Reddit and Facebook Veteran On How to Troubleshoot Troublemakers

Bethanye McKinney Blount has a very particular set of skills, skills that she’s acquired over a very long career. But unlike Taken’s Bryan Mills, her ability as a “fixer” extends to corralling troublemakers at technology companies. That guy who decides to rewrite an entire system in his off-hours in a new language without telling anyone else? Know him. The dev who won’t share any of her code while it’s in progress? Seen it. The person whose interactions with colleagues sends them all to your desk five minutes later? Yes indeed. Blount’s managed and worked with each one of them.

For the last 20 years, Blount has led technical teams at a range of companies, from tech titan Facebook to Second Life creator Linden Lab to music recording company EMI. She was recently the VP of Engineering at reddit and has founded two companies: Cathy Labs and MailRank, which Facebook acquired. Over her career, Blount’s seen both sides of the coin with troublemakers: supremely talented and opinionated people who can also be brash and bullheaded. On many occasions, leadership transferred troublemakers to Blount, introducing her as their new “mentor.” Quickly she transitioned from debugging code to debugging coders.

In this interview, Blount tackles the complexities of troublemaking and how to frame, diffuse and redirect it in a startup environment. She offers general principles about rabble-rousing and outlines the four main troublemaker archetypes that she’s come across as a manager. Any company that seeks a lifeline when employees cross the line will benefit from her guidance.

It Takes One To Know One

Blount’s insights into troublemakers didn’t start with managing them; she was one herself. In fact, she’s gathered as many insights on troublemaking from others as she has from reflecting on her own actions — both as an individual contributor and manager. “As an engineer, there were times when I was very meddlesome, pissed off and never feeling as if my managers were doing enough. I was on the the receiving end of what I felt like was not enough data or context to make good decisions,” says Blount. “When I first started managing engineers, I became a different kind of troublemaker. I thought my job was to get people to do stuff for me. That really shook the beehive. Instead of focusing on how someone was going to get something done for me, I should have been figuring out how we were all going to do something together.”

Broadly speaking, technology companies produce a special flavor of troublemaking. “It’s super common in many companies, but especially among people in tech: we have this idea of what we believe is the one true way to do things — whether it’s how to design, collaborate or ship,” says Blount. “I, myself, would get very attached to the idea that my way of doing something was the right way to do it. I’d have a list of my reasons ready in case I had to back them up.”

Blount has gathered some guiding principles around troublemaking that are less to vindicate troublemakers and more to put their actions into perspective. Here are her three tenets on troublemaking:

Your founders are the first troublemakers — don’t make them the last.

The more common take on troublemaking is that it disturbs the harmony of a collective, but an equally concerning symptom is the prevalence of homogeneity if troublemaking is absent. If a startup’s first goal is survival, that means evolution. Too much uniformity can halt progress.

“It’s the specific cases of troublemaking that you want to troubleshoot, not the role or presence of troublemaking abstractly. After all, the founders are the first troublemakers. They noticed some inefficiency or gap in a market and stirred something up,” says Blount. “But here’s what often happens: founders continue to see their companies as a physical extension of themselves. They need to get the hell over themselves! I’ve seen it happen at companies of all sizes. Founders wonder why there are people among their hundreds of employees who aren’t doing precisely what they once wanted exactly the way they envisioned. Everything at a startup — its vision, people and leaders — is dynamic, can change and should outgrow where it once was.”

Have some tolerance for troublemaking. Otherwise, you might end up with a homogenous organization that a single virus could knock out.

Couch troublemaking in the context of company stage.

As a startup matures, the particularities and definition of troublemaking will change. “The exact behaviors that make it so that the organization can stay alive, move fast, be scrappy can be exactly the same actions that cause a negative disruption later in the life of your company,” says Blount. “Troublemaking brings signs of large tectonic shifts, releasing pressure into the atmosphere. Specific rumblings are almost all borne fundamentally of some kind of frustration: moving too fast, not moving fast enough, taking too few or too many risks. These are signals — and opportunities — to assess underlying changes and growth in an organization.”

Leaders should take these instances of troublemaking to revisit what it may mean in a broader context for the company or market, rather than treat it as an isolated issue to be solved. “There’s a danger to be the manager that just forges ahead to stay the steady course. Again, what works is a moving target and about being responsive to your company’s stage. Don’t be the manager who instinctively throws dissenters overboard in favor of a smooth running ship,” says Blount.

Troublemaking is often done unconsciously.

