Tooling Collaboration [Kwok]


A friend shared this fascinating read by Kevin Kwok

The Arc of Collaboration

It’s a thoughtful thesis on the state of enterprise/business tools and the apparent tension between productivity and collaboration, as epitomized by the use of Slack. 

Starting with Slack as the jumping-off point, Kwok acutely observes that, currently, Slack usually serves three main functions: 

1. “Else” statement. Slack is the exception handler, when specific productivity apps don’t have a way to handle something. This should decrease in usefulness, as the apps build in handling of these use cases, and the companies build up internal processes.

2. Watercooler. Slack is a social hub for co-workers. This is very important, and full of gifs.

3. Meta-coordination. Slack is the best place for meta-levels of strategy and coordination that don’t have specific productivity apps. This is really a type of ‘else statement’, but one that could persist for a while in unstructured format.

The first one is worth digging into. In essence, the prominence of Slack is a result of existing business tools not supporting some essential collaboration capabilities. Slack fills these collaboration gaps (as well as supports 2&3 above). To use Kowk’s eloquent yet slightly hyperbolic metaphor: 

Slack is not air traffic control that coordinates everything. It’s 911 for when everything falls apart.

And we are seeing some of those functional gaps starting to get closed, by native, in-app capabilities. All “GitHub for X” collaboration-first products fall into that category. Kwok highlights Figma (Design), to which I’d also add Abstract (Design) and GitBook (Docs) to show that this more than a single-product trend. The ripples in the collaboration pond originated in engineering (GitHub) and permeate outward starting with engineering-adjacent roles (designers, technical writers) with the first ripples reaching as far out as HR

But there seems to be a huge missed opportunity here, since the need for collaboration is function/work-product agnostic. By building in-app collaboration capabilities the walls between apps become higher and cross-app interoperability becomes harder. Not to mention the increased cognitive load on the user. 

Kwok looks at Discord as a different potential direction/inspiration for a tool that provides a set of collaboration capabilities (text and voice chat) across a set of functional workflows (games), stemming from a similar unfulfilled gap around collaboration caused by the poor in-game chat/collaboration capabilities. While the analogy has its limits, it does highlight an exciting path forward. 

The depth of desired collaboration on an MMORPG game and a business app (if you need a mental image: think a PPT/Keynote/Gslides presentation) is different, while the former often stops at coordination, in the latter we aspire for co-creation. This has a couple of concrete implications: 

1. Functionality-wise, lofty “collaboration” can be decomposed into a set of shared cross-product capabilities:

This list is probably incomplete, but the immediate capabilities that come to mind are: 

  • Unique user identity — mostly already solved today via “login-with-Google” type solutions. 
  • Hyper-granular permissions — providing edit/comment/view access to a subset of the work product. Think a single slide in a deck or a set of rows in a spreadsheet. 
  • Synchronous and asynchronous co-creation — I’m making a distinction here between “two people writing in a GDoc at the same time” and “Person A using the “suggest” feature to offer specific changes to Person B”. Both are needed. Both are relevant across all work products. 
  • Versioning —used here as a catch-all for the entire GitHub functionality including but not limited to: fork, branch, pull request, diff, and partial/selective merge. 
  • In-line commenting —having a dialogue about a specific piece of the work-product
  • Decision-making — decision-making is used here in the narrow context of making decisions about changes to the work-product, not in the broad context of making business decisions facilitated by the work product. Today, only a single decision-making mode is supported, by some of the products: a single autocratic “owner” accepting changes made by “collaborators”. 

2. An ideal solution will seamlessly integrate with the existing functional UIs

The breadth of work-products that we want to collaborate on justify the existence of multiple “creation/authoring” UIs. Any UI that will try to reduce collaboration on code snippets, presentations, and spreadsheets, just to name a few various work-products, into a single UI will most likely have to do so at the expense of depth of collaboration that it can support. An ideal solution will look more like Grammarly’s browser extension, which provides cross-product writing quality support, or like a “collaboration SDK” which multiple products can adopt. 

Tooling Collaboration [Kwok]

The score takes care of itself [Walsh/Rekhi]

Continuing the accountability/collaboration arc of the past few months, today I’m building on Sachin Rekhi’s insights from reading Bill Walsh’s The Score Takes Care of Itself.

A key motivation for implementing a traditional organizational goal-setting/OKR system is often to use it as a mechanism to drive accountability. Therefore, the push-back for eliminating or overhauling such system is often the concern that if we don’t ask people to set goals, what is it that we will hold them accountable for? 

Walsh, via Rekhi, offers a compelling alternative: a Standard of Performance.

