Driving effective behavior change with Prism

A neat set of frameworks for creating the organizational behavior change you seek

source: affective-advisory.com

So much of the organizational work we do aims to change (or “sustain” as a special use case) certain behaviors in our teams. What’s the point of articulating a strategy if it doesn’t cause our teams to change their default behaviors and take a different set of actions to pursue it? What’s the point of a training or a workshop if the behavior before and after it is exactly the same. 

The team at Affective Advisory developed a pretty neat framework for driving strategic behavior change: 

The D.R.I.V.E Prism for identifying and evaluating effective nudges in practice

The framework builds on the core premise that human behavior is context-dependent and therefore, behavioral interventions have to be tailored to an individual context. Therefore, there are no universal interventions that are effective independent of context. Theoretical concepts need to be adapted into practice using a model-based, evidence-led approach and then tested and validated. 

The overarching framework for applying behavior interventions is outlined under the acronym D.R.I.V.E: 

  • D.efine strategy as a set of preferred target behaviors. 
  • R.esearch actual (current) behaviors and review related contexts relevant to the strategic challenge. 
  • I.dentify, evaluate, and adjust suitable science-based solutions. 
  • V.alidate the selected and tailored interventions across a representative sample. 
  • E.xecute behavioral interventions realizing behavior change at scale. 

Other than the neat acronym, there’s nothing earth-shattering here: define the change you need to make → understand the current situation → select an intervention → do a small pilot to ensure it drives the desired outcome → scale. 

The non-trivial piece comes in the middle of the process. Given the premise, how do we identify and adapt the right interventions that are most likely to drive the desired outcome in this particular context

This is where the prism comes in: 

source: affective-advisory.com

The prism is a three-dimensional taxonomy for categorizing different interventions and selecting the ones most likely to be effective in the specific context. 

Dimension I: Intervention levers

The underlying thesis here is that behavior can be changed by a combination of four different levers: 

  • Contextual triggers
  • (De)Motivators (automatic <-> reflective)
  • Individual capabilities (psychological & physical)
  • Feedback

Different interventions use a different mix of these levers. 

This construct can also be mapped to a similar behavior change model that I covered here providing further support to the taxonomy: contextual triggers → reinforcements mechanisms, motivators → understanding and conviction, individual capabilities → confidence and skill-building, feedback → role-modeling. 

Dimension II: The cognitive level

The levers outlined in dimension I can be designed to influence behavior through two cognitive levels: 

  • System 1 — unconscious, automatic, affective, effortless.
  • System 2 — conscious, deliberate, controlled, effortfull.

Interventions working through system 1 aim to either leverage or mitigate some of its unique attributes, for example: auto-saving documents based on a time trigger. 

Interventions working through system 2 aim to intentionally activate it to correct a system 1 driven behavior, for example: opening a dialogue box reminding users to save their file when they try to close it. 

Dimension III: The intervention level

Here, the taxonomy distinguishes between: 

  • Adding new enablers.
  • Removing existing blockers.

For example, a sign showing your current driving speed adds an enabler to drive the desired behavior. While default options and opt-out remove blockers by eliminating the need for a decision to reach the desired behavior. 

In Sum 

As it stands today D.R.I.V.E and specifically, prism, are useful tools for honing in on potentially effective interventions in a particular context. Especially if a specific intervention has been tried and didn’t work — exploring a different assumption around one of the prism dimensions may help identify a strong candidate intervention quicker. While contexts are inherently different from one another, I wonder if there are contextual patterns that make a certain type of intervention more likely to succeed than others. If that’s the case, a similar contextual taxonomy can be developed and more resilient mapping between contextual patterns and effective interventions can be drawn. 

Driving effective behavior change with Prism

Inclusive organizations change their systems, not just train their people

The Bias Interrupters Model

My ongoing quest to improve organizational equity and inclusion got me to the Center for WorkLife Law’s Bias Interrupters model.

