How do you hold meetings that work for everyone’s schedule when your teams are spread around the world? For First-Round backed founder, Sidharth Kakkar, the answer is – you don’t.
Let’s rewind. After his first startup, Freckle, was acquired, Kakkar went through a self-reflection exercise where he captured every lesson he’d learned over the course of his six years as a founder in a massive 35-page document. He articulated – among other things – he didn’t need his employees on-site in San Francisco to find success. Over the course of the startup’s history, Freckle had undergone an evolution from an in-office to hybrid workplace before transitioning to fully remote.
So when it came time to start Subscript, a subscription intelligence platform for B2B SaaS, Kakkar knew he wanted a fully remote workplace from day one. It’s a seed that was planted by the founding team, with his co-founder Michelle Lee living across the country from Kakkar and tending to work very different hours within the day. Ditching geographical requirements, Kakkar and Lee believed, would give Subscript a leg up by being able to tap into high-performers from a global talent pool, as well as give folks the flexibility to do their best work.
“I personally find that there are just times of the day when I am much less productive than other times in the day. One of our earliest engineers, Brandon, likes to be active and take a dance class after lunch, and he comes back to work refreshed,” says Kakkar. “You don’t want people sitting in front of their laptops when they aren’t going to be able to be productive.”
But he had a problem: meeting times. With folks spread across the globe (and working whatever hours best aligned with their schedule and productivity), someone was bound to be getting the short end of the stick, either joining a meeting in the middle of the night or before the sun rises. Kakkar didn’t like the idea of that. So, he canceled meetings — all of them (well, except for the fun optional ones like social hours).
Now, not only has Subscript opened up a global talent pool, but he also freed up his own calendar as a founder and CEO, allowing himself the time to focus on the tasks only he can accomplish. In this exclusive interview, Kakkar unfurls the blueprint for a radically different workplace that’s fully asynchronous. The three pillars he emphasizes for an async company includes: no micromanagement, documenting everything, and treating hiring as a segmentation exercise.
Even if your workplace skews more traditional, you’ll find these insights can be implemented in minor – or major – ways to improve your company culture and make sharper, quicker decisions.
FROM ON-SITE TO ONLINE: THE ASYNC PLAYBOOK
So just how asynchronous is Subscript? Here’s the quick rundown of how it works in practice:
There are no required meetings.
Folks can work whatever hours best align with their schedule and productivity
Rather than a standard all-hands, the leadership team sends a context-setting email every Sunday night, which includes a living document and a recorded video going over the OKRs and goals for the week.
Any team standups are conducted in Slack, where folks can post updates on their progress or ask for help unblocking an issue.
There are monthly social meetings, like playing an online board game together, or pairing up folks for 1:1 get-to know-you sessions. There are also regular all-team offsite weeks where folks get together in person.
To keep the culture buzzing, there are plenty of casual Slack channels dedicated to topics like “food” or “parents.”
But setting the parameters for when — and in what channels — folks communicate is just the scaffolding for the company culture. At a fast-paced startup, it’s important that decisions don’t get delayed and projects don’t grind to a halt just because someone’s stepped away from their desk. You’ve got to bake in a culture that prioritizes autonomy — and give folks the context they need to make sharp decisions without gathering a group of colleagues on a Zoom call.
PILLAR #1: NO MICROMANAGEMENT
Reflecting on his early years as a founder, Kakkar observes, “I started out the way a lot of people start out as managers, which is as fairly micromanaging. I would have scoffed if someone called me a micromanager, but in reflection, I did a lot of the typical things that I would now consider quite micromanaging.”
But to run a company with no meetings, you have to loosen your grip.
“There are very minimal benefits to micromanaging people, but there's quite a lot of downside to it,” says Kakkar. Instead of reaping the benefits of hiring top talent, you now have an entire company dependent solely on you and your ideas. The time you freed up by canceling meetings is now filled with making decisions that you hired a team to make.
