Autonomy in the Workplace: How To Achieve Zero Regret Attrition With Sidharth Kakkar

17 min read
Headshot of Sidharth Kakkar smiling, in an interview on autonomy in the workplace and Human First Leadership.

Meet Sidharth Kakkar, the founder and CEO of Subscript, a subscription intelligence platform empowering B2B SaaS leaders. 

Bringing a unique approach to our Human First Leadership series, Sidharth’s methods, including offering complete autonomy in the workplace, can be described as both exceptional and intriguing.

In this interview, led by Mindmaven founder Patrick Ewers, we look inside Sidharth’s operations that have allowed him to achieve zero regret attrition. A remarkable organizational accomplishment that indicates a prowess in effectively managing and retaining top-tier talent and building a stable, high-performing workforce.

Read on to gain the pragmatic insights and strategies that can help you achieve similarly remarkable results and redefine your business’ approach to productivity and fulfillment … 

Plus, download your free copy of our ‘My North Star Objective’ Notion Template. An invaluable resource to help you consolidate your goals, providing the clarity and direction needed to navigate your journey toward success. 

Let’s get started … 

Championing a Company Culture Where Everyone Wins 

Subscript is on a mission to empower finance leaders of subscription companies to better understand and manage their businesses and support their CEOs and leadership teams. 

Revealing how they are driving this vision, Sidharth states: “The way we’re operating the company and building things is some of the principles that you mentioned around giving people a lot of autonomy.”

What Is Autonomy in the Workplace?

Sidharth opens up about what autonomy in the workplace means for his business, explaining:

“Almost complete autonomy in terms of how they go about their work, what they work on, when they work, all of those things.

Really treating people with the respect that I think they deserve as intelligent human beings. 

And they are intelligent human beings because we spend a lot of time finding the right ones to join our team. 

We hire them all around the world, but we also don’t want people waking up at 3:00 AM to attend some pointless standup. So we do this all without meetings at all. 

That has resulted in a work culture that is one that I personally really love working in, and so does the rest of the Subscript team.”

While Sidharth has found great fulfillment in offering complete autonomy in the workplace, many organizations are more hesitant to explore such visionary methods. 

But what are the consequences of not establishing such high levels of trust and transparency with your team members? 

In our next discussion point, we explore Sidharth’s leadership journey and why he found becoming the antithesis of micromanagement through offering autonomy in the workplace the key to success.  

What Is Micromanagement? And Ways To Reform  

It’s likely that you will have encountered micromanagement in the workplace at some point in your career. 

However, if you’re not so familiar with this workplace faux pas, micromanagement can be simply described as the need to be super-involved in every little thing your team does. 

Even if this comes from a good place, needing to know every detail and control each next step is, in our experience, an extremely inefficient way of getting the best out of your team. 

This lack of autonomy in the workplace often leaves team members feeling untrusted, like you don’t believe in their abilities, and can be pretty frustrating for everyone involved.

When questioned on what made him think his methods are the right way to operate, Sidharth reflects on his own leadership journey: “It came out of something that was true for me in my last company I started when I was 26 years old. 

I was really quite clueless about the world but quite confident that I knew everything there is to know. 

I was a first-time manager and my first time building a company … 

I feel like I made every mistake in the book.

The mistake that I think most managers make in the beginning is that they micromanage. Because what made them good before was they were able to really get into the details of their work and be very good at what they do – that’s how they became managers.

But then you start doing that with people, and it turns out that it’s a completely incorrect way of actually getting work done with a team.

You have to unlearn your habits that made you good so far, and you have to relearn new habits.”

How Sidharth Became The Antithesis of Micromanagement

While this wisdom is impressive, Sidharth will be the first to admit he wasn’t born a great leader: 

I was in the beginning, in retrospect, a pretty bad manager. 

And then, over the course of building my last company, about six and a half years, I grew a lot and realized this is not working. 

I need a better way to do some of these things.

That led me to how I do things now, which is the antithesis of micromanagement. I’m taking that path to its logical other extreme, and it’s been perfect for me.” 

As summarized by Patrick, there are two main takeaways from this approach: 

  1. Hire people because you trust them in their ability to do the job. 
  2. Let your team completely autonomously decide what they will work on.

When discussing how to succeed at building the highest-performing teams out there, Sidharth adds: 

“It’s certainly about getting the right team, and then it’s also about making sure that they are able to do their best work.

If you get amazing people, but then you stifle the creativity out of them, or stifle the productivity out of them because they had to sit in meetings for six hours a day … 

Well, then, what was the point? Why did you bother?”

Why Is Autonomy in the Workplace Important? 

Curious to know more about the day-to-day reality of Sidharth’s unique leadership approach, Patrick asks about the impact autonomy in the workplace has had on his business. 

Sidharth explains: “It’s been going really well in terms of getting really good people on board because I think this appeals to a lot of people. 

It also does not appeal to some people, but that’s what you want in company culture. 

