Expert Round-up: Lessons from a decade of remote work
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Lessons From a Decade of Remote Work – Expert Round-up

Post Author - Dajana Berisavljević Đakonović Dajana Berisavljević Đakonović Last Updated:

In the beginning, there was an… office

It is 2014 in Tallinn, Estonia. Our small team is having the time of their lives building a successful startup from their beautiful, centrally located office. There are office parties, free snacks, and those stunning 7th-floor views. And no world pandemics in sight! Who could ask for more, right?

But then, one day, our co-founder and current CEO, Alari, gets a crazy idea to switch from our office fairytale to something called remote work?! I love hearing Alari re-tell this story and how back then people thought he had totally lost it.

Why would you do it?

It’s so risky.

How are you going to know if people are actually working?

How are you going to make sure they actually work 8 hours every day?

The questions were endless, and answers were nowhere to be found.

Back in 2014, for most people and companies, the remote work concept was as unexplored and unknown as the center of a black hole.

So where did this risky and dangerous journey into the great unknown take us?

Fast forward to today. From a small Estonian start-up, we’ve become a successful global business with 1.5m users, 4 different products, and a fully remote team of 130+ people from 40+ countries around the globe.

Not bad, heh? But why did we do it in the first place? And what did we learn along the way?

Along with our own unique experience running a remote business, we’ve gathered together a range of People Ops leaders and remote work experts (huge thanks to Chase Warrington, Iwo Szapar, Alina Jesien and Jessica Zwaan) to share their own insights and advice.

So sit back, relax, grab a cup of tea (or coffee) and discover the highs, lows and lessons learned from almost a decade of remote work…

Dajana Berisavljević Đakonović, Head of People at Toggl

1: Global hiring will change your business forever

It all started with our hiring pains back in 2014. Hiring was slow, and resumes lie. We struggled to get enough candidates for our job openings and struggled even more to get those who had the right skills for the job.

Two things changed our business forever – we built Toggl Hire to help us evaluate skills (instead of spending time reading resumes), and we took the bold decision to start hiring remotely. Suddenly, hiring was no issue at all, and we were steadily building a strong and diverse team of A players.

Being remote gives us an opportunity to hire from the widest possible talent pool and allows us to bring the best of the best to our team.

2: Trust for breakfast, lunch and dinner

Once you hire a team of A players, you want to give them full freedom and trust to do their best work. We don’t monitor. We don’t micromanage. Both our culture and our products have a strong anti-surveillance stance because we strongly believe that trust fuels a sense of ownership over our work.

You might still wonder how we know if people are actually doing their work.

One simple word: results.

First, we provide the team with the high level strategy, business direction and objectives. Then, we give people freedom and trust to work wherever they want, whenever they want (we don’t have official working hours), and in any way they want, as long as their work is producing the desired impact.

Trust is our core value, propelling our team as confidently as a spacecraft navigates the boundless expanse of space – guided by stars, yet free to explore.

3: …people are businesses are people…

Our third biggest learning from a decade-long remote journey is the realization that people and business are not just interconnected; they are interdependent.

Many HR teams see themselves as peace-making forces between the conflicting demands of people and business. I often hear worries when talking with fellow HR colleagues about protecting people’s interests from business or vice versa.

Today, I firmly believe that people and business are two sides of the same coin. There is no strong business without an engaged and motivated team. And there is no motivated team without a successful business that can provide a healthy company culture that attracts and keeps the A players.

It’s a delicate and crucial balance that extraordinary HR professionals will know how to nurture.

Jessica Zwaan, Chief Operating Officer at Talentful

When building a culture centred on remote, and particularly distributed working, creating an autonomous culture was essential to how we positioned ourselves at my previous role in Whereby.

When you are working on different timezones, often async, autonomy in a remote environment empowers employees, giving them the agency to make decisions, solve problems, and direct their work without delays or fatigue.

This shift from a parental-style management, to a culture of trust and independence can transform a remote organisation, but requires discipline and trade-offs. Rather than instructing employees on every aspect of their roles, companies should focus on providing the tools and support needed to foster self-sufficiency, such as leaning on written communications which detail a decision “flow”.

Ultimately, by treating employees as adults capable of managing significant life decisions, remote-first companies can encourage a faster, higher agency, and responsible approach to work.

This not only enhances productivity but also aligns with the intrinsic motivations and personal growth goals of the healthy remote team.

Alina Jesien, Senior Director of Human Resources at Ergeon

At Ergeon, a fully remote construction tech company, we navigate the complexities of operating across various time zones, cultures, and skill sets. Trust doesn’t come automatically in our diverse environment—it needs to be built over time and can quickly erode with a single misstep. Establishing solid frameworks early on has been key to fostering and preserving trust.