The Standard of Performance clearly delineates what excellence looks like in each role. It includes each of the skills that someone who is excelling at the role is expected to have. And even beyond job skills, it includes the attitude that’s expected of each individual as well as interpersonal dynamics.

In a sense, I’m thinking about it as an expanded/modified career ladder that focuses on those three elements: skills, attitude, and interpersonal. Under such system, people are held accountable to the behaviors that eventually lead to long-term success, rather than to a defined outcome with a fixed time horizon

The one aspect where my views differ from what Walsh/Rekhi advocate for is around who defines these Standards of Performance for each. In their opinion, it should be the coach/manager who does that, but they also acknowledge that this approach poses a real challenge: 

Bill expects leaders to be functional experts in the roles on their team in order to develop the Standard of Performance. These leaders are not just people managers. They are the very best at what they do… But Bill admits that to do this well, you need to posses incredible knowledge and develop expert intuition in your domains of expertise. And this takes a lifetime of experience to hone and develop. There are no shortcuts in Bill’s leadership approach.

In my opinion, this falls into the “unicorn manager trap”: so we’re looking for people who are not only highly competent and motivated people managers, but they’re also functional domain experts capable of defining the standard of performance in each of the roles that report into them? Good luck finding them…

The good news is that I don’t think this is a hard requirement, and an alternative can actually move us on the path of unbundling the managerial responsibilities package: the skills piece of the Standard of Performance is a function, well, of the function (or role). I believe it should be identical for people doing the same role in different organizations and there’s no need for each organization to reinvent the wheel here. I do expect inter-org (but not intra-org) variability in the attitude and interpersonal pieces since those should be reflecting the company values/culture. However, those should be defined at the company (not team) level and co-created in a participatory process. 

Is this the end-all-be-all solution for humanistic accountability? No. But certainly a piece of the puzzle. 

The score takes care of itself [Walsh/Rekhi]

The Silent Meeting Manifesto [Gasca]

Continuing another arc that I’ve previously explored here in previous posts, first in 2014 and more recently, at the end of last year, I recently came across David Gasca’s The Silent Meeting Manifesto

The get the meta nerd-out out of the way first, this arc is a really cool example of the evolution/adoption of an organizational practice: from “here’s this unusual practice that Amazon uses and seems to be working really well for them” (2014) through “we’ve tweaked and adopted this practice in our company and it seems to be working well for us as well” (2018) to “here’s the manual/playbook for how to implement this practice in your company” (now). 

Since Gasca’s post is a bit verbose (Medium estimates the reading time at 26mins) here’s a quick summary/teaser that’ll hopefully convince you to commit the time to read the full thing: 

Silent meetings aim to address these 10 challenges with the traditional (“loud”) meeting format: 

  1. No agenda
  2. No shared reading material for the whole group
  3. Unequal time-sharing
  4. Bad presentations — too slow, too fast, and meandering
  5. Most meeting attendees don’t comment
  6. Reading is faster than listening
  7. Favors native speakers
  8. Bad for remote attendees
  9. Rambling questions
  10. Comments from the meeting often get lost and aren’t captured in any doc

Silent meetings address these challenges by making 4 key changes to the way meetings are typically run: 

  1. Ahead of the meeting, create a basic agenda that defines the meeting goals, non-goals and format and explicitly appoints a meeting facilitator and a meeting note-taker (two different people). 
  2. Create a “table read” document, that will be read during the meeting in order to provide all participant with the shared context needed to accomplish the meeting’s goals. This differs from a “pre-read” in that there’s no expectation that the document will be read ahead of the meeting. 
  3. Read and comment on the “table read” — this is done during the meeting. Participants read the doc and post comments and questions in the doc. Then they read other participants’ comments and questions. The facilitator monitors the process and tags specific individuals that are best equipped to answer particular questions. 
  4. Facilitator synthesizes comments and leads discussion — identifying the themes in the comments, the facilitator triages them and leads a discussion on the themes that will make the best use of the attendees’ time. 

The silent meeting format has its boundaries. It will not work well the meeting aims to address interpersonal dynamics, be an inspirational talk, or cover a broad/multi-issue agenda. It also doesn’t address more systemic meeting issues such as having a true need for a meeting, to begin with, the right attendees, and a clear decision-making process.