In the vast majority of cases, Blount has found that troublemakers don’t intend to make waves that drown the organization. “There are exceptions. Some people really do just want to watch the world burn. It makes them feel good about themselves to tear down others. They’ve actively decided to be the schoolyard bully and are enabled by being an asshole to people around them. I’ve only helped a few of those really bad cases unlock what truly bothered them,” says Blount.

In most cases, the root cause of the troublemaking is unintentional, partially developed or temporary. “I’ve been in situations where troublemakers weren’t empowered or self-actualized because they couldn’t name what frustrated them. In those cases, it’s about basic management skills — working through their surface-level frustrations to get enough signal of the real issue at hand,” says Blount. “Given how talented many of these colleagues are, I often diagnose — and frame — their troublemaking as self-sabotage. Any manager’s job is to help her people be as badass as possible. In the end, they want that, too. Troubleshooting why they're doing it is one way to enable an organization to be much faster, stronger and better.”

If you subscribe to the premise that most troublemaking is done unknowingly, the corollary is that you must go into any interaction with troublemakers having decided that you want them to win over the long term. “Whether it’s a first warning or the last strike, you absolutely must be rooting for that person. Every time you go into a performance review — which is difficult especially if they continue to fail themselves and you — you must have their back, even if they don’t,” says Blount. “If you can’t make that pact, it may be a deeper issue, and one that involves you. If you’ve tried and been pushed long enough that you’ve stopped rooting for a person on your team, it’s better for her — and you — to find another alternative, regardless of expense. It may be time for her to leave the company. Be careful to not just hand off the problem to another team and a new manager. Own the process and the decision you’re making.”

How to Manage Four Types of Troublemakers

Early in her career, Blount started to manage engineering teams because she wanted to work on projects that were bigger than she could accomplish on her own. She not only gained an appreciation for the managers who dealt with her when she was a troublemaker, but also for what it meant to handle those who were complaining about the troublemakers. “Of course, you have to debug the troublemaker,” says Blount. “But then there’s everyone else, who instinctively blames the manager for the troublemaker. They’ll say, ‘This guy’s a jerk. Fix it.’ There’s a big ripple effect when it comes to troublemakers.”

Over the years, Blount has identified four of the most common troublemakers. Here are her tips on who they are, how you recognize them, why they act the way they do and what to do about it.

THE HERMIT

The hermit labors independently on his own project or piece of the puzzle and won’t let anyone see his work while it’s in progress. His isolation doesn’t stem from honing his craft or toiling for perfection, but is driven by fear. Regardless of the team’s established process, workflow or deadlines, he finds ways to hide his work until he deems it suitable to share.

“The guy who works in a silo is actually relatively common. Typically, this style is a vestige from a previous workplace,” says Blount. “There’s a couple of ways that he could’ve learned those habits. First, the shipping culture of the organization could’ve been that each person was responsible for his own part of the pie. Or it could be that it was a more toxic environment in which the hermit had to protect and defend his work.”

Both root causes prompt reform, but often the second requires more repair. “When you work collaboratively, you make a deliberate choice to be vulnerable. It may be just a sliver of vulnerability, but you're making a choice to share ideas that aren’t fully formed. It only works if you trust that the team is operating similarly,” says Blount. “I think the best products are built that way. You bring an in-progress idea to the table, thunderdome it with a team and it comes out better than anyone could have done independently.”

Not putting a stop to the hermit’s approach can signal that you condone that behavior on your team. Not only can this jeopardize the quality of the products being built, but help spread a culture of compartmentalization over collaboration. “One time I worked at this company where, if you showed anything early, everyone would tear your ideas and you apart,” says Blount. “It was a very toxic environment and people trained themselves to protect their work at all costs. The only way to debug that ingrained behavior is to get them to build trust. To start, tell a hermit that you’ve been there, know how that culture forms and can pledge that’s not how it’ll ever be.”

How you combine that acknowledgement and assurance with a plan to acclimate and integrate the hermit is key. Blount suggests grouping them with at least two other peers who are attuned to a more collaborative style. “I’ve experimented with both pairing and grouping, and find the magic number is a cohort of three. Just pairing a hermit with one person really relies on an ideal match and doesn’t emphasize group dynamics. If you get too large, the hermit gets lost in the mix,” says Blount. “Form a three-person group where the team is tasked on the same project. It’ll still be a steep learning curve for the hermit, but he’ll be stronger for it. It’s a relatively inexpensive exercise and can unlock bad habits and fear for an otherwise talented contributor.”

