TL;DR: Feeling out of the loop with your team’s work creates exhaustion and prevents true delegation. The solution is implementing three core systems: reframing how your team thinks about work (deciding, designing, doing), setting up a project management tool like Asana or Notion, and creating communication rhythms including team meetings, call recaps, and regular updates. These systems build trust through visibility and free your brain to focus on high-value work instead of worrying about dropped balls.
You: “Hey, what’s going on with that project? I haven’t heard anything in a couple of weeks.” Your team: “Oh yeah, I got stuck because…” OR ” I’m working on it…why don’t you trust me?”
Sound familiar? Almost every client I’ve ever worked with deals with big communication gaps with their teams. It’s hard for entrepreneurs to trust that things are being handled because they can’t see what’s going on.
This feeling of being out of the loop is exhausting for everyone involved. You can’t truly delegate when you’re worried about dropping the ball, and your team feels micromanaged.
You know I’m a systems person, so you know where this is going – this is a systems problem with a systems solution! What you need are good rhythms for visibility across your team (ESPECIALLY if your team works virtually).
Here are the three things we always talk about when our clients are dealing with this issue:
How Should Teams Think About Different Types of Work?
Everything we do has four types of work:
- Deciding – what are you going to do?
- Designing – processing and managing the work
- Doing – actually implementing the work
- Decompressing – resting and resetting for another round
That second category—designing—includes all the behind-the-scenes project management: breaking a plan into steps, keeping notes, setting deadlines, updating people on status, blocking off implementation time, and organizing information for future reference.
Too often, teams see design work as a distraction from the “real work.” But processing the work IS work. It’s an incredibly important part of what you do, and it’s even more critical for virtual teams because no one can see each other working. Everything has to be communicated.
When we deploy Operations Managers in our clients’ businesses, one thing I tell them over and over is that the trust they build through great processing is 50% of the value they provide to their clients. Our clients need to know beyond a shadow of a doubt that they can mention something once and forget all about it because they know we’ve got it.
This isn’t intuitive, but I’ve seen it play out dozens of times. When we ask our clients what’s most meaningful to them about our work together, they never mention a deliverable we created. They mention the relief they experience when they have the visibility they need to feel confident in trusting us.
Trust is built through making promises and keeping them, and through communicating OFTEN. It’s worth the time it takes to take great notes and update people regularly (sometimes saying the same thing a few times).
I’ve never met a team that communicated too much, but I’ve met plenty that didn’t communicate enough because they were ‘too busy getting things done’ and were surprised when things went sideways.
What Project Management System Should You Use?
You need somewhere outside your brain to capture everything that needs to be done. Your brain is excellent at having ideas, but it’s terrible at file management. Using your mind as a storage system will burn you out.
You know that nagging feeling in the back of your mind wondering “Am I missing something? Is there something else more important I should be doing right now?” That’s exhausting. Plus, when one task bounces in and out of your awareness five times throughout the day (usually pinging you about a task at particularly unhelpful times), it feels as heavy as five different tasks even though it’s only one.
The solution doesn’t have to be expensive. The free version of Asana works great, or you can use Notion like we do. What matters is having a system where:
- Everything you and your team need to do gets captured and can be accessed outside of your head
- You can assign tasks and see what’s on everyone’s list
- You can track the status of projects
You know your system is working if your brain rarely dives into a “crap! I forgot about that!” spiral.
I’ve seen businesses making $20M a year who didn’t have one of these and didn’t see the point of one (showing up at an event to find you have no tables and chairs because you forgot to reschedule them is why). I’ve had a project management tool since day one- this is a nonnegotiable system.
What Communication Rhythms Prevent Micromanagement?
Without regular communication systems, you’ll end up in one of two frustrating scenarios:
Option 1: You’re talking all the time. Your team pings you constantly with questions, you get information in scattered pieces, and you spend all day in reactive mode responding to Slack messages and texts and emails.
Option 2: You hear nothing and have to actively check in with people about everything.
Instead, set up a communication rhythm that works for everyone:
Team Meetings
Schedule a regular meeting to review priorities and what everyone’s working on. Keep it concise and focused. Some teams benefit from 15-minute daily stand-up huddles; others can meet once a week. You can use this time to update the team about new developments, answer questions/unstick things, and hear what everyone is working on.
If Option 1 sounds familiar to you, these meetings can also consolidate the questions you need to answer. You can turn down the volume on incoming messages because people are just adding questions to a list they can ask you in a batch.
Call Recaps
After every meeting, a team member should send a recap covering what was decided and what everyone committed to work on. They can build this from an AI notetaker to make it easy!
Regular Updates
Each team member should send you regular updates with three sections:
- What I’ve done
- What I’m doing next
- What I need from you
Emails once or twice a week may be enough, or maybe you’d prefer a daily Slack message. If you’re meeting live every day, you could do these less often! Having an overview like this written down becomes a really helpful reference point, too – we always think we’ll remember more than we do.
Why This Matters
Your brain won’t release something if it believes the ball might drop. You need systems you can fully trust to keep tabs on things, so you can actually let go and focus on your highest-value work.
You’re spending a lot of time/energy/money on your team. Setting up a good system so you have visibility into what, exactly, you’re spending that money on is worth doing. It also spares you those annoying ‘quick question’ texts, and spares your team those annoying ‘hey, where are we with x’ messages too. Everyone wins!
I’d recommend picking one thing to start with and layering on more pieces as you go. Remember, processing the work is a critical part of the work – and having something like this will make your vendors and attendees happier, too.
Frequently Asked Questions
How often should my team send me updates?
The frequency depends on your team’s workflow and meeting schedule. Most teams find success with email updates once or twice per week, or daily Slack messages. If you’re already meeting live every day, you can reduce written updates. The key is consistency – pick a rhythm and stick to it so updates become a reliable habit rather than an afterthought.
What’s the best free project management tool for small teams?
Asana’s free version is excellent for most small teams and includes task assignments, due dates, and project tracking. The learning curve isn’t very high, so we tend to recommend this to teams who are upgrading from sticky notes. Notion is another popular choice that combines project management with documentation (and it’s what we use). The “best” tool is whichever one your team will actually use consistently – start simple and add complexity only as needed.
How do I get my team to stop seeing project management as busywork?
Reframe it as “designing the work” – an essential step between deciding what to do and actually doing it. Emphasize that for virtual teams especially, processing work through documentation and updates is how trust gets built. Share examples of when poor processing led to problems, and celebrate when good processing prevents issues before they happen. And of course, walk the talk! Invest in good tracking and communication for yourself, too.
My team says they’re too busy to send updates – what should I do?
This is a red flag that usually leads to bigger problems down the road. Explain that updates take 5-10 minutes but save hours of interruptions and miscommunication. If they’re genuinely overwhelmed, your team meetings can serve as verbal updates while you work on workload management. You can also consolidate communication – batch questions for weekly meetings instead of constant messages.
How long should team meetings be to review what everyone’s working on?
Keep meetings concise and focused – 15-30 minutes is ideal for most teams. Daily stand-ups should be even shorter (10-15 minutes maximum). The goal isn’t detailed project reviews; it’s a quick sync on priorities, progress, and blockers. Detailed discussions should happen separately with only the relevant people involved.
