How remote work can work on real life

An interview with Darcy Boles, Director of Culture and Innovation at TaxJar, a company that operates 100% remotely and is very happy about it.

About this article

I decided to write this article to share with you the best remote work practices to manage and motivate teams.

Since I started working remotely in 2017, I dedicate time to study ways to improve productivity and engage people in virtual environments.

Recently I came across Darcy Boles profile on LinkedIn and decided I needed to know her and asked for an interview. It was amazing!

Darcy is the Director of Culture and Innovation at TaxJar, a company that operates 100% remotely, and is very happy about it. 

I wanted to check how some of the studies on people strategy and leadership practices were taking place on a company that took remote working to its highest level.

We talked about leadership, company culture, how to create a sense of belonging, and best ways to communicate when working with remote teams.

Many of the practices you will read in this article could be applied to onsite work as well.

The acceleration to online platforms made us look into our practices in order to adapt and survive in the digital world.

I hope you will enjoy this interview and take as many valuable lessons as I did.

How to Motivate and Create structure on virtual environments

Darcy states her mission as the Architect of Company Culture. That reminded me of a recent World Economic Forum report about leadership and people strategy in the Digital Revolution. 

According to the study, the borderless organization requires new mechanisms to unite teams, so the Company Culture becomes the glue that holds it all together. It permeates the processes, the daily routine and has to stay agile to the changes in business’s needs.

Culture-driven companies know that following values is much more motivating than following rules. Once you have the team aligned with the company’s values, you will find it easier to achieve goals and increase productivity. 

Using Culture as a structure is now considered to be one of the most important leadership skills for dealing with uncertain and complex scenarios. That is why I asked Darcy how that was done at TaxJar, especially to foster and nurture a sense of belonging.

It was clear that this was one of her main concerns and that much effort is put into finding ways to promote the sense of belonging.

“It starts with our integrated values system which sets the stage for a deep sense of belonging, mastery and autonomy which breeds intrinsic motivation.”

“We build relationships that matter, based on honesty. We teach people how to build trust.”

According to Darcy, Cultural Values must lead all the other practices, including recruitment. TaxJar made the culture fit a requirement for anyone who wants to join the company. Although strategic recruitment is a base strategy, they know that the job is not over. To be a value-driven company is a continuous effort.

When you are talking about a 100% remote working environment you can expect a cultural shock”. That is how Darcy explained the reaction some people have when they start at TaxJar. 

Most people are not used to all the flexibility and trust, even when they agree with the values and principles it may be hard to break behavior patterns and act in a new way. To address this reality, Darcy and her team work on making the company values tangible and real.

According to her, people are stimulated to reflect upon their behaviors and check if that agrees with the company’s values. Employees are even encouraged to challenge one another when they step outside the values by saying things like “This doesn’t feel like the company.” “You have the company’s permission to say that”, Darcy made clear. 

You might now be trying to understand how that can be done in a remote working environment. There are no posters on the wall, no fun office with meditation rooms or ping-pong tables.

Although some companies decided to create fun offices, it is not uncommon to hear that employees work overtime regularly and that the work is very stressful. Most people would trade all that for working with purpose, being respected and cared for.

At the end of the day your boss has a bigger impact on your productivity and motivation than most of the other factors in your professional life. It is the leader who puts all practices in motion, playing the role of cultural ambassador when you work in a value-driven organization.

I asked Darcy to tell me more about leadership and how they knew if leaders were actually nurturing the company’s values.

Leadership in Remote Environments

There is one thing all studies and researches on leadership agree on, in order to engage, motivate and organize work at a distance leaders must change their mindsets. They must believe in the company’s values and trust the people they work with

When leaders are practicing what they preach, they are staying true to their own principles and therefore will be highly motivated to work. And a highly motivated leader will motivate their teams.

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When companies shift to remote work the cultural values that are actually practiced comes to light. It is like all that we know that was wrong with the workflow, the communication, and the leadership becomes obvious and unbearable. 

This is when distrust becomes so clear.

One of the most common reactions when a company first starts working remotely is micromanaging. Some leaders want to guarantee that the team is working, so they schedule constant online meetings and calls or ask for reports on everything the team does. 

These leaders are still trapped in the control and command mindset of the industrial revolution. Beneath this micromanaging behavior is the belief that people won’t work if they are not constantly supervised or pressured. This is a huge distrust of the team and it just disrupts the focused time they need to reach high performance on their tasks.

“The beauty of remote work is that it doesn’t kill culture, it reveals it. All that is left are the values.”

That is why it is so important to hire leaders that are already aligned with company culture, according to Darcy. 

Although TaxJar uses the values as a priority on recruitment, that does not mean that all leaders and employees know how to practice them on the day-to-day work as soon as they are hired. 

As they arrive at TaxJar, leaders take part in an intensive leadership course they call the Leadership Academy, based on the organization’s values and how to practice them.

To be a cultural ambassador and act as a purpose-driven leader, they must change their mindsets about how to best manage teams. Instead of wanting to impose command and control, the leader must work as an orchestrator of talents. 

This mindset shift is usually the first thing I address with my clients. It is the starting point and also the condition for making the most of the digital working environment, so I was glad to see that Darcy takes this matter as seriously as I do.

We train our leaders to lead with authenticity and vulnerability which creates a deep sense of psychological safety. We also in no way monitor our employees’ days, so our employees feel like they can show up how and when it works for them as long as they produce high-quality results.” 

TaxJar takes this mindset shift so deeply that they made trust a core value. In order to have flexible schedules, be vulnerable and authentic you must trust the people you work with. 