You do not want it to appeal to everybody. 

It works really well in terms of retaining exceptional people, and it works really well in terms of productivity. 

Everyone at Subscript is exceptionally productive. It is not because they’re working 80 hours a week. It’s because they have all these other things that are set up really well for them. 

And then it’s working well for the business. We’re a startup that’s growing quickly, and we have customers who are extremely happy with what we’re building. 

It’s a small team having an outsized impact in terms of going towards that grand vision.”

By operating in a way that most startup founders would find completely counterintuitive, Sidharth has discovered it’s possible to have an exceptionally productive company, all while working remotely.

The takeaway: Change the mode of how you’re operating to fit how high-performing people actually like to work. 

Real-Life Examples of Autonomy in the Workplace

Granting complete autonomy in the workplace isn’t an instinctive approach for most CEOs. In fact, it challenges the traditional structures upon which many businesses are founded.

But is it about time we embraced a more trusting and empowering future? 

Sidharth presents a real-life example of how giving everyone autonomy in the workplace, irrespective of their years of experience, is a risk that pays off …

Sidharth shares: “This person realized that a portion of the code base was getting a little bit tangly and a little bit harder to work with. 

So they essentially wrote up this documentation around how we’ve organized it currently, which are the ways in which we want to reorganize certain parts of it, which are the super high priority items that we should address immediately … and then went ahead and did half those things.

No one asked this person to do it. No one told them that this was even a thing that someone does. It was just, ‘How do I make this whole thing better?’ 

This is someone who’s using their best judgment, which is what we hired them to be able to do. 

I think in an environment where someone was just assigning them tickets … I don’t think this would’ve happened. 

Or they’d be like, ‘I’m thinking about working on X, Y, Z project. What do you think? Should I work on it?’ Essentially, seeking approval from their manager. 

That’s what normally happens. That does not happen at Subscript. 

This vastly reduces the number of things where I am a limiting factor. Because no one needs to even ask for my permission.”

Solving the Bottleneck in Business 

As Sidharth touched on in his previous example, one of the main benefits of offering complete autonomy in the workplace is that it removes you, the leader, as a bottleneck. 

When decisions would usually wait for the CEO’s approval, this takes a much more team-centric approach. 

Sidharth explains: “It works out really well that the people who are most qualified, in that they have the most context around the technical parts of it, the design parts of it, the like customer-facing parts of it, the rest of it, the customer’s part of it, they weigh in a bunch. 

So you get a lot of essentially expert opinions on that specific topic.”

However, Sidharth points out that the key to making autonomy in the workplace successful relies on leaders providing the correct cultural context. This includes sharing with your team the plans for the next month, quarter, six months, and even the year ahead. 

With this information in mind, your team can bring their expert opinions in their area, identify any risks, and also consider the company’s overall strategy. 

Once all those factors are considered, your team can decide whether or not a project will move forward. 

Sidharth enjoys this approach, stating: “There’s a lot of things where you’re not sure with a startup. But I think what I appreciate is the process is so good. Even when the decision is not the one I would’ve liked to make, the process is so good.

I’m comfortable with people making the decision I would not make – even with big things.”

Stop Fearing Catastrophic Outcomes

Entrusting your team with complete autonomy in the workplace and making decisions on what they feel is best for the company’s goals is a notion that would naturally make many CEOs nervous. 

Especially when dealing with inexperienced team members, allowing them to commit significant resources to a decision you don’t know is right could make some disregard this as a feasible leadership approach. 

Patrick investigates these questions about autonomy in the workplace further: “I can just imagine how most people would have this urge of wanting to double check this. 

Did you get rid of this completely? And more importantly, how do you manage those moments?”

Sidharth replies: “The main thing I would say is this fear of catastrophic outcomes based on these things … 

Whether someone worked on the wrong thing and therefore the most important thing didn’t happen because their time is spent elsewhere. Or someone rewrote a thing, and there’s massive security vulnerabilities … 

Those things just don’t happen.

The people you’ve hired are too smart for that. And if they aren’t, you need to hire new people because it’s just these things don’t happen. 

In my experience, what instead ends up happening is that when there is a thing that is the most important thing to work on, and you as a leader do the right job setting the context. For example, we’re launching this new thing … 

This is the most important thing for the company right now. Let’s make sure we get this new thing. 

I promise you everyone will figure out how to make that happen. 

No one is going to refactor something that is completely irrelevant. And if that person does, be curious, ask them, ‘How did you think about that?’

Find a time where you do one-on-ones or feedback, and ask them about it because you might end up getting an answer that will be really surprising to you. 

So many times that collective wisdom will be better than just your opinion.”

The Benefits of Autonomy in the Workplace  

Granting autonomy in the workplace to build trust within your team is not just about fostering better collaboration; it’s also about improving your own life as a leader. 

While this visionary approach to autonomy in the workplace may not be the most well-trodden path, Patrick and Sidharth provide valuable insights on achieving alignment and handling challenges within the system to help you and your team thrive …

Patrick states: “What I hear you say is … 

With this methodology, your rewards can be exceptional.

