Managing Remote Teams For The First Time

Remote work only works when people feel connected. That’s the hardest and most important part of being a remote manager. I was hired during the pandemic and have now spent four years managing a fully remote technical team. Last year, I brought my team to Muir Woods. We stepped away from screens, walked under redwoods that have stood for centuries, and just… talked. No slide decks. No Slack notifications. Just people, connecting. That day reminded me: 👉 Remote work only works when leaders build connection with intention. Here’s what I’ve learned managing remotely for four years: 🌲 Clarity or chaos. Without crystal-clear OKRs, people drift. 🌲 Hire adults. A senior team that can self-manage is non-negotiable. 🌲 Respect human rhythms. Some work at 6 AM, others at midnight. Flexibility builds trust. 🌲 Norms > assumptions. Define core hours and Slack expectations—or miscommunication will do it for you. 🌲 Meet IRL. Even once or twice a year. No Google Meet call replaces breaking bread or walking trails together. 🌲 1:1s are lifelines. Weekly conversations (and sometimes same-day check-ins) stop issues from festering. 🌲 Recognition matters. A quick shout-out in a virtual call or Slack message makes people feel seen, valued, and motivated. 🌲 Make progress visible. Jira epics, Kanban, monthly reviews. visibility = accountability. And right now, as remote jobs are being cut faster than in-office ones, two things matter more than ever: 💡 Show value. Invisible work too often looks like no work. 💡 Work loud. Share updates. Celebrate wins. Make your contributions known. Remote leadership isn’t easy. But when it’s done right, you don’t just manage a team—you build a resilient, independent group of people who can thrive anywhere.

5 hard-earned lessons on managing a remote team of 70+: 1 - Embrace the chaos (but add some structure) Look, I'm the first to admit I'm not a fan of rigid processes. But when you're dealing with a large team of remote workers, you need some guardrails. We've implemented just enough structure to keep things moving without killing creativity: • Use project management tools religiously • Set clear deadlines and expectations • Allow flexibility when you can 2 - Overcommunicate, but don't micromanage. Culture Isn't Just for Offices Just because we're not all in the same room all the time doesn't mean we can't have a kickass company culture. At Taktical, we've gotten creative: • Virtual happy hours (yes, they can actually be fun) • Online game nights (nothing builds team spirit like crushing your coworkers in Rocket League) • Random coffee chats (our Slack bot pairs people up for casual convos) Culture is more than just forced fun. It's about creating an environment where people feel valued and connected. 3 - Hire for Self-Motivation When you can't see your team, you need to trust them. That means hiring people who can get shit done without someone breathing down their neck. What we look for: • Track record of delivering results • Strong communication skills • Ability to manage time and priorities Remember, in remote work, output matters more than hours logged. 4 - Tech is Your Friend (Most of the Time) We live and die by our tech stack. But here's the thing – more tools doesn't always mean better communication. We've learned to be intentional about our tech choices: • Slack for quick chats and team bonding • Zoom for face-to-face meetings (camera on, people!) • Notion for documentation and knowledge sharing And yes, sometimes a good old-fashioned phone call can solve problems faster than a string of Slack messages. 5 - Mental Health Matters Remote work can be isolating. We've made mental health a priority at Taktical: • Encourage regular breaks and time off • Provide resources for mental health support • Lead by example (I make sure to unplug and recharge regularly) Remember, burnout is real, and it's your job as a leader to prevent it. Building a remote team isn't easy, but it's incredibly rewarding. We've been able to tap into global talent, reduce overhead, and create a flexible work environment that attracts top performers. Sure, there are challenges. But with the right approach, you can build a killer remote team that's not just productive, but thriving.

