Stop Chasing Updates

The infrastructure team just launched a major performance improvement. Marketing rolled out a campaign that's driving record signups. Your biggest client renewed for two more years.

Great news, right? Except you found out about all of this through Slack messages, hallway conversations, and an offhand comment in someone else's meeting.

When you were managing 5 people, keeping track of everything felt natural. Decisions were visible, information flowed organically, and you could easily stay in the loop through regular check-ins and casual conversations.

But as your team grows, the complexity of the product grows, the velocity and the amount of work increases, and the demands on your time to play more of a strategic role become more important, this approach breaks down completely. What once happened organically through hallway conversations and informal check-ins now requires intentional architecture.

The scaling challenge isn't about working harder; it's about working systematically.

From Chasing to Receiving

The foundational shift that successful leaders make when their responsibilities increase is moving from reactive (constantly chasing updates and details) to strategic (having information flow to you systematically).

It’s impossible to know everything that’s going on, nor is it particularly valuable. It’s about building systems that help you stay informed, filter the signal from noise (and yes, there will be a lot of noise), know when something requires your direct involvement, make informed decisions, and represent your team and organization effectively.

Staying Informed at Scale

Any one of these five strategies alone will help to make you more informed about what is going on with your team, your projects, and company — but together, they start to have compounding effects.

Lean on Your Team

Your team should be accountable for keeping you informed, not the other way around. This is a fundamental part of “managing up,” and you can set the expectation by helping your team understand what you need to know and when you need to know it.

When they proactively flag "The CEO might ask about this in the board meeting" or "You'll want to know this before your next status report meeting," they're not just keeping you informed, they're helping you stay ahead.

Of course, this doesn't mean they have to bring everything to you. Work with them over time to understand what level of detail is important and in what format. What makes sense for weekly written updates versus what makes sense in-the-moment? When do you need high-level updates versus when do you want to get in the weeds?

Over time, they'll learn to recognize high-visibility items and potential escalations before they become problems and articulate them to you in a way that allows you to best address them.

Focus on Outcomes over Outputs

The more responsibility you take on, the more “stuff” there will be to keep track of — all of the things being built, all of the problems being solved, all of the things going on day to day. You can’t keep track of all of these individual things, so you’re going to have to come up with a mental hierarchy of what matters: tie them all back to the “why.”

The team is already focusing on and tracking all of the outputs on a day-to-day basis, which means you need to focus on the next level above: the business outcomes they roll up into and why the work matters. By tracking things at the higher level, you'll get higher-level signals that will let you know when things are running smoothly and when to dig deeper.

Think like a newspaper editor: know the key stories and why they matter. You need enough understanding to make informed decisions and ask the right questions, but not enough to second-guess every tactical choice.

Then, when your curiosity is piqued or something doesn't sound right, you should still be able to get into the weeds. But make it a conscious choice, not a default mode.

Information Doesn’t Flow Through Org Charts

By leveraging diverse intelligence sources, you’ll build relationships and learn more about what’s going on within and beyond the team. For example, prioritize having skip-level meetings (within your org, and above you in your org chart) and meetings with your cross-functional partners. These relationships can give you unfiltered insights into team dynamics, potential issues, and opportunities that might not surface through formal channels.

But these intelligence sources don’t just have to be other employees. They can also be competitive insights, market trends, and what’s going on in the industry. These will help you contextualize internal information and identify strategic opportunities or threats.

And, probably most importantly, getting information directly from the customer, whether through analytics, interviews, or feedback, will help you to validate and triangulate if your internal signals are aligned with external reality.

Build Systems That Think For You

Of course, the updates you receive don't just need to be qualitative in nature. Build systems that deliver you insights without requiring any human intervention. What type of data would be valuable to you that you can build dashboards around?

Think about how you can leverage these dashboards to give you leading indicators that signal potential issues before they become problems. For example, if customer support tickets spike in a specific category, or if deployment frequency drops below your team's normal baseline, or if code review cycle time starts trending upward. These early warning signals let you intervene proactively rather than reactively.

These automated reports, alerts, and summaries (just think about everything you can do with AI and agents these days) will help reduce the overhead of staying informed while ensuring consistency in what you're tracking.

Sometimes It’s Not Systems, It’s People

In the end though, the challenge simply may not be about improving the systems, it could be about capabilities.

If you find yourself constantly diving into the weeds or feeling like you can't trust the information you're receiving, you may need to ask yourself whether you have the right people in the right roles. This may be a signal that your scaling challenges are really talent challenges.

Your job is to develop your team's ability to operate independently, not to become better at doing their jobs for them — and one of the harder realizations many leaders face is that these talent challenges are ultimately holding the rest of the team back because it prevents you from operating at the capacity that you need to best serve them.

The fortunate part is that every moment in this process is an opportunity for learning. You should use every decision-making moment to coach your team on judgement, priority-setting, and communication — building their capability to manage up effectively. And if and when the time comes to part ways with a team member, you'll be very clear the type of support you'll need going forward.

The Dual Challenge: Systems + Capability

Here's the thing: you can't just build these information systems in isolation. You need to simultaneously develop your team's capability to operate within those systems effectively.

This means coaching your team members to filter and escalate appropriately, teaching your team to recognize when something needs strategic input, and creating decision-making frameworks that help everyone understand when to act independently versus when to involve you.

When your team succeeds at this dual capability — both the systems and the judgment to use them well — you succeed at scale.

The Long Game

What starts as these information systems quickly becomes something much bigger: it's the foundation for how your organization learns, grows, and adapts. When you get this foundation right, positive behaviors begin to emerge organically. Teams collaborate more naturally, people see clear paths forward, and your best talent can envision a real future.

But, if the foundation is shaky, you'll spend your time patching cracks that keep reappearing.

Stop chasing updates. Start building systems that bring information to you. The real question isn't whether you can afford to invest your limited time in building these systems — it's whether you can afford not to.