Product Management Confessional

My entrepreneurial focused career has provided me with the good fortune of leading and influencing a wide range of “fail fast” accelerators and products. More often than not, I found myself stumbling into an unexpected product management role on top of my other responsibilities. These happy accidents have led to a handful of success stories, but I had to commit over a dozen “sins” with less successful iterations to get there.

As penance, I’ve prepared my top five lessons learned as an act of contrition for product managers of all stripes.

Bless me, readers, for I have sinned. It has been ten years since my last confession. These are my sins.

Sin #1 — Techno-Lust

A Loving Couple: ‘Lust’, Jacques Jacques de L’Ange (1630–1650)

“Beloved, I urge you as sojourners and exiles to abstain from the passions of the flesh [i.e. whatever the latest cool technical thing is], which wage war against your soul.” ~Peter 2:11

My first and most prolific sin is being blinded by “techo-lust“ at the expense of all other market fit considerations. This is where I’ve fallen in love with a new shiney solution, but without consideration for what actual business problem it solves. This situation firmly falls within the ”Type III“ quadrant when visualizing products & problems:

Product Management for Dummies, Brain Lawley, Pamela Schure (2017 p.g. 109)

In a Type III scenario, you and your technical peers have defined or often prototyped an innovative and well defined product based on novel technology. For me, I was allured by innovative real-time decisioning systems, personalization engines, model visualizations and custom user interfaces wrapped around generative AI. In all these cases, our best customer reaction might be “that’s kind of cool”, but almost ceremoniously followed by a “meh” or “so what?” as they all failed to address a well defined business problem.

Remediation starts with accepting why I keep finding myself in Type III situations: it’s me, but also the company I keep. Possession of a technical background and hobbies is almost a guaranteed predictor of committing this sin. Likewise, if most of your friends and work interactions are with engineers, you’re more likely to fall into the trap of talking about technology for technology’s sake. When the market (and especially business decision makers) don’t share your enthusiasm for the product, you’ve almost certainly committed this sin.

My engineering-minded colleagues worshiped at the altar of newly emerged real-time architectures and visualization. We stood triumphantly above newly developed prototypes and MVPs, only to struggle when answering questions about justifying each solution:

• Did the solution really need to be real-time, or would batch processing meet the need?
• Does visualizing a predictive model in a creative way help, or is accuracy more important?
• Did low level personalization actually move the needle on key business metrics, or was it just an excuse to demonstrate a neural network and sound cool?
• Was a custom user interface necessary, or would a chat interface have sufficed?

While it shouldn’t be interpreted as an excuse for these transgressions, many of these initiatives had indirect benefits beyond the goal of a successful product with recurring revenues. In most cases, these exercises were a training ground for the consulting arms of the business. They were differentiators that helped to open new doors with new name accounts, and demonstrated the firm’s technical acumen and creativity.

Sin #2 — Micro Market Bacchanal

Adoration of the Golden Calf

At last. The chosen one. We had found it. This was the product that was sure to augment our burgeoning consulting technical professional firm with a new source of revenue and horizons. We worshiped this golden calf, as it had already proven its divinity with prestigious early adaptor Fortune 500 enterprises.

Alas, the product was a false idol. Our dissolute party ignored the warnings signs of the micro market sin.

The solution was born out of the realization we could capture and analyze the data exhaust from enterprise marketing campaign solutions — system logs. Instead of traversing cryptic and verbose incessantly growing log files, users and administrators alike could visually analyze and pinpoint the causes of performance issues with ease.

Growth was fast. Our professional services firm was already working with many of the firms that would ultimately become product customers as well. These were marquee clients that would normally be challenging for a solo SaaS start-up to take on as their initial customer. All of these buyers had high-performing marketing operations as a core part of their strategy, and they had already made significant investments in related people, process and technology. In fact, early buyers sometimes defined their identity by high-performance marketing operations, in the case of loyalty programs or agencies — the technical performance and runtimes of their campaigns had a direct correlation on their revenue and profitability.

