Five things that helped me become a good remote People Ops Partner

Stefania Chiorboli leads Global HR at Boundless. Passing through and leaving an impact in companies such as Automattic, Booking.com, and Status, she knows what it takes to make remote employees happy, engaged and productive. A remote worker for the past five years, she has learned from the best and shares her lessons on the blog.

Falling in love with People Ops was an accident meant to be. 

I had been a Product Owner for years and enjoyed the work. I was a team lead for a Content agency before that, and a mentor/supervisor of a call centre before that – it felt like my career had a path. Over time, however, I noticed that I enjoyed building a team of product owners more than product work itself. I found helping others become better at their work far more interesting than focusing on being the best tech person I could be. Eventually, I asked myself: if what I enjoy the most is coaching others and supporting their growth, am I in the right role? Shouldn’t I be spending all of my time supporting people?

The answer was clear to me: I wanted to build up people, not products. My very first HR role had a direct people happiness element to it, and this was also my first time working fully remote. All of that came with a steep learning curve. Five years on, here is what I have learned about navigating People Ops in remote companies and making sure people are their best at work. 

My vision of the People Ops role

After I officially transitioned to People Ops, I noticed something I didn’t expect – people were acting differently with me. When I was leading product owners, translators, support agents – we chatted effortlessly. But when I was seen as someone representing HR, it was different, more rigid somehow. It didn’t feel like they were being their authentic selves. They picked every word carefully, making sure they didn’t say the wrong thing or didn’t expose any mistake they had made. The only thing I could compare it to is how people act around law enforcement. It felt they were hiding the hard stuff from me. 

I found it hard and frustrating because the very reason I had moved to People Ops was to authentically connect with people and coach them. I realised this was neither my fault nor theirs. It was instead a byproduct of the lousy reputation “HR” had built historically and the fact that not many employees understood that People Ops existed to resource people not treat them as resources. It’s a challenge that many in People Ops can relate to. 

Tech giants such as Google, where people happiness and people operations functions originated, have been advocating for the better perception of the role for years. One book in particular, Work Rules, has made a massive difference in stating the alternative vision – one which is more authentic to the motivation driving People Ops. But more often than we like, the bad rep notion of managing resources still lingers, so it’s on us to proactively show that we care about people’s well-being. It’s on us to communicate that People Ops is ultimately about helping people be their best while at work.

I believe that we can only achieve this by showing that we genuinely care about people and how they feel. It’s on us to instigate changes that make our companies a better place. We have to prove we are someone who is passionate about diversity, inclusion and equality, and a champion of employees, through all of our actions, such as the ones I outline below. 

  1. Elevate different cultures 

One of the most extraordinary things about being part of internationally remote organisations is what melting pots of culture and diversity they can be. A different way of thinking, speaking and understanding the world can help to create truly robust company cultures that build great product and customer experiences, and are exciting places to work. Being surrounded by and learning from colleagues from around the world has been one of the most significant upsides for me personally when it comes to working remotely.  

I have been deliberate about making the most of this proximity to other cultures, however, I have learned that this may not come naturally to everyone on the team. A core part of my role is making sure everyone is exposed directly to the cultural richness of remote organisations by creating opportunities to share experiences. 

At Boundless, which is currently a company of 11 people, we are fortunate to employ people from eight nationalities. Since I joined on the cusp of the Covid19 pandemic, I have been making sure that, as we build the world’s first global employment platform, we also get to know and understand each other. For example, during our most recent team social gathering, we asked people to share a picture of their favourite place and tell us something special about it. Through this experience, we learned about Matthew’s favourite lake in Macedonia, Irina’s fascination with Grace O’Malley, a badass pirate queen from Ireland, and some of the extraordinary fruits in Brazil such as Jabuticaba that Vivian dearly misses.

It’s such interactions that slowly help build understanding about people from other cultures. 

Other things that I have found to be helpful is to run workshops where we get to know each other by completing and sharing results of tests such as 16 personalities or the High5 strengths finder. Separately, in our company handbook, we have a section where people can share how others can work best with them, which is based on the how to work with me philosophy. 