The premise of the model is capture clearly by the team who developed it: 

Bias interrupters are tweaks to basic business systems that interrupt implicit bias in the workplace, often without ever talking about bias.

In many ways, it’s an evidence-based response to the failure of more culture-centric/training-centric approaches to significantly move the needle on eliminating bias in the workplace. 

The Bias Interrupters Model focuses on five core business systems: 

  1. Hiring & Recruiting
  2. Performance Management 
  3. Compensation
  4. Meetings
  5. Assignment

While the first three are capturing most of the current limelight as areas that required heightened attention to bias, conversations around inclusive meetings are still at their infancy and assignments are at the “inclusion frontier” as far as the broader conversation goes. Therefore, I found Bias Interrupters to be one of the most holistic approaches for driving this much needed systemic change.

The Bias Interrupters approach advocates for an iterative process consisting of:

  1. Establishing relevant metrics.
  2. Implementing evidence-based bias-interruption interventions.
  3. Assessing the impact the interventions had on the metrics and using the insights to inform the next iteration of the cycle.

Change to each of the five business systems listed above is supported by a recommended set of metrics to track, and a list of evidence-based standalone interventions. The idea here is that not all interventions have to be implemented at the same time, and different organizations can choose different paths to getting to bias-resistant business systems. For example, one organization may start tackling performance management by explicitly separating evaluating performance from evaluating potential, another may start by offering alternatives to self-promotion, and a third may tackle both of them at the same iteration. 

Furthermore, Bias Interrupters supports the systemic change needed in those systems on three different levels: 

Each level is supported by a toolkit including guides, worksheets, checklists, talking points and other relevant training materials. 

Different organizations take different stances on social justice issues and that can sometimes muddy the water around core DEI initiatives. The beauty of the Bias Interrupters program is that it’s completely agnostic to that stance, as if focuses on systemic bias which has no upside. It offers a blueprint for a way to run these core business systems that is flat out better than the alternative. 

Inclusive organizations change their systems, not just train their people

Changing the world with Heat AND Light

A balanced approach to social change


On a recent MindGym webinar on The Future of Inclusion, I had a big a-ha moment, when they introduced their model of persuasion for changing behavior based on the work of Prof. Dolly Chugh.

Chugh’s model defines two approaches for pursuing social change: light and heat.  

Pursuing change through light-based means, puts the comfort of the target audience as a high priority. It aims to meet people where they are, recognizing that making people too uncomfortable will cause them to resist your message. It takes the time to educate, using factual, descriptive language, and a framing that focuses on our shared humanity. 

Pursuing change through heat-based means is specifically designed to make the target audience uncomfortable and to force acknowledgment of the problems and the need for change. It confronts the issue straight on, recognizing the subtlety may lead to a complacent response. It uses more emotive, visceral language and doesn’t shy from actions like protest and civil disobedience. 

One of Chugh’s most important insights from her research was that:

When historians study social-justice movements, they find that movements that only have heat or only have light tend to not make as much progress. Successful movements have both a more moderate and a more radical flank, if you will.

When I reflected on my own change strategy through this lens I noticed that I’m leaning more heavily towards the light-based approach. This also explained why I viewed heat-based strategies as less effective and, in some cases, moving us backward, even when we were all striving for the same social outcome. 

Shifting my perspective from looking at those strategies as an either-or choice to a both-and polarity, allowed me to recognize the importance of a combined strategy: too much light and not enough heat leads to complacency. Too much heat and not enough light leads to backlash and resistance. Effective social change requires a healthy mix of both. 

Changing the world with Heat AND Light

Choosing the right remote talent strategy for your business

It’s definitely NOT a one-size-fits-all


Building on my personal experience leading distributed organizations, and my deliberate study of highly-remote organizations over the past six months, two key factors informed my approach to strategy development outlined below.

First, this challenge is shared by many organizations. Therefore, having your business come up with a solution from scratch will just repeat old mistakes that others have already made and learned from. Instead, I chose to synthesize their experience and lessons learned focusing on identifying the contextual elements that impact the outcome, so the approach can be adapted to fit an organization’s unique context.