That said, there are times when debugging a hermit just won’t work. “Sometimes there’s organ rejection and hermits just won’t integrate. They’re exhausted. The energy that they’d use to do their job they’ve expended trying to work with others,” says Blount. “This profile will normally opt out. I can't recall many cases where I had to actually ask a hermit to leave. In most every situation, they tried for a month and couldn’t make the switch to a more collaborative workstyle. It was too difficult and emotionally draining.”

NOSTALGIA JUNKIE

A nostalgia junkie frequently expresses frustration that times are changing at her company. She harkens back to old days and talks of “the way” we’ve always done it. Her battle cry is “We’ll never turn into that big company!” Given their allegiance to their initial vision of the company, nostalgia junkies can be obstructionists when the company scales or pivots.

Often confused with valuable veterans with institutional memory, Blount has found one statement to be a reliable tell for nostalgia junkies. She says, “They always think that two years ago was the best time to be at the company. Once, on my first week at a job, my new colleague said to me, ‘Too bad you weren’t here a few years ago. It was great.’ Then three years later, the same guy said, ‘I really miss the old days. Like when you started. It was so great back then.’ That’s crap! You can’t have a moving window for the good old days, but nostalgia junkies do.”

The underlying frustration of the nostalgia junkie is not that the company is growing, but that she’s being left behind. “Nostalgia is very powerful. It drives people to recapture a time, even if it means running the events of the past through a filter,” says Blount. “They don’t remember nearly running out of cash, rounds of layoffs or botched launches — essentially how much wasn’t pleasant in the past. They recall getting off the rollercoaster and saying, ‘Man, that was fun. Look, we survived.’ They wear their survival like badges of honor.”

Many startup survivors, who have been through trials and trauma, become suspicious not only of new ways but also of new faces. “On one hand, they’re excited that others get to experience ‘their baby’ but, on the other hand, new people bring new reference points and changes. At once, they want to share, but not let go of something that they’ve loved,” says Blount. “This manifests in nostalgia junkies as eventually becoming obstreperous, caustic and inhospitable. You’ll often see them cooling off to anything or anyone that’s new after an initial warm welcome.”

As an engineering manager, she encountered nostalgia junkies frequently. “The rate at which a startup cycles spins out a lot of them. Many of the earliest employees are developers, making nostalgia junkies especially common on engineering teams,” says Blount. “The programmers that were expert at launching a product are rarely those who are good at running it and those aren’t typically the ones who scale it. Sometimes they have to go, which is hard because they’ve been good for so long to an organization that they may not fit with anymore.”

There are two key questions that Blount uses to try to debug nostalgia junkies. “First, I ask what they are not looking forward to next week. This does two things: it puts them firmly in the future and lets them air out and hone in on what’s bothering them exactly,” says Blount. “Then I ask them about the qualities of the company that they miss most. Often, that leads to their moment of glory, when they once stepped in to be the hero or broadly influential. If I can think of an existing project or team that could use their skills and help them recapture that feeling, there’s a way through. But, either way, this line of inquiry has often helped me satisfy their hunger for recognition, which is usually the root cause and route forward with nostalgia junkies.”

TREND CHASER

“I’ve read about this on Twitter and I’m installing it,” says the trend chaser. This troublemaker loves what’s trending, novel and shiny. As a first mover, he’s seduced before something becomes a buzzword, an established programming language or tested collaboration platform. An alpha on betas, he’s the opposite of the nostalgia junkie.

The challenge with this troublemaker at a startup is that he very quickly acts on what he’s recently absorbed. “This guy just starts popping the next newfangled thing into production without thinking about the consequences,” says Blount. “This tends to happen earlier in someone’s career or with the chronic conference attendee. They have the extreme energy or exposure to a lot of new, cool things, and the result is unfocused exuberance.”

The blindspot of the trend chaser is that they care about ingenuity, not continuity. That can be a fatal blow to the integrity of a product — and startup. “The truth is that very few of them have actually maintained a system that they’ve built. They’re very good at surfacing what’s on the horizon, but not so adept when considering the maintainability of their technology choices.”

“Years ago, I worked with a guy who owned one of the systems that our company really depended on. I had heard through the grapevine that he’d decided to rewrite the whole thing in C#. No one else at the company knew about his decision,” says Blount. “Even more problematic is that nobody else even knew the language. Plus, he was just learning it as he went along. He thought it made sense. But if he got hit by a bus, the company would be under the tires, too.”

The first way to debug this troublemaker is to consider the gravity of the choice. “With the trend chaser, it’s about risk and reward, because there is also a benefit to the type of technology and information that this guy can bring to an organization,” says Blount. “In the case of guy learning C#, his decision could have jeopardized the startup. But it’s usually a net positive to have developers staying curious and advancing their skills. If it were a smaller, more contained test, then I would’ve let it slide. If that were the case, perhaps it would have taken him a week to try out a new language. Worst case, it would’ve taken just three days for the team to rewrite it, if needed.”

