Anti-Misalignment

Nobody knows what alignment is, but everyone knows what misalignment feels like.

A funny thing happens when you’re praised for something. Suddenly you’re on the lookout for more opportunities to do that thing. In fact, some things that are not that thing start to look like that thing so that you can do that thing and get praise for it because praise is nice, right?

For the past 10ish months, that thing for me was alignment.

“Driving critical alignment across platforms, orgs, cross-functional partners, and leadership”

^ this is a cornerstone of my performance review, and for good reason! Alignment work is hard, requiring you to dive deep into the gaps, build missing connective tissues, and then market the essence of your findings to everyone so that issues can be resolved before they even appear.

But also, isn’t it totally bullshit and a huge waste of time? If we have alignment, why do we have a meeting tomorrow for “Launch alignment” and one the following day for “Scope alignment”? Isn’t the point of alignment to enable autonomy? And also, why is “alignment” often the “goal”? Shouldn’t alignment be how we get to the goal?

These questions and more have haunted me for months. I’ve asked everyone what alignment is, inhaled everything I could find on the topic, and written perhaps 10 drafts of this essay.

So, here is Thesis #1 - Nobody knows what alignment is, but everyone knows what misalignment feels like.

Alignment is group flow

Nobody knows what alignment is. Sure, there are essays that define it, and everyone I asked had a coherent response to what it meant to them. But in practice, it doesn’t matter if you’re in a thousand-person company, working on a side project with a friend, or planning a wedding, the word “alignment” often feels handwavy and disconnected.

So, here’s my definition based on feeling: Alignment is flow between people. The group feels like a trusted extension of yourself. You feel fully utilized to focus, make decisions, and move.

Just like flow, alignment is hard to define, but it feels fantastic and you know when you’re in it. Another similarity is that losing flow always has a clear culprit:

• You got a text from your mom → flow broken

• You switched tabs and got distracted by a news article you saw → flow broken

• Someone tapped you on the shoulder to ask you a question → flow broken

• Your Spotify queue suddenly started playing a podcast. → flow broken

But what about getting into flow? Do you remember the last time you were in flow and why it happened? A common answer:

“I woke up early, brought my work to the library, turned off my notifications, quit all my apps, deleted Hinge, threw my phone in the trash, turned on white noise, and just stared at it until it started happening.”

Isn’t it interesting that ☝️ this isn’t how to get into flow, but how to prevent falling out of flow? Why? Because flow is mystical and hard to define, and it’s so much easier to notice what took you out of flow.

In the same way, alignment is hard to define, but it’s easy to notice misalignment - what took you out of alignment.

So let’s extend the thesis - Nobody knows what alignment is, but everyone knows what misalignment feels like. Thus, most “alignment” is just preventing misalignment (i.e. "anti-misalignment").

Anti-misalignment is lazy alignment

Anti-misalignment (noun) ​
1. The act of stamping out misalignment as a brute force strategy to achieve a feeling of alignment.
Synonyms: ​Lazy alignment, reactive alignment. ​
Antonyms: misalignment, proactive alignment

During the months thinking about this essay, I made an interesting discovery. People struggled to truthfully define alignment, but I couldn’t stop them from going on and on about misalignment. From those conversations (and my own experience) here’s what I found:

Misalignment is felt when you discover a decision that feels both surprising and harmful to your goals. Some examples:

1. Discovery: An engineer quickly builds an ugly design for an edge case. After launching, they find there is no traffic to the edge case, so they don’t bother sharing the decision with designers. Misalignment is not felt by designers because they did not discover the decision.

2. Surprise: Every week you share with your team lead that engineers are struggling with a certain “non-essential” feature. Eventually, you decide to cut the feature from scope. The lead doesn’t feel misalignment because while this decision is harmful to their goals, it is not surprising.

3. Harm: After launching an email campaign you notice that the graphic is different from what you expected. Apparently, this new graphic performed better in testing. As an engineer, this decision was surprising but not harmful to your goals, so you do not feel misalignment.

From this misalignment-focused lens, here are some bad ways to achieve alignment:

1. Reduce the discoverability of decisions. For example, make sure that all decisions happen in secret, with no record, in private invite-only forums. If people never discover what decisions are being made, they can't feel misalignment.