For example, we’ve implemented standardized pay rates per region and role, eliminating pay bands and negotiation. We strive to offer equal benefits, including health insurance, equity, and paid time off, to all staff, regardless of their location.

However, our journey hasn’t been without its challenges. In our eagerness to move quickly, early on, we made some hiring decisions based solely on manager recommendations, bypassing the crucial step of posting the position internally—even for a short 48-hour window.

This taught us that fairness doesn’t necessarily mean slow; it means transparent and inclusive.

Now, we ensure our policies and philosophies are clearly documented to prevent ambiguity. Yet, the real test is in the explanation—if I can’t explain a policy and its purpose in a few sentences, it’s a sign that further simplification is needed.

These experiences remind me that continuous improvement is essential in maintaining an effective, inclusive remote work environment.

Chase Warrington, Head of Operations at Doist

At Doist, our 17+ years of being a remote-first company have taught us that building products remotely hinges on effective communication. The following communication values are central to our company culture, so I recommend PeopleOps leaders adopt a similar set of concepts that are central to their way of working. Writing down what is inherently assumed can be extremely powerful!

1 – Async not asap.

We value thoughtful, well-considered work over speedy, one-line-at-a-time communication. By embracing asynchronous communication, we empower our team members to collaborate effectively without the constant pressure of immediacy.

2 – Disagree and commit.

Diverse perspectives are our strength. We encourage healthy debates, but once a decision is made, we commit as a team. It’s about unity in action, even when we hold differing views.

3 – Remote first, not remote only.

Flexibility is key! We prioritize remote work but maintain the option for intentionally curated in-person interactions a few times per year.

4 – If it’s not a hell yea, it’s a no.

There are a lot of good ideas, but if everything is a priority, then nothing is a priority. We believe in focusing on what truly matters, so if a project or idea doesn’t align perfectly with our goals, we owe it to everyone on the team to pass, even if the potential outcome is positive.

5 – Decisions drive action.

We don’t dwell in analysis paralysis. Once we make a decision, we act on it promptly, ensuring our ideas turn into impactful outcomes.

6 – Radical Candor.

Honest and caring feedback can be especially difficult to elicit in a predominantly async-first environment since non-verbal communication represents 80% of how we express ourselves (and we lose a lot of that in the virtual world). So it’s imperative we foster an environment where open, direct communication is valued, and where constructive criticism leads to personal and professional development.

7 – Deep work.

We champion deep, focused work, and we value creating dedicated time for meaningful tasks, while minimizing distractions and interruptions, to maximize productivity. Chatting isn’t working, being present doesn’t equate to output.

8 – Document it.

Knowledge sharing is key in a remote environment, so we make it a point to document our processes, decisions, and insights so that everyone can access and benefit from our collective wisdom. When something is mentioned in passing, we’ll often say “document it”, to ensure it’s hardcoded into our employee handbook.

Iwo Szapar, Founder at Saudi AI Leadership Forum, and Co-founder at Remote-First Institute

At the Remote-First Institute, our deep dive into the remote work landscape has illuminated the profound role of Artificial Intelligence (AI) in reshaping success narratives for remote and hybrid businesses. Here’s a closer look at how leveraging AI can profoundly enhance operational efficiency and employee satisfaction in such settings:

  • AI-Assistant as a Productivity Partner: It acts as an intuitive coach that not only sets daily agendas but also strategically allocates time for deep work and reflective practice. This vigilance ensures that individual productivity is continuously optimized, supporting a balanced and fulfilling work life.
  • AI-Assistant as an Employee Engager: Through AI-driven micro-conversations, this tool periodically gauges employee wellness and workload, offering managers actionable insights. This proactive approach helps in timely addressing potential issues, ensuring a supportive work environment.

To harness AI’s full capability, we advocate for two strategic approaches:

  • Organizing AI Hackathons: Encouraging teams within distributed organizations to create bespoke AI solutions that cater directly to their roles and challenges. This not only fosters a culture of innovation but also ensures that the solutions are aptly tailored to the needs and workflows of the employees.
  • Implementing the Jobs-to-Be-Done Framework: This involves crafting AI assistants designed to perform specific tasks identified by employees, thus freeing them to focus on more complex, value-added activities.

By integrating AI into daily distributed work operations, we pave the way for a more structured and responsive working environment.

AI doesn’t replace the human touch; instead, it enhances our capabilities, allowing us to function at our best by taking over routine and repetitive tasks.

At the Remote-First Institute, we see AI as essential to not just sustaining but actively enriching the fabric of remote work productivity and employee engagement. This technology is not a distant future—it’s an accessible present, ready to transform how we work and thrive in distributed work settings.

Dajana Berisavljević Đakonović

Dajana is the Head of People at Toggl, where she has been part of scaling the team from 30 to over 130 members across more than 40 countries. She excels in orchestrating remote team operations, ensuring that each team member is engaged and productive, regardless of their geographic location.

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