Coleman McCormick

Archive of posts with tag 'Company Culture'

July 2, 2024 • #

How Cultures Accumulate →

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January 23, 2024 • #

This book is dense and fascinating. Highly recommended to anyone intrigued by how companies, organizations, or groups in general operate — the driving psychologies behind different types of orgs.

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January 22, 2024 • #

The Cynefin Framework →

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Coordination Headwinds →

October 11, 2023 • #

Transaction costs are unavoidable, and with a scaling team, these drags of coordination slow every team down. It’s a law of business physics.

Here’s Venkatesh Rao, commenting on this excellent slide deck from Alex Komoroske:

There is no villain responsible for this. Coordination simply becomes vastly more difficult far earlier along scaling trajectories than people realize. Things get worse than you expect, sooner than you expect. This is coordination headwind. It’s an exponential snowballing phenomenon.

I agree that it’s an inevitability. And that the headwinds sink their teeth earlier than you think.

One note I’d add is that some companies create coordination headwinds for themselves — trying to “play company” and “get ready for scale” too early; I describe it as “copying the worst parts of a big company without getting any of the benefits”.

Here’s Venkat again:

People routinely and radically underestimate the massive size of this effect, and misattribute it to bad management, individual incompetence, or malice, and systematically under-react to it, doing too little, too late, and letting the problem grow to crippling, existentially threatening levels before even recognizing it.

I’ve seen teams encounter these headwinds, but then rather than recognize the onset of natural coordination costs, they misdiagnose what’s causing underperformance. Without an idea of what to do, they hire consultants, begetting more coordination. A coordination headwind vortex.

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Big Firms Need to Be Sluggish →

May 16, 2023 • #

Arnold Kling raises interesting points here about the nature of big companies. The incentives and physics of large company dynamics essentially demand that they move slowly. Sometimes this slowness looks like indecision or lack of conviction (and sometimes those are in there), but for the most part it’s a function of the upside/downside balance. As a business expands, the downside for failure starts to outweigh the upside of success:

Amar Bhide, in The Origin and Evolution of New Businesses, classifies business opportunities along two dimensions: capital and ambiguity. If a project requires a lot of capital, then it is not suitable for a small business, unless it can somehow obtain a lot of funding from venture capitalists. If a project has a lot of ambiguity, meaning that the path to success is unclear, then it is not suitable for a large, established business.

A useful explanatory reasoning from Kling here.

There are exceptions that prove the rule, though. One could argue that the Amazons, Shopifys, and Teslas are able to maintain a sense of forward progress and risk comfort out of band with their size. Disruption theory tells us that the conservative, rear view mirror-oriented view of a large business is baked into the cake. In a lot of ways it’d be rash and illogical not to service your existing customer base and prioritize preservation of business over creation of new markets. But even given these rational perspectives, BigCos have more control over their destiny and their internal cultures than they’d admit. Maintaining “builder” mentality is entirely possible.

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Anti Portfolio Theory of Product →

October 18, 2022 • #

Often you hear product teams talking about their roadmap in investor-like terms. Managing their upcoming initiatives like a financial portfolio, distributing their bets among things of various categories, sizes, and risks — like a portfolio manager would do to hedge risk. Umang Jaipuria makes the case that product teams should be inverting this logic: concentrating their bets (and therefore, money and energy) behind fewer things.

All product teams should have ONE bet they are making, and put all their effort into making that successful. The fact of the matter is that a product team is not an entire company. A product team does not need to “survive” against all odds and hedge their risk. A product team needs to build a successful product. Even if that means failing after a while and having to start anew or go into maintenance mode or join other product teams that need to scale (that dreaded phrase ‘get reorg-ed’).

He also references the world-class investor Stanley Druckenmiller, and his similar philosophy that’s helped him to generate ridiculous returns over his investing career through this type of extremely calculated, concentrated betting:

“Yeah it’s completely contrary to what they teach in business school which is if you’re highly diversified you have less risk than if you’re highly concentrated. I don’t believe that at all. As an investor when I think most people get in the most trouble is when they have stale longs or stale shorts. When you’ve got 15-20 percent of your asset base or sometimes in macro positions I’ll have two or three hundred percent. Believe me they’re not getting stale and you have to have ruthless discipline and you’re coming in every day just to quote Andy Grove “you could not be more paranoid” and you’re constantly reevaluating.”

As Druckenmiller has famously said, “It’s not whether you’re right or wrong it’s how much you make when you’re right and how much you lose when you’re wrong.”

