Tuesday, March 28, 2023

No More Meetings: Sidharth Kakkar

EPISODE 62 Want to go totally asynchronous? Sidharth Kakkar on remote teams & autonomous cultures
The Secret to an In Sync Startup? Ditch Your Meetings and Try an Asynchronous Culture
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. ................. 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. ........... One of our earliest engineers, Brandon, likes to be active and take a dance class after lunch, and he comes back to work refreshed .......... “You don’t want people sitting in front of their laptops when they aren’t going to be able to be productive.” ....... he canceled meetings — all of them (well, except for the fun optional ones like social hours). .......... 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 ........ a radically different workplace that’s fully asynchronous .......

no micromanagement, documenting everything, and treating hiring as a segmentation exercise.

.......... 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.” .......... 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. ......... But to run a company with no meetings, you have to loosen your grip. ......... 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. ......... “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.” ........ “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” ......... 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.” ........... 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.” ......... 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). ........... 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 is not the same as no feedback. ....... 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. ...... Make it simple. ...... Don’t skip your high performers. ........... 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.” .............. 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. ..........

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. .......... 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.” .......... 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.’” ............ “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. ........... 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. .......... 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. ........... “OKRs are a tool that are very simple sounding but actually executing on them can be quite hard and nuanced,” warns Kakkar. ......... 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. ...........

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.”

....... 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.” ......... 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. ........... 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. ........... The result is that everyone feels useful because they are being useful. .......... 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. ............... Clear communication skills are just as important as clean code. ............. “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. ........... “It's incredibly freeing once they've made that transition, but at first it can feel a little uncomfortable.” .......... 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? ............. “What we've gained is this incredibly written, permanent, documented technology that has made so many things so much easier.” ............. “That’s one of the nicest things about being a founder — you get to build the company in which you’d want to work.”

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Sidharth Kakkar

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