About Me

I am just some guy with a cool wife and funny kids who likes making things that probably don’t need to exist, like this website, a bunch of albums, and all these words.

About Me

I am just some guy with a cool wife and funny kids who likes making things that probably don’t need to exist, like this website, a bunch of albums, and all these words.

You Fix What You can Reach

Elephants

One consistent factor across the now numerous early-stage companies I’ve worked at for the last decade or so is the presence of proverbial “elephants in the room”. Everywhere I’ve been, there has always been something bigger and more fundamentally important than the things we were working on, that everyone senior-enough knew was more important, but that we all knew wouldn’t/couldn’t ever be addressed. Sometimes it was a business model issue, and what we were selling just wasn’t as valuable to people as we wanted/needed it to be. Sometimes it was a product issue where we built out too many mini-solutions to user issues and ended up with a confusing mess that no one would ever get permission to purge (because everything that comprised the mess, individually, solved a customer issue somewhere). Oftentimes the issue was a technological one, especially when our business leader wasn’t sufficiently technical, and our technical leader was perfectly happy to watch the ship slowly sink as long as it continued to prove he was the smartest guy in the room.

On the other hand, I have never worked at a company without at least a couple of talented people (often many, many more) who really impressed me, and this has been especially true during my startup binge from 2008-2022. So there have always been voices — loud, frustrated, pleading — calling out these elephants, suggesting ways to engage with them, and ultimately giving up and either accepting the way things would have to be, or moving somewhere where the elephants were either more palatable, or less obvious.

No Refunds

Although the “talented” adjective is debatable, I’m pretty sure I’m from the bucket of people who have trouble looking past the elephants. I’ve left all of my jobs pretty amicably, but I can tell you the exact moment when I knew I had to leave each one. So far, every single time it’s been over the collision of what the company wanted me to do, and one of these elephants. My favorite was back at Bamboo — I wasn’t even 30 yet — where our new CEO and his consultants wanted us to create a “Bamboo Way”, not unlike their favorite store Bauhaus, where we’d guarantee that customers would be happy. This sounded very ambitious, so I asked if we’d be expanding our refund policy for customers who weren’t happy, since we’d usually get a decent amount of those. The CEO looked at me like I was crazy. “No, definitely not. We’re not talking about refunds, here. This is more of a feeling than a specific policy.”

At 28 or 29 or whatever I was at the time, I thought this was rank hypocrisy, but now that I’ve had more C-level bosses, I realize that it was really just garden-variety self-justification. Customers should always be happy, yes, but there are LOTS of ways to make customers happy, and we should just do the ones that don’t require us to ever give them money. We should build better products, and provide better support. Easy!

But ultimately the elephant in the room was that we weren’t actually built to do that, and we were cutting costs at the same time with a mandate to increase profitability, so there was no reason to think we would suddenly become more capable anytime in the future. We were setting ourselves up to not only fail, and lie to customers, but then to allow everyone to blame nebulous factors and boogeymen for that failure once it happened. When there was no real counterargument to this existential assessment other than “it’s more complicated than that” without any follow-up explanation of what those complications actually were, it was pretty clear what was about to happen. Over the next couple of months, some people left, some people didn’t, but for everybody in that room it was pretty clear you were either able to ignore the elephant in the room or you weren’t, and if you weren’t you needed to go. For the first time in my career, I was one of those people who needed to go, so I did, despite an incredible amount of affection and loyalty to the place.