As a founder, Kakkar believes your role should be thinking “about the system level things I should do differently so that bad decisions – or misaligned decisions – don’t happen.” In an autonomous workplace, employees are trusted to find solutions to the problems you hired them to solve. It’s shifting your attention from instructing an employee on how to precisely format an email to providing the foundation that they need to make their own choices.
“Everyone who works for me is better at their thing than I am at their thing,” points out Kakkar. Allowing people to work independently creates what Kakkar calls a “collective Subscript brain.”
Anytime you’re telling someone what to do you’re not actually solving the bug. You’re doing a really bad patch.
Here’s how that looks in practice. Previously, in the engineering team’s daily standup (conducted over Slack), folks would answer three questions:
What did you do yesterday?
What are you going to do today?
What are your blockers?
Kakkar has whittled this process down, “I only find the last question to be essential and the first two are actually quite micromanaging. So I cut out the first two and now we only talk about blockers.” Everything else, he leaves up to the individual to decide.
“Even if you think someone's making a mistake, just let them,” advises Kakkar. “Plenty of times, what appears to be a misstep might instead be just an alternative route. The rest of the time, the person will learn a ton and will make fewer mistakes in the future”
It's important as a founder to know the difference between having a correct answer and just having an opinion.
Opinions Come at a Cost – Spend Wisely
Forcing your opinions on others can do immense damage to your workplace culture. Not only are you potentially wrong, as Kakkar says, “As CEO, I’m wrong very, very, often and I don’t think that’s unique to me as a startup founder.” But even if you’re right, it’s a risky move. According to Kakkar, “There’s a question of how right you are because there’s a cost to telling someone what to do.” Here’s why:
Employees lose confidence in their skills. “You’ve squashed their creativity and you’ve squashed their ownership chops.”
Employees become more concerned with your opinion than finding the right solution. “You want to avoid folks thinking through problems like, ‘If I don’t do things Sidharth’s way, then that means he’s going to think less of me.’ Which is quite detrimental to the business.”
Employees become dependent on you to make decisions for them. “Then you condition folks to think, ‘I better just run all my decisions by Sidharth.’ And that is the worst possible outcome that you could imagine.”
Of course, there’s no one-size-fits-all solution here. “How do you apply our beliefs on autonomy and not micromanaging to more junior members? I think the principles will still apply, but the specifics may vary a little bit more,” says Kakkar. While junior folks may need a bit more handholding for some of their larger projects, it’s important to still leave space for them to build up their confidence on smaller tasks (and learn from mistakes that inevitably crop up).
No matter where you work or what role you’re in, you can use Kakkar’s advice to weed out your own micromanager tendencies.
Before you give an opinion, ask yourself, “Am I right or do I just have an opinion? If I am right, what’s the cost of being right?” You might discover what you have to say is better off left unsaid.
Trust others to do what they do best. Focus on the things that only you can do and leave the rest to everyone else.
No Micromanagement ≠ No Feedback
It’s important to point out — no micromanagement is not the same as no feedback. “Everyone should give each other feedback, but without a dedicated forum feedback always feels a little more offensive,” says Kakkar. Remove the sting by letting employees know what to expect and when to expect it. Creating a predictable, regular feedback cycle is critical here.
Make it regular. Subscript operates on a monthly cadence. “It’ll feel like a lot, but it’s so worth it,” says Kakkar.
Make it simple. “So it doesn’t feel like a big, onerous task that you want to put off.” He suggests the Start-Stop-Continue framework.
Don’t skip your high performers. “Don’t rob these folks of the chance to improve, even if they’re already operating at a high level.”
PILLAR #2: DOCUMENT EVERYTHING (AND MAKE SURE IT’S EASY TO FIND).
Several years into a startup, you might find that your memories about the early days – and your early decisions – have gone fuzzy. Repeat founder Kakkar remembers from his Freckle era, “There were so many things that we basically ended up re-litigating that we had figured out three years ago because teammates come and go and you easily forget what you decided, why you decided it, and you end up asking the same questions all over again.”
