Managing Remote Teams

Bridging the Gap: Leading with Intention in a Remote-First World

In the past five years, we’ve seen a significant shift in how companies approach work, with many moving towards remote-first environments. While some champion this model, others question whether it harms workplace engagement, raising concerns about maintaining strong connections and collaboration. Personally, I believe remote-first work can be just as enriching and fulfilling as any other structure no matter the distance—when it’s approached with intention and care.

"True workplace engagement isn’t about the overarching policies or processes alone—it’s about people leaders intentionally investing in people, and that investment starts with you."

I’m Sam Blinde, and I’ve been an engineering manager at Nearform for the past two and a half years. During this time, I’ve held the responsibilities of being both a senior software engineer on client projects, and a manager who is directly responsible for the growth and well-being of my direct reports. Each of my direct reports works on entirely separate projects, with no overlap between them. Because consultancy projects vary in length, our structure intentionally pairs direct reports with managers for the long term, regardless of project assignments. This approach allows direct reports to build lasting, meaningful connections with their managers over time.

As a caveat, our managerial structure presents its own challenges. With team members spread across different projects, the risk of isolation is very real—each person working within their own silo at times. It requires deliberate and consistent effort on a manager’s part to foster connection and a sense of community within their teams. Over my time as a manager, I’ve come to understand that true workplace engagement isn’t about the overarching policies or processes alone—it’s about people leaders intentionally investing in people, and that investment starts with you.

Finding Your Leadership Compass

There’s a quote by Ira Glass that I often reflect on when I think about the work I aspire to—it’s commonly referred to as ‘The Gap.’ In the quote, he describes the gap between where you are and where you want to be, and he refers to what ‘got you in the game’ as your ‘taste.’ Now, you might be thinking, “Sam, what does this have to do with management?” Bear with me for a moment—I promise, it connects!

Take a moment to think about what led you to pursue management. What’s driving you toward your path? Was it a manager you admired and wanted to emulate? Or perhaps a manager whose example taught you exactly what not to do? Maybe it’s a desire to create the change you’ve always wanted to see or to carry forward a legacy that inspired you, or the opportunity presented itself and you were the right person at the right moment for it. Reflect upon your team next. How do you want them to feel when they log on and off of work each day? How do you envision their relationships with one another in this remote working environment? How do you want them to feel about the work they do and the impact they have?

Let’s go back to the Ira Glass quote. The ‘taste’ that got you into the game—think of it as a metaphor for your values, the core drivers that compelled you to step into management or aspire to leadership. It’s the sense of purpose, the thing that anchors you to your current role, or motivates you to pursue the path you’re on. Whether you feel you’ve arrived at where you want to be or you’re on the journey, it’s that internal compass—the shift in mindset—that set you on the course and will connect you to where you want to be in your career journey. The questions I asked, they’re at the heart of that compass. It’s what led you to read this post today.

Before you move further, I’d encourage you to reflect further on your values. What truly matters to you as a leader? What kind of values do you want to cultivate in your team? These ideas might not fit within one single statement or sentence, and that’s okay. Crafting a value statement—one that resonates with your mission—will help ground you in your role as a leader and manager. Chances are, there will be some overlap between your values, the values of your direct reports, and the company you’re a part of. A well-defined mission statement can help guide you in creating connections within your team that feel both meaningful and authentically you.

One-on-One Engagement with Purpose

Once you’ve reflected on what sparked your interest in management and developed your value statement, it’s time to consider your one-on-ones with your direct reports. If you don’t already hold regular one-on-ones, now is the time to begin creating these intentional spaces on a consistent basis.

As we’ve discussed, your values play a significant role in your approach to management and shape the philosophy behind how you lead. For me, trust, respect, advocacy, honesty, ethics, and transparency are my core values. While I acknowledge that being a manager places me in a position of power, I view people management as a mutual journey—one where I feel privileged to walk alongside my team members. It’s a mutually beneficial relationship: I grow through the process of managing my team, and they benefit from the strengths I bring to the table.

When I onboard new direct reports, I begin with a one-hour meeting to get to know them, share my management philosophy, and establish the foundation for our future conversations. For the first month, I meet with them weekly for half an hour, always leaving room to extend our time to an hour if they wish to dive deeper. After this initial period, I allow them to set the cadence of meetings—weekly or every two weeks—based on what works for them. For my established team, they meet with me every one to two weeks at their preference, and we adjust the timeframe based on need or circumstance.

In our one-on-ones, I always want to allow space for individuals to check in about how things are going, both in their projects, their work life, and their personal lives that they are open to share with me. On a practical level, understanding their projects helps me know where I can advocate for them, provide guidance, and support them in achieving their goals. Every person has their own individual needs, wants, motivations, and drivers, and you have to be considerate of these things for each individual. Being in touch with your direct report in this way also helps you be in tune with them, and notice patterns that may repeat over time throughout their career. These patterns could be subtle or more obvious, but they can vary, and the more you continue regular one-on-ones and mentoring your team, the better you’ll get at recognizing these patterns.

Beyond work-related discussions, I leave room for other topics to arise. I believe one-on-ones should not solely be a status update—they’re a space for us to connect beyond our roles of manager and direct report. What are they interested in? What drives them? To me, it doesn’t matter if these passions extend beyond work—those conversations are valuable to me. Because of these conversations, I’ve learned so much about my team members as people, and I’ve grown from those experiences. My team has inspired me in countless ways: from inspiring me to return to college, to recommending books and films that have touched my heart. They’ve even introduced me to new tools and perspectives that I’ve applied to client projects and my own life.