Second, I view organizations as complex systems with emergent properties, where the relationship between cause and effect is not fully known/understood. Therefore, while an initial, directional approach is essential, the plan needs to include scaffolding for learning as we go: creating the space and the method to observe the impact of changes as they are made, and the willingness to adapt both direction and plan based on what is learned.

Step 1: Align on the “why?”

A remote talent strategy offers a diverse set of benefits[1] and challenges[2]. For example, at the organizational level, it offers access to a broader candidate pool but requires deeper intentionality in designing and scaffolding how work gets done. At the individual level, it offers more flexibility in schedule management but requires stronger communication and organization skills to get work done. Your business may have already experienced some of these, as Stripe had through its remote engineering hub[3]. Different organizations choose to pursue a remote work strategy for a host of reasons, placing varying premiums on the benefits they want to capture and the challenges they need to mitigate. This variability leads to choosing different remote talent strategies. Therefore, Your business’ starting point needs to be articulating its specific “why?” — scoring these key benefits and challenges and creating clear criteria to evaluate alternative remote talent strategies.

Step 2: Converge on the desired end-state

Remote talent strategies lie on a spectrum between “fully co-located in a single office” and “work from anywhere” where the extreme ends are the best option only for a minority of organizations. Strategies in between those extremes differ from one another primarily in how much they constrain the location from which work can be done, and how much they constrain the time-of-day in which work should be done synchronously. Quora[4], for example, opted to keep its office, allow employees to work from any country in which they can be legally employed, but defined 9am to 3pm PT as “coordination hours” where most employees will be expected to be available for meetings and impromptu communication, regardless of where they are located. Market research[5] identified additional points along the spectrum that can serve as anchors for different remote talent strategies. Flexibility in location and synchronicity has a varying impact on specific roles based on their unique attributes: providing on-site client interaction, accessing specialized equipment or facilities, the need for supervision and regulatory oversight, reliance on collaboration and interaction, and focus on innovation. Therefore, your business needs to conduct a role-by-role impact assessment of each candidate strategy. Coupled with the weighted criteria defined in Step 1, it will have sufficient insight to converge on the right end-state and determine whether a single end-state can fit across the entire company or bifurcation by role type is required.

Source: BCG analysis

Step 3: Define success and how to measure it

Defining success targets and how they will be measured will heavily influence the way organizational changes will be rolled out to support the strategy.

Success should be looked at through two key lenses: work, reflected in a set of business KPIs, and workforce, reflected in a set of employee-reported data. The specific benefits your business wants to capture and key drawbacks it wants to mitigate with its remote work strategy will determine the selection of specific KPIs and data. Since this strategy heavily impacts the way employees interact and collaborate, those standard success metrics should be complemented with Organizational Network Analysis[6] metrics collected both actively and passively.

Ideally, changes will be rolled out as randomized, controlled tests that will allow your business to isolate the impact of the strategy and distinguish between correlation and causation. Pragmatically, in some cases your business will have to move backward from that ideal, thoughtfully making trade-offs between reducing success attribution and increasing roll-out feasibility.

Step 4: Perform gap analysis and formulate a plan

With a clear end-state and approach to measurement defined, your business can now perform a gap analysis between the present state and the desired end-state to determine the pace by which it can move forward. The analysis explores the same two lenses of success: work and workforce.

Work — effectively working remotely requires deliberately changing the way work in the organization gets done across several dimensions[7]:

  • Routines, tools and capability building
  • Cyber and internal data security
  • Coaching and development
  • Productivity and performance management
  • Senior leadership and culture
  • Recruiting and onboarding
Source: BCG analysis

Workforce — effectively working remotely requires deliberately preparing the workforce to work remotely across several dimensions:

  • Motivation
  • Skills
  • Experience
  • Other needs (childcare, physical space, etc.)

Understanding the current gaps and ways to address them will enable your business to set a realistic pace for the change. Understanding the variability in current gaps will inform whether a uniform pace or multiple paces will likely yield a better outcome.