I wasn’t always a fully-remote CEO... But when I launched Squad App, I wanted it to be 100% remote from the start. I’ve been working in tech my entire life— With international teams across different time zones my entire career. Here’s how I leverage my experience to build a world-class culture with no office 👇 1. Flexibility as a rule You can’t lead an international team without being flexible. I built my daily schedule from the ground up to accommodate different time zones— Starting early with our European teams, focusing on American activities during the day, and wrapping up with our teams and partners in Asia. 2. Proactive communication Working remotely exposes any flaws in your communication style. Remote teams don’t get the exposure of in-person conversation— You MUST learn to express ideas clearly over Slack, Zoom, and Loom, and get it right the first time. Otherwise? People will carry on with misunderstandings, and you’ll find out hours later they did something completely wrong because of poor communication. 3. Fully embracing technology for connectivity Coming from a tech background, leveraging Notion, Workspace, Slack, and other async-friendly tools for collaboration came naturally to me. Simply put, the right tech stack will 10x your productivity. Even if you’re not a remote leader, get serious about the tools you use. They say great photographers aren’t people with the best cameras — it’s those who understand how to take full advantage of what they have. It’s the same for remote teams. They understand how to leverage collaboration platforms to their full potential, no matter which they’re using. 4. Fostering a culture of flexibility and trust You can’t build a remote team without placing your full trust in them. Why? Because you can’t hover over people’s shoulders, or force everyone into a meeting room to hash things out in-person. You need people who can turn around quality work without you controlling the process. Remote teams are self-starters working together toward a common goal— Trust matters here more than ever. 5. Prioritizing employee well-being Not seeing your team in-person makes it harder to pick up on struggles they might be facing that you’d notice in the office. You don’t see anyone sad, happy, frustrated, or anything else. You see them for a few minutes on Zoom calls, and that’s it. That’s why it’s crucial for remote leaders to be proactive about team health — because they won’t share it otherwise. Ask them how they’re doing. Ensure they’re using their time off. And most importantly, emphasize an open-door culture. All this is the backbone of Squad App’s success in remote work, and why we’ve been so effective — despite being 1000s of miles apart — from day one.

I've worked remotely for 12 years. Here are some "best practices" I've developed and/or seen from other CEOs of remote-first companies: (Honestly, these would work well whether you are a CEO, senior leader, or middle management at a remote-first, hybrid, or in-office company... ...so if you're a People Leader that's new to remote work, no stress!) 1. One-on-Ones Have regular 1:1 meetings w/ your direct reports. These are not meant to check on the work. It's meant to check on the person doing the work. This time is for coaching, unblocking, offering feedback, planning for the week/month/quarter ahead, career development, etc. Most managers want a "status update" in these meetings, which can be done async. The best managers use this time for feedback and strategy. Whether you meet for 15 minutes, or 1 hour. Meet every week. 2. Lead By Example Work and communicate in front of your team about everything - except of course for personal matters. Communicate in public Slack channels instead of DMs, like if you had an open floor plan office. Be accessible and visible, especially as a manager or anyone taking on a leadership role within the company. Your action reinforces positive asyc standards and also shows people the quality and speed of work you are getting done. Show them you care by showing up. 3. Document Everything. The best remote-first companies like Remote, GitLab, and Automattic all have public and/or company-wide handbooks with standard operating procedures on how to manage all aspects of the business. These are massive companies with tons of people decentralized around the world. And yet their leadership and their CEOs are "in the trenches" documenting things themselves, writing up SOPs, and communication best practices async for the entire company to see now and into the future. Don't be "too big" as a manager to write up a how-to document. 4. Check In On Your Team's Workload People think remote workers don't get anything done. The reality is most remote workers work too hard. It's so much easier to overwork when you work from home / work from anywhere. As a leader, you may need to force your team to take PTO, take a break, or take on less work. Don't wait. Take a load off your team right now. Rest is essential if you want top-performers to remain with you for years to come, and if you want top-performers to remain productive. 5. Be Available This mostly means limiting direct reports. No manager should have more than 8 direct reports. I have 4 right now at Offsite, plus a couple contractors who report to me. My main job is to equip my leadership team to do great work. I am also an "individual contributor" for marketing, but my most important work is supporting my leadership team through tough problems and exciting opportunities. - - - Again, this is good for remote-first, hybrid, and office-first managers. What am I missing though? Comment below! Then, repost. 🙏