So, at Subscript, everything is documented, “We try to make sure that all the logic of every decision we make is reflected in our collective Wiki – everything, even the smallest things.” The goal is that every discussion is in writing.
To illustrate this in practice, he points to one of his favorite examples: The Journal of Product-Market Fit. The series of journal entries, which was started in the second month of Subscript, documents the startup’s path toward product-market fit and the problems they were thinking through at the time.
Kakkar says you can see how their journey went from high-level discussions around customer solutions and problems to more recent discussions about the core buyer, which is the finance leaders and other stakeholders and how they work together. “Over the course of reading through these documents, you can watch our thinking and our business evolve,” says Kakkar.
Here’s another fictional example of how decisions at Subscript get documented in real-time:
Emily runs the Client Success section. “She’s thinking about changing the process for how Client Success becomes involved in a customer relationship during the sales and data set phase.”
She creates a Discussion Area document. She provides background on why she’s thinking about this and possible additional reading. She’ll also identify what’s working, what’s not working, and what might work a little better with the current process. No decisions have been made yet.
Emily owns it, but it’s a team effort. “In that doc, she might tag people who need to work with her on this. They can leave comments on what they do or don’t agree with, as well as, “add a section at the bottom, write their name, and say ‘Here’s some other thoughts I have’” or present a slightly different idea on how it can be done.
A discussion evolves.The natural next step, at least at Subscript, is an asynchronous, multi-threaded discussion coming together. Kakkar says the advantage here is, “You get a much richer discussion and clearer communication because if you misread something, you can ask more questions, and then if other people also misread it, then they can also see the explanation within the doc.”
Next steps and Emily’s choice. The discussion has been had, buy-in has been procured, so a decision is imminent. As the Directly Responsible Individual (DRI) for the project, Emily is the final decision maker. “Although opinions and discussion is welcome, no one else gets to make the decision.”
The loop is closed with feedback. Any significant project or strategic shift will probably have both aspects that went well and ones that could be better — capture retroactive feedback in the same doc so it can be applied in the next cycle.
Because this decision-making process was documented, time spent re-litigating can now be spent refining a process. “Let's say a new Client Success person joins and they start wondering about a particular process or project, ‘Wait, why do we do it this way?’ They now have a comprehensive document where they can get up to speed on context,” says Kakkar. And if they have new ideas, they can just create a new section at the top or create a new doc, reference this one, and then we could continue iterating.’”
How to Organize Massive Amounts of Information
As you can probably imagine, an asynchronous work culture with an obsession with documentation creates an incredibly long paper trail. To keep the knowledge amassed manageable and accessible, it’s important to have an organizational strategy. Otherwise, you’ll just have lots and lots of orphan documents that no one ever takes the time to review or reference because they’re impossible to find.
At Kakkar’s previous startup, Freckle, they attempted to manage everything using Google Docs. However, Subscript has gone a different route, “In Google, you can create and share a doc with someone that doesn't live in any folder or hierarchy. That means a lot of things basically go into the ether and you will never find it again.” Kakkar prefers solutions like Confluence or Notion that enforce hierarchy so documents can be located easily in the future.
So when Subscript folks go into the documentation hub, there are sections like Goals and Planning, Product and Design, Client Success, Go to Market, Culture, Team, Engineering, General Operations, and Security.
Each section has discussion areas for storing relevant documents. You’ll also find RFCs or Request for Comments, “I really like that name because it very explicitly says, ‘These are not ‘decisions’. This is a work-in-progress hub where I'm looking for input from other people.’”
Depending on the section, there are specific sub-categories. For example, in Product and Design, in addition to RFCs, there are Discovery Interviews, Feature Requests, and the Journal of Product Market Fit.
While you might not be in the position to overhaul your company’s entire process, you can get your own documents in order with these simple tactics:
Think outside the Google Docs box. Don’t be afraid to stray from what’s comfortable. Play around with some of the more hierarchical solutions and see if they unlock additional organization potential for you.
