Fixing the Remote Disconnect: Real Strategies That Make Collaboration with Your Executive Assistant Work
Remember when hiring an assistant meant someone sitting outside your office, overhearing your calls, and anticipating what you needed before you even said it? Yeah, that world doesn’t exist anymore. Well, the third one does still happen at Alpine, but gone are the days of your assistant sitting at a desk outside your office.
I’ve been helping clients get started with their first remote assistant for six years, and for a decade before that, I was the remote assistant helping clients adjust to the whole remote thing. I’ve heard all the advice out there, and most of it is overly simplistic and not very helpful. "Use project management tools!" Okay, but how? "Schedule regular check-ins!" Sure, but what does that actually look like?
After five years of helping business owners figure out how to make it work with an executive assistant, I’ve learned what separates teams that thrive from those that are just getting by. If you want to hire an assistant or have a remote team working for you, here are some strategies that have helped our clients transform their remote collaboration from chaotic to seamless.
The Foundation: Over-Communicate, Then Over-Communicate Some More
The biggest mistakes clients make when starting with an assistant usually sound like this:
I don’t have time to delegate or properly communicate this task.
I feel bad delegating this when I could easily do it myself.
My assistant can read my mind and already knows what I want and how I want it done.
I don’t need to give clear instructions or communicate much because there’s no way this task could be done wrong.
The underlying issue in all of these is communication.
The difference between working in the same office as your assistant and working remotely is that, in an office, your assistant naturally picks up context. They see your stress levels, overhear your phone calls, and notice when an angry client walks in. Remote work removes that layer of awareness.
The good news is that your virtual assistant can still stay on the same page. They see the messages in your inbox and how you respond. They review your expense reports. They notice that your calendar is full of back-to-back meetings and that you have a major project coming up next week. But even with all of that visibility, you still carry the responsibility of clear communication.
Here's what actually works:
Document your thinking, not just your decisions. When I assign a project now, I don't just say what needs to happen. I explain why we're doing it, what success looks like, and what we're not trying to accomplish. For example, instead of "Update the client onboarding document," A cleint would write: "Update the onboarding doc to include the new intake form. Goal is to reduce back-and-forth emails during week one. Don't worry about making it pretty—we just need the info there. This is blocking three new client starts, so prioritizing this over social media updates this week."
That extra context takes 90 seconds to write but saves hours of confusion.
Create a communication hierarchy. Not everything deserves a meeting. Here's a great system:
Slack message: Quick questions, updates that don't need responses, casual chat
Async video (Loom): Explaining something complex, giving feedback, walking through a process
Slack Huddle: Something urgent came up that would take too long to Slack about, but it requires a discussion and a mutual decision
Scheduled call: Decision-making, brainstorming, relationship building
Email: External communication, formal records, detailed briefs
Then put this in our team handbook so everyone knows where to go with what.
Embrace redundancy. I used to think saying something once was enough. Then I was wondering why people missed it. Important information gets repeated in multiple formats. A big deadline, for example, goes in Slack, on our shared calendar, in the project management tool, and gets mentioned in our team call. Yes, it feels like overkill. In a remote setting, when you feel like you’ve overcommunicated, you probably haven’t communicated enough.
Time Zone Matters
One member of my core team is an early riser. She’s also two hours ahead of me in Eastern time. Trying to coordinate her availability, my availability, and our other core team members’ availability always felt like it took longer than it should have. The key was figuring out what we actually needed to meet about, and making a plan for the rest.
Here's how we handle it now:
Find the overlap hours and protect them fiercely. We have a two-hour window when everyone's available. That's it. So we use those hours for actual collaboration - meetings, brainstorms, quick syncs. Everything else happens async. I put those hours on the calendar and block them off. No client calls during overlap time unless it's an emergency.
Default to async. Most things don't need real-time discussion. We use Loom for complex explanations, comment threads in our project tool for feedback, and shared documents for collaborative writing. A five-minute Loom often replaces a 30-minute meeting and gives people the flexibility to watch when they're actually alert.
Make meeting recordings standard. Every call gets recorded (with permission) and uploaded to our shared drive with timestamps. Can't make the meeting? Watch the recording at 1.5x speed during your productive hours. Someone confused about a decision? They can go back and review the exact conversation.
The Tools That Actually Matter (And the Ones That Don't)
Every tool promises to be the fix you need for your problems. Let me save you some money: you don't need 15 different tools. I’m naturally frugal so I took the time to learn what we needed on our team and what was a waste of our time and money.
Here's our actual tech stack:
Slack for daily communication. We have channels for different projects, a random channel for personal stuff, and direct messages for quick questions. The key is setting norms: we don't expect instant responses (that's what phones are for in emergencies), and we use threads religiously to keep conversations organized.
One of my favorite tips for Slack is channel-specific Do Not Disturb. Team members can mute non-urgent channels during focus time without missing critical updates.
Asana for project management. I might get cancelled for this opinion, but we spent hours trying Monday.com, ClickUp, and all the fancy project management platforms. Asana/Trello stuck because it's flexible enough for different work styles but structured enough to keep things from falling through cracks. We used automations to keep projects movin,g and every project has clear owners, due dates, and subtasks. No more wasting time asking for updates on projects’ progress when I can just open Asana and see where we are at. We review it in our Monday sync so everyone knows what's moving.
I also love Templates. We built templates for recurring projects (client onboarding, blog production, monthly reporting) so we're not reinventing the wheel every time.
Google Workspace for documents. Shared drives, collaborative docs, comments, version history - it's all there. We use suggested edits instead of just changing things so people can see what shifted and why.