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Against Recurring Meetings

October 5, 2022 • #

I have a bone to pick with recurring meetings. They’ve become a scourge that’s been amplified with fully distributed teams. What may start with clear intent as a space for a team to coordinate continuous work eventually devolves into a purely ceremonial affair. And they’ve gotten 10x worse since the pandemic turned every meeting into a remote one. This effect was visible long before COVID, but I think remoteness has magnified the negatives without adding any positives.

Recurring meetings

Since no one has to book a conference room, the bar to generating tons of ceremony “sync” sessions has dropped to the floor. Even worse, remoteness makes a bloated 15-person meeting not feel any bigger than the 4-person meeting it should’ve been. In person, the bloated attendee list would be an obviously bad idea — very few meetings should leave some attendees with standing-room-only.

These meetings show up on the calendar with positive intentions. A subset of folks from different teams might need to regularly stay in touch with one another on specific projects, or perhaps there’s always some active work to be coordinated. Maybe it’s a stand-up intended to be a high-signal-per-minute short session to sync team members as quickly as possible1. There are good reasons the repeating function exists. But it’s overused. The decision to spawn a cross-functional recurring meeting isn’t considered deeply enough in terms of the cost, and the long-term purpose. Almost every time I’ve seen one appear on my calendar, there’s triggering project or event that compels someone to create it.

The “value per minute” of a recurring meeting might start high, but it decays over subsequent weeks. It’s like there’s a half-life on the value of a particular meeting, with its potency to get work done and problems solved waning substantially by month 3. But why does this happen so often?

For one, they’re too easy to create, and too hard to cancel. It requires the team as a whole to fundamentally not want to have the meeting, to be in favor of a meeting because it needs to happen. Gradually the utility : time ratio degrades, people get less and less out of their weekly session and are less engaged, just going through the motions. The whole group (especially meeting-originators) need to be on the lookout for ways to obsolete the need for having the meeting in the first place. I liked this from Aakash Gupta on Twitter, who says “meetings are like gravity”:

Different personalities and roles have differing preferences for what medium to use for each type of work. Some will always lean toward a meeting to communicate. Some want long-form writing. Some like incessant email chains. Choosing the right medium is Step One to escaping the recurrence gravity well. To quote myself from a previous post, meetings are just one medium for communicating and getting work done. A core contributor to “meeting fatigue” is when we’re choosing the wrong medium for work:

I know when I find myself in a useless meeting, its “meetingness” isn’t the issue; it’s that we could’ve accomplished the goal with a well-written document with inline comments, an internal blog post, an open-ended Slack chat, or a point-to-point phone call between two people. Or, alternately, it could be that a meeting is the optimal medium, but the problem lies elsewhere in planning, preparation, action-orientation, or the who’s who in attendance.

So what to do?

I recall this interview with Shopify founder and CEO Tobi Lutke. He mentions how they periodically mass-delete all recurring meetings from the corporate calendar:

That was a tangent, but to get back to the question you asked, we found that standing meetings were a real issue. They were extremely easy to create, and no one wanted to cancel them because someone was responsible for its creation. The person requesting to cancel would rather stick it out than have a very tough conversation saying, “Hey, this thing that you started is no longer valuable.” It’s just really difficult. So, we ran some analysis and we found out that half of all standing meetings were viewed as not valuable. It was an enormous amount of time being wasted. So we asked, “Why don’t we just delete all meetings?” And so we did. It was pretty rough, but we now operate on a schedule.

I don’t know if this is apocryphal or real, but it’s an interesting experiment in refocusing. Like a brush fire that clears the undergrowth for new life.

A few things we could do to minimize meetings, to force more thoughtful selection of medium for the message:

  • Make fewer in the first place — Seems obvious. Can we just do 1? If one isn’t enough, can we just schedule 3 and go from there?
  • Set end dates - 1 month, 3 months, whatever. This function exists, but I don’t think I’ve seen it used once in my career. The normal move is to say “we’ll cancel it later if we need to.”
  • Don’t make anything? — Do we even need to meet? Could it have been an email? Do you need to write up thoughts/ideas? Maybe record a Loom? Make a Miro board?
  • What if calendar tools let you see how many collective hours you’re scheduling? “For the next 1 month, this schedule will cost 60 hours of human time.” Not that this would stop some people, but may make you do a double-take to see the volume of time you’re about to commit.

Tyler Cowen says “context is that which is scarce”, meaning that we’re never lacking in information in our modern lives, but the means to make productive use of the information. Meetings often stem from people lacking context. The craving for context — to have a window into what’s going on, why it’s happening, and what to do next — generates temptations to “set up a quick meeting”. And if we know something is too big a topic for a single session, it’s too easy to say “let’s sync up weekly on this”.