Make discussions documentation-first. If you hope to document things after the fact, you won’t do it. So, instead, make writing the first step in big decisions. Then, it’ll be natural to update the document with the conclusion, and the documentation becomes a by-product of the process.
Make it a team effort. Consider how you can document the ideation and discussion phases to ensure group buy-in.
Goal Setting in a Document Heavy Culture
“OKRs are a tool that are very simple sounding but actually executing on them can be quite hard and nuanced,” warns Kakkar.
Subscript’s approach is to keep it simple. Rather than spend an hour-long monthly all-hands meeting going over the goals for the period, at Subscript, OKRs reside in a combination of a living document and a 15-minute weekly pre-recorded video. “People comment on the video and on the doc so there’s a robust discussion on it. In my view, it’s a significantly more powerful thing than an all-hands because you can engage in discussion way more frequently, which I think is quite important,” says Kakkar.
Here’s how it works (and his tips for implementing a similar process at your own company):
Keep it simple: “We have monthly OKRs with usually only one, or sometimes two, objectives, and only 2-3 key results per objective — focus is really important.”
Set the context. “Every week, either myself or another member of the team, will record a context-setting video for the week. This video is essentially, ‘Here’s what our goals are, here’s our KRs, here’s our progress to date on those KRs. Then we outline ‘Here’s a set of ideas for the week that can probably help us move toward those KRs.’”
Share ideas, not directives. “The set of ideas isn’t, ‘Do X, Y, Z. It’s more, ‘Problems A or B or C are the types of things standing in our way.”
Collect reflections to share org-wide. “Reflections can be anything from an awesome win that we had that is a great thing to celebrate together. Or it can be someone saying, ‘I’m really drowning in notifications.’ In the following week’s video, we pick a few reflections that make the most sense for everyone to have context on and use this as a prompt for more in-depth discussion, that obviously, happens asynchronously.”
PILLAR #3: TREAT HIRING LIKE A SEGMENTATION EXERCISE.
At Subscript, Kakkar says, everyone gets “the unvarnished truth” and the startup operates with full transparency. This style is often shied away from with executive leadership, because there’s a fear of discouraging employees by reporting on the negative. But if you want employees to operate autonomously, they need the full picture.
At Subscript, transparency means that big decisions are made in public — litigated in documents that anyone can access. Drafts of OKRs are in public, so anyone can comment. Both good and bad news is discussed publicly, so nothing is a secret. “Conversations that technically only involve two people are still held in public Slack channels, so that everyone can see how decisions are being made, and can potentially chime in, or reference those decisions later,” says Kakkar.
If you treat people like adults they'll act like adults, and if you don't treat them like adults, well, you're gonna get what you asked for.
By trusting everyone with the positive and the negative developments in the journey, Kakkar says you’re communicating to the whole company, “You’re a huge part of this journey, just like everyone else here and you have significant things to contribute.”
In practice, this looks like trusting the right team and the right person to tackle the right task. Here’s an example of how that conversation might go:
Identify what you’re attempting to accomplish. “We're working towards product-market fit. And here's how we'll know we got there.”
Provide the necessary context. “Here’s the data available. It seems like the best strategies are X, Y, and Z”
Gather feedback. “What do you think? Where is the logic potentially missing information you have? Let’s get all the information out, and then agree collectively”
Empower the employee. “Please figure out what you think makes sense in your role to help the whole team succeed in the strategy, which will help us get towards product-market fit.”
The result is that everyone feels useful because they are being useful.
But you can’t achieve this outcome without rethinking your hiring philosophy. Kakkar says, “If everyone can make their own decisions, then you have to make sure that you're hiring people who are going to be able to make those decisions.”
Why you want candidates to realize that your company isn’t for them.
