Management should never lose sight of what the team does daily
The higher you climb, the less you see of the work that happens below you.
Every promotion moves you one step further from the work itself. First, you’re doing the work. Then you manage the people who do the work. Then you manage the people who manage the people who do the work.
At each step, the daily reality of the job gets a little further from your line of sight. You may no longer be aware of the tool that no longer meets the team’s needs, or the client requests that have started absorbing entire afternoons.
I went through a few iterations of this throughout my career. I moved from a role in enterprise software implementation to the company’s product manager. Though I was no longer talking directly to customers, I was still “touching” the product constantly as I tried to figure out how to make it better.
Then I moved to an executive role. Though I was still the product manager (dual role), I no longer had time to tinker with the product. I was meeting with my team of seven people, preparing reports, and organizing vast swaths of data for the development team. The longer I was in the role, the more I realized that I no longer understood what the new features of the product did. I was also removed from the pain points that customers were experiencing — the kind that the customer service team had to deal with every day (and made their work harder).
The further you move up in an organization, the easier it is to lose sight of what the people below you do all day. It’s even true of self-employed people who may start to outsource some work. It’s imperative to stay in touch with the work in some shape or form. Being too removed from the work is what causes bad decision-making.
The disconnect happens because of distance
Each rung up the ladder adds a layer of abstraction between you and the work.
When I was an individual contributor, I lived inside the daily friction of customers. As a manager, I was only hearing about it. My boss (COO) and the CEO only heard the summaries I provided. At larger companies, these are reduced to quarterly metrics.
By the time the information reaches the top, it’s been compressed so many times. The context is gone, and the context is how people actually understand the problems. (This is part of why so many people feel trapped in the middle as a middle manager.)
When I moved into a product manager role, I was responsible for reviewing issues reported by customers. I wasn’t receiving them directly, but I looked at the tickets. The tickets would contain notes from the customer support rep (if a phone call) or the direct emails from the customers. I could get a sense of the urgency or level of pain that the issue was causing. But the other members of the executive team (the COO and CEO) only saw numbers: how many customers reported the issue? It was my job to convey urgency, but this was often stacked against other priorities.
In Glassdoor’s Worklife Trends 2026 report, mentions of “disconnect” in reviews that reference leadership rose 24% year over year. “Miscommunication” rose 25%, and “misaligned” jumped a whopping 149%. Employees are well-aware of the structural distance — and when they feel like they’re not heard, they may check out entirely.
Part of the problem for managers is the endless barrage of meetings and reports. Your calendar is filled with strategy reviews, daily standups, and quarterly planning, and you stop having time to understand the work itself. You spend your days staring at dashboards and tracking outputs instead of staying tuned in to how work actually gets done.
A manager who only sees the metric can’t tell the difference between “the team is behind schedule” and “the team is behind schedule because something in the process is completely broken and the workaround takes three times as long.”
Freeing up time to stay involved in the work
I remember the intensely uncomfortable feeling that I no longer understood the product that I was supposed to manage. My days no longer had any time built in to get my hands on the product and play around.
But the fix isn’t to swing to the other extreme and do everyone’s job for them, which is what some managers do. That’s a failure mode all on its own: the leader who refuses to let go and hovers over every decision. (And founder mode is the worst version of this.)
Stepping back so people can do the work they’re good at is the entire point of building a team — you hire smart people precisely so you can let go.
The ideal is informed distance: close enough to understand how the work actually gets done, far enough to let people do it without you breathing down their necks. You step aside on every single detail, but stay connected to the how.
I’m an advocate for AI when it’s actually useful (i.e., not slop), and it has a place here: buying back in a manager’s day. I think back to the hours spent prepping for meetings, compiling information scattered across five different systems, and turning raw numbers into a summary for the CEO — a lot of that is now work that can be done with AI.
And the point isn’t more output. If done correctly, that reclaimed time flows back into understanding the work itself. In an episode of the podcast How I AI, host Clare Vo says:
I know so many people who feel like they’re in meeting after meeting after meeting. And when they’re not in meetings, they’re preparing for meetings… You would much rather your managers be hands-on doing the work, filling a creative impulse, than prepping for meetings.
Management roles can often suck the fun out of work. There’s creativity in being an individual contributor that disappears with a promotion to a manager role. Imagine if managers actually had the time for creativity. They’re more connected to the team and get to keep work interesting.
Most of the conversation about AI at work is about cutting headcount or increasing output. But for managers specifically, the most valuable thing added is giving them more time for attention — the time to actually watch (or put their hands on) the work again.
For managers
The structure of most managerial roles causes a disconnection that most managers feel. The system moved you away, then handed you responsibilities that make it impossible to stay connected.
The best leaders stay curious about what the work feels like, not just what it produces. They know the difference between a number on a report and the context behind it. They get that story by talking to the people living it. That only happens when you have time in your day for curiosity. The management team above you won’t give you that time, so you’ve got to find ways to claim it for yourself.
For self-employed people
The same management scenario applies the moment you stop being a team of one. When you hand off work — to a contractor, a VA, or a subcontractor — you need to understand more than just the end result.
You should absolutely hire people more capable or more specialized than you, but it’s too easy to forget about the work altogether. Distance creates the same blind spot for a solopreneur, the same way it does for a VP. You stop thinking about the “why” or “how,” and the work loses meaning.
So as you hire help, resist two urges: the pull to micromanage (let the person do their thing!) and stepping so far back that you lose sight of the work. Stay close to the process even when you’re no longer the one doing it.
The goal is always to keep your eyes on the work without constantly putting your hands all over it. And to build time into your day that lets you do just that.
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