My Comments Are in the Google Doc Linked in the Dropbox I Sent in the Slack

This post is like watching “Portlandia” as a Portlander (or HBO’s “Silicon Valley” as a tech worker). It’s obviously satire but too close to reality to be funny… My Comments Are in the Google Doc Linked in the Dropbox I Sent in the Slack:

You still don’t see the link? It’s right there on the bottom of the Slack thread from yesterday about which shared drive folders link to Dropbox folders that contain all the shared PDFs. Oh, my mistake; it’s actually at the bottom of a thread about what everyone had for lunch yesterday. Here I’ll send it to you again. I just replied to an email to Jeff with the link and asked him to forward it to you. The subject line is ‘Email.’

Say the quiet part out loud: simplifying communication in high context environments

The Culture Map by Erin Meyer is a great book about how to improve communication between different cultures when you work at a company with a global workforce. Recently I’ve been thinking about how these concepts apply not just at a (geographical) global level, but within the systems of a single organization. What are the norms of how people communicate with each other in meetings, in email, over Slack? What type of confusion/misalignment might happen because of those norms, and how can it be improved?

There’s one dimension the book covers that I think applies particularly well to modern organizations, and that is the difference between high context and low context communication.

High context settings are those where communication relies heavily on implicit understanding. The assumption is that everyone has the same frame of reference, which means a lot is left unsaid, with the belief that everyone “just gets it.”

Low context environments, on the other hand, are those where things are spelled out more clearly. There’s less assumption that everyone has the same background information or knowledge, leading to more explicit communication.

For instance, if you often don’t know what people are talking about in meetings and it makes you feel like you missed something obvious, you might be in a high context environment. Perhaps things move so fast that there’s an assumption that everyone already has all the context of the previous 10 meetings that happened about a topic. It’s natural for this to happen—but it reduces the effectiveness of our work and the health of our relationships.

I’ve been trying to be more deliberate about addressing this issue—at least for myself and the people I work with most closely—by actively going more “low context” in my communication. When something is implied through context, but not explicitly stated, I aim to go out of my way to make it explicit.

The goal is to ensure that no one has to feel like they can’t contribute (or be scared of making the “wrong” contribution) because they weren’t part of every conversation. By making the implicit explicit, we level the playing field. It’s not just about adding clarity to our communications, it’s about fostering an environment where everyone, regardless of their starting point or level in the organization, has the same opportunity to understand and contribute.

By breaking down our messages into clearer, more accessible information, we’re not dumbing down—we’re opening up. We’re building a foundation where everyone can work confidently, equipped with the knowledge they need to contribute meaningfully.

Keep an eye out for opportunities to say the quiet part out loud. To clarify a statement, or state the thing that appears to be said between the lines. It takes work and concentration, but it’s a shift that can make a big difference in how we work and relate to each other.

How Group Chats Rule the World

This essay on How Group Chats Rule the World (NYT Gift Link) is really great, and I agree with all of it.

The group chat can sustain indefinitely this thin wire of connectedness. Some might argue that this feeling is a deception, another screen-based way to stave off loneliness; I would say instead that it glows with potential. Because there is no practical end to the group chat, it can be a means of keeping the lights on, constellating a set of people who would otherwise be entirely separate.

Taylor Swift and the Good Girl Trap

You know an essay is going to be good when this is the preamble:

I am writing this piece in good faith (that you, as a reader, like to think more about the culture that surrounds you, whether it’s culture you love or hate or are ambivalent about) and that you are in turn reading in good faith (that I do not hate Taylor Swift, that this is not a takedown, that we’re talking about Swift’s image but we’re also talking about people’s reaction to that image).

But yes, this is a really timely and poignant piece by Anne Helen Peterson about Taylor Swift and the impossible trajectory of celebrity:

But sometimes, when you keep on winning — awards, sure, but also in your career — it doesn’t matter who you are or how hard you worked for those achievements. People are going to find it harder to root for you. It’s when domination turns into over-saturation: when honest missteps become weaponized, when the interpersonal comes to feel emblematic, when every move becomes overdetermined.

Whose job is it?

This is another fantastic post on career development from Johnathan and Melissa Nightingale. This bit really resonated with me:

I want to feel like I’m making progress. And to feel like the various work experiences I’ve had are all building toward a thing. I want to be able to talk about work, not as a string of jobs I’ve done, but as a career.

The Law of Propinquity And The Work From Home Dilemma

Here’s a solid, research-based take on remote work by Paul Taylor. He discusses what type of work is usually more successful when done in person vs. remotely:

If you are doing solid repeatable work, or work that requires intense solo concentration, you can work from pretty much anywhere. If you are in a discovery phase of work, and trying to fuse ideas together from multiple viewpoints remote working might be a hindrance.

