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Building Brex 3.0, March 2024

I wouldn’t want to work in an environment like this because even though delivery is a fun part of building product, I find that for most PMs it’s so much more fulfilling (and you usually get better results!) when they are part of strategy and discovery as well. That said, I’m now long enough into this product journey to recognize that as long as you have a team of people who love execution and are excellent at it, this is a completely valid way to build a company:

We changed this model with Brex 3.0. We killed our planning process, and now have One Roadmap for the entire company. I [Brex CEO] am the ultimate editor of everything that ships. We release 4 times a year, and each release has no more than 3 big themes. This forces me to choose what truly matters, allowing us to make a large, company-affecting investment in the few things that are step-function changes to the customer experience, and drop everything else.

Basecamp works in a similar way, and it works for them. I do appreciate that both companies are honest about how they work, so PMs know what they’re in for and what’s expected of them. The frustration only sets in if PMs think they have some autonomy over their work, and then slowly find out about the “shadow roadmap” they weren’t aware of. Just bring it all into the light, I say.

Can AI therapists do better than the real thing?

My wife is a therapist, so the story Can AI therapists do better than the real thing? (oh hello, Betteridge’s law of headlines) piqued my interest, since we’ve had lots of conversations about this kind of thing.

The story starts off with some really interesting anecdotes about people forming “relationships” with their therapy chatbots, but it then turns towards some of the concerns and drawbacks, and how one client (not a fan of the use of “patient” in the article) ultimately dealt with the bot they created.

One example of the things that AI therapy bots can’t replace:

Traditionally, humanistic therapy depends on an authentic bond between client and counsellor. “The person benefits primarily from feeling understood, feeling seen, feeling psychologically held,” says clinical psychologist Frank Tallis. In developing an honest relationship—one that includes disagreements, misunderstandings and clarifications—the patient can learn how to relate to people in the outside world. “The beingness of the therapist and the beingness of the patient matter to each other,” Grosz says.

Oops, I did a Manager-README

I know the concept of a Manager-README (a document where you explain to your team some of the ways you like to work) can be controversial, so I’ve avoided it up to now. But this week I got curious and read up on the pitfalls and how to avoid them. Then I took a stab at an outline and it was actually really helpful—even just for myself—to clarify some of my own views on product work. It starts like this:

The purpose of this document is to summarize some of the values and principles I try to adhere to at work. But we are human and this is a relationship not a contract, so I see it as a way to kick-start how we work together, not the end result.

I also recognize that documents like these can be abused by managers, so this is not a way for me to excuse any bad behaviors. If you see me doing something that is not reflective of these values, please call me out so that I can improve.

I then go into talking about my leadership style, product philosophy, communication preferences, decision-making, and feedback loops. I would love to hear if this type of outline is helpful to anyone, and if you have any feedback!

The Trap of Tying Your Identity to Your Job Title

Elena Verna makes some really great points in her post on The Trap of Tying Your Identity to Your Job Title. If you are struggling with questions around title and importance and what it all means, this one is for you. This point on external expectations particularly stood out for me:

Perhaps most concerning is the inclination to make career decisions based on perceived market expectations rather than personal happiness and well-being. This mindset propels individuals down a path not of their choosing, driven by the desire to conform to societal benchmarks of success rather than pursuing what genuinely brings joy and satisfaction.

What is strategy—explained with a useful puzzle metaphor

This is about content marketing but Fio’s post What is strategy—explained with a useful puzzle metaphor is very relevant to product people as well:

At its core, that’s what strategy is: taking a problem, discovering what makes it hard, and finding the right way(s) to solve it. The concept is super obvious when applied to a puzzle: you intuitively know that picking random pieces from the pile and expecting them to slot right into place is not a sensible approach…

…and yet, that’s often how content folks expect marketing programmes to work: we bypass the diagnosis and guiding policy phases, jump straight into picking tactics, and expect that all the pieces will automagically fit together in the end.

Another reminder (which I think we need to hear almost every day) not to jump into implementation too quickly. Take time to understand the problem and the opportunity first.

Why I love Buttondown

This is a bit of a meta post, especially if you’re reading this as an email as opposed to via RSS or the web… but bear with me please!