Then, the growth slowed precipitously to a mere whisper.

We had been so enthralled by our licentious gatherings that we initially didn’t notice that the number of inbound leads and word of mouth was slowing. The sales cycles were extending deep into the horizon, as the next cohort of prospects did not seem to share the same urgency to adopt our solution.

While technical marketing campaign performance was a strategic imperative for the narrow set of our initial buyers, our next target segment was not nearly as enthusiastic. Organizations with less complex needs, and fewer performance challenges were not as interested. We were puzzled when we encountered organizations that did have sufficient complexity and performance challenges, yet they were unmotivated to solve the issue; in this case, there wasn’t a strong enough organizational push to improve the situation.

The true market size started to come into focus. We were addressing the needs of an incredibly narrow market: IT administrators within large enterprises, who operated a specific marketing automation solution, having sufficiently complex campaigns and the ongoing motivation to optimize the technical performance of their campaigns with low runtimes and high predictability.

We knew that we were targeting a niche market, perhaps in the hundreds of clients. However, it became clear that our market was even smaller than we anticipated — perhaps a micro market of a small handful of customers. We recognized that having a product principally focused on IT performance needs meant that we were only addressing a small IT performance problem, and we weren’t offering anything compelling enough for the larger marketing business teams.

Ultimately, this product was a strong fit for a niche of customers, but we had priced the solution assuming that we would be able to easily repeat the sale hundreds of times. Outside of the micro market, customers opted to invest in their existing multi-product performance monitoring tools and make do.

Our premature revelry led us to a product dead end, which was not without a silver lining. The product was instrumental in playing a supporting role for the larger professional services organization, which prodigiously used this story’s product to break into new markets and key accounts.

Sin #3 — War with “Good Enough”

The Intervention of the Sabine Women, Jacques-Louis David (1748–1825)

Built on bleeding edge technologies. Flexible. Powerful. A long list of features and pre-built integrations. Who wouldn’t want a solution that sounds like that? Yet, these attributes don’t do anything to overcome the biggest hurdle: the “good enough” status quo.

This lesson was most obvious and humbling with my go-to-market initiative for a home-grown real-time decisioning engine, which was designed with feature parity with powerful equivalent tools from vendors like SAS and IBM in mind.

The solution was a flexible one, which could cover use cases as diverse as anti-fraud/AML, marketing personalization to credit decisioning. To start, the initial target market focus was on lenders looking for a more powerful real-time credit decisioning solution.

Our outreach showcased how the solution could help lenders to realize complex credit decisioning strategies. We touted the virtues of visually building complex credit strategies, which could combine a complex web of alternative customer data. We also demonstrated how we could enable an agile way of testing and experimenting new strategies. The problem? The incumbent solutions were most often “good enough”.

We learned that these lenders were working with an existing ecosystem, which already had some limited credit decisioning features. We found that although the features found embedded within existing core lending systems were vastly inferior to our solution’s specialized decisioning capabilities, customers were generally content.

Tools with more power and flexibility are not universally more desirable. As in this case, the added complexity that came with our solution made it a non-starter. Experimenting with A/B testing, novel data sources, intricate credit strategy flows are all interesting academic possibilities, but are meaningless if the sufficiently skilled and motivated talent to operate the new solution doesn’t exist.

The product was intrinsically superior, but it had no chance against business as usual.

Sin #4 — Business Environment Blindness

Christ Healing the Blind Man — Eustache Le Sueur (1617–1655)

Meeting a real business need? Check.

A solution that is easy to operate and priced right? Check. Check.

Sometimes, a solution can organically emerge from enlightened customers and stakeholders, which can seem like a sure thing (spoiler alert: it’s a trap). In these cases, you and your coach have stumbled upon a new opportunity, but it isn’t one that can thrive within the surrounding environment, like a sprout marooned on mars.