Step 5: Do → Sense → Adapt. Repeat.

Once the plans for closing the gaps identified in Step 4 are set in motion, on-going measurement of the success metrics defined in Step 3 will inform progress and drive continuous adaptation of both the strategy and the plan to implement it.

Putting it all together

For those of you who share my preference for visuals and illustrations, the following diagram summarizes how all the steps fit together: 


  1. All-Remote Benefits
  2. All-Remote Drawbacks
  3. Stripe’s remote engineering hub, one year in
  4. Remote First at Quora — The Quora Blog
  5. How companies can make remote working a success
  6. Organizational network analysis — gain insight, drive smart
  7. Remote Work Works — Where Do We Go from Here?
Choosing the right remote talent strategy for your business

True wellness (at work)

Physical, emotional, social, cognitive, spiritual, environmental

Photo by Aleksandr Ledogorov on Unsplash

I’m going to keep it short and sweet this week. 

Wellness is the collective label used in many companies as an umbrella term for projects and initiatives aimed at improving the lives of their employees. It often manifests itself as a set of perks including but not limited to: gym stipends, meditation/yoga classes, healthy snacks in the kitchen, ergonomic workstations, etc. 

But ask an employee or even an HR practitioner about their company’s vision for wellness, and you’ll get something between a blank stare and a fumbling response. 

In the age of pandemic, wellness is perhaps more important than ever, and yet many of the programs mentioned above stop making sense while working from home and doing your best to socially distance. 

In comes Brad Stulberg with a pre-pandemic piece that rings event truer today: 

We’ve Reached Peak Wellness. Most of It Is Nonsense.

Stulberg lays out a six-point evidence-based wellness manifesto: 

  1. Physical: Move your body and don’t eat crap — but don’t diet either
  2. Emotional: Don’t hide your feelings, get help when you need it
  3. Social: It’s not all about productivity; relationships matter, too
  4. Cognitive: Follow your interests, do deep-focused work
  5. Spiritual: Cultivate purpose, be open to awe
  6. Environmental: Care for your space

This short manifesto seems like a perfect “north star” for corporate wellness programs —  mapping a specific program, training or experience to a particular element in the manifesto. 

True wellness (at work)

The startup heartbeat

Orchestrating product, marketing, sales, and finance

Photo credit: Diuno

In a recent post, David Sacks ex-COO of PayPal (in the “PayPal mafia” days) and founder and CEO of Yammer (acquired by MSFT for $1.2B in 2012) laid out an integrated framework for orchestrating the operations of the four major departments of every SaaS startup: product, marketing, sales and finance. 

The Cadence: How to Operate a SaaS Startup 

While some design elements can be modified to meet the differing needs of non-SaaS startups, this framework is a fantastic starting point, that can save many startups years of discordant operations and cross-departmental friction and missed hand-offs. I’ve taken a stab at summarizing it below: 


  • In a SaaS context quarterly goals (and therefore, planning) seems to be ideal time-frame. Yearly is too rigid/unresponsive and monthly is too volatile. This dictates the heartbeat for everything else.  
  • The quarter begins with a Sales Kick-Off (SKO) where the sales team receives their new quotas, commission plans, and territories. Learnings from the previous quarter are shared, and Product demos the latest version of the product and reviews the roadmap for the current quarter.  
  • Once the plan is clear and in play, sales leadership focused on pipelines review and support. The sales team is immersed in active sales efforts supported by news, awards, and recognition generated by the marketing team. 
  • The third month is dedicated to heads-down closing and making the numbers with minimal interruptions.