After measuring the degree of risk associated with trying the new technology, get trend chasers to project ahead into the future. “I ask them to explain to me why this is the route they’re going to take with the technology or tool over the next year. This gets them to think about how we’re going to deploy, roll out and support it. It’s a prompt for prototyping,” says Blount. “There are some organizations where everything must be in Python or Java. I like to give people a little bit of space to experiment, schedule permitting. I'm a big fan of finding the right tool for the job and not necessarily making everything so homogeneous. But, in order to stay, trend chasers must anchor a bit more to a goal. The potential has to worth the expense of the experiment.”

SMARTEST IN THE ROOM

For lean, bootstrapped startups that punch above their weight, there are frequently very sharp, savvy people turning the gears. In their ranks can be a troublemaker who just wants to be the smartest in the room. According to Blount, there are a few permutations of this person, but the simple reality is that this person’s an asshole — though not always an unredeemable one.

“There are two main manifestations of this troublemaker: the first kind is the woman who actually thinks she’s the smartest gal in the room and front-loads that persona every chance she gets. The second type comes off as an asshole because she’s very direct and believes that politeness is inefficient,” says Blount. “They both read as the same jerk, but one is consciously cultivating an image, while the second is ignorant of what she’s projecting. The first wants you to know she’s the smartest in the room; it’s an unintended byproduct for the second type.”

The smartest person in the room becomes most apparent in the context of other people. “You may get a different signal when you’re one on one with the person, but from a distance, it becomes more clear. Group dynamics really showcase this problem in action. It’s because this troublemaker feeds off her environment and the reactions of others,” says Blount. “With these types, it’s easier to see them for who they are from a distance. You may even learn more about them secondhand. That makes them especially difficult to handle. Debugging them also entails cleaning up after their interactions with others.”

To complicate matters, you may not only manage these troublemakers, but report to them. “They can be found at the top. It's super common for these guys to be one of the founders in the company or somebody who was a very early employee, who did something magical,” says Blount. “And that’s real. They likely did something amazing that allowed for the company to exist at all. But just like the nostalgia junkie, they’ve typically been there a long time and still hold on to those times. Because of their attitude, seniority, style or all three, their colleagues hesitate to raise the flag early. So this troublemaker keeps hitting the same spot until there’s a bruise.”

Debugging the smartest person in the room doesn’t always work. “This one’s often not salvageable. When you’re tiny, you might get away with having her around, but as you get bigger it gets expensive to have this person,” says Blount. “The most successful tactic I’ve used with this archetype is coaching her to take 30 seconds to ask what the goal was with her communication. I ask her what she wants written into memory when others read it into themselves. What should she say to get through all the buffers and busses and written to disc?”

The Hail Mary tactic is an appeal to efficiency. “I list out to them all the tasks and time it took for me to clean up after their shit. This only works if there’s enough of a foundational relationship (read: consistent 1:1s) that she cares about your experience,” says Blount. “Tell them that you’ve reached your limit and that we’re not going to have this happen anymore. This appeal has both worked and failed, but it’s typically my last, best attempt to drum up awareness and empathy.”

These aren’t fables. These troublemakers exist. They’re out there in the wild.

Troublemakers play many roles in organizations. They can be arsonists or bellwethers, your founder or a newbie. When you’re managing them, remember that a troublemaker’s spirit is part of a startup’s DNA, but must be calibrated according to the stage of the company. Rarely are people intentionally destructive troublemakers. There will be instances when you won’t be able to decode them, but knowing how to recognize and troubleshoot them will save and benefit the organization and them — and ideally both. Be able to identify a hermit, nostalgia junkie, trend chaser, and smartest person in the room. Go into conversations with them rooting for their relevance and redemption.

“I remember one troublemaker who couldn’t walk down the hall without stepping on someone’s feelings. He was as talented as he was expensive to deal with. But, through time, we reached an understanding where he’d start to manage the impact of his troublemaking. He’d stir up situations just enough to see if there was anything brewing that was harmful to the company,” says Blount. “He’d send me warnings like a scout. His eagle eyes saved the company from dangers more dire than his troublemaking. I remember several instances when it took a few deep breaths to keep me from kicking him out. But today he leads a team and triages the troublemakers he once was. Sometimes when you save a troublemaker, you’re saving a team they’re not yet on.”

Photography by Bonnie Rae Mills.