In one example, an existing customer helped identify the need for a new business intelligence (BI) product for the non-profit sector. The product generated insights on the perpetual inflows and outflows of donor cohorts into various segments, lifecycle stages and milestones.

Although these insights were intrinsically valuable, there was no obvious answer for who should purchase, operate or be responsible for the solution. The non-profit organization itself was an unlikely suitor, as they assiduously seek to keep headcounts and their number of tools low. The other potential buyer — their 3rd party agencies — were also a poor fit, as their commercial arrangements were most often output based (time & material), with little incentive to improve efficiency.

In a second example, my team identified some innovative solutions that were some early attempts to bridge the marketing & ad technology worlds. As 1st party data experts, we knew there were obvious use cases such as where we knew a customer had already made a purchase, and there was no need to continue to target them using 3rd party ad networks.

We were surprized when our prospects didn’t share our enthusiasm for an easy ad spend efficiency win. When we pressed to understand why, we learned that the way that ad spending was forecasted and negotiated wasn’t aligned with other past efficiency business cases; waste was recognized, but already accounted for in a complex ballet of volume discounts and other negotiated enterprise adjustments.

While the business environment can change, it’s important to read the room for the here and now. You may not be able to change the modus operandi of today, but you can be aware of and cure your own blindness. Once you have regained your vision, it may be time to park your product, or limit your efforts to persuading innovative early adopters.

Sin #5 — Founder’s Pride

A Woman at Her Mirror, Gabriël Metsu

The HiPPO (“Highest Paid Person’s Opinion”) effect is a well discussed phenomenon we have all likely experienced at one time or another within a meeting or discussion. When the HiPPO’s opinions extend beyond a meeting or two and start to drive product prioritization, you may be witnessing the deadly sin of founder’s pride.

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Whoops! We weren’t supposed to send that to those customers.

Marketers who have been around long enough know all too well the kind of panicked frenzy that ensues after a marketing campaign goes wrong. Angry customers, uncomfortable questions from leadership, or worst of all, the media.

This is a serious problem. It’s no wonder that it inspired a technical firm’s founder to hypothesize and propose a grand solution to this problem. Marketing campaign quality issues and their associated embarrassment would become a thing of the past. Any marketing VP that neglected to adopt the solution would be negligent and clearly making a career limiting move. An automated quality control solution would become an imperative.

Except, that it wasn’t.

Early buyer interviews and prototype demo sessions never seemed to surface the expected underlying critical business need. Although there was an acknowledgement of past failures and crises, buyers were not interested in exploring how new tools could proactively prevent future issues.

Instead of embracing a “fail fast” mentality and moving on, we dug our heels in deep. We had to. This was the founder’s baby.

After countless further demos, interviews, and prototype testing, the development and product teams were exhausted with little to show for ourselves. We had to accept that although there was a real high-level (and public) pain present, the operational teams within the organization were not interested or willing to change. Yes, reducing errors and improving marketing velocity is a good thing, but reducing those risks needs to be weighed against the finite resources of any team, and their willingness to adopt and take on new tools, roles and processes.

Ultimately, the solution wasn’t addressing a real pain point for our buyers and it was time for everyone to take a hard look in the mirror.

Redemption

I am sorry for my sins of poor product management decisions, but I pray that chronicling my transgressions here may serve as a small atonement.

Recognizing these and other sins early has always been key to prioritizing and investing in the right products that have the greatest chance of success. I hope you can learn from my trespasses, and avoid similar fates.

Consider these five ‘sins’ as a toolkit for your next product venture. Before diving into development, ask yourself: Am I driven by techno-lust, or a true market need? Have I truly gauged the market size? Am I battling a ‘good enough’ status quo? Am I blind to the business environment? And finally, am I letting founder’s pride cloud my judgment? By mastering these questions, you’ll be well on your way to building products that truly resonate.

If you’re ready to confess your own product management challenges and seek guidance, let’s connect. Send me a message, and we’ll schedule a private discussion (no confessional booth required).