A good “Table Read” is a vertical document (Word/Gdoc) rather than a horizontal one (PPT/Keynote), often covering the following topics: 

  • Meeting agenda
  • Problem/Situation background
  • Solution principles/parameters
  • Options identified that can solve the problem
  • Recommendation
  • Discussion questions
  • FAQs
  • Appendix/ add’l info

Lastly, a silent meeting is not without pitfalls, particularly around the key interventions/format changes that it introduces: bad facilitation, low-quality table read, or ineffective handling of comments (including lack of follow-through) will likely lead to a silent meeting not accomplishing its goals. 

The Silent Meeting Manifesto [Gasca]

Goals Gone Wild [Ordóñez et al.]

Stumbled upon an interesting 10-year old paper by Lisa D. Ordóñez et al. 

Goals Gone Wild: The Systematic Side Effects of Over-Prescribing Goal Setting

Their core thesis (supported by academic references and case studies) is that the beneficial effects of goal setting have been overstated and that systematic harm caused by goal setting has been largely ignored. Rather than advocate for getting rid of goals altogether, they use a medical metaphor to convey their recommendation and suggest that the practice of goals setting should not be used as a benign, “over-the-counter” treatment for motivation (the way it’s used today), but rather as a “prescription-strength medication” that requires careful dosing, consideration of harmful side effects, and close supervision.

They group the systemic “side effects” of goals into the following categories: 

  • Goals that are too specific: narrow goals lead to narrow focus often at the expense of the “big picture” and other important non-goal objectives. The specificity can also lead to an abundance of goals, which in turn lead to overwhelm and a focus on a single goal as a coping strategy. Finally, specificity around the time horizon increases the likelihood of getting it wrong and making the goal either too hard or too easy to have the desired effect on motivation. 
  • Goals are too challenging: overly challenging goal often leads to counter-productive behavior in an effort to achieve the goal by all means necessary — from excessing risk-taking, through unethical behavior, to dissatisfaction and the negative psychological consequences of failing to achieve the goal. 
  • Friction with learning and cooperation: (performance) goals can create a dynamic where the stakes are too high to engage in activities that promote learning: from exploring different ways to achieve the task, through setting time aside for reflection to “playing it safe” in fear of making mistakes. Furthermore, individual goals can support and reinforce a culture of competition and individualistic focus.
  • Crowding-out of intrinsic motivation by the extrinsic goal 
  • In a multi-person context (read: organizations) a calibration challenge also emerges: using the same goal for different people ignores their individual capabilities, and will result in different outcomes on motivation and in turn, performance. Yet idiosyncratic/personalized goal-setting is not without its challenges either, especially around managing perceptions of unfairness. 

The authors advocate the use of goals in the narrow context outlined by King and Burton (2003):

The optimally striving individual ought to endeavor to achieve and approach goals that only slightly implicate the self; that are only moderately important, fairly easy, and moderately abstract; that do not conflict with each other; and that concern the accomplishment of something other than financial gain.

Lastly, they offer a set of reflection questions for people who consider the use of goal-setting in a particular setting to determine whether goal-setting can be effective in that setting and mitigate the side-effects to the best of their abilities: 

  1. Are the goals too specific? Narrow goals can blind people to important aspects of a problem. Be sure that goals are comprehensive and include all of the critical components for firm success (e.g., quantity and quality).
  2. Are the goals too challenging? What will happen if goals are not met? How will individual employees and outcomes be evaluated? Will failure harm motivation and self-efficacy? Provide skills and training to enable employees to reach goals. Avoid harsh punishment for failure to reach a goal.
  3. Who sets the goals? People will become more committed to goals they help to set. At the same time, people may be tempted to set easy to reach goals. 
  4. Is the time horizon appropriate? Be sure that short-term efforts to reach a goal do not harm investment in long-term outcomes. 
  5. How might goals influence risk-taking? Be sure to articulate acceptable levels of risk. 
  6. How might goals motivate unethical behavior? Goals narrow focus, such that employees may be less likely to recognize ethical issues. Goals also induce employees to rationalize their unethical behavior and can corrupt organizational cultures. Multiple safeguards may be necessary to ensure ethical behavior while attaining goals (e.g., leaders as exemplars of ethical behavior, making the costs of cheating far greater than the benefit, strong oversight). 
  7. Can goals be idiosyncratically tailored for individual abilities and circumstances while preserving fairness? Strive to set goals that use common standards and account for individual variation. 
  8. How will goals influence organizational culture? If cooperation is essential, consider setting team-based rather than individual goals. 
  9. Are individuals intrinsically motivated? Assess intrinsic motivation and recognize that goals can curtail intrinsic motivation. 
  10. Consider the ultimate goals of the organization and what type of goal (performance or learning) is most appropriate? In complex, changing environments learning goals may be more effective.
Goals Gone Wild [Ordóñez et al.]