One of the team members that has been here for long is hard to work with, another one left because he got an amazing offer, we do not finish our sprints half the time, and every non-developer is pushing towards building our own AI (am I the only one tired of people trying to shove AI into everything?). I still suffer from anxiety, but haven't had a panic attack in months and I'm pretty sure I won't stay here for a lot longer.

Again, before wrapping up, here are some key takeaways from this year (and some of them might be the same as previous year):

• Create fear-free environments: allow your team to make mistakes. They will fix them and learn from them. Fear of failing will lead to inaction. And this applies to your coworkers, but also to yourself.

• People leave, and that's ok: very high rotation is bad, but some rotation is actually positive. New people brings new ideas. Avoid inbreeding within your team. "We have always done it that way" is probably the worst answer to any question.

• Talk about your feelings, do not let intrusive thoughts snowball. Talk to your friends, family, loved ones, coworkers, psychologists. Talk to people and you'll see you are not alone.

• Your loved-ones will not leave you because of your mental health status. My wife is amazing and she has supported me all this time.

• Maybe the most important one: change takes time. It takes time at work, it takes time out of work. Be patient.

• I regret saying I would leave and then staying. From my point of view, I lost credibility there. Biggest mistake this year.

This past year has been intense, and probably even worst than the last one, when I though I was at the very-bottom. I really hope this helps anyone out there that's been facing similar problems.

TLDR: Second year has been even worse for most of it, but the past few months has improved a lot. Had some panic attacks, tried to quit, decided to stay, fired some guys, hired some other guys, things are getting better.