When Product Management Goes Wrong – Part 5 – the Dread Pirate Roberts

In part 1 of this series, we looked at the underminer product manager. In part 2 we talked about the dinosaur. In part 3, we looked at the erratic driver. In part 4, we looked at the micromanager. In this post, we will discuss the Dread Pirate Roberts product manager.

The Dread Pirate Roberts manager threatens people in a misguided attempt to motivate them.

This is the final post in this series on product management anti-patterns. While it seems outrageous, and maybe amusing, I can assure you it is not the least bit funny to the people who suffer under it.

SPOILER ALERT.

In the book (and movie adaptation) The Princess Bride, there is a character called The Dread Pirate Roberts. Another character, Westley, is captured by the Dread Pirate Roberts. Every night, the Dread Pirate Roberts says to him: “Goodnight, Westley. Good work, sleep well, I’ll most likely kill you in the morning.” The Dread Pirate Roberts never does kill him, but this goes on for three years.

END SPOILER.

Dread Pirate Roberts

The character in the movie is fantastic and likeable, but if you analyze their behaviour, much of it is deplorable. This scene is so memorable that I have named this particular anti-pattern after it.

There are some product managers who think this pattern is a good tool. “We can’t let people get too comfortable, and there is nothing like a threat to motivate them, right?” Well no, fear is a terrible motivator. You’ll get a minimal level of compliance, but you will not motivate people at all. In fact, you’ll do the opposite and demotivate people. (You might also might end up being disciplined by HR, or by legal authorities if you do this.)

Here is an example.

I was helping a software company with some process tuning and advisory work. I would drop in for a couple of days a week and help them with whatever came up. They had created a new team to work on emerging technology, and they worked independently from everyone else on a brand new product line. It was an experiment to try to jolt some new thinking into a company that was resting on past success a bit too much. They had assembled a young, inexperienced but highly talented and motivated development team. They also had communications, marketing, PR and visual designers from the rest of the company working on the same floor. The office was in a gorgeous brick building that was a former factory and it was warm and inviting. The team used an open environment that practiced hot-desking, meaning no one had assigned space. You arrived, plugged in your laptop into a docking station, and claimed that space for your own that day. The next day, someone else might be sitting there, and you would find an alternative.

The development team had staked their claim on one side of the office and found it more productive to sit together. They would pair, diagram, brainstorm or play with nerf guns or have foosball tournaments to ease some stress. The marketing, sales and PR folks claimed another area on the other side of the office. The kitchen was closer to them, and they laid claim to a couple of vintage arcade games for stress release. Everything else in between was a free for all. There was a bit of an empty gap between the teams, but they tended to sit closer or further away depending on what they were working on, and there was a lot of positive energy and good natured joking.

One day that all changed for the worse.

I walked into the office that morning and instantly felt tension and stress. Heads were down, conversations were short and hushed, and the product owner had stopped working in the dev area and set up shop on the other side with the marketing ands sales people. The visual designer dragged herself into the office, clearly fighting the flu. Normally she would have spent the day in bed or worked from home. There was nowhere else to sit, so with reluctance, she set up near the developers. A mountain of kleenexes began to build around her and there were copious amounts of hand sanitizer being used by by everyone else. She looked nervous and afraid.

When the daily standup started, the individual reports were short, guarded and the usual joking and camaraderie was completely absent.

The product manager had returned that morning from a two week trip out of town visiting various client sites. Obviously, they had done something to throw off the team. Whatever they had done was clearly having a negative effect on productivity. The build server was quiet and when I checked the feed for source control, there wasn’t the usual pace of checkins. When I checked the productivity software, stories weren’t moving through the process like usual.

This was odd because they were self-organizing team with strong DevOps practice and they usually pushed several builds to a staging server every day. There was at least one production push per week that included bug fixes, new features and other things that customers and stakeholders were interested in.

Over the next couple of weeks, there were no pushes to production. I monitored source control and build machines, and found code check-ins to have slowed down considerably. The quality of conversations on new designs lacked the creativity that they did before, and the product owner would only show up briefly to clarify or discuss an issue, then would scurry back to the other side of the building. Everyone got sick because they were stressed and working too much, and they would struggle to work from home, or drag themselves in to meetings.

I couldn’t get much out of anyone other than “Talk to the product manager”, so I made sure to track him down. I asked what was going on and that I had noticed some changes with the team. He explained that senior managers weren’t happy with the team’s productivity, so he called a team meeting and threatened them. He told the team that he had picked each of them for this project, and he could easily get rid of them and replace them with other people who were coming off of other projects in the company, or hire new people. He had created this team and he wasn’t afraid of tearing it down and starting over if they didn’t start working faster.

“Are they afraid for their jobs?” I asked.

“They should be.”

Wow.

You can imagine my reaction. I tried to be calm and not ask if he was ****ing crazy, and if he really wanted the product to fail. Well, I did say it, but in much more diplomatic terms. The product manager told me he was directed by senior management to “put the fear of God in the team” and they wouldn’t relent. They understood it was killing productivity and it had a negative effect, but they were just doing what they were told.