Justin Duke is one of my favorite internet people—ever since I met him while I was working on Postmark and we tried to convince him to switch his email provider for Buttondown. I now use Buttondown to run my little RSS-to-Email newsletter (yes, via Postmark!), and it was such a joy to chat with a fellow Open Web Enthusiast™ last week about owning your words, and what makes this partnership so special to me. He somehow managed to edit my ramblings from the interview into something that makes sense:

Despite sounding cliché, I hold a strong belief in the importance of owning your content, a sentiment echoed in the challenges faced when migrating from platforms like Substack. Their network is essentially their product, monetized in a way that complicates leaving, especially when payments are involved. […]

The internet’s enduring spaces, free from central ownership, are RSS and email. These technologies prompted my switch, betting on the most basic, reliable forms of digital communication. Embracing the POSSE model—Publish (on your) Own Site, Syndicate Everywhere—resonates deeply with me.

I think this is also where I’m supposed to mention that if you’d like to help cover the cost of hosting this site (and paying for Buttondown!), you can become a Friend of Elezea for $3/month. Bargain!

On kindness and decisiveness

Mike Fisher reminds us how important it is for leaders to be excellent listeners in Listen or Speak. This part particularly resonated because it’s a misconception about me that I’ve had to deal with my entire career:

Just because we speak softly doesn’t mean we act with hesitancy or indecisiveness. We can be a strong leader, setting the example, and making the tough decisions all the while communicating in a manner that keeps the conversation going and open to other people’s inputs.

I believe strongly in acting people-first as a leader, and I’ve found that when I’ve gone through interviews and/or job changes in the past there is a very common worldview that equates kindness with indecisiveness. It always takes a little while for people to realize that just because I believe we make better and more successful products when we treat each other well and truly listen to everyone’s input, it doesn’t mean I don’t know how to make decisions.

I haven’t quite been able to put my finger on why this misconception exists in the corporate world, but my current hypothesis is that collaboration gets confused with consensus, and there is a fear that “speaking softly” will result in a consensus culture where decisions take forever to be made. With that part—the dangers of consensus cultures—I do agree with. Consensus cultures often produce watered down, unexciting products. Products where endless rounds of give-and-take have worn down the original idea to a shadow of what it once was. Consensus cultures also wear down the teams working on the product, because no one really gets what they want, they just get some of it.

So I always try to make the point that I prefer collaboration over consensus. In collaboration cultures people understand that even though everyone gets a voice, not everyone gets to decide. People are able to voice their opinions and argue (kindly!) for how they believe things should be done. But it certainly doesn’t mean that everyone has to agree with every decision. That seems to help—so if you find yourself in a similar situation, give that framing a try!

Since this is something I have felt in my own career, it’s also something I try to be cognizant of in my dealings with those around me. Just because someone doesn’t dominate the conversation (see the “babble hypothesis”, which states that those who talk the most tend to emerge as group leaders), or refuses to engage in combative conversations, it doesn’t mean that their viewpoints and opinions are weak or invalid. In fact, the opposite is likely true.

Figma’s CEO on life after the company’s failed sale to Adobe

Alex Heath has a really interesting interview with Figma’s CEO Dylan Field, covering life at Figma after regulators forced Adobe to abandon its $20 billion acquisition of his company. It covers a wide range of topics, but I wanted to highlight Field’s thoughts on generative AI, which largely matches my own viewpoint:

If I was to zoom out even further to knowledge work, we’re very much in a paradigm of AI as a tool and AI helping people get work done, but it’s not necessarily a replacement. I really think that there’s a human in the loop going forward in that AI might be a useful tool, but we all know its limits in terms of hallucinations, in terms of potential inaccuracies. Even if you apply it to rote tasks, it’s important to check the work. And you know better than anyone as a writer that the current models do not match your ability to write, let alone gain context in a conversation to ask the right questions or show the intelligence that you have as a journalist.

If you think about what it takes to create great design, there’s so much in that context window that’s emotional or thinking temporally about a brand experience or a user flow. I just don’t see how, in the near term, AI is able to have that as part of its context, which means that humans are providing that.

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