The *real* haunted house: What truly scares Product Managers (a Halloween special) 🎃🕷 🕸

Jonathan Bennun
4 min readOct 31, 2020

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A tech company — any tech company — can feel like some kind of a haunted house because of all the eerie things you might find there, like scary glowing evil eyes in the boardroom, severed heads of sales reps who underperformed, or, uh, crazy, wild-eyed scientists running secret experiments in the basement. I mean, chilling stuff.

“Come, join us! We have candy… and stock options.”

If you believe it can get pretty strange and spooky for the average candidate or employee, understand that this goes triple for product managers who have to work cross-functionally with the entire company, including at hidden spots and secret pathways which some ghosts have made their home and where many dead bodies might actually be buried. Did you mistakenly go into such a haunted house? The writing is on the wall. GET OUT NOW. You’ve been warned.

For your reading pleasure, I’ve crafted a special Halloween piece about some of the things that product managers fear the most.

Zombie Companies 🧟🧟‍♀️🧠

Arguably the most critical factor in joining a new company is momentum: at least 2x-3x growth YoY in users and revenue, hiring like crazy, and lots of excitement in the air.

For that reason, for ambitious product managers, a stagnant company that is not seeing any growth, AKA a Zombie Company, is one of the scariest things you can find — and yes, these companies do eat brains. There will be noticeable decay and cobwebs around the office, fatigue that leads to zombie-like behavior, and lots of people who seem to have already checked out mentally and otherwise.

“Yeah, sure, let’s, uh, get the product working again sometime this year.”

Skeletons in Engineering 💀

Everyone hides a few skeletons in their closet. For some, it might be a failed professional experience that we crossed out of the resumé. For others, it’s a couple of dead ex-husbands who were “accidentally” stabbed 43 times. Tech companies are no different, with common skeletons being miscalculating simple SaaS metrics, or that time marketing somehow flipped on free shipping for all customers in the East Coast (oops).

What scares product managers the most is unearthing many of these skeletons in engineering. Where is all the data we’re supposed to store about our customers? What do you mean by “we don’t actually secure any transactions” ? How come this form doesn’t actually do anything? These are some of the many horrifying thoughts that can potentially throw product planning into chaos and flying blind for months if not years of catching up with good product practices.

“Hi, I’m Bill and I wrote the payment function. You’re saying it doesn’t work for most users?”

Frankenstein’s Monster Monolith 🤖

Another creature related to the skeletons in the engineering closet, yet much more difficult to hide, is Frankenstein’s Monster Monolith.

The Monster Monolith — that single-tier , unmodular codebase that is so hard to maintain — is not only real but also fairly common in early-stage companies. While these unfriendly giants are not too harmful and quite the necessary evil for building and deploying applications fast, they can get really big and then become incredibly destructive for future product work. The Monolith Monster can be unpleasant even for fast-growth companies that manage to raise a monstrous round to grow engineering, shrink some of the monolith, and keep what’s left on a tight chain. It’s often because of the Monolith that product managers are left in the dark and frustrated that it takes a few weeks and endless meetings to fix a stupid button.

Blood-Sucking Creatures 🧛🏻‍♀️🧛🦇

As momentum and excitement are arguably the most important things at a good tech company, who or what is most likely to slay them? That’s right: Vampires and other people who suck the joy out of work and out of you.

They often hide in the shadows and so might not be easily noticeable. They are most often senior managers, but can be anyone who is for no good reason in a power role, where his or her toxic behavior and negative attitude can not only dampen the mood but also truly stifle and hamper productivity and the creative process. Contrary to popular belief, direct sunlight won’t kill these blood-sucking fiends, but will sometimes make them scurry to the nearest Slack channel where they can do the most damage.

While having garlic breath can help ensure these vampires don’t come so close to you, your best strategy might be to just accept that these creatures do exist and then go work for a different company.

“Ouch. I’m guessing you don’t like my little office drama?”

The Ghost of Product Past 👻

Virtually every company experiences setbacks, failures, and pivots. One of the scariest things that a product manager may experience is seeing some of those failures and pivots in the form of The Ghost of Product Past. Often dressed in a pale robe, The Ghost roams the halls at night and whispers fables about that legendary product that failed once but could totally succeed the next time… even though the users, the customers, the analysts, the investors, and the rest of the market all say otherwise. Many times The Ghost of Product Past is nothing more than your friendly neighborhood spider-ghost, who entertains people around her with folk stories, but every now and then it pans out to be a deadly creature who completely derails the product and the company.

“Come play with our product, Danny. REDRUM”

The Grim Reaper ⚰️☠️

How are you going to die? Do you lie awake in bed, tossing and turning, fearful that The Grim Reaper could knock on your door at any minute?

Will it be a a fire sale? Will it be a failure to fundraise that gets you the axe? Perhaps some epic managerial clusterfork that sends the entire company packing, who knows. But The Grim Reaper is very real, and he is out there, waiting… for you.

Happy Halloween everyone! 🎃

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Jonathan Bennun
Jonathan Bennun

Written by Jonathan Bennun

I’m a human Swiss army knife. A hacker and engineer turned product leader and entrepreneur. Ex-Cisco, OneLogin. Venture Partner@NextGen. Founder@Security Dojo.

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