Of course, not every one-on-one fits into the above structure: this does not address goal management, performance reviews, delivering and addressing feedback, or identifying and managing burnout, which require different approaches and deserve their own dedicated discussion. These are challenges that every manager faces, but they are topics for another day.

Building Bridges Within Your Team

Once you’ve started crafting connections with individuals, it’s time to take the next step: expanding your focus outward and fostering meaningful connections across your team.

If your team has never had a social casual event, start small. Schedule a twice monthly, 30-minute event over Zoom or Google Meet. Keep it optional, but encourage participation by choosing a time that works for everyone across schedules and time zones. Make it clear from the start that this isn’t about work—it’s an opportunity to relax, connect, and have fun.

To help break the ice, have a few topics on hand, or a short activity for the initial conversation, especially if your team has a few quieter members. Keep in mind your team members who may be more jaded by the most common of conversation starters: don’t rely solely on small talk to spark that first conversation. Let people engage in a way that feels comfortable for them—don’t require cameras on if that’s not everyone’s preference.

When you create a space like this, it opens the door for vulnerability and authenticity—not just for your team, but for you as well. It allows your direct reports to get to know one another, but also to get to know you beyond the role of manager. In turn, it helps build trust, not only between you and your team members but amongst team members themselves. They start to see each other as more than just colleagues—they become peers, collaborators, and even friends. These connections become forged in a space of openness and can lead to a stronger, more supportive team dynamic that might not have otherwise existed.

Fostering Leadership Collaboration

Beyond your team of direct reports, think of the other managers within your organization. How often do you connect with your peers, and those who manage those peers? Building connections at all levels of leadership can have a meaningful impact—not just on you, but on your organization as a whole.

In our organization, we created several spaces specifically for managers to connect. As an example, we have a regional channel where managers can discuss topics that matter to us—from clarifying questions about performance review cycles, sharing important announcements, or simply navigating the challenges of our roles. We also host a monthly Managers’ Roundtable meeting, an optional meeting where we can choose a topic in advance and come together to share experiences, give advice to one another, and support one another. The goal of this space is not to build policies or give official updates; instead, it is to build a sense of community as peers. Over the years, this intentional space has fostered connections that have become an invaluable support network.

It’s worth taking this effort a step further. One of the steps I take beyond the team level is building individual connections with other managers and directors. Doing so—whether managerial peers or other members of leadership—makes a difference. Forming these relationships creates a ripple effect, strengthening the culture of the entire organization. By engaging beyond your own team, you contribute to a larger sense of community, ensuring that the work you’ve started does not end with your immediate circle, but grows to shape the organization as a whole.

Strengthening the Bonds Over Time

Now that you’ve started to make shifts across your reports, your team, and your organization, it’s important to keep the momentum going. You’ve likely started to notice positive shifts in your direct reports, with the benefits becoming clear across the team. As you build connections across your organization, you might even be experiencing some of those benefits yourself. To sustain and deepen these connections, there are plenty of simple actions you can take. While the suggestions here can serve as inspiration, I encourage you to lean into what feels most authentic for you and your team. Stay open to their input—they may bring their own ideas to the table, and lean into your own values as well.

1. Shared Team Channel. Providing a private space for your team to communicate is always a good idea. It creates an easy way for team members to share pictures during your casual meetings, post updates, celebrate good news, or simply ask questions. This kind of space fosters a sense of belonging—a place where your team feels comfortable reaching out, sharing what’s on their mind, or just chatting about topics of interest. A small, but meaningful step, towards building a supportive and connected team culture.
2. Utilizing a Budget. If you have a team budget, consider using it to add some fun to your meetings. Encourage a team lunch for a session, or share a food item from their region for a team show-and-tell. Play a game together—Jackbox games are fantastic for remote play, but there are plenty of options to explore.
3. Working Without a Budget. No budget? No problem. Get creative with what’s available. Build something collaboratively in code during a session, or use a tool like Miro to create something fun as a team. You might even organize a yearly show-and-tell where team members share something fun they’re proud of from the past year. It doesn’t have to be work-related—just something meaningful to them. These activities can bring energy and connection to your team in impactful ways.
4. Take Team Collaboration to a Larger Scale. Beyond the casual meetings, think bigger. What about taking your team’s collaboration and creativity to the rest of the company? Is there something your team would enjoy making and sharing together? Collaborating on something that reaches beyond your team can foster pride and a sense of purpose. The possibilities are endless, you and your team have the power to shape what that can look like for all of you.
5. Stay Consistent. Most importantly, show your team that your social team meeting matters to you just as much as any other. Avoid canceling it unless absolutely necessary, and don’t treat it as an afterthought squeezed into the end of a Friday. Give it the consistency it deserves, and your team will see it’s a priority for you. This goes for all of the efforts outlined above, not just your social meeting with your team. Be intentional, be proactive, be thoughtful.

Closing the Gap: Leading with Purpose

As a manager and leader, you are a catalyst for change, driving the growth and connection you want to see in your team, its individuals, and the broader company culture. By intentionally addressing isolation and fostering engagement in a remote-first environment, you are actively creating a space where everyone around you benefits. Not only do your team members benefit from your work, but you, your team as a whole, and your company. These intentional efforts to build connection and engagement transform the remote experience, creating a sense of belonging that is often difficult to replicate in a virtual setting.