  • Synchronizing the finance calendar with the sales calendar simplifies and clarifies financial reporting since the numbers then reflect a complete quarter’s sales activity.
  • A fiscal year ending on Jan 31 rather than Dec 31 avoids the end-of-year holiday crunch and disrupts customer expectations around end-of-year discounts.
  • Board meetings occur two to three weeks after the end of the previous quarter allowing for


  • The product roadmap gets reviewed and prioritized quarterly with external input from the board meeting and a customer advisory board informing the process. 
  • The goal is to align on the “major rocks” of each release, giving individual PMs a lot of autonomy in determining the “pebbles” and “sand” that fill up the overall capacity. 
  • Development projects are scope so that they can be shipped within one quarter. The rule at Yammer (where Sacks was CEO) was that projects would be assigned 2 to 10 engineers for 2 to 10 weeks. This is conceptually very similar to Basecamp’s 6-weeks model and other incremental software delivery approaches. 


  • The overall marketing approach should be event-based — orienting around a central quarterly event that can combine launch announcements and demos of new features with news about customers, financing, market share, metrics, or other milestones.
  • There’s a benefit to tying the product and marketing calendars together so the externally committed deadline can become a motivating factor. A lot has been said about the delicate balance that’s required in order to avoid the downside of this coupling. The product approach outlined above (projects’ scopes + release planning) is one essential component in enabling that coupling. 
  • Not all four quarterly marketing events have to be big ones. An annual user conference + three smaller webinars/city events can sufficiently drive the desired discipline around product delivery. 

Putting it all together 

Shifting to this orchestrated heartbeat starts with determining the fiscal year (Dec 31st. vs. Jan 31st, etc.) which derives the fiscal quarters. Sales plans are then lined up with the fiscal quarter, deriving the timing for SKOs and quarterly closing. Scheduling the marketing event in the middle of the quarter offsets the marketing calendar from the finance and sales calendar by 45 days, positioning the surge in marketing activity to best support on-going sales efforts. Lastly, the product cycle is aligned with the marketing calendar to hit the event deadlines. 

The coordinated heartbeat creates natural opportunities for internal “all-hands” meetings (not all should be used): after the books are closed, after the board meeting, before/after the launch event.  

This is another example where a picture is worth a thousand words, and in this case, the final picture looks something like this: 

The startup heartbeat

The best kind of CEO shadow

This program for top performers is a true win-win

Photo by Daniel Polo on Unsplash

The shift towards distributed/remote is causing many companies to revisit their core HR programs with the realization that simply “doing what we did before, but virtually” is not a long-term solution. In particular, engaging, developing and retaining top talent has been top of mind for many leaders since this shift unlocks new opportunities for these individuals, creating a critical “shields down” moment. 

 Luckily, this is another area where many companies can (should?) take a page out of GitLab’s handbook (pun intended) and consider implementing a CEO shadow program for their top talent: 

GitLab’s CEO Shadow Program 

In typical GitLab fashion, the link above describes their CEO Shadow Program in full transparency and almost-excruciating level of detail, resulting in an 8,5000-word document. Below I’m hoping to do my best in highlighting the key design elements that are worth considering when implementing a similar program elsewhere, using 95% fewer words. 


The goal of the program is to help participants globally optimize their work by gaining a deeper understanding of how GitLab works, and what it aims to accomplish, as well as building cross-functional relationships with other members of the program’s cohort. For the CEO, it’s an opportunity to build a personal relationship with team members across the company and learn about challenges and opportunities through their unique perspective. 

Eligibility & Application

In addition baseline tenure (at least 1 month, preferably 3) the eligibility criteria aim the program at employees on the managerial track with large spans of control, senior individual contributors, cultural leaders and under-represented groups (both minorities and geographies). The application process is driven by the employee, requesting a particular slot on the schedule, highlighting how they meet their eligibility criteria and providing confirmation from their manager that they meet the criteria.  


The program runs on an on-going basis with a few rare exceptions (CEO PTO, etc.). Participants shadow the CEO for two weeks with one week overlap, so during the first week a participant is trained by the outgoing person and during the second week, they train the incoming person. This is a good place to highlight the extra consideration that GitLab made for parents — highlighting specific “parent-friendly” slots in which full week participation is not required or the weeks are inconsecutive, and paying for childcare while parents participate in the program. 