The goal here is not to cast an extremely wide net. In fact, to hire for a unique culture, Kakkar views hiring as a segmentation exercise, similar to product-market fit. “Think of your company and culture as a product your employees experience. The people you need are the people who are interested in the product you're offering. This gives us very specific segmentation,” he says. “It's actually a non-trivial number of people who start interviewing at Subscript and say, ‘I'm sorry, actually, this thing is not for me,” says Kakkar. There’s even a “reverse sell” interview step in which Subscript co-founder Michelle Lee sits down with the candidate to unpack if they’re sure they’re up for the unusual culture.
So, what does Subscript look for when hiring? People who:
Really care about managing their own schedule.
Are very good at motivating themselves.
Are very comfortable with ambiguity and making their own decisions.
Are very good at communicating in an asynchronous way – written or video.
When you review this list of must-haves, the constraints they can do away with are also clear. They aren’t limited to hiring people who:
Live in or are willing to move to San Francisco.
Require being in the office full-time.
Are willing to wake up for an all-hands at a particular hour.
Hiring For an Autonomous Culture
So, how do you interview with an autonomous culture in mind? For Subscript, it’s a combination of having the right skills for the role and an extraordinary ability to communicate what they’re doing and why.
Take their interview process for hiring engineers. The process starts by taking a problem and recording an asynchronous video where the candidate talks through their thinking and the solution they've reached in real time on camera. They’re looking to see if the engineer plans ahead, communicates their plan, and is comfortable completing the work and talking through it on camera. Clear communication skills are just as important as clean code.
Plenty of companies leverage a take-home assignment — but Subscript’s next step is a bit more unique. Next, engineering candidates are asked to simulate a real working environment where they collaborate with someone else. If the candidate has a back-end focus, their job is to show how they’d collaborate with someone who’ll work on the frontend, “Your job is to create documentation that will help the person working on the other half of the feature know what to do and how to do it,” says Kakkar.
With this trial pair project, Kakkar says they’re able to observe:
How they communicate. Could they be communicating more? Could they be streamlining the information they’re sharing?
How thoughtful they are. Are they considering their teammate’s needs? Are they offering information in a way that is easy to consume?
How deep they go. Are they providing an excessive amount of information? Are they sharing all the knowledge necessary for their teammate to accomplish their objective? Are they being completely transparent?
How much they anticipate needs. Are they operating on a timeline that helps them hit their deadlines? Are they packaging the deliverables in the most convenient way possible for your teammate?
Even with folks tested for async chops throughout the interview process, there’s still the matter of helping people come on board to a new way of working once they join Subscript — which is a major shift for folks who are used to a traditional synchronous, highly monitored workforce. “There are questions that come up, like, ‘What do you mean I'm not assigned a ticket? What do you mean I can just do anything?’ That can be hard when you've spent a decade or two doing the opposite,” says Kakkar.
But after overcoming the initial mental roadblock and gaining more context around how Subscript operates, Kakkar says buy-in becomes easy, “It's incredibly freeing once they've made that transition, but at first it can feel a little uncomfortable.”
WRAPPING UP: THE ADVANTAGE OF ASYNC
Although a meeting-heavy culture is the default for most companies, from early-stage startups to BigCos, there are serious advantages to asynchronous communication. Yes, offices allow for unplanned water-cooler moments, but what happens to the knowledge that comes out of those moments?
Kakkar predicts, “You get the serendipity of solving a problem side-by-side, but you've also now created a bunch of knowledge between the two of you that no one else is privy to. And maybe some version of it gets documented, but other folks don't have nearly enough context.”
So along with tapping a global talent force, plugging this knowledge leak keeps Kakkar committed to an asynchronous workplace, “What we've gained is this incredibly written, permanent, documented technology that has made so many things so much easier.”
Ultimately, Kakkar advises that an asynchronous, autonomous workplace might not be right for everyone, “There are people who believe the exact opposite of me about whether sync or async is best and many of them are much smarter than me. I don't think one of us is right, and one of us is wrong. There are multiple right answers,” he says.
For founders, the question is: what company do you want to work in? “That’s one of the nicest things about being a founder — you get to build the company in which you’d want to work.”