Are you an experienced software buyer? I could use some help.

I'm writing a bunch of chapters on Observability Governance for the second edition, and I would love to hear your stories about buying software...the good, the bad, and *especially* the ugly. 😉

If it seems like I’ve been relatively quiet lately on social media and my blog, that’s because I have. Liz, Austin, George and I have been busy toiling away on the second edition of “Observability Engineering” ever since April or May. I personally have been trying to spend 75-80% of my time on the book since May.

Have I been successful in that attempt? No. But I’m trying. Progress is being made. Hopefully just a few more weeks of drafting and we’ll be on to edits, and on to your grubby little paws by May-ish.

The world has changed A LOT since we wrote the first edition, in 2019-2022. Do you know, the phrase “observability engineering teams” doesn’t even occur in the first edition of the book? Try and search — it can’t be found! Even the phrase “observability teams” doesn’t pop up til near the end, and when it does, we are referring to those few teams that choose to build their own observability tools from scratch.

These days, observability engineering teams are everywhere. Which is why we are adding a whole new section, a sizable one, called “Observability Governance.” The governance section will have a bunch of chapters on topics like how to staff these teams, where they should fit in the org chart, how to buy good tools, how to integrate them, how to manage costs, how to make the business case up the chain to senior execs, how to manage schemas and semantic conventions at scale, and much much more.

The problem

The problem is, I’ve never really bought software. Not like this. I’ve never even worked at a  truly large, software-buying enterprise tech company. So I am not well equipped to give good advice on questions like:

• How do you shop around for options?

• What are some signs you may need to suck it up and change vendors?

• What does a good POC (proof of concept) look like?

• Who are your stakeholders? What are their concerns?

• How do you drive consensus when millions of dollars (and the work experience of thousands of engineers) are on the line? What does ‘consensus’ even mean in that context?

• What are the primary considerations should you take into account when making a decision? What are secondary considerations?

I’m looking for the kind of advice that a principal engineer who has done this many times might give a staff engineer who is doing it for the first time. Or that a VP who’s done this many times might give a director who is doing it for the first time.

Can you help?

This is me wearing Leia buns and projecting a unicorn-shaped rainbow bat signal out into the sky for help. Do you have any advice for me? What guidance would you give to the readers of the second edition of this book?

Please send your advice to me in an email, addressed to my first name at honeycomb dot io, with the subject line: “Buying Software”. Include any relevant context about how large the company or engineering org is, and what your role in purchasing was.

I may respond with more questions, or reply and ask if you are able to talk synchronously. But I will not quote anything you send me without first asking your permission and getting a signed release. I will not mention ANY vendors by name, good or bad.

I am not fishing for honeycomb customers or buyers, I assume most of you haven’t tried honeycomb and don’t care about it and that is fine. This is not a Honeycomb project, this is an O’Reilly writing project. I just want to gather up some good advice on buying software and funnel it back out to good engineers.

Can you help? Your industry needs you! <3