Where the Dude is, and likely to stay for the long term (7-8 years until retirement age) things are, interesting to say the least. In the Dude's 5 years, he has worked under 6 different senior leaders (VP/GM's), each has entered with a "new" grand vision. The latest is probably the most interesting.

Some Background

We do education. Providing training for our corporate products and technology, as well as validating competencies for people who are entrusted to use the technology at companies, well, everywhere.

In our mission, over the last 27 years or so, we have built an internal tool chain that provides an outstanding experience for people trying to gain skills. Our offers are considered leading edge, at least capability wise, and frankly, other companies with solutions like ours, benchmark themselves against us. This is frustrating, as it buggers our competitive analysis, when everybody looks to you as the leader. Le Sigh.

Is our toolset great? No. It was largely developed in the early 2010's, and it looks like it was. But it works, and it is part of our unique value proposition, and that keeps the smaller, more agile players at bay.

Buckle up for the next 1,700 words or so...

The New Leader

A long time mid level executive in the company, this was their first General Manager role. Their last stop was in a developer relations team, and this will be important later.

Anyhow, this is their first post in a true P&L group. As such, we have to generate enough revenue and profit to support our operations and development (this will become more important later in the post, Dude's word). Since we are considered important to the company (the more people in the world who know, understand, and can effectively use your products, the more of your products you sell, a "win-win") we are not held to the same margin targets as the other business groups, and we tend to reinvest more of our profit into building more offers, rather than in contribution margin. This is a good thing.

But the new leader looks to the commercial offerings in this space (think Udemy, Coursera, and the other MOOCs) and thinks that our future is to build a glimmering platform, and then rely on independent agents to build out the library.

What this means is that our current product team isn't aligned to this mission. But we still make a lot of money to fund us.

What is the leader to do?

Call who you know, and build a second product team.

The Second Director of Product was hired to build this forward looking business, starting with the platform, and then the strategy.

When they were hired, the Dude looked them up on LinkedIn, and he was not surprised by what he saw. A shit-ton of software engineering, full stack web development, some serious security chops. But what was missing?

If you said "product management", give yourself a gold star.

Seriously, a fucking "SENIOR" Director of Product Management (that title outranks the Dude's director) with not once scintilla of prior product experience.

Dafuq is this world coming to.

Shortly, the Dude did the "dude" thing and scheduled an introductory call. The Dude noticed that they were looking to hire a couple of product managers to be under this Sr. Dir. Product, and the Dude wanted to first gauge the new guy, and second to see how their search was going. Ya know, be neighborly.

The Dude came away somewhat impressed by their technical chops, somewhat surprised that the desired "platform" product manager was difficult to fill, because all the applicants were, well product people, not coders, and with a healthy desire to not get in their way. Hey, this strategy is way above the Dude's paygrade, but honestly, he couldn't figure out if they truly believe that "if you build it, they will come". That strategy almost never works in real life, and especially within markets that are fairly mature and well populated with strong incumbents.

That doesn't mean that leader after leader won't try cutting their teeth believing that they will be the one to crack the code.

In all honesty, after this, the Dude put his head down, and just did his thing, delivering value day in and day out.

The New Director of Product

As the Dude said, he had his introductory conversation, and kept his thoughts about the wisdom of hiring full stack developers as mere product managers to himself.

From the outside, he saw some encouraging signs. The initial plan to build from scratch (NIH anyone?) was scuttled, and a search for one of the seemingly myriad SaaS solutions was commenced.

One of the Dude's peers were coopted to guide because she had some direct experience in the design and sale of products similar in a B2C space. Some of the things he heard from her were encouraging. That the team was small, and everybody just pulled tasks from the pile and worked on it. There was no compartmentalizing of data and information, it was just all shared, so that whoever was doing a task could just get on with it.

In short, it sounded like a little start-up in the organization. Perhaps we were going to break out of our stultified rut.

