What do we mean when we say “feedback”?

A short feedback taxonomy

I’m expecting a few shorter than usual posts in the coming weeks as I’m adjusting to my new work circumstances, but will stay committed to quality > quantity. 

Feedback is a word we love to use in professional settings, yet I’ve had a recent realization that we tend to use it to mean different things. 

Oxford Languages (Google’s English dictionary provider) defines feedback as: 

Information about reactions to a product, a person’s performance of a task, etc. which is used as a basis for improvement.

While this definition seems somewhat lacking or incomplete, it’s a good starting point. Feedback is information about a reaction to <something> used as a means with a particular <end> in mind. The different somethings that the feedback is a reaction to and the different ends that providing the feedback is meant to accomplish are two key differentiators that will allow us to distinguish between different types of feedback. To those two, we can add a third, which pertains to the period of time that the feedback is provided as a reaction two. 

Let’s get a bit less theoretical and a bit more practical. The following is a draft taxonomy that’s likely incomplete. Even in its nascent form, it provides some useful distinctions and insight. 

In a professional setting I find it useful to discern between: 

A. Feedback about the work

The work refers to a work product (deliverable), a project, a plan, a decision that needs to be made, etc. 

The trigger for further distinction between types of feedback about the work is the lifecycle stage of the work: 

  1. Problem validation — am I trying to solve a problem that’s worth solving?
  2. Solution exploration — what are all the potential ways so solve this problem? 
  3. Problem-solution fit — which solution (out of the now known set) will likely best solve the problem? 
  4. Continuous improvement — how well is the implemented solution solving the problem? 

B. Feedback about how we work 

This can potentially be further decomposed to “feedback about us” and “feedback about you” but I’m keeping those grouped together for the time being. 

The first trigger for further distinction between types of feedback about how we work discerns between different ends, and the second discerns between different time periods: 

1. Evaluatory / performance feedback — usually the responsibility of the manager).

2. Developmental feedback — how can we work better together? Can come from all collaborators and customers of the individual. Decomposed further by the period of time covered: 

  • Situational feedback — delivered in the moment or right after the moment. 
  • Episodic feedback — looks at broader behavioral and relational patterns and, usually facilitated by a formal quarterly/semi-annual/annual process. 

These different use cases of feedback often require a different process or structure to support them. A catch-all structure that does not account for the different types usually leads to a “jack of all trades, master of none” outcome. 

What do we mean when we say “feedback”?

Finding a job in unusual times

5 reflections on a months-long journey

Photo by Caleb Jones on Unsplash

I left Grammarly at the end of 2018 and after taking 2019 as a Sabbatical year with a pretty lightweight consulting load, I started my job search in earnest in Feb-March 2020. Consulting was never a thing I aspired to do, but certainly an experience that I was eager to explore. When it was time to ramp up my professional intensity (and income) I chose to focus on another tour-of-duty in an in-house role rather than on building my consulting practice up to a full-time-equivalent volume. 

There was only one wrinkle. COVID-19 hit the US at full speed, and my target sector, private tech companies, was holding its breath: freezing hiring, furloughing staff, and in some cases, conducting painful layoffs in an effort to extend cash runway faced with a future that just gotten way more unpredictable. I could not have picked a worse timing to look for a job. 

In late August, my job search concluded successfully, accepting an offer from a wonderful company for a dream role. This is a great time to reflect on my journey and share some lessons, for my own future reference, and hopefully for the benefit of others as well. 

1. Establish a rhythm

At the beginning of the search, I was following a very loose plan. I’ve been spending a lot of time in the previous year thinking about goals and how to pursue them wisely. Knowing that I’m not fully in control of the outcome, and without an external feedback mechanism: am I doing too much, overestimating my ability to influence the outcome and exhausting myself unnecessarily? or doing too little, resting on my laurels, underestimating my ability to influence the outcome, and unnecessarily prolonging an extremely uncomfortable situation when I could have done more? 

The insight came from looking within, reflecting on past challenges and situations and realizing that in this particular case, I’m likely doing too little than too much. That gave me the conviction I needed to push myself harder and put together a more disciplined plan. I certainly consider myself a creature of habit, so designing and scheduling a recurring set of activities was the best way for me to ensure that my actions reflect my intention. 

My job search rhythm consisted of the following: 

  • Daily — Review LinkedIn jobs emails that were pushed to my inbox based on 3 keywords I set up in advance, and take action on any relevant opportunities. 
  • Weekly — Go through the VentureLoop job board. Given my target sector, this was the job board most likely to yield relevant opportunities. 
  • Weekly —Continue to publish content on OrgHacking. The content I published on OrgHacking over the past 6 years has become a powerful tool to demonstrate what I’m bringing to the table in a way that a resume never could. I created a sample portfolio with some of my best posts and referenced it in my outreach emails. 
  • Bi-weekly — Go through a set of GlassDoor job searches. Lower ROI but still a very popular option with my target sector. 
  • Monthly — Exec search outreach — I built a list of the 15 top exec search partners in my domain and checked in with them on a monthly basis to see whether they’re running any relevant searches. 
  • Monthly — VC talent partner outreach (at a 2-week offset from exec search outreach) — I built a list of the 15 top VC talent partners and checked in with them monthly to see whether they know of any relevant openings in their portfolio companies. 

2. Manage the pipeline

As my rhythm was picking up steam and starting to bear fruit, I needed a system to keep track of the opportunities and ensure that I’m not dropping any balls. 

It was helpful to distinguish between a “lead” — a job opening that I saw/applied to, or a person that I was introduced to. And a “viable opportunity” — a job opening where I had at least one real-time conversation (phone or video) with the hiring manager or recruiter. 