Even previous to Boundless, whenever I encountered working with someone from a new country, I always made an effort to interact with them to get a sense of how they communicate, how they think and how they see the world. A thing I have found very helpful is asking people about suggestions of books or films about their countries and nationalities they would recommend to understand their experience and background better. Some books I have recently been suggested are The Portuguese, The Irish Paradox, and Geography of Bliss.

All these initiatives are important because, as beautiful as multicultural exchange is, it can be prone to misinterpretations, especially in remote settings. Establishing rapport can be a great antidote. As a People Ops leader, I have to lead by example and prioritise building cultural awareness and competence about subtle (or more obvious) differences. 

  1. Attune your communication style

In internationally distributed companies, different cultures, nationalities and humans come with varying styles of communication. Some prefer to jump on a call, others like instant messaging, while others still would really insist on asynchronous communication where they respond in their own time. One of the things that I have had to learn very fast as I transitioned to a People Ops role in a remote setting is becoming fluent in all of these. 

Beyond the communication style, what also matters is the language itself. For pretty much any remote company, English will be the primary working language. For many people, however, English isn’t their native language and is at varying degrees of fluency, which determines whether subtleties will be lost in translation or not. Even when English is their native language, different English-speaking countries do have their own expressions, which might be misinterpreted. In People Ops, you have to make sure that everyone understands everything – any policies, charters, or messages sent from leadership. I have always seen my role as interpreter, making sure that information I pass on to the team lands the same way to people in Spain, the UK or Bulgaria. 

I know this because early in my career, I used to misinterpret indirect, politically correct statements coming from North American colleagues as mere ideas. They, however, fully intended them as actual instructions. When I took on the role of People Ops, I wanted to prevent that from happening to anyone else, so I read The Culture Map, which has helped me immensely since.

Keeping language as direct and straightforward as possible is key to avoiding any misinterpretations. Take, for example, very emotional things such as salary or benefits like time off, maternity leave, pension contributions, etc. Any information relating to either has to be very straightforward, and very accessible, almost scannable. There is no room for misinterpretation. Arguably an example of that is unlimited time off. Studies show that when in place in a company, people actually end up taking less time-off than if there was a set number of days. That’s because it lacks clear guidance and people look for subtle signs of what is acceptable and what isn’t and err on the side of caution.

Using a language that doesn’t sound overly autocratic is also very important. This is a bigger problem in Europe, where complex Latin languages have permeated in a lot of legal and official communication domains. As the person representing other humans in the organisation, you have to make sure you spare them from that. 

Another example of misinterpretation between cultures happens because some cultures treat the concepts of “yes” and “no” differently. This could play out in different ways. In certain regions of the world people do not mean the same affirmative ‘yes’ that we mean in the West. It’s not that they are being deliberately deceiving, it’s that in their culture, the word ‘no’ isn’t taken lightly, and in the context of work, there are many subtle nuances which make it very unlikely to be used. This can also happen through non-verbal communication. People from Balkan countries such as Bulgaria, Greece, and Turkey nod their head when they mean no and shake their head when they mean yes. 

It will be on you to reframe your communication and to observe the subtle differences in the ‘yes’, so that you can understand when a challenge is presented and offer the support needed. You need to be able to read between the lines, and the words and gestures that are being used.

  1. Connect as often as possible

There is a significant variation in the perception of how people feel valued in a shared physical space versus being distanced geographically, and this can negatively impact their professional development. As People Ops professionals, we need to consider this fact, when we field concerns or questions from team members. For starters, frequent check-ins allow for regular acknowledgement of people and their work, keeping morale and motivation high, and most importantly catching the early signs of and preventing burnout. However, remembering that people may feel less confident, also dictates how to approach the check-in. 

Every team member in Boundless has access to my personal calendar and can schedule a meeting at any point. They are encouraged to book a session whenever they want. If they don’t, I will still try to reach out and have a virtual coffee every 6-8 weeks. For each check-in, the format is free – they can talk about anything they want, and even just vent if that’s what they need at that time. Check-ins are confidential by default.

