When Product Management Goes Wrong – Part 2 – the Dinosaur

In part 1 of this series, we looked at the underminer. In part 2 we will look at the dinosaur product manager.

A dinosaur is a product manager who is out of date, and they obstinately refuse to consider anything that is current. They have their model of the world, and they refuse to learn anything new. They might be out of date with any or all of the following: the market, competing products, their customer’s current expectations, pricing, monetization models, marketing and sales approaches, current technology and design trends.


Tyrannosaurus image from Wikipedia.

Of all the product management anti-patterns, the dinosaur is the one that I find to be one of the most painful to witness. As a technical product manager who works with new and sometimes cutting edge technology, I run into the dinosaur quite often. It’s painful to observe because you see all these people working so hard, and the team inertia is moving in a direction, yet one person is getting in the way. It sucks the life out of teams, and it’s also one of the most difficult behaviors to deal with.

Dinosaurs are people who for whatever reason have stopped learning. They have a specific approach and they are frozen there. Often dinosaurs are more experienced people who are fatigued with learning new technology, or they might be jaded after too many campaigns. Software is a tough, demanding business.

I get the learning fatigue. As you have more experience and have learned a lot, it is tiring to learn yet another web framework, a new set of productivity tools and yet another design paradigm. Right now I am learning some new approaches to mobile development, and a whole new templating engine for web applications using responsive design. It isn’t as much fun to learn as when I was new in the industry, and I have to fit that in between engagements and deliverables.

However, I have also met dinosaurs who had very little experience, but they have still chosen an approach and refuse to update their thinking.

Recently, two executives asked me to help them with a difficult problem at their company. They were creating a new product to expand their product line and steal market share from an emerging, lucrative market. Their existing customer base was maturing, and there were strong economic forces at play that they felt threatened current revenue streams. They didn’t want to get caught when an inevitable decline hit the market, so they were looking seriously at other sources of revenue that better fit emerging market conditions. They implemented a “20% time” for technical teams to spend time coming up with product ideas, held facilitated brainstorming workshops, and engaged heavily with their enthusiastic supportive customers and trusted industry contacts.

As usual, the problem they posed to me and the real problem were two different, yet related things. They didn’t say anything about the VP of Product Management, other than mentioning them in passing. In fact, they said the problem was an alignment issue between the experienced people in the company, and a young engineering team. The execs gave me the impression that the engineering team on this project were the problem here – they weren’t respecting the more experienced people in the company. But the execs said they would let me figure out what the problem was. All they wanted was a great minimally viable product they could start introducing to the market.

As I met with more people in the company, alarm bells started to go off. I didn’t meet the VP of Product, and it felt like people wanted to shut them out. Any mention of the VP of Product was met with a silent tension. When I met with the technical team, they seemed depressed and were checked out. They sauntered into the meeting with me, and most of them were late. The product owner was the last to arrive, and while she was pleasant and polite, she spent most of her time with her face buried in their smartphone. The lead engineer on the project took me through an abbreviated walkthrough of their prototype, and aside from some UX and design issues and some unfinished parts here and there, it looked solid. In fact, the fit with the market was obvious, and the technology had a lot of potential. I found it exciting, but the rest of the team were sombre looking and weren’t engaged. I started asking clarifying questions and they slowly started to wake up.

They had stumbled on a very difficult navigation problem, and asked if I had any ideas from my UX experience. I suggested looking at game design, because this sort of problem is well addressed in video games, but often poorly addressed in enterprise applications. After a couple of shocked moments, engagement turned to excitement. We brainstormed, some team members started researching compatible game engines, and looked for examples on the web. At the end of the hour, the team asked if they could extend the meeting further, and most of them were able to stay in the room with me. The frenetic pace of excited brainstorming continued for another 45 minutes, and then we realized we were all tired. The lead engineer wrapped up the meeting, and the product owner took me aside and told me it had been the best meeting they had ever had for that product. In fact, in the two years she had been in the company, it was the best technical meeting she had attended.

Next up was a meeting with the VP of Product. They had been in the industry since the early 1990s, and had seen a lot of past success. You can guess what happened next.

The VP of Product spent the first 15 minutes of the meeting name dropping and telling me all about their accomplishments. When they asked me a question, they interrupted before I could finish answering and began to berate me. This continued on for the remainder of the meeting – any time I spoke I was interrupted and ridiculed. When I changed tack and asked for a demo of their ideas, they showed me a PowerPoint slide deck with an outdated theme, and the product screen examples they had created looked straight out of the 1990s. With a bit of probing I found that they didn’t just treat me with derision and aggression, they were that way with just about everyone. It was obvious that a dinosaur was derailing an important product effort and potential new revenue stream.

I advised the executives of what the problem was, and you guessed it, they already knew. Instead of dealing with the issue, they were trying everything else but having a difficult conversation with the VP. The VP still had a lot to offer the company, but not in product management. They had hoped that a consultant would have some sort of magical solution idea that would get them off the hook, and would somehow get the VP on board.