A lot of coordination between people is about setting or sharing context. “Syncing up” is about sharing context. You can lean on recurring meetings to share context, which is occasionally okay if meeting trade-offs are worth it (in time required, efficiency). But sometimes we choose the wrong method for context-sharing between teams, and the need for too many meetings is merely a symptom of poorly-communicated context.

  1. I think short standup-style meetings, 10-15 minutes, are fine for the most part to recur. Of course there are alternative methods for getting the same job done (mutual info sharing between team members), but a quick call is fine. Tools like Loom show some promise to even make these obsolete, making asynchronous collaboration simpler. â†Š

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Don't Confuse Motion With Progress

January 13, 2022 • #

When I read Cal Newport’s Deep Work a few years ago, one of my favorite ideas in the book that I keep coming back to in conversations is the idea of “busyness as a proxy for productivity”. Here’s how he puts it:

In the absence of clear indicators of what it means to be productive and valuable in their jobs, many knowledge workers turn back toward an industrial indicator of productivity: doing lots of stuff in a visible manner

We’ve all worked with violators of this. People that always have fully-booked calendars, can never find a time to get tasks done, and constantly talk about how busy they are. One of the reasons people do this, whether subconscious or not, is that in the world of knowledge work, it’s seen as a virtue to be busy. “Man, that guy is always in high demand, it’s impressive how many things he’s doing every day.”

But behind the scenes, the impact of each unit of time spent “being busy” is miniscule. It’s a classic mismanagement of time and attention, but one that has obvious roots given the incentives in business to be seen. And when a behavior is rewarded, in this case with attention and sometimes even respect, it perpetuates.

But we're moving!

So let’s talk about motion. Busyness is a form of motion, usually described in an individual context. Motion and progress are terms that apply more at a team or organizational level. What is progress anyway? Clearly progress isn’t just “Stuff Happening.” There’s got to be an outcome for any of it to be worth it. There should be specific and consistent directionality to goals, and measurable steps to get there.

The motion of the team doesn’t necessarily tie back to an outcome anyone cares about, though.

One example where this happens in practice is the infamous Recurring Coordination Meeting — the Standup, the Check-In, the Sync Meeting. Someone sets up a weekly recurring meeting, often with few specifics as to the outcomes expected from each one. In subsequent weeks, the team now pulls itself away from other duties to distract itself with Another Meeting. Now I’ve rarely met anyone who enjoys these kinds of meetings in the absolute sense. At best we tolerate them, or see them as some form of ritual necessity. But so often some initial hangup or friction point triggers someone to decide “we need to stay in sync on this topic”, and they make the Check-In Meeting. In a snap we’ve committed several people to an unknown number of future hours for an often poorly-defined expectation. We’d have been better off with one-off meetings until we feel the team going wayward again, if we need to regroup.

An aside: I remember an anecdote about Tobi Lutke, CEO of Shopify periodically deleting all recurring meetings to reset commitments. Like a brushfire routinely clearing the corporate undergrowth of recurring time-sinks that may have long since outlived their usefulness.

But let’s get back to the “motion” piece of this. You’re now meeting once a week on a subject, and because the time since the last one is so short, you end up discussing the same topics again and again. You run through a loop with each meeting, repeatedly discussing the same things, with a tad more detail each time. Because we’re touching the topic regularly, sometimes beating the same topic to death in more than one of these meetings with different permutations of attendees, we feel like we’re “doing a lotta stuff”. We’re moving around, Trello cards are getting edited, Jira tickets are moved up and down the list, a few commits get made. But none of these motions are, necessarily, indicators of actual forward progress along the line we want. They might be, but they just as likely make us feel like we’re making progress when we’re really not.

I can get in the car and drive around the block over and over. Motion is happening, but am I getting anywhere?

Just measuring ticket throughput, or cycle time, or stories-per-sprint, or any other metric doesn’t mean you’re making progress in any meaningful sense. Those metrics might be directionally positive, but are they doing the thing you think they’re doing?

It’s imperative to have good yardsticks by which to measure progress, rather than motion.

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Hard Edges, Soft Middle

January 2, 2022 • #

Have you had that feeling of being several weeks into a project, and you find yourself wandering around, struggling to wrangle the scope back to what you thought it was when you started?

