I don't have anything particularly deep to say on this one. But I've spent a bunch of time thinking about how skepticism, uncertainty, and critique are really a form of learning. This is something that's decently prevalent in higher education, but is often missing in tech. If there's any sort of behavior I've noticed that gets the most policed, it's expressing skepticism about a technical or business direction. I still remember my first job as a project manager, the look of "why can't you just get on board and stop being so obstinate" and feeling "I'm sorry I don't actually know how to be any other way". It sucked.

But on the other hand, the best relationship I've had with managers are the ones that let me express my skepticism in a healthy way, regardless of whether or not it leads to immediate change. At a previous job I was probably one of the most skeptical people when it came to the switch from Javascript to Typescript. But my manager at the time invited my disagreement and gave me an opportunity to do more research until I ended up becoming a Typescript champion on the team.

Being on the Receiving End

Look, I'll be honest, as someone who's spent a fair amount of time now trying to get other people onboard, at various places of work, of ideas that I thought were good. Skepticism can be fudging frustrating. It can occasionally feel like I'm trying to do a good thing and someone is just standing in my way out of obstinacy or a decision just not to educate themselves on what I'm trying to accomplish here, dammit.

The irony is not, in fact, lost on me.

But, at some point I have to recognize that my frustration with that situation is less a reflection of someone else's incompetence and more a reflection of my emotional attachment to a decision I've made.

What Skepticism Isn't

Being skeptical is one of the more policed forms of communication, and I think it comes down to a couple different phenomenon. Firstly, the concept of bringing your "whole self" to work. In emotionally inclusive spaces there's a kind of belief that if everyone can be their "whole self" that any single given opinion is indicative of their "true opinions". So it's less "this person is uncertain and this is how they're expressing uncertainty/confusion" and more "you're choosing to be a problem".

Firstly, I think skepticism cuts against the incredibly popular aphorism "disagree and commit". The idea of disagree and commit is that "we're a team here so once we make a decision, in order to continue being a part of that team, get on board".

Confusion expressed as skepticism is typically not obstinance in my experience. It’s someone who doesn’t know where to start and is expressing that uncertainty through critical language. Disagree and commit doesn’t work here because there’s no earnest disagreement. The issue is that there’s no material knowledge to disagree with or to commit to to.

Secondly, it's ironic to me because it cuts against the concept of the learner's mindset that Carol Dweck popularized, but it's also just not representative of the situation. Often the best way to learn is to say "This looks weird and wrong to me for X, Y, Z reasons" and then to have a conversation about why that's not the case. At least for me, trying to reframe my perspective that's not critical just isn't possible. It's not that I'm actually trying to be a jerk it's that the way my brain is perceiving this situation is through critique. And with that explanation, I can move forward with growth and learning.

But more importantly, all of these sorts of alignments are really about the end stage fof the process, not the start. The goal of collaboration on a project isn't actually to be in alignment at all points in time. It's about addressing points of disagreement and then moving forward together once a decision has been made. Being comfortable with people's "whole selves" means being ok with the fact that some days they're going to be less in alignment and some days they're going to be more in alignment. And trying to create a situation where they can be equally effective in both modes.

What Skepticism Is

Skepticism, in my experience is someone who is being open about their thoughts and bringing their "whole self" to the situation. It's often "unwarranted opinions based on knowing very little". While it can be frustrating to be on the receiving end of that, people being open about those very opinions is the best way to start a productive conversation towards future alignment.

I actually really love hearing people's unwarranted opinions now, because it gives me a clear sense of where they're at, and what sorts of information or techniques we can talk about to move towards having a productive conversation.

Meeting that skepticism with frustration has the potential to reinforce the sorts of ("command and control") emotionally unsafe behaviors we really try to avoid in tech. Some of my most productive conversations on Pull Requests have been when I say something like "this looks weird and wrong" and the developer who wrote the code walks me through what's happening.

I think it's important for both parties to extend grace in these sorts of situations. As the skeptic, I've tried to reframe my initial criticisms less as raw frustration and more as a reflection of my own lack of knowledge. But I also think it's important to respect people's skepticism (even when less than ideally worded) as a real piece of useful information that can be used productively in the future.

Actions Matter

I want to end with a reflection on the heart of "disagree and commit". I think when we hear that phrase we conjure these images of people arguing in a boardroom 12 Angry Men style and saying "I don't agree with you, but dammit do I respect you". But the truth of what actually happens is way more subtle. It probably looks more like someone leaving a bunch of comments on a PR and approving it anyway, or someone disagreeing in a conversation one moment and then shipping code related to the agreed upon direction.

Words matter, but I would much rather be around people who express frustration and still productively take action towards a shared goal, than people who are quiet and do not. The ideal is always that our words, actions, and emotions are in alignment, but we're all human, occasionally those arrows are going to be moving in different direction and in those cases it's important to differentiate genuine productive emotions (skepticism) from unproductive action (obstinance).