In two other recent experiences, I have met inexperienced dinosaurs. Both were startup CEOs who had product ideas, and managed to attract friends and family investment to hire technical teams. They didn’t have product managers, and had decided they were going to play that role in their company to save money. They had immediately latched onto the first technology ideas that were presented to them, and refused to learn anything else. Unfortunately, in both cases, they had outsourced development to teams that were inexperienced and placated customers, and made complex, risky development efforts sound simple, quick to implement and inexpensive. Both of them approached me because they had spent a lot of money on solutions that didn’t make it to market.

They were afraid. Yet, in the face of losing their businesses, they refused to listen to contrary advice from people with experience and track records of shipping software. They clung onto their initial ideas and conclusions they had made a year or two ago, and refused to budge. This was likely a controlling dysfunction borne of easy wealth and the arrogance that can come with it. They were intimidated by people who understood technical things, even though they had hired those people precisely because they had technical expertise.

The dinosaur product manager:

  • Believes in “one true way” approaches to marketing, sales, products and process. (This tends to coincide with their way.)
  • Scoffs at new technology or pricing models
  • Scoffs at design trends
  • Makes fun of consumers who buy products or services they consider to be fads
  • Talks more about “the old days” than being productive in the present
  • Dismisses ideas that aren’t their own
  • Makes fun of new technology environments
  • Equates every new design, marketing or technology paradigm with one from the past
  • Blocks efforts to update technology or architecture, even when when it’s needed
  • Underestimate the risks, complexities and efforts of their solution ideas
  • Reacts strongly to people with more technical knowledge, and especially more recent knowledge and skills than they have. They may be antagonistic, belligerent, use ad hominem attacks, or they may be passive aggressive and simply undermine them.

How do you deal with a dinosaur?

One of the most difficult things when dealing with experienced dinosaurs is that they are often right about a lot of things. They often express their ideas poorly, so it is easy to dismiss everything they say. Sometimes what seems like scoffing and denigrating behavior is simply an attitude problem borne out of harsh experience. The trick is to figure out when they are blustering due to fear, obstinance or unwillingness to change or if they are complaining about a valid issue. This requires patience and trial and error.

  • Talk to the person, and ask them what is going on, and point out how their behavior can be damaging and misconstrued if it is well-intended. Ask them to work with you and help the team move towards something successful, even if it means compromising.
  • Training and knowledge gaps are common, particularly with more experienced people. See if you can set up training or online materials to help them get confidence in something new and threatening.
  • Set up a safe place for ranting and complaining about new models, even if they seem to be consumer or process fads.
  • Play to their strengths and experience, and divide labor so that they have input and crucial parts to play in direction, but others are in charge of revenue models, marketing schemes, technology and look & feel.
  • Have them do competitor analysis, and have them perform user experience heuristic evaluations and pricing research of competing products.
  • Make sure they engage with customers who have differing views from their views and preferences
  • Take technology, design and other decisions out of the conversation, and have them provide constructive feedback in a neutral way. Their concerns may be valid, and if so, they will be happy to abstract them and present them differently. If they are not valid, they probably won’t do anything but bluster.
  • Let them win at times. A lost battle on a non-core issue is better than losing the war.
  • Be consistent and patient. It can take a while for them to win respect of other people with new and different ideas, and to get on board with new ideas and approaches.

If the person is coming from a place of fear, most of the above points won’t really help. In that case it will likely require some repositioning of their work and power. Following a process that uses team-based decisions and approaches can really help in this case. In many of these situations, a hardline approach is necessary, because a team member who obstructs can kill productivity and hijack business initiatives of the entire company.

Ask the champion of the new approach to present their approach to the group.

Next, hear out any criticisms of the approach, because there may be valid points. A dissenting opinion presented constructively is incredibly valuable.

Then make it clear, once the decision has been made, that the decision must be supported by the team, and anyone undermining the position will be asked to leave the team. (Also make it clear that undermining behavior will be monitored and will not be tolerated.) Often people who appear to be on board with the decision will undermine by amplifying problems and use that as evidence to criticize the decision. Peter Block calls this “resistance through compliance” and it is insidious and dangerous in organizations.

Here are two dinosaur examples with different outcomes.

An organization had grown from a two-person startup to a thriving company with close to 100 employees. They had created an MVP, tested it in the market and attracted a lot of initial investment. Trouble was, the market changed drastically and suddenly. The product manager became a dinosaur, slavishly sticking to their initial idea. Their product concept and understanding of the market had worked for over a decade, but they couldn’t get on board with the new market reality. There were also a lot of retirements and younger people moving in to replace their existing customers. That meant that during purchasing decisions, younger people (who use a lot of apps on smartphones and are more fashion conscious) were brought in to provide opinions. A middle aged CTO might have a social media marketing person sitting in meetings analyzing the offering from their perspective. Their expectations were much different, but were taken very seriously.