It’s an easy trap to fall into. It’s why I’m always thinking about ways to make targets smaller (or closer, if you’re thinking about real physical targets). The bigger and more ambitious you want to be with an objective, the more confidence you need to have that the objective is the right one. What happens often is we decide a project scope — a feature or product prototype we think has legs — but the scope gets bigger than the confidence that we’re right. A few weeks in and there’s hedging, backtracking, redefining. You realize you went down a blind alley that’s hard to double-back on.

I heard an interesting perspective on scopes and approaches to building. Think of the “scope” as the definition of what the project is seeking to do, and the approach as the how.

Hard edges, soft middle

In an interview on David Perell’s podcast, Ryan Singer made a comparison between having a hard outer boundary for the work with soft requirements on approach, versus rigid and specific micro-steps, without a solid fence around it, an unclear or amorphous objective. In his words: “hard walls with a soft middle” or “hard middle with a soft wall”:

I’ve had this mental image that I haven’t been able to shake that’s working for me lately, which is what we’re doing in Shape Up. We have a very hard outer wall for the work. And we have a soft middle. So there’s a hard outer boundary perimeter — it’s very fixed, it’s going to be six weeks and we’re doing this, and this is in the project, and this is out of the project, and this is what this solution more or less. Clear hard outer boundaries. But then the middle is totally like “hey, you guys figure it out.” Right now what a lot of companies have is the opposite. They have a hard middle and a soft boundary. So what happens is they commit to this for the first two weeks, we’re going to build this and we’re going to build that, and we’re going to build that all these little things. And these become tickets or issues or very specific things that have to get done. And then what happens the next two weeks you say, okay, now we’re going to do this. You’re specifying exactly what should go in the middle, and it just keeps growing outward because there’s no firm boundary on the outside to contain it. So this is the the hard wall and the soft middle or the hard middle in the soft wall. I think our represent two very, very different approaches.

This requires trust in the product team to choose approach trade-offs wisely. If you encounter a library in use for the feature that’s heavily out of date, but the version update requires sweeping changes throughout the app, you’ll need to pick your battles. A team with fixations on particular steps (the “hard middle”) might decide too early that an adjacent feature needs rework1. Before pulling up to a higher altitude to look at the entire forest, the team’s already hitched to a particular step.

Setting a hard edge with the soft middle sets what the field of play and game plan look like, but doesn’t prescribe for the team what plays to run. The opposite model has a team hung up on specific play calls, with no sense for how far there is to run, or even how large the field is in the first place. When you grant the team the freedom to make the tactical choices, everyone knows there’s some freedom, but it isn’t infinite. The team can explore and experiment to a point, but doesn’t have forever to mess around. If you choose to work in the Shape Up-style 6 week cycle, decision velocity on your approaches has to be pretty high to hit your targets.

Any creative work benefits from boundaries, from having constraints on what can be done. The writer is constrained by a deadline or word count. The artist is constrained by the canvas and medium. A product team should be constrained by a hard goal line in terms of time or objective, or preferably both.

Some of the best work I’ve ever been a part of happened when we chose particular things we weren’t going to do — when we intentionally blocked specific paths for ourselves for some cost/benefit/time balance. Boundaries allow us to focus on fewer possibilities and give greater useful, serious attention to fewer options. We can strongly consider 10 approaches rather than poorly considering 50 (or, even worse, becoming attached to a specific one before we’ve explored any others).

Premature marraige to specific tactics pins you to the ground at the time when you need some space to explore. Because you’ve locked yourself into a particular approach too early, it may require tons of effort and time to navigate from your starting point to the right end point. You may end up having to do gymnastics to make your particular decided-upon solution fit a problem you can find (a solution in search of a problem).

Hard edge, soft middle reminds me of a favorite philosophy from the sage Jeff Bezos, talking about Amazon’s aggressive, experimental, but intentional operating culture:

“Be stubborn on the vision, but flexible on the details.”

  1. What you “need” to do is a dangerous trigger word. Almost always the perceived need is based on a particular understanding of trade-offs that could be misguided. One engineer’s need to recover some technical debt (while noble, of course) might be the opposite for CEO, who might be seeing a bigger picture existential need to the business. A thing is only “more needed” relative to something else. â†Š

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Peak Meeting Efficiency →

September 15, 2020 • #

An epic post from Steven Sinofsky about all forms of meetings, when to use them, when not to use them. The list of dysfunctions and countering tactics is full of gems.

The thing is that most people say they don’t want to have meetings. Most say “oh that meeting could have been handled with an email or slack message”. They might be right. But that is only if you take the meeting literally. Meetings mean so much more to a company than conveying information or deciding.

Meetings are literally how cultures are formed, values expressed, and companies made.

See also, previously on the blog: Andy Grove on meetings.

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