If nothing comes up, I have questions that can spark the conversation, such as how things are, what they are finding challenging right now, and what they would like to change. But also what is going good, what new things they’d like to learn, what they are enjoying the most out of all the things we get to do. We’re a new team, and we each get to wear many hats. It’s an amazing place, especially for the youngest team members, to try things out and discover what really makes them excited about work.

  1. Build trust every day

To maintain a healthy connection with everybody my role as a People Ops person is to build trust with them every single day. This can be more difficult when working remotely because people do not see me as often. This means that having difficult conversations, raising tough questions, or flagging HR concerns is more intimidating and as a People Ops person, I have to take extra care to make people feel comfortable. That starts with trust. To make sure I build it effectively, I have established rules for myself in how I connect and communicate with everyone, which I make a point never to break.

  • Keep strict confidentiality. I start every check-in by being very explicit that things will always be confidential. If by context, that’s not the case, I explain exactly what I may need to disclose. This way people can get into the conversation not feeling manipulated, and knowing where they stand. And when I said that something was confidential, I have kept it that way. Even nowadays when I am asked to share some of my own experience and give anecdotes, I decline that because I steadfastly want to keep people’s privacy. It’s a bit like client/attorney privilege – I feel the responsibility to act in their best interest, and to keep what they want private.
  • Be clear who is advising them. As people have sought my opinion, there are always two places where it can come from: the official company policy and stance, or my own personal two cents. People must know who they are talking to – Stefania, the People Ops manager of company X or Stefania, the colleague, and friend who has good instincts about things. Knowing which one it is, builds trust, and helps me be seen as a more trustworthy person.
  • Be honest if you can’t help. There are certain circumstances where I am not the right person to offer advice or help. It is essential to be clear with that and not create false expectations of being able to help. 
  1. Approach conflict with care

Interpersonal conflict can disrupt healthy workplaces, and remote settings are no exception. The fact that people are not working from the same physical space should not be an excuse not to deal with them. When I have encountered conflict in previous organisations, my role has been to diffuse it. One might assume that resolving conflict is more difficult in a distributed setting. I, however, find it somewhat easier. That’s because working from home or simply not being in the same physical space provides more safety in these tough situations. It gives the headspace and protection that people in vulnerable positions, such as during a conflict, need. Here is a conflict resolution framework that I have found helpful: 

  • Validate whether my input is in fact needed. I approach conflict situations by trying to hear out both sides independently, give some advice, and if it’s possible, to let them try to deal with the problem themselves. Sometimes all people need is an impartial opinion, and they can take it from there. I’ve often done pre-conversation coaching, and post-conversation debriefing – to support the process, but let the relationship build itself without interfering unnecessarily.
  • In situations where my input is needed I start by making sure that I create a context where I can hold some space. Each party needs the opportunity to tell their truth independently, and why they found what was said or done as an attack, betrayal or abuse of trust. They need to feel heard. This helps everyone understand where the heart of the conflict is. Only after understanding where the breach of trust happened can you bring people in the same physical or virtual space to face each other. 
  • After I have heard each side, I create a sense of support and safety before we all speak together. I focus on the future and encouraging everyone to see the conflict as an opportunity to learn from what happened so we can build a better way to work together. 

The bottom line is that conflict is usually a misunderstanding of a point of view between two different personalities, both moved by the best of intentions. That may happen more easily in a remote setting where different communication styles, possible cultural differences, or lack of good rapport between the two sides contributes to the clash. As a people expert it’s important to remember that most people are, in fact, inherently good, but very fragile and can be pushed beyond their boundaries. It’s quite a human thing. Understanding that may be one of the most important things you can do as a People Ops partner.

Conclusion

I hope my experiences can help others become the best People Ops professional they can be. Learning from peers in other organisations is a great way to broaden your perspective and get great ideas. Because of the belief that people learn best when surrounded by individuals they can learn from and be challenged by, we have started a community for People Ops leaders. It’s our safe space to talk about all the difficult challenges and help each other. Drop us an email to peopleops@boundlesshq.com if you want to join and get involved. 


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