Participants are expected to prepare for their time in the shadow program by connecting with co-shadows and program alumni, preparing a formal onboarding program (off a template), and getting up to speed on the work currently in-flight (projects and calendar) and the CEO himself. 


The format is pretty straight forward. Participants are expected to perform a set of small administrative/operational/documentation tasks that can be completed during their time in the program and be part of almost any conversation that the CEO is having with a very small subset of explicit exceptions. Detailed guidance is available on everything from what to wear, through how to present yourself and act during meetings, to how to navigate the CEO’s home office (aka “Mission Control”). Of note is the awesome expectations to “speak up when the CEO displays flawed behavior” which probably merits a post of its own. The specificity in both describing them and validating/inviting the way you can respond to them is truly inspiring. 

In Sum

A CEO shadow program can be a phenomenal opportunity to help retain top talent. If you’re considering starting such a program in your own organization, the GitLab handbook page is a comprehensive jumping-off point that can help ensure that you got all your bases covered. You can refine, modify and iterate from there.

The best kind of CEO shadow

Does your team discuss the undiscussables?

The 4 types of team undiscussables teams should start discussing more 

Source: MIT Sloan Management Review

A neat piece by Ginka Toegel and Jean-Louis Barsoux expanding on element from the psychological safety piece from a few weeks back: 

It’s Time to Tackle Your Team’s Undiscussables

Tackling undiscussables, a set of issues that are holding the team back but the team is reluctant to discuss, is a good example of taking an interpersonal risk in support of the greater benefit of the team. The reluctance to discuss them often stems from fear that doing so will sap the team’s energy, surface unresolvable issues, or expose the person to blame for the part they played in creating the issue. Where in fact, it is often the case where tackling the undiscussables brings relief, boosts the team energy and generates team goodwill. 

Toegel and Barsoux offer a taxonomy with 4 types of undiscussables, differing in their source, the way they should be approached, and the sequence in which they should be tackled: 

  1. You THINK but dare not say — risky questions, suggestions, and criticisms that are self-censored out of fear of the consequences of speaking. Often due to past erratic or uncharitable responses from team members. Beginning the fix: leaders can explicitly acknowledge they may unwittingly have created a climate of fear or uncertainty, invite discussion about sensitive issues, draw out concerns, promise immunity to those who share dissenting views, and lighten the weight of their authority in the room.
  2. You SAY but don’t mean — spoken untruths. Discrepancies between what the team says it believes or finds important, and how it behaves. These issues are often left undiscussed not based on fear as much as on an unquestioned and distorted sense of loyalty to the team, its leader, or the organization. The intent is to maintain the team’s cohesion, even if that cohesion is based on a shared illusion. Beginning the fix: leaders need to make the hypocrisy of saying but not meaning explicit and acknowledge their part in the charade. Collecting anonymous examples of empty proclamations (“We say we want to…, but in fact, we….”) and challenging the overprotective mindset that inhibits the airing of criticism can kick-start the fixing process. 
  3. You FEEL but can’t name —negative feelings that are difficult for team members to label or express constructively, often failing to see the difference between manifesting one’s anger or resentment and discussing it. At a more basic level, they are not discussed because the antagonists experiencing negative emotions don’t test their inferences. Based on their own worldviews and self-protective instincts, they presume they know why the other party is acting in a particular way and let that drive their behavior. This leads to escalating tensions. Beginning the fix: help the feuding parties investigate the differences — in personality, experience, and identity — that sustain and fuel their apparent incompatibilities, rather than ignore the feud and the negative emotions associated with it. Enable them to share their experience while staying on their side of the net.  
  4. You DO but don’t realize — collectively held unconscious behaviors, such as instinctively developed defensive routines to cope with anxiety. Beginning the fix: Warped interaction patterns may be readily discernible to outsiders. A trusted adviser or an external facilitator can be invited to observe the team and give feedback on their communication habits through humble inquiry

Toegel and Barsoux recommend tackling the “SAY but don’t mean” undiscussables first, as the gap is between two elements that are visible to all team members — the things we say and the things we do. And leaving the “Do but don’t realize” undiscussables for last, as they require outside intervention that will predicate on enough internal goodwill being built by tackling the other undiscussables first. 