But then the Dude saw some externally visible cracks in the foundation. A new "Director" of Business Development was hired to help this Sr. Director of Product with the business side. Of course, we already had a Director of Business Development, but hey, if we can have two Directors of Product, why not have two Directors of BizDev?

Then a high $$$ consultant was brought in, and he began nosing around the legacy business, ostensibly to "see how efficient" we were. But in reality he seemed to be looking for talent to pull in.

In the interim milestones were set, big bold strategy slides shared at all hands meetings. A public demonstration to key partners in 4 months, public roll out by the end of the year. Contracts inked with content creators to populate the system with tons of quality titles on day one. Rah rah, it all sounds great.

On our side, we were preparing for the tectonic shift, designing our new programs to fit into the new system, rejiggering ongoing projects to help fill out their catalog, but there was a problem.

We kept asking what we needed to build to (aka what is the expected format, and output. What capabilities could we count on. How to provide the best, seamless experience for users) to be told that it hadn't been nailed down.

Look, the Dude wasn't expecting a bible of design guidelines, but he wanted some hints at what would and wouldn't work.

He didn't get it. Turns out that none of the commercial solutions fit the expansive vision of the leaders and this Senior Product Director, but they were struggling to weigh the options and make a decision. Sound familiar?

Sure it does. One of the key problems with engineers, even fantastic engineers, moving into product is that they want to weigh every decision, consider every contingency, not compromise on any detail, no matter how trivial it may seem. That old adage "Analysis Paralysis" that the Dude has lived many times before had reared its head.

If the Dude hears the term "zero technical debt" one more fucking time, he might go postal...

The Dude's peer was venting in their 1:1 that the Sr Director just couldn't make a decision. This led to the scrapping of the public show and tell, in less than 2 months now, delayed a minimum of 3 more months, and the project that the Dude is working on, a first to highlight the full capabilities of the new platform will no longer be needed until June or July next  year.

Whoa. And as of this writing, the decision isn't made. The team is still struggling with the tradeoffs (hint: no solution is going to be perfect, and even a fully build in house tool stack will have some shitty parts to it (as ours currently has) so just pick and move on) and still there are a couple of sandboxes that various people are playing with.

No bueno.

Oh, and that high dollar consultant? He was brought aboard as a Director (yes, what our team really needs are MOAR Directors). His title is Business Development. If you have been keeping count, that makes it THREE directors of biz dev.

Funny thing that. The job requisition for this "plum" position read straight up business development, but the title advertised was for Director of Engineering. The Dude guesses that the corp HR team looked at the title, looked up the responsibilities in Radford, and said "nope". There's a story there that the Dude will tell later about the affinity of our latest leader for "Engineers"

The Sr. Director of Product

Last week, the Dude had a conversation with someone close to the Sr. Director of Product. The Dude didn't seek this out, but it came up.

Turns out that the Leader who tapped him for the role sold it as:

  • You will have free rein to build a new modern platform from the ground up
  • You will be able to hire/assemble a hand picked team of developers to accomplish this (internal people and external recruits)
  • You will have ample budget to accomplish this
  • A true clean slate

But quickly, the Leader learnt from the ELT level that they had about 15 months to build and deliver this "transformative" strategy. That they couldn't count on dollars that we didn't generate from the business (we are a P&L), and that there will be severe headcount restrictions. As in he might get 2, instead of 20+. And you have 6 months to get to a saleable version (aka, not a MVP in any real sense)

The Engineer cum Product Leader finally is learning that product management is a world of compromises, half measures, and making due with what you are allotted. And what you are allotted is never enough to do the job right. (but if you are crafty, you can still do the job well)

In a way, the Dude feels sorry for him. He is not a bad guy. He truly has some mad chops and skills. He would be a great partner to build a business with. But the Dude can't alter reality.

The Dude suspects that we will be late, it will be massively short of the initial promise, and it will not gain traction, as a Me-Too product with some tweaks. The early movers have way too much market presence, and our shift will remove some of our competitive advantages and make us compete in a space that we really will be unable to.