Once a lead graduated to a viable opportunity, I added it to a simple Google Sheets tracker that I updated daily with the following info: 

  • Status: Open, Closed, On-hold
  • Company
  • Role
  • Hiring Manager
  • Hiring Manager role
  • Source
  • Stage: Recruiter screen, HM screen, assignment, on-site, final round
  • Last contact 
  • Notes

3. Introductions, introductions, introductions

In my almost-20-yr career, I have never gotten a job by blindly submitting a job application. And not for lack of trying. With the hyper-competitive market dynamic that COVID-19 created (scarcity of jobs and abundance of candidates), I figured that’s not going to change and focused on finding someone that can introduce me to the hiring manager (preferably) or the recruiter, regardless of how I first learned about the opportunity. 

4. Ask for help

This is a personal growth area for me that I’ve intentionally focused on in this search. My independence has been a deep source of strength in my life, but it’s not without its shadow side. While asking for help showed up in many ways in this journey, these were the key ones: 

  • Leaning on friends, family, and especially my partner, Kimberly, for moral support and sage advice. 
  • Adding the “open to work” frame to my LinkedIn profile. Publicly admitting that I’m looking for work. My inner daemons told me that there’s still a stigma around it and that it can come across as desperate. I decided not to listen to them and do it anyway. 
  • Working with a career coach. A good colleague and strong executive recruiter happened to complete a coaching training and was looking for his first coaching clients. I took him up on his offer and found the added accountability and advice to be extremely helpful. I tend to think of myself mostly as a “think first, talk second” kind of person, but more and more I’m learning that talking about unbaked thoughts out-loud is a powerful way to advance and distill my thinking. 
  • Making semi-open requests to my immediate network. This was the hardest and most valuable for me to overcome. I had no issues asking a specific person for a specific introduction, but felt extremely uncomfortable with a generic network-wide blast of “hey I’m looking for work, send relevant opportunities my way”. Partly because I think it’s ineffective, but partly because of my inner daemons. I landed on a middle-ground solution where I reached out to a dozen people in my network who I trusted the most, asking them to introduce me to three connectors or relevant hiring managers who are hiring or may be hiring in the near future. The combination of a more targeted outreach with a more targeted “ask” got me over the hurdle. The job offer I accepted can be traced back to one of those emails. 

5. The 5 Fs

At the end of my search, I needed to choose between two very compelling but very different opportunities. It was a tormentous decision, but one I was lucky to have to make, and at the end of the day, a clear winner emerged. 

In hindsight, had I used the “The A Method for Hiring” 5Fs framework, making the decision would have been a bit easier: 

  • Fit ties together the company’s vision, needs and culture with the candidate’s goals, strengths and values.
  • Family takes into account the broader implications of the job to the candidate’s family. 
  • Freedom is the autonomy the candidate will have to make his or her own decisions. 
  • Fortune reflects the stability of the company and the overall financial upside.
  • Fun describes the work environment and personal relationships the candidate will make. [personally, I have a more profound definition for fun]

While the differences were far more nuanced than this, one opportunity was stronger on “fit” and “fun” while the other was stronger on “fortune” and “freedom”. “Family” ended up being the area that tipped the scales quite heavily towards the winning opportunity. 

Finding a job in unusual times

The one formula every leader should know

It’s been a best-kept secret for more than 80 years

No. Not this one. 

I love it when seemingly disparate posts come together in a surprising way and culminate in an “a-ha” moment. 

What do posts about a behavior change model, DEI program, self-engagement, and change management have in common? The answer: 

Lewin’s Equation

Kurt Lewin, a Jewish psychologist who immigrated from Germany to the US in 1933 as antisemitism was rising in Europe, first presented his formula in his 1936 book Principles of Topological Psychology: 

Lewin suggested that behavior (B) is determined by two key elements: the person (P) and the environment (E). 

The variables in the equation (P,E), can be replaced with the specific, unique situations and personal characteristic. 

The equation is even more powerful when written in a dynamic form: 

A change in behavior is a result of a change in the person and/or a change in the environment. Or put more prescriptively: to change behavior, we need to change the person and/or change the environment. This is where nuance comes in: some behaviors will be more sensitive to changes in the person, while others will be more sensitive to changes in the environment. And, of course, both person and environment can change and be changed in multiple ways. 

To see the powerful explanatory power of Lewin’s equation, here are the key insights from each post, articulated using it: 

  • Getting personal about change — offers an expansion, or decomposition of Lewin’s equation. It breaks down P into “confidence and skill building” and “understanding and conviction”. And it breaks down E into “role modeling” and “reinforcement mechanisms”. 
  • D.R.I.V.E and prism — offers a slightly different decomposition. It breaks down P into “individual capabilities” and “(de)motivators”. And it breaks down E into “feedback” and “contextual triggers”.
  • Self-engagement — argues that traditional employee engagement efforts are not as effective as they could be, because they focus solely on changing the environment (ΔE), completely ignoring the opportunity to help people change (ΔP). 
  • Bias Interrupters —argues that many DEI efforts are not as effective as they could be, because they focus solely on helping people change (ΔP), completely ignoring the opportunity to change the environment (ΔE).

While I noted some of the similarities between the first two posts in D.R.I.V.E, the equation helps organize the patterns a lot more clearly. 

The focus reversal (from ΔE to ΔP) in engagement efforts vs. DEI efforts was a big “a-ha” insight to me and enabled me to capture the approach to improve both under a single thesis. 

There’s no leadership role in which behavior change is not a large and critical part of the role. Lewin’s equation should be part of any Leadership 101 textbook or training. 

The one formula every leader should know

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