Hard to work with.

Managing teams has taught me a lot about my own behaviors and motivations. For example, I overworked for a long time. This left me continually teetering on the brink of burnout, and I had no energy left to absorb the typical sorts of organizational changes that happen at any company. Despite doing good work, I handled change poorly, and I picked up the reputation for being difficult to manage.

I’d like to say that I learned from my mistakes directly, but the honest version is that I came to understand this dynamic mostly through working with folks struggling from the same issue. After seeing it in others several times, I came to notice it in myself. This culminated in joining Stripe with the explicit goal of pacing myself to be more valuable after four years rather than getting exhausted after two years like I had at Uber.

Overworking is an interesting vice because it’s socially acceptable and some view it as a necessary precondition to outsized success. The category of “socially-acceptable professional vices” is an interesting one because these vices will hamper your career progress in non-obvious ways, and this is indeed my segue to the actual topic I want to dig into: individuals who have higher standards for those around them than their organization supports.

It’s a truism that you always want to hire folks with very high standards, but I’ve seen a staggering number of folks fail in an organization primarily because they want to hold others to a higher standard than their organization’s management is willing to enforce.

I’ve seen this happen so many times in my own work, in friends’ work, and in emails that wind up in my inbox. A few examples:

• An interim Vice-President of Engineering (VPE) at a company whose CEO won’t finalize the role because one peer is upset they didn’t get the role. That peer has been struggling for some time, but the CEO doesn’t want to “rock the boat” so leaves them both lingering. Attempts to hold their peer accountable are viewed as “evidence they’re not ready” for permanent VPE role
• An engineering manager working with a product manager whose proposals are both very expensive to implement and misaligned with the company’s goals. The engineering manager flags the issue to product leadership and it gets reframed from a concern about the product manager’s performance into an issue of two peers not collaborating well. Both are pushed to “collaborate better” but the team’s impact remains poor
• Engineering directors at a company who instituted company-wide bar raisers because one of their peers was unwilling to maintain the shared hiring bar. The CTO was unwilling to hold that director accountable, so the other directors followed the only solution they could think of that wouldn’t be interpreted as “interpersonal conflict” by the avoidant CTO

As you look at enough of these scenarios, you can back out a common pattern. The main character is trying to do their job effectively, but can’t due to the low performance of a peer. They escalate to the appropriate manager to address the issue, but that manager transforms the performance issue into a relationship issue: it’s not that the peer isn’t performing, it’s just that the two of you don’t like each other. Instead of being the manager’s responsibility to resolve the performance issue, it’s now the main character’s responsibility. By attempting to drive accountability in their peer, the main character has blocked their own progress (“they’re just hard to work with”) without accomplishing anything.

What I’ve come to appreciate is that the appropriate manager is almost always aware of the underlying issue, and for some reason they’re simply unwilling to confront it. You think that you’re bringing a new problem to that manager to solve, but what you’re actually doing is trying to hold that manager accountable for not solving a known problem, which more often than not ends poorly when they’re more senior than you.

If you still want to have a direct discussion, you can usually have a direct conversation about why they’re comfortable maintaining the status quo. You can even add more context about how it’s impacting you or the team you work with. Sometimes this will lead to change, but it’s a slow process. You’re not going to change their mind overnight.

What I’ve found effective in these cases is to lead with constructive energy directed towards a positive outcome. Even if you can’t get your peer’s performance addressed directly, you can often overcome your peer’s bad performance by generating excitement in the direction you want to go. Enough excitement will give the resolution avoidant manager a way to solve their problem without actually engaging with the situation that they’re unwilling to address.

I know that folks don’t want this advice: it is unfair to be forced to overcome a peer’s poor performance, that’s the manager’s job, but work isn’t a perfect place. Success is finding a path forward among the options that actually exist. Grinding yourself down in frustration about paths not existing doesn’t solve anything. It may take a few tries to learn this lesson, I certainly devoted quite a few years to learning it the hard way.