You have a more performing team, but you also are living your life as the founder and CEO with a lot less mental load, with a lot less stress, and probably with the ability to do what you need to do most. 

Which is basically: 

  1. Set the agenda,
  2. Set the vision, and 
  3. Make sure that the people are making the decisions on what they’re working on based on the fundamental belief that there’s strong alignment.

But you have to first get comfortable with that. We can both recognize that’s not easy for everybody to do. What do you do to get that alignment?”

Sidharth expands on why he believes autonomy in the workplace should be embraced: “Like I said, catastrophic outcomes don’t happen. 

Like, in the driving analogy, if you’re going from San Francisco to LA, no one’s going to start driving north. That’s not going to happen.

But you might have someone who takes the wrong exit on the highway.”

Discussing how he operates in such situations, Sidharth adds: “I think about it at a system level. I assume the person is smart, and I can trust them, and they’re doing their job. 

If those things are not true, then I have to figure out how to deal with that. 

Then I go:

What was wrong with the system that they didn’t make the right call?’ 

Often, the answer is: I have forgotten to talk about XYZ thing because it was obvious in my head – but literally obvious in no one else’s head. I forgot to tell everyone. 

You, as the leader, have more context than everyone else. 

To me, that is more or less your job, to have that ‘more context’ and to make sure that everyone else has that ‘more context.’ 

And then making sure that they’re able to use that context to make great decisions and produce great outcomes.” 

Recognize Your Team Are More Than Cogs in a Machine

As Mindmaven’s founder, Patrick is passionate about helping leaders achieve phenomenal success without sacrificing what matters most (something we like to refer to as True Greatness). 

Celebrating Sidharth’s unique Human First Leadership approach that champions autonomy in the workplace, Patrick explores: “So what you’re saying is your job as a CEO becomes one that actually sounds to me exceptionally fun. 

Your job is just to make sure that people know where we’re aiming for long term, but also short term. Then provide whatever context anybody needs to be able to make the right decisions on how they want to use their time.”

When discussing what Human First Leadership means to him, Sidharth summarizes: “In my view, the more micromanaged approach is sort of treating people like cogs in a machine.

This approach is much more: 

You are an intelligent person who has the ability to understand complex ideas and then to produce outcomes that literally no one else can. 

You are able to connect the dots that are provided to you in a way that only you can. That is going to be extremely positive for the company and positive for the team.

That is, I think, at its core where the person goes from cog to human.”

Curious to hear the human impact Sidharth’s approach of granting autonomy in the workplace has had on his business, Patrick asks: “Would you say it’s fair that you’ve seen that play out in terms of statistics like attrition rates or loyalty?”

Sidharth states: 

“We’re a young startup, but we have had zero people leave. Zero voluntary turnover so far. 

You never see people phoning it in or slacking off. 

There’s no artificial carrots and sticks situation going on that motivates them to do it. 

We’re creating the situation in which they can be excited and motivated.”

Embracing the Long-Term Vision of Autonomy in the Workplace

Always looking for new ways to develop and grow, Patrick wraps up this inspiring discussion by asking the big question: “What is your vision for the future? In 10, 20 years, how are we going to be working?”

Sidharth offers his thoughts: “I think the thing that you are doing here, and that a lot of people are reaching up to, is that leading people is a skill. 

Listening to a series like this or being mindful about what that means and what the impact you’re having on other people and what you’re creating. It’s just so good for everybody. 

It’s good for the leader because you’re not fretting about the random little things anymore, and you’re much more free to do your best work. 

And then the people being led because it’s just so much more inspiring. 

It’s just good for the world. 

That’s what I hope happens. I hope there’s just more inspiring leadership out there as a result of this, and ideally, people who feel more fulfilled by their work.”

Download Your Free “My North Star Objective” Notion Template 

We hope you enjoyed this inspiring Human First Leadership discussion on autonomy in the workplace with Patrick and Sidharth! 

To help you implement these insights into your own leadership journey, we’re offering a free copy of our “My North Star Objective” Notion Template. 

This template is designed to help you consolidate your goals, giving you the clarity and direction needed to navigate your journey toward success. 

Just like the way sailors view the North Star, your North Star Objective is how you can stay on course, no matter where you are. Whenever you feel like you don’t know where to go or what to do, all it takes is a quick glance to get back on track!

By adopting elements of Human First Leadership and using this Notion template, we hope you, too, will be inspired to create a workplace where autonomy, trust, and fulfillment are the guiding principles.

Click here to access your free My North Star Objective Notion Template now and start your journey towards a more empowered and successful Human First Leadership approach.

Share this article
Radical Delegation isn’t your typical business book.

No theory here—It’s a pragmatic, conversational handbook for leaders designed to free up 12+ hours a week

Receive exclusive updates to help unleash your superpowers on your journey to True Greatness.