Practically Remote: Leadership

Written by Dom Kirby

Former MSP Owner, CyberSec Practitioner, Modern Work Pro, Evangelist, Husband & Father

February 5, 2024

A lot of folks I work with say that managing remote teams is dramatically different than managing in person teams. In many ways, I agree. However, I also think that fundamental principles of modern leadership apply – the most important among them being trust.

Key Considerations of Remote Management

There are a lot of leaders who have grown accustomed to “managing seats” (as the book Remote puts it). That is to say that they aren’t necessarily managing around outcomes, but more so around seeing their people on Monday through Friday from 8AM to 5PM. I don’t think that’s the right way to lead, and I don’t think that was ever the right way to lead. Fundamentally, I don’t believe you can drive high-yield results without managing the work and leading the people. With that approach, it doesn’t really matter where the people are physically located (assuming you aren’t leading a manufacturing line or something like that). If today, you’re finding yourself leading seats, start to think about managing work and leading people.

Managing Work: It’s all about the Data

As the saying goes: “Inspect what you expect.” If you’re going to transition to managing work, you need to know and be able to measure your team’s expected outcomes. There is no single dataset to use for this because every team is doing some unique work, but here are some general ideas.

Task Management

If your team doesn’t already have a central place to manage workload and general tasks (like a PSA), get one in place right away. Ideally, something the whole team sees and collaborates on. A simple tool to start with is Microsoft Planner, but there are plenty of other like Wrike, Asana,, etc. Task management is also an essential piece of the puzzle to avoid overloading your team. I’ve been guilty too… We have a quick call, delegate something, and go on. Your team-member wrote it down. Rinse and repeat that too many times and you’ve overloaded your team! If you have a central/shared space, you can see just how much work you have dished out and where people are at.

Transparent Reporting

This is key. People need to see the fruit of their labor (or at least most people do). Be as transparent as you can with your team about the company goals and results. I think you’d be surprised how good it feels when your whole team is celebrating hitting that big target you kept talking about!

Missions and Outcomes

Mission and Vision are critical for any team, as are attainable goals. Whether you use OKRs, KBOs, Rocks, wish lists. It doesn’t matter, but you need to have a purpose, and steps to achieve that purpose. This becomes even more critical in the remote leadership landscape because you don’t always get the same level of human connection you get in the office. Leverage technology to lay out your goals in a central space and allow the whole team to keep each other accountable. Some tools for this include Viva Goals, (for EoS folks), and a few others on the market. I trialed Viva Goals to check it out and it seems like a powerhouse of a tool for the price!


People are complicated, it just is what it is. However, that complexity is a thing I’ve come to love. It means that everyone on your team has a unique mission and vision of their own. Empowering your people to find and own their mission helps them connect their work to that mission (or not, and then they are empowered to find a place where that connection exists). A mission doesn’t have to be a big, majestic thing, either. Someone’s mission could be to work forty hours per week doing something they like and to make a livable wage. That’s okay! If they like what they do, then there’s no problem! Some people have grander missions, I know I do. My work aligns with my mission, so I put a whole lot of effort into it.

When leading remote people, you need to lock on to their mission, and connect their work to it. And notably that mission may someday no longer align to your mission. That’s okay too, empower them to embrace their own mobility and find a new role in your company or elsewhere!


if your follow some version of the guidance above, I think the performance part can come pretty naturally. If tasks are clearly and transparently laid out, and aligned to projects or goals, your performance management becomes simple. Were things completed on time? Are the goals on track? Did we communicate properly when the goals were off track? There are all really simple metrics you can use. And, if you used a team/task management platform, they are at your fingertips in real time.


People are typically social creatures. At a minimum, we should be having some sort of contact with our boss! One on one meetings should still be a thing remotely, at a cadence that works for you and your employee. Additionally, productive team meetings are welcome (BUT PLEASE DO NOT OVERDO IT). I hold a bi-weekly team call where we review wins, any headlines that are necessary, and share feedback with each other. This gives the team a space to connect with each other and share wins (or learnings). We’re also known to host the occasional virtual happy hour or team lunch – it’s just a space to have fun and talk about not work stuff (we host them during work hours).


In Conclusion

At the end of the day, I don’ think there’s a massive difference between remote and in-person leadership, assuming you’re leading people and managing work/outcomes. If you only wanted to take one key takeaway: You must be more intentional about connecting with and empowering your people. You won’t have the impromptu in person interactions that you may have been used to in the past, you have to forge the path.


P.S.: ALL leaders should have this, so it goes without saying. Maintain a virtual open-door policy! My people can ‘bug’ me any time they need, drop time on my calendar, or just call if I’m green on Teams. You should always be available for your people.

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