The dinosaur product manager became more entrenched and combative, and taking any criticism (real or imagined) quite badly and personally. They became more isolated, and the rest of the team were realizing they needed some big changes. The dinosaur also hated any usability issues and was quite scoffing of UX practices. “Our customers don’t need something that is usable…” was often their response.

One Monday morning, the product manager came into work a changed man. We didn’t know it at the time, but the CEO, the CTO and a major investor/advisor had taken him out to dinner that Friday night. They asked if he wanted to continue being obstructionist, or if he wanted to work with everyone else to solve the problem? After all, the company and a lot of investor dollars were at stake, and his behavior wasn’t going to help the team. They had decided early on that the core members of the team would agree unanimously on decisions moving forward. To get unanimity meant that if a person was a lone dissenter, they would be asked to leave. The manager told me later on that the discussion hit him really hard, and he spent the weekend mulling over options.

He moved quickly once he made a decision. He immersed himself in new pricing models, spent hours with potential customers doing field research, and hired a UX expert and visual designer to help them create a new product. The results were dramatic. They turned around a failing product into a big seller, and they sold the company to a larger player in the industry for a tidy sum.

In another situation at a large, established company, a dinosaur product manager was stuck in her ways when it came to marketing and sales. That was one thing, but she also refused to allow the technical team to pay off technical debt through refactoring, and would rarely allow them to update tools and infrastructure. She was also, bafflingly, incredibly stubborn about the look and feel of their e-commerce site. It was six years old and really showing its age. Any UX improvement or change, no matter how small, was met with enormous resistance.

This was flat organization with an open environment, and anyone could suggest ideas for improvements or new revenue streams, and field reports were frequent. No matter what anyone said, she would argue against anything she saw as a threat. She would often literally frighten away younger employees who had good ideas based on observations.

Senior managers tried to work around her, then ordered her to help implement an add-on feature to help increase sales. She appeared to be enthusiastic when they were around, and made all the right noises, but she was resisting through compliance.

She didn’t understand SaaS style pricing models, and her views of pricing, marketing and sales were hopelessly out of date. The projected numbers were staggering, but every meeting she was involved with was a painful fight. A marketing designer described a particularly painful “pixel by pixel” review meeting of pre-release marketing designs that took hours. Everything seemed to be painful, took way too long, and people asked to leave the project in droves.

Since the team was moving one way with executive directives, and that didn’t suit her outdated ideas, she actually hijacked efforts to secretly develop the solution the way she wanted. Part of the team at any given time were also working on her competing ideas. We found out because there was an anonymous tip about this from an abused employee to a politically powerful person. Her revenue model was so outdated and wrong, the legal department got involved and sent out a cease and desist warning internally. She continued in her undermining and obstructionist behavior, so she was let go. After she was gone, the teams moved quickly, and after 9 months of fighting, implemented the new feature with a completely new redesign in 3 months.

Avoid Dinosaur Behavior

It’s easy to fall behind in a massive industry that is constantly changing. It will happen to all of us eventually. The important thing to remember is that no one knows it all, and it’s ok to say: “I don’t know.” Very few people will look down on you for not knowing something, and if they do, they aren’t worth paying attention to anyway. Here are some tips:

  • Stay current by reading industry news, a little bit each day
  • Talk to your customers and ask them about problems that haven’t been solved yet, and about other applications they like to use
  • Study User Experience and keep abreast of developments in that field
  • Aim to be a lifelong learner
  • Take online training courses. There are a lot of free and inexpensive courses out there that allow you to work at your own pace
  • Attend conferences, workshops and local events in your community
  • Delegate to people who are more current than you are
  • Check your attitude – are you resisting change, or is your discomfort due to a deeper, important issue that needs to be addressed?

Any new revenue generating, marketing, design or technical change will involve problems and stumbling blocks. There will be fear of the unknown, resistance to change, and there should also be healthy dissent. In fact, any decision without some healthy dissent will likely be a poor one. The trick is to not let the dinosaurs hijack decisions or turn teams away from new initiatives just because they stopped learning and don’t want to help anymore.

4 thoughts on “When Product Management Goes Wrong – Part 2 – the Dinosaur”

  1. Hi Jonathan. Great blog. Unfortunately, it seems I’m more of a dinosaur than not! I’m pretty resistant to things like e-signatures, preferring to use the old-fashioned pen and paper method, and at the moment I see no immediate reason to make the change to things like that and cms. I guess it all boils down to how comfortable someone is with the technology and how organized they are without it.

    1. Hi Matt, thanks for the comment. The point here isn’t about being open to all new technology without serious thought and skepticism. I work with emerging tech, but I don’t always like the latest and greatest ideas. I need to be won over. Sometimes it feels like I am constantly shooting down new tech ideas that I don’t see solving real problems in the real world. It’s how we figure out how to use tech in a useful way, and a lot of what we do is working to overcome the weaknesses of the new designs.

      Bottom line: there is a happy medium between being skeptical of the tech and making sure it solves a real problem better than existing tech does, or just being obstructionist and dooming the product to failure by because you’re stubborn and intransigent.

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