Deck Chairs

At most of the other places I’ve worked, the elephant in the room is usually related to the nexus of product, technology, and business (which makes sense at the kind of growing technology startups I’ve spent my time at). I wrote about this in other post, but the venture capital treadmill makes many of these elephants almost inevitable. You start with something powered almost exclusively by vision, and then begin the process of delivering that vision with resources that have extremely specific strategic and operational milestones and timelines attached to them. They aren’t articulated, but they’re there — you start burning money at a rate that necessitates more funds than you can generate from customers (which means going back to VCs or finding new ones), and those new funds rapidly become contingent on promising to operate a certain way or focus on certain things (“we are moving upmarket!”). Having only vision (versus an operating strategy) allows you to accept resources that — eventually, inevitably — dictate your operating strategy further down the road, vision be damned, and that’s exactly what happens. Vague visions will survive (self-justification!), but they will quickly become eye-rolling corporate totems of resentment to everyone outside of new-employee orientation groups or ask-me-anything sessions with founders, because the vision is secondary to the operating requirements, and the operating requirements get more onerous every year. And no matter how far away the vision still is from reality, it’s not getting any closer once the idea of product development becomes nothing more than a liability, and technology becomes nothing more than a cost.

Elephants all the way down, man.

At a certain size — and it’s not really that big — the relevance of what you’re working on to the actual stated purpose of a company (whether that is making money, or something else) can get pretty vague. You start to have goals that, if reached, seem to indicate that you are good at your job, and your function/department is a high-performing function/department, but if unpacked, may not actually have a whole lot to do with the stated purpose of the company as a whole. If you are in Marketing, you will probably get some sort of lead goal, and the way to succeed at work is to hit that lead goal, or maybe come up with a good, believable excuse for NOT hitting that lead goal. It is not to say “wait, do we actually need more leads?” Partially that’s because that question is annoying, but mostly it’s because the answer to that question is often complicated and opens up additional, cross-functional questions that are even more complicated, or worse, NOT that complicated but quite uncomfortable to answer honestly. Here’s an example.


Q: Why do we need more leads?

A: To make more money.

Q: Can’t we make more money off the leads that we have?

A: No.

Q: Why not?

A: Most of our leads don’t buy anything.

Q: Why is that?

A: They don’t think the product is worth paying for.

Q: Should we make a different product?

A: No. Product development is very hard and takes a long time, so we are better off getting better at selling what we have.

Q: But you just said most people don’t think the product is worth paying for. Should we charge less?

A: No. In fact, so few people want this, we should probably charge the few people who DO want it a lot more.

Q: But then… won’t an even smaller percentage of leads buy anything?

A: Yes.

Q: But… you want more leads?

A: Of course, we need more leads because even fewer of them are going to buy the same thing at a higher price. It’s basic math.

Q: But if this product makes sense for such a small segment of people, isn’t the pool of possible leads not just finite, but actually pretty small?

A: This other software company has a blog post that says they generated eighty kazillion leads last quarter, that’s a lot more than us.

Q: Does our product do something similar to this other company’s product?

A: It’s software. We also make software.

Q: Right, but our software calculates the number of steel beams required to build bridges of different sizes, their software is for taking online payments.

A: Exactly, B2B software. We have some of the same investors.

Q: (blinks)

A: (stares)

Q: Is it possible that we’ve built a business that requires people to pay a lot of money for something they don’t want that badly, but that also has extremely aggressive growth targets?

A: I have a hard stop at 2:18.


The correct move here, from a career development perspective, is to start visibly working on lead generation while simultaneously looking for a job at a different company. The correct move here from a management perspective is to provide at least somewhat better answers. I have been on both sides of this conversation, especially as I got older and got into management. Just as I became a parent of two very curious, very question-oriented children, I also became a manager facing a lot of these same questions from people who sounded like better educated versions of me from ten years earlier.

And there are better answers, to be sure. When the market for your product seems constrained, you can almost always expand it — with a lot of effort — at least a little bit more. When the product seems critically limited, there are almost always ways to make it a little more useful with non-technology tactics like templates, guides, and services. I learned about those avenues from smart, creative managers, and I did my best to suggest them when appropriate to people I managed. It went okay. I never got fired, and most of the places I’ve worked have ended up basically okay.

But the elephants are there for every one of them, and I don’t expect them to get addressed… probably ever.