Lastly, Toegel and Barsoux offer a lightweight diagnostic tool, to help identify what type of undiscussables may be present in a certain team, based on the most common symptoms and team patterns: 

Source: MIT Sloan Management Review
Does your team discuss the undiscussables?

HEY, it’s about time we reinvented email

Basecamp’s new email client is a tour de force of the “jobs to be done” approach in all aspects but one


I rarely cover specific products in this publication, but decided to make an exception this time for the following reasons: 

  1. It’s a collaboration product, and collaboration is a core organizational need.
  2. It’s quite transformative in the way it approaches some big challenges with the existing solution (email). 
  3. Many of the issues it’s addressing and the approaches that it’s taking to solving them apply to broader collaboration mediums that extend beyond email.

You can check-out the feature-by-feature overview here or watch this tutorial video. I’ve decided to take a stab at organizing the features by the challenges that they are addressing. 

Screen and triage

Emails from new senders arrive at a “screen queue” where they can either be rejected or accepted and triaged to one of a few “work queues”: 

  • Imbox (default)
  • Reply later — non-urgent emails that require a response.
  • The feed —newsletter and other non-urgent recurring communications.
  • Set aside — short-term reference: information about an upcoming event/meeting, document that needs to be reviewed, etc. 
  • Paper trail — long-term reference: receipts, reservation confirmations, etc.

Read and respond

Each work queue supports a slightly different workflow for handling the emails in it: 

  • Imbox — split between “new for you” (unread) and “already seen”. A “read together” feature opens all unread emails in a single screen enabling the batch review of all unread emails together. 
  • Reply later — offers a “focus and reply” feature, with similar UX to “read together” but adding a reply box to the side of each email. 
  • The feed — a news feed view with the most recent email at the top offering a preview of each email and an ability to expand (“show more”) the whole email. 
  • Set aside and Paper trail — a Pinterest board view with a visual digest of each email 
HEY “focus and respond” workflow

In addition, email threads have the following additional features, impacting only the particular user (not all thread recipients): 

  • Rename the subject line.
  • Merge threads of the same topic.
  • Notify when new responses are added to the thread or when an email is received from a specific sender. (notifications are off by default).
  • Clip (save for later) a portion of the email. 
  • Add a “note to self” to the thread — “response” that only the user can see.
  • Add a “sticky note” to the thread that shows up under the subject line in the various work queues. 
  • Send large files. 
  • Unfollow (mute) — feature parity with existing solutions.
  • Labels (tags) — feature parity with existing solutions.
HEY “note to self” feature


Finally, recognizing that email is also used as an archiving system, HEY added the following features: 

  • “Paper trail” queue (discussed above).
  • List of all the content clipped from emails. 
  • Contact view showing all correspondence that involved that contact, surfacing files separately.
  • Files-only view 
HEY contact view surfacing files separately and supporting granular notifications

There’s also a neat privacy feature proxing all images and therefore preventing unauthorized data collection using a tracking pixel

There is, however, one area where HEY misses the mark and fails to extend the “jobs to be done” approach into a critical element of the user experience: migrating work into the service. It is unlikely that users will rush to leave their native email address and immediately start using they @hey.com address. For many of us, our email addresses serves as a better unique identifier than our physical address. We change apartments more frequently that we change our email address and therefore this change is associated with non-trivial switching costs. While HEY does support auto-forwarding of email from your native email address, it does not (as of the writing of these lines) support defining a different “reply from” email address. Therefore, email responses from HEY will go out from the @hey.com email address, creating a confusing and discontinuous experience to the email recipient. 