The product manager felt the approach was drastic, but appropriate. When I also talked with senior management, they said they had no intention of letting people go, but if they feared for their jobs, they would work harder. No matter that people were so stressed out now that they were getting sick, no matter that productivity had plummeted, no matter that some team members weren’t even hiding the fact they were looking for new jobs, no matter that the development team had packed their belongings in boxes, waiting for the inevitable tap on the shoulder from HR. They felt that eventually people would work faster and do exactly what they wanted.

The opposite occurred. Productivity cratered, and people did get some work done, but the creativity, unique and amazing solutions disappeared. (There go some of your product differentiators.) After advising that this was abusive and not a suitable way to treat people, I left the project. It seemed that leadership were far more interested in feeling in control than creating a great product and having a productive, happy team. Their egos were stroked by controlling people, so that trumped everything. (This is likely why the Dread Pirate Roberts behaved the way he did in the movie threatening and toying with a captive.)

As you can imagine, the product didn’t succeed. Yes they managed to force compliance, but they created a weak imitation of their competitors’ offerings and it went in the market. People on the team left the project and most eventually left the company for more suitable working environments. (ie. non-abusive ones.)

As a team member, if you feel a constant threat hanging over you, you are going to feel fearful and not at your best. All this brain power is needed to deal with your fear and worry about what might happen instead of using that brain power for problem solving. It is horrible to experience. In fact, it is a form of abuse. People will respond to abuse in non-deterministic ways. ie. you have no idea how they will react, but it won’t be good. It won’t be good for the individuals, the team, the product or the company. It won’t be good for you either, if you are the abuser.

Threats and fear are tools that will enforce some level of outward compliance, but they are terrible motivators. Managers who think that they will increase productivity or get products or features out the door faster if they use empty threats are abusing their colleagues. Much like in the movie The Princess Bride, they may feel a sense of control and justify using empty threats. That was a movie though, in real life, pirate behaviour is abuse at best, and criminal at worst.

The Dread Pirate Roberts:

  • Makes threats, either explicit or implicit
  • Never follows through on said threats
  • Believes in antiquated management theory (ie. that fear is a good motivator)
  • Manipulates people to get their way
  • Changes their mind all the time so you never feel like you can make them happy
  • May deny making the threats when confronted, expecting you to doubt your own version of events. (Also known as gaslighting.)
  • Is likely a psychopath, or is directed by one

In another case, I witnessed an accidental Dread Pirate Roberts, but the outcome was the same: demoralized staff who weren’t as productive as they could be.

I had worked with the CTO of a rapidly growing startup at a couple of other organizations. We weren’t close, but we had mutual respect for each other. He told me that their product teams needed some help, but wanted to make sure there was a good fit with me and the VP of Product at his current venture. The VP of Product was a big, good natured man, with full sleeve tattoos and a shaved head with a large beard. He looked intimidating, even though he was kind hearted. He played up the look, wearing black t-shirts, designer work boots and a wallet on a chain. He joked that he was the king hipster of the company. He had a loud voice and a loud laugh, and because he had a nagging shoulder injury, he frequently crossed his arms when talking or listening.

The office, like many software companies, was dog friendly, and he brought his Rottweiler in to work every day. The dog was large and imposing, but quiet and would stare at people. Since it didn’t have much of a tail, it was hard to tell if it was happy to see you or not. It silently followed him around. It was an intimidating creature, especially if you weren’t used to dogs.

Prior to working at this company, I had heard rumours of this “big biker type VP” who would walk around the office with his dog yelling at people. I chalked it up to campfire project horror stories that programmers tell to scare each other. When I met with him and other leaders, I didn’t find him intimidating at all. He was open minded, kind hearted and quick to laugh. Reputations usually have a grain of truth to them though, so I was wary.

It seemed like a good fit, so I was brought in initially to help with User Experience (UX.) The UX folks had done a fantastic job, but the VP of Product had decided to forgo usability testing prior to shipping. The CTO asked me to come in and do an expert review and a heuristic evaluation. My work product was a report, and I made a few recommendations. I was careful to back up all the recommendations with at least two citations from UX experts. The UX team loved the report (I independently verified their concerns), but I was a bit worried when a nervous CTO told me to be careful, the VP of Product might need to be “treated delicately”.

The next morning, the VP of Product marched into my office, with his dog right behind him. His huge frame filled my doorway, and he threw a printed copy of my report on my desk and started yelling at me. His dog peered from behind him, and it felt like the dog was scowling at me too.

Picture in your mind a large, slightly heavyset man with a trucker hat, large framed glasses, Harley Davidson t-shirt, full sleeve tattoos with crossed arms yelling at you. His mouth was open wide and his large beard was wagging. Not to mention both he and his large, intimidating dog are blocking your only exit.