2. Make decisions less surprising. For example, all decisions must be democratically agreed on by every member of the project. Or, only the lead can make decisions. Everyone else just brings the decisions to the lead. If people can’t make decisions on their own, you can’t feel misaligned.

3. Make decisions less harmful to your goals. For example, only work on projects that <1% of users will use. If you launch something nobody can possibly want then no decision can be harmful.

4. Stop making decisions. If nobody makes any decisions, then nobody can feel misaligned!

Hopefully none of these obviously ridiculous examples hit too close to home, but if they do, you might be on a project more focused on stamping out misalignment than finding true alignment!

“Anti-misalignment is lazy alignment” is the title of this section and I don’t mean that pejoratively from an individual’s perspective. I literally mean that any organization which doesn’t proactively and intentionally strive for true alignment will default instead to cauterizing the symptoms of misalignment. This is especially true the larger an organization gets.

Let’s once again expand the thesis: Nobody knows what alignment is, but everyone knows what misalignment feels like. Thus, most “alignment” is actually “anti-misalignment”, which is less effective than true, proactive alignment.

Alignment is more than anti-misalignment

We’ve talked about what alignment isn’t. But what is it, really? Well, let’s return to the previous answer for “how did you achieve flow?”:

“I woke up early, brought my work to the library, turned off my notifications, quit all my apps, deleted Hinge, threw my phone in the trash, turned on white noise, and just stared at it until it started happening.”

Now let’s consider a new answer to “how did you achieve flow?”:

“I hopped on the pottery wheel and found flow”

Doesn’t the pottery answer feel more authentically “flow” in some way? When you read that you say, “yeah, that’s flow, the library answer is some weak diluted knock off flow.”

Flow requires more than just preventing distractions. You can’t delete all your apps and hope to find it. You have to actively connect some deep part of yourself to the core of the work.

Alignment is the same. Just preventing misalignment (“anti-misalignment”) is a weak knockoff compared to finding true, deeply connected alignment. The group has to connect some deep part of itself to the core of the work to actually be aligned.

Let me see if I can illustrate this:

Alignment by setting the context, goal, strategy, and priorities.

In this example, it doesn’t really matter what decisions we make and whether people disagree. What matters is that we deeply understand where we are (the context), what the destination is (the goal), and what the boundaries are (strategy & priorities). Since that is deeply clear, we’re all fully empowered to make our own decisions, disagree & commit, and move!

Anti-misalignment - tries to align by stopping misalignment

Anti-misalignment doesn’t aim for clarity—it aims for control. Since no one understands the strategy well enough to act independently, the only way to stay “aligned” is to move in lockstep. Every decision is a potential landmine. Disagreement isn’t something to commit through—it’s something to avoid entirely.

(Examples included in the appendix at the end)

Now What? Policing Terminology?

"There are only two hard things in Computer Science: cache invalidation and naming things" ​- Phil Karlton

Your instinct may be to jump straight to being the "alignment police", but I have found that this is not effective.

The problem with “alignment” is it means everything and nothing at once. Sometimes it means "alignment", "agreement", "decision", “strategy”, “context”, or sometimes it's a filler word. Everyone has a different idea of what it means, so questions like “are we in alignment?” rarely lead anywhere useful.

However, I’ve found that getting everyone to agree to a new idea of what alignment is adds more confusion than clarity. In the few rooms where I prototyped a distinction between “alignment” from “agreement,” it just led to a confusing tangent about terminology. Most people tuned out. Remember that misalignment is painful, so if you suggest that we aren’t actually in alignment, the fear of another meeting kicks in and people might defend that in fact, we do have alignment.

Instead, here are three strategies I’ve found useful in making alignment less painful (and more effective) day to day

Strategy 1: Use Different Words

First, the most useful strategy is to just stop using that word. Just pick another one. “Strategy” is a good one. “Context”, “motivation”, “priority”, “clarity”, “approach”, “agreement”, all good words. Prefacing them with “high level” is helpful if the conversation is too in the weeds. If “alignment” is vague and not helpful, switching the word can shake out a new perspective.

