It Depends

Matthew • April 20, 2021

As I start thought-leadering publicly and consider the subjects on which I might opine, I keep coming back to the phrase "it depends." By which I mean, "context matters."

When I read books and blogs these days, I'm kind of gobsmacked by how infrequently people say, "this is good advice for people like X but not people like Y." Everything is Maximum Certainty. It just rubs me the wrong way, because I know that none of it is certain at all.

And here I am, poised to foist my thoughts and beliefs on the world, and I'm (possibly irrationally overly) concerned that the wrong folks might end up trying to take my advice. I mean, sharing one's thoughts publicly is already harrowing enough without worrying you'll cause harm, yeah?

(Basically, this blog post serves as a giant disclaimer for all of my public statements. Consider yourself notified! Your continued reading constitutes implied consent.)

I once was on a panel at a small conference expounding on the glory of agile development practices and DevOps. This event happened before those ideas became part of the universal word salad. Among my firmly held beliefs was the idea that too much planning and looking too far into the future was Old Fashioned and Bad. (Or something--I don't remember the exact words.)

One of my fellow panel members replied, "My company has purchased a Super Bowl commercial, and the URL it will contain has to work." (For those not in the US, the Super Bowl is basically the World Cup for Americans and commercial timeslots cost a millionish dollars.)

What he was saying was that he did not have the luxury of letting his ship date slip. And as he described the details (which I don't remember), it was also clear that he had limited latitude around scope as well. His team couldn't take it sprint-by-sprint. Agile was probably not the tool for him and his colleagues.

"Oh," I said. (Probably. But probably something dumber.) I suddenly realized that the tool or approach I employed should depend on the particulars of the situation: how flexible is the schedule, how many unknowns are there, how much risk is there, what are the strengths and weaknesses of my team, what resources are available to me, and so on.

So, that was an epiphany for meā€”kind of embarrassing, honestly. Maybe you figured all of this out a lot sooner. I'm a late bloomer. (Still!)

And that was only the beginning of that journey. The more I do and see, the more I say, "it depends."

The next significant milestone on my journey was when I read Donald Reinertsen's "The Principles of Product Development Flow: Second Generation Lean Product Development." I'll elaborate on this book (AT LENGTH) in future posts. I've never seen another professional book be so up-front about saying "it depends." (And I think that's one of the reasons it's a difficult read.)

That book or blog about software development or hiring or whatever--who is the intended audience? Is it for a startup SaaS shop? A media consultancy? An internal technology team at a Fortune 500 company? Fast or slow-growing? Pre or post-product-market fit? Mostly, authors don't say. It's incredibly unhelpful. I would encourage authors to identify their target audience.

And, of course, as a reader, you should be mindfully asking, "Is this for me?" It might not be!

These days, I find this lack of context especially grating and exhausting because it presents the writer as lacking in empathy. And, Dear Reader, here in April 2021, my tolerance for that is utterly depleted.

So here's my experience and where I am credible. I'm a seasoned technology manager with experience growing teams from 0 people to under 100 people, from $0 to $100M in revenue, at companies in SaaS, eCommerce, marketplace, and enterprise software. My time has typically been at fast-growing VC-backed companies mostly using Ruby on Rails where I've been senior management often reporting to the CEO. (I've also written a Ruby on Rails gem with over a million downloads.)

That's it for now, friends. I hope this finds you in good health and good spirits. If you've got questions or comments, hit me up at @mjbellantoni on Twitter.

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Matthew Bellantoni is a seasoned technology manager experienced growing teams from 0 people to under 100 people, from $0 to $100M in revenue, at companies in SaaS, eCommerce, marketplace, and enterprise software. His time has typically been at fast-growing VC-backed companies, mainly using Ruby on Rails, where he's been senior management usually reporting to the CEO. (He's also written a Ruby on Rails gem with over a million downloads.) You can contact him at or at @mjbellantoni.