The horror stories were true! I was witnessing it in person. I could hardly believe it and I almost burst out laughing at the absurdity of it.

I can’t remember everything he said, but I got the gist of it: my report was garbage and he was going to rip up my contract and send me on my way. Once I got over my initial shock, I told him that his behavior was unacceptable, and I wasn’t going to put up with it. That escalated the situation, so I invited him in (so he wasn’t blocking my exit) and I asked if he would sit down. He declined, but he did at least come in to the office and loom over me. I was rescued by a call on his mobile, (which he took and talked at length in front of me) and that seemed to calm him down. When he returned to me, I distracted him by asking about his tattoos. Eventually, we found some common ground, had an awkward conversation about tattoos and then he picked up the report he had thrown on my desk and walked out. The dog gave me a look over its shoulder as it trotted after him. I almost felt like it was trying to get in the last word and give me one last scolding.

I’m not easily intimidated, but it was an incredibly unsettling experience. As a consultant, I had a lot of power and could walk away. What about employees who weren’t used to people who dressed and acted this way? What about subordinates or others who felt they had to do what he said to keep their jobs? This would be frightening to endure.

I immediately walked to the CTO’s office and told him what happened and that behavior was completely inappropriate. I said I would not work in an environment like this. He agreed, and asked what we should do. I said we needed to meet with the VP of Product and see if there was a way we could deal with conflict in a more healthy way.

The next morning I met with both the CTO and a now contrite VP of Product. We explained how his behaviour was intimidating, and that the threats, no matter how empty they might be, were distressing and abusive. We also explained that having his dog around while he behaved like this made it the situation worse. It was bad enough for us dog lovers. People from cultures that aren’t obsessed with dogs like North Americans are found it absolutely terrifying. He was shocked and visibly upset. He said he knew he had a temper problem, and that he was working on it. He said he had become angry because he felt that my feedback had criticized the product, and it was his heart and soul, so he felt personally threatened. When we explained that my job was to help the product be better, and not to tear anything down, and I asked if there was anything I could do to help with delivering the information so it felt less threatening. He said he had over reacted, apologized and asked for help.

As we talked, he told us that his father was a successful entrepreneur, and was a big “Theory X Management” believer. He felt that employees are inherently lazy, and need proper motivation to work for you. That upbringing had rubbed off on him, so he resorted to it at times.

In his father’s factory, in another era, it had worked. (Or so he claimed.) However, software companies tend to be egalitarian, and technical people prefer meritocracies. You might be able to yell and scream and get your way, but it isn’t the only factory in town. They can leave. Conversely, theory Y management works well in knowledge fields, where you assume people are intrinsically motivated, and with proper encouragement will work hard and thrive. He mimicked his father’s management style, and when you combined that with his large size, loud speaking, intimidating mannerisms (not to mention his large, intimidating sidekick dog), he tended to get his own way a lot.

He was asked to leave his dog at home for a while during office hours, and to not behave aggressively because of the way it made team members feel. If he felt threatened or angry, the CTO said to come into his office and talk to or yell at him first, if needed. Once the emotion was vented, he should then have the uncomfortable conversation with a peer or subordinate.

At first there was a dramatic improvement, and he really tried hard to adjust and grow personally. Eventually, he was able to bring the dog back to the office, but didn’t bring the dog with him to meetings or when he wanted to confront someone.

I would love to tell you that this story had a happy ending, but it doesn’t. Even though he said the right things, and seemed to sincerely want our help, he quickly grew to resent it. As time went on, the behaviour came back as his attitude soured. He had trouble taking responsibility for his actions, and while he would feel terrible after each outburst, he would rationalize it. He said that people knew that he didn’t mean it when he threatened them anyway, it was just his style. But not following through on threats is even worse than following through with something drastic. At least people know where they stand and what to expect. Furthermore, empty threats cause people to lose respect for you and your ability to tell the truth.

He was eventually forced out of the company, and it took a terrible toll on him afterwards. This was a case of someone really needing to grow up, it didn’t seem like the behaviour was intentional. His motivations aside, the company rightfully saw him as a liability, and got rid of him. Sadly “the Veep with the dog who yells at people” story was spread by every employee who left the company. (And for a while, there were a lot of people who did.)

I don’t have much to say about how to deal with the Dread Pirate Roberts product manager, other than to run away when you encounter it. Unlike the movie (or book by Goldman), I have yet to witness a happy ending. (Sorry for the spoiler.) I have seen this sort of abuse many times, and it never ends well for anyone. If you’re a product manager and you ever feel the need to threaten someone, don’t. Just don’t. Stop yourself and do something to distract yourself to get yourself under control. Take a walk. Count to ten. Drink a glass of water. Go home for the day and collect your thoughts. If you do this regularly, get some counselling and take a courses on managing people.

Bottom line: this behaviour is abusive and you should never do it, even if directed to by someone else. It isn’t worth the cost to the person you threaten, and you’ll not only destroy the people who you inflict it on, you will eventually destroy yourself and your reputation.

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