Loom for async video. This replaced probably 60% of our meetings. Need to explain a complex process? Record a Loom. Want to give feedback on a design? Loom with your face and screen. Training someone on a new tool? You get it.
That's basically it. Yes, we use Zoom for calls and Calendly links for scheduling, but the four above are our core. The goal isn't to have the fanciest tools - it's to actually use the tools you have.
Building Real Relationships Without an Office
This is the hard part. People have always been my favorite part of my job. When I first went fully remote, I missed the random hallway conversations, the lunch breaks, the Friday afternoon decompression. You can't replicate that exactly, but you can create new rituals.
Start meetings with personal check-ins. Our Monday team call always starts with "weekend wins and lows." Three minutes per person. Did you finally fix that leaky faucet? Tell us. Did your kid have a rough night? We want to know. It sounds cheesy, but it's the glue that keeps us connected. Remote work only works when we remember we’re working with people, not Slack avatars.
Create space for non-work chat. Our Slack has a random channel where we share memes, recipes, pictures of our kids, a book we are reading, whatever. It's optional, but most people pop in. Those micro-interactions add up to real friendship.
Do virtual co-working sessions. Once a week, we open a Zoom room for anyone who wants company while working. Cameras optional, mics muted unless you want to chat. It's like working in the same room without the commute. Some people love it, others never join - both are fine.
Celebrate wins publicly. When someone crushes a project, it goes in our wins channel with specific details about what made it great. When someone's struggling, we troubleshoot together. Recognition and support are even more important when you're remote because you don't see the daily grind.
Meet in person when possible. We're not fully remote by ideology - we're remote by practicality. When budget and logistics allow, fly your assistant out to join your company retreat or help at your conference. The buy-in is worth every penny.
Boring Systems that Make It All Work
Boring systems are what make remote work great. Here are ours:
Daily end-of-day updates. Each team member posts a quick Slack message at the end of their workday: what they finished, what's in progress, any blockers, what they need from me. Takes two minutes, prevents so many "wait, I thought you were handling that" moments.
Weekly planning syncs. Monday mornings, 30 minutes, entire team. We review the week's priorities, flag potential conflicts, and make sure everyone knows what's critical. The great thing is that over-time this weekly planning session usually becomes bi-weekly or monthly as you get “in-sync”.
Project kickoff docs. Before any significant project starts, the project owner creates a one-page brief: objective, deadline, who's doing what, success metrics, communication plan. Everyone reviews and asks questions before work begins. Sounds formal but it prevents massive confusion later.
Decision-making transparency. When a decision gets made outside a team meeting (which is most of the time), the decision-maker posts in Slack: what was decided, why, and who can provide input if they have concerns. This prevents the "I didn't know we were doing that" problem.
Feedback cycles. We don't wait for quarterly reviews to give feedback. It happens in real-time, in writing when possible, so there's a record and time to process. Positive feedback goes public, constructive feedback goes private.
What to Do When Collaboration Breaks Down
Even with great systems, remote work can feel isolating and confusing. Here's how we troubleshoot:
Audit your communication. If someone seems confused or disengaged, look at the last week of interactions. Are they getting enough context? Too many messages? Wrong format? I once realized I was sending wall-of-text Slacks to a team member who processes information better via video. Switched to Loom, problem solved.
Schedule face time. Sometimes async just doesn't cut it. If a project feels stuck, get on a call. Screen share, talk it through, rebuild the connection. Ten minutes of real-time conversation beats days of confusing message threads.
Check in on workload and boundaries. Remote work makes it dangerously easy to overwork. If someone's consistently missing deadlines or seems burned out, talk about it. Maybe they need help, maybe expectations are unclear, maybe they need permission to log off at 5pm.
Revisit your tools and processes. Every six months, we ask: what's working and what's not? Do we need this weekly meeting or could it be async? Is this tool helping or just adding clicks? If something isn't serving us, we change it.
The Real Talk About Remote Collaboration
Remote collaboration isn't inferior to in-person work, but it's not automatically better either. It's just different. Some things are easier (focus time, flexible schedules, hiring beyond your zip code), some things are harder (building trust, reading the room, spontaneous problem-solving). The teams that thrive remotely are the ones that acknowledge those trade-offs and build intentional systems to address them. They over-communicate. They invest in relationships. They iterate on their processes. They use technology as a tool, not a replacement for human connection.
After six years of running Alpine Virtual remotely, I can honestly say I'd never go back to a traditional office or hire in a traditional office. My core team is 100% remote and because of our systems, this works better than an in-person setup ever could. But that's because we've built communication strategies that work for us - not because remote work is magically easy.
Your team's needs will be different than ours. Maybe you need more structure or less. Maybe video calls drain you or energize you. The key is paying attention to what's working, being willing to experiment, and remembering that collaboration is about people, not tools.
Your Next Steps
Want to improve your remote collaboration starting today? Here's where to start:
Pick one communication channel for each type of message (quick questions, complex explanations, decisions, etc.) and share that guide with your team.
Schedule a 15-minute async check-in where everyone shares one thing that's working well about your current collaboration and one thing that could improve.
Create one template or system for something you do repeatedly - project briefs, weekly updates, client onboarding - and use it consistently for a month.
Have one non-work conversation with a remote colleague this week. Ask about their weekend, their pets, and their favorite lunch spot. Build the relationship.
Remote collaboration isn't about having perfect tools or processes. It's about staying curious, communicating clearly, and treating your team like humans who deserve context and connection. Start there, and everything else follows.
Working remotely in Denver, Colorado Springs, or anywhere in between? Alpine Virtual has been mastering remote collaboration since 2019. We believe the best work happens when people have the freedom to work in ways that fit their lives - with the right systems in place to keep everyone connected.
