How would you know what good looks like if you have never seen it?

The other day I was discussing observability and monitoring tools with an experienced CTO.

For many years across different companies and teams I have been using some kind of unified monitoring solution. Datadog, NewRelic, Honeycomb, Sentry, or similar. Tools that help a team understand how their product is working (or breaking) on a technical level in real time.

This experience has made it obvious to me how much more effective these tools make troubleshooting and understanding your system. Especially compared to what you did in the old days: manually logging in to different servers and looking through endless log files.

After some discussion I asked the CTO what they are currently using. They explained what they have been doing since forever, and added:

These new tools sound really interesting. You need to tell me more, because I have never seen or used anything like this before.

The reply made me realize that what I regard as the reasonable good way of doing something was completely unknown to this person.

And how would you know what good looks like if you have never seen it before?

Before encountering a better alternative, it might be hard to imagine its existence.

Marty Cagan gives a similar explanation for why there are so many bad product companies: the leaders have never worked at strong product companies and never seen good.

I’m sure this explanation can be generalized even further: leadership, teamwork, engineering practices, sales, user research, communication…

What good looks like today is being redefined constantly, and you have to do some amount of work to keep up.

So how do you get to know what good looks like? There are a lot of different ways, for example:

📚 Read books and blog post, listen to podcast, and watch conference talks to get new perspectives.

🪓 Work on side projects or take on responsibilities in your spare time that allows you to grow and explore new ways of thinking.

👔 Catch up with former colleagues and network with people in other companies to learn from what they are currently doing.

🤝 Change company and team every now and then to be exposed to different ways of working.

How do you stay up to date with what good looks like today?