It reminds me of a saying I heard somewhere: “In-person is where decisions happen, remote is where work happens.” I also really like this (new to me) concept:

The law of propinquity states that the greater physical (or psychological) proximity between people, the greater the chance that they will form friendships or romantic relationships. Other things being equal, the more we see people and interact with them, the more probable we are to like them.

No running in airports

Every time I travel, just before I leave the house, I do a weird thing. I stop at the front door of our house, look myself in the mirror, and say out loud: “Remember, no running in airports today”. Travel is inherently stressful and I’ve found that once it boils over into having to run to catch a flight, I lose my ability to deal with things well. So I try to remind myself to keep calm and walk on.

Of course, there are a lot of variables in the “no running in airports” equation that are out of my control. A delay might cause a tight connection. A messed up security line could take longer than expected. I could miss a gate reassignment and try to board the wrong flight (yes, that happened). And yet, that statement helps to ground me in the two most important things I can do to stay in control of my travel day: be prepared (know when to go where, renew my Flighty subscription, etc.), and pay attention to detail (um, just, you know… read the gate assignment right).

I was thinking about this as I was getting ready to head into another workweek. There seems to be a lot of “running in airports” going on in the tech world right now, and it sometimes feels like it gets too much to handle. So what would it mean in a work context to look in the mirror on Monday morning and say out loud: “Remember, no running in airports today”? Yes, lots of variables are out of our control, but how could we be prepared and pay attention to detail in a way that reduces some of the likelihood of that happening?

For me? I could be prepared by looking ahead at my calendar and making sure I am spending my time in the right meetings—and that I go into them knowing exactly what is expected of me and what we expect to get out of them. I could try to anticipate “delayed flights”—those unexpected wrenches in projects—and what I could do to get things back on track if that happens.

I could pay attention to detail by listening intently when people speak, by hearing the meanings and feelings underneath the words in meetings where things seem a little wobbly. By noticing when “a gate assignment changed” (no, I’ll never stop being embarrassed about that one) and preemptively figuring out how and why it happened and what I can do about it.

There are, of course, no guarantees. But I still firmly believe that teams make better products in calm environments. Just like in travel, we can’t really create calm. The planes are going to do what they do. But we can remind ourselves that the goal is not to run, and that we have some agency over that.

Here’s to not running in airports this week.

Why using a Now/Next/Later roadmap might be right for you

I was recently asked by a colleague to write up our team’s reasoning for using a Now/Next/Later roadmap to plan our work (instead of quarterly/annual roadmaps with dates). If you already use Now/Next/Later nothing in here will be new to you, but I thought I’d share what I wrote for this internal document in case it’s useful to anyone hoping to make this shift as well.

We use an adapted version of a Now/Next/Later roadmap to plan our work. You can read more about this approach in Introduction to Lean Roadmapping by its creator, Janna Bastow. In short, here are the guiding principles for using this roadmap and why it is effective:

  • Deadline-driven development is fraught with issues that make it a fairly ineffective way to plan delivery work. This includes:
    • Long-term priorities frequently change based on new data and developments, so any planning past a few months out is mostly fiction and rarely happens as planned.
    • Deadlines are often set without input from the delivery teams who are building the product, which makes estimates inaccurate and difficult to attain.
    • Because deadlines are often arbitrary, delivery teams have to make quality tradeoffs to meet the dates, which introduces unnecessary technical debt into the system.
  • Using a Now/Next/Later approach helps delivery teams know what is most important to work on, and what is coming down the road.
    • “Now” means Now–it is literally the work that is in flight. This work should be limited to 1–2 projects per team to ensure effective delivery.
      • Changes to “Now” should only happen in the rarest of occasions so as not to interrupt work in flight.
    • “Next” means anything from 2–8 weeks from now. This is work that is planned and ready to go as soon as a team becomes available. It has been spec’d and scoped, and everyone agrees it’s the next important thing. We limit not only Work In Progress (Now), but also Work in Next, so that there are not too many priorities vying for attention.
      • Changes to “Next” should happen infrequently since the work is planned and the team will be ready to go at any moment.
    • “Later” means anything from 2–6 months from now. This is work we believe is important to be prioritized, but it hasn’t been fully spec’d and scoped yet.
      • Changes to “Later” can–and often does–happen whenever new data becomes available that makes us shift priorities. This is expected and encouraged, until the project moves to “Next” where it gets locked in and fully spec’d.
    • We cheated and added “Much Later”, which lists things that we think will be 6–12 months out. The likelihood of these projects changing are high, but it is good to have a long-term view on what we believe, with the current information we have, will be important for the business and our customers to work one.

We do acknowledge and recognize that delivery dates are important. We prefer to work with high-integrity commitments, which are dates that delivery teams commit to once they have had a chance to properly scope out a project (which sometimes means getting started without a completion date set).

The teams are accountable to these dates because they have been involved in setting them, and though they can change based on unknowns, these changes should be infrequent.


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