In sum, HEY creates a transformational email experience by acknowledging three deep truths and building them into the user experience:

  1. Different emails, different use cases — users engage with different types of emails in a different ways. We engage with an email from a good friend, a newsletter and last month’s internet subscription receipt differently. Therefore, the email client should support different workflows.  
  2. Different users, different preferences — traditional email forces complete symmetry in the way two people view the same email thread. HEY breaks that symmetry and allows users to modify and annotate the threads in a way that makes sense to them. 
  3. Communicate AND document — building on the framework I covered here, while email is primarily used to communicate, it’s a sufficiently good system of record for documenting/archiving some critical content. Supporting that secondary functionality needs to go beyond good indexing and a search box. 

If we zoom out, these truths apply to other non-email collaboration tools such as chat and discussion boards as well. Therefore, considering similar approaches to addressing them in those other mediums opens some thought-provoking opportunities. 

One of the beautiful things about HEY is that it’s a “dumb” email client from a technical standpoint. There’s no AI/Machine Learning involved in any of the features I listed above. It screens the emails you tell it to screen, it triages emails to where you tell it to put them, it notifies you about emails you tell it you want to be notified about. 

On the one hand, it’s an incredible testament to how far just deeply understanding what your customers are trying to do with your product can take you. 

One the other hand, it may also be HEY’s biggest business risk. A HEY subscription currently costs $100/yr. But if HEY starts getting serious traction, how hard would it be for Gmail to catch up? 

HEY, it’s about time we reinvented email

Community of Practice twofer [Webber, FabRiders]

This is one of my rare twofers combining two posts that only loosely share a theme, and don’t justify a standalone post individually. 

The first is Emily Webber’s research:

Social group sizes, Dunbar’s number and implications for communities of practice

Through not-the-most-scientifically-rigorous method (a survey on Twitter) Webber collected ~150 responses on different communities of practices capturing information about their community size, number of leaders and frequency of meetings. The results are captured in the following graphs: 

  • Business communities of practice mimic natural social communities, sharing a similar fractal distribution of size. The intuition of drawing on insights from natural social communities when addressing issues with business organizations have existed for a while and provides some additional evidence for the validity of that analogy. 
  • There’s a notable community threshold at about 40 participants. Below that threshold it’s more likely to see purely democratic (leaderless) communities and they meet fairly frequently (monthly or less). Above that threshold it’s more likely to see more definitive “leader” roles and meeting frequency increases substantially. 

The 40 person threshold was interesting to me as it’s notably smaller than the Dunbar Number that’s estimated to be around 150. While it’s not discussed in the article, I’d hypothesize that the looser nature of the business community leads to the need to introduce structure in order to maintain them sooner (at smaller scale). 

The other piece I want to cover today is by FabRiders titled: 

What are we building: communities or networks?

It notes the recurring conflation of terms between “community” and “network” and posits that the short longevity of many efforts to create self-sustaining peer expertise exchanges is a result of unrealistic expectations for having those networks become real communities.

After providing a few “classical” formal definitions of community, they make a minimally compelling case for “network“ being a better framework for thinking about these groups than “community” arguing that:

We should not have expectations that a group of people coming together to share expertise will form a community, and in particular, that it will become self-sustaining… [peer expertise networks] provide an ability to establish connections that can deliver knowledge sharing in ways that strengthen the communities we are aiming to serve.

While there’s definitely some merit in this argument where the knowledge gain through that group is often used elsewhere, earlier in the post Paul Jame’s definition of a community is also covered: 

It is a group of people who are connected by durable relations that extend beyond immediate genealogical ties, and who mutually define that relationship as important to their social identity and practice.

For many of us, our professional identity plays a big role in our overall sense of identity. While the criticism of it playing an outsized role is mostly justified, the activity that we spend such a large portion of our waking hours engaged in should play a meaningful role in our identity. 

So while other references to “communities”, for example around certain product brands, easily fail both tests, the professional community seems more complex. 

The distinction between a peer expertise network and a community is helpful, and I wish that the authors had provided clearer definitions of each. Yet as the article does point out, regardless of how the group is labeled, a clear and focused group purpose will be essential to its success. 

Community of Practice twofer [Webber, FabRiders]