Whether we have “alignment” is not actually the goal because remember, nobody knows what “alignment” is. Instead, make sure people have clarity. Make sure they understand the strategy. Make sure they know our priorities and the context behind the decisions we make. If the goal isn’t “alignment”, then the goal is progress, flow, movement, autonomy.

Strategy 2: Treat Alignment as Variable

Second, don’t expect alignment to be static. I know this essay implies that alignment could be set once and then enable a glorious era of autonomous productivity, but in reality, it changes. New stakeholders and variables weigh in, priorities change, people leave, and new information can be discovered.

Instead of aiming for one perfect alignment artifact at the start, focus on enabling group flow right now, and be ready to adjust as things evolve.

Strategy 3: Advocate for Autonomy

Finally, advocate for autonomy. This especially helps with understanding the line between “alignment” and “agreement”. Ask “what kind of situations would require us to have this conversation again?” Sometimes, just asking that question will reveal something that prevents that conversation from being needed in the future.

Here is an example that tries to capture all 3 strategies:

Meeting host: the goal is to align on what to do about issue XYZ that came from our project colliding with a new company initiative.

Group: (discusses, arrives at a decision)

You: Sounds like we made this decision because Y priority now outweighs Z. Do you think that tradeoff holds more broadly? If so, we could share it with our partner teams to help them make similar decisions without needing to sync every time.

Great job avoiding the word “alignment”, understanding that alignment can change, and advocating for autonomy 👍!

Conclusion

The thesis again:

Nobody knows what alignment is, but everyone knows what misalignment feels like. Thus, most “alignment” is actually “anti-misalignment”, which is less effective than true, proactive alignment. - Mr. Boots Too Big

This is roughly three ideas on alignment. According to my notes, I have ~75 more snippets tagged with “alignment.” Now admittedly, most of them are probably garbage, but I definitely cut some good ones from this essay (with much difficulty).

So if you’re also interested in the topic, I think I roughly know what I want to say in a second and third part on alignment. Just give me six more months and 20 more drafts and I’ll get them straight to your inbox!

More about me (Mr. Boots Too Big): I fixate on ideas, and this project helps me distill them into concrete artifacts. Originally, I hoped to write about ideas discovered on my journey to a Staff promotion, but well… it happened! So I hope to publish something probably once a quarter. Nothing timely, nothing monetized. If that sounds interesting to you, feel free to follow along:

Appendix: Agreement vs Alignment

Some examples:

We know from past projects that this page is really sensitive. Small changes often lead to really big results (both good and bad). So, we prioritize testing assumptions iteratively over launching big bundles of features all together.

• This is a high level strategy. It gives the group a way to make decisions in the future.

Let’s align on the process of communication between our two teams for how we will operate.

• This is an agreement, not a strategy. This doesn’t help determine how to make changes in the process in the future, just agreeing on a decision right now. Agreement isn’t a bad thing and is probably what is necessary in many cases for speed. The purpose of drawing the distinction is not to discredit "agreement", but to encourage people to actually seek alignment after the agreement is made.

• How this could be alignment: "Let's align on what the goals are for our teams and derive a process that matches those goals. Hopefully we can preempt some of the gaps that emerge, but if not, let's discuss how we will adjust and improve our process over time”. You can see that this takes more depth, so a short agreement could be appropriate depending on the context.

We are in a phase of discovery to find our next big thing. We should use data, research, prototypes, and quick experiments to try every idea and see what sticks. We should not be afraid to take a slight brand hit by launching something unpolished. We also should not be afraid to end an experiment that is working, but won’t be a huge opportunity

• This is also a high level strategy. It provides clear priorities and tradeoffs to give a wide breadth of autonomous decision making.

Here is what we are launching next quarter! Notice that XYZ is not in the build, but ABC is in the build. The reason is 123, but we’re happy with that trade off. If we’re in alignment, let’s lock it in and finalize the roadmap!

• This is an agreement on what we are building, it doesn’t enable individuals to make tradeoffs and decisions. What happens if an issue is discovered and another feature can’t make the build? We would have to “align” again.

• It is close though! If you add "we're happy with that trade off because priority X takes precedent over priority Y for our goal to Z", then that could enable future decision-making.