Communication best practices

Communication is essential for productivity, motivation, and talent retention. So finding the best ways to communicate with a remote or hybrid team is a key factor for success.

Once I heard from a programmer who worked from home that he always felt like his boss was demanding something urgently. The messages he received were so objective that they were misinterpreted by him as orders.

Another developer was working in the client’s office and he felt no connection to the company that hired him. He talked and felt like he worked for the client.

In a third example, a hybrid team always forgot to invite the remote workers for the birthday celebrations at the office. And even when they remembered, the remote employees felt left out because they couldn’t be there.

I could go on and on with examples of how you can lose a talent, or demotivate a team if you don’t know how to show intentions, emotions in your messages or if you fail to create a sense of belonging.

That was the most impressive part of the conversation I had with Darcy. TaxJar really focuses on communication strategies that are designed to create a sense of belonging and improve productivity.

Many of the executives I speak with are telling me they will choose a hybrid team arrangement after the pandemic is over. 

Darcy has worked in both models and she thinks hybrid teams are challenging and will only work if you put remote practices first. That means that if part of the team is at the office everyone will use their own computers to join the online meeting, for example. All workers must have the same experience to ensure the sense of belonging. 

I agree with Darcy. People think that going hybrid is a middle way, less radical, but it might be harder to manage than a fully remote team. You might end up losing the benefits of both sides instead of taking advantage of them. 

Flexible working hours are more productive

Here is where the mindset shift is so important for leaders. The industrial revolution needed everyone to be at the plant at the same time. That is not necessary anymore.

Darcy showed me how much you can accomplish if you believe that work can be done when you trust people will do their tasks delivering with high quality and on time. They have a strong focus on results instead of effort.

TaxJar uses synchronous and asynchronous work in a very strategic way. By offering technology and workflows for the best use of asynchronous tasks they give autonomy for people to work at their productivity peak. That allows a flexible lifestyle and increases productivity.

We ask our teams to record what they have done for asynchronous work. Briefing people should always happen.”

Recording briefings is just one example that shows how many possibilities and technologies are available for organizing work when you rely on asynchronous communication whenever possible.

Having the best talents

Another advantage of remote working that few companies are taking is the possibility to find the right talents regardless of geographic location. Remote working is already being demanded by

top talents and people often compare each other’s company’s policies during the quarantine periods.

TaxJar has employees all over America and they can work from anywhere they want, as long as they deliver as expected. Who says that a project done at the beach will be worse than one done at home or at the office? This makes remote working a lifestyle and a great employer brand. As Darcy puts it…

You allow people to design their lives around work and not the other way around”.

You can feel how proud Darcy is of her work. The sense of purpose and belonging she has with the company is clear. Darcy is herself a great enthusiast of this lifestyle and often writes about where she is working from and how that flexibility makes her happy. 

As a remote worker myself I can honestly say that I have the lifestyle I have always wanted.

I miss lunches and meetings in clients’ offices, though, and I am eager to go back to that. But since the covid-19 pandemic stroke, everyone shifted to online meetings and some will remain remote even after we can meet each other. 

Meetings in fully remote or hybrid teams

Online meetings can make remote work hell. The problem is that people left the office, but the office is still in them. The sudden shift to a digital environment caught many companies by surprise, so they just moved the same practices and workflows from the office to the Zoom room.

The success of a high-performing team is evidenced by the way it conducts meetings. One of the most important parts of my job as a team coach is to observe them. Most of the time people are not briefed about what has to be discussed and even less about what decision has to be made as a result, so the meetings take longer, have more people than needed, and are less productive.

When I talked to Darcy about meetings it seemed to me like that was a basic step for any remote working. Having clear goals and a communication structure to follow.

If you need to disrupt someone’s focused time of work, you must have a good reason, one that demands everyone to be together at the same time.

Meetings are no longer a waste of time when you know what is expected from you, how you can contribute, and what decision will be made after that. In the end, having clear objectives with your communication leads to effectiveness, productivity, and motivation in online and onsite meetings.

The need to use online meetings during the pandemic accelerated innovation and made it possible to re-imagine meetings from their core. When you finally see what an effective online meeting is like, you will be amazed at the possibilities for co-creation and decision-making it offers.

In order to guarantee a sense of belonging and productivity in online meetings, two things are essential: infrastructure and digital tools. You must see that everyone has the infrastructure needed to have the same experience, like cameras and a good internet connection. Also, you must train your team on using digital resources like collaboration tools, breakout rooms, and instant polls. Make your team digitally savvy


Talking to Darcy made me hopeful for the future. When you see so many companies struggling with remote working and just waiting for things to get back to “normal”, you may get frustrated. But there are some companies that want to move forward and take this chance to speed up the digital revolution to adapt to our times.

If you are part of these companies, TaxJar can set an excellent example and serve as a benchmark. 

Their success in being 100% online begins with understanding that you must create a productive and happy virtual working environment. It is thinking outside the box to take full advantage of the benefits and possibilities of the digital world. 

That can only be achieved when the CEOs support and encourage this way of working. Darcy told me that at TaxJar “founders give support, they champion it. They know that it is their DNA that is being transmitted.”

I have been working with leaders and teams to find the best way for each company to move to a remote working environment. Some want fully remote teams, others a hybrid team design, but everyone wants high performance and a good lifestyle.

That can be done by challenging our ideas of work relations, designing workflows and agreements that will nurture people’s potential and get results.

Count on me If you need any help with that.