Remote work: Some People Need the Office. Some Don’t.

Remote Work Isn’t One-Size-Fits-All: A Tech Leader’s Perspective

I know the conversation around remote work has been going on for what feels like forever. Every few weeks, there’s another headline about companies demanding people return to the office, or someone claiming remote work is killing productivity. It’s been argued from every angle.

So I’m not here to pick a side. I just want to share my experience. This is what I’ve seen and lived, both as a team member and a leader. Today, I work mostly remotely as the founder of Timberline Digital Consulting. Most of my time is spent in my home office, but I still visit clients when it makes sense. Some conversations are just better face to face.

Before Timberline, I spent almost three years as the Director of Technology at a fully remote accounting firm. And before that, I managed IT at a transportation company. That role started out 100 percent remote during the height of the pandemic, and later shifted to hybrid as COVID went endemic. So I’ve had a front-row seat to the evolution of remote work and how it impacts teams and productivity.

Here’s what I’ve learned.

Structure Is Key to Remote Work

Remote work gives you a lot of flexibility, but that flexibility only works if you’ve got structure in place. One of the first things I figured out was how important it is to time block. I use my calendar religiously, planning out each day before it starts. I set clear work hours, map out what I’ll focus on, and stick to those boundaries as much as possible.

It’s the difference between feeling in control of your day or constantly reacting to things. Without a structure, you drift. Without a plan, you start each day playing catch-up. And in a remote setup, there’s no visual reminder of what others are doing, so it’s easy to lose momentum.

Clarity Beats Oversight (Especially the Tech Kind)

As someone who works in tech, I’ve seen a lot of companies try to solve trust issues with software. Mouse click trackers. Keyboard activity logs. Screenshot apps. I understand the impulse, but honestly, I think those tools do more harm than good.

They create a culture of surveillance instead of accountability. They make people feel like they’re being watched instead of trusted. I’ve never wanted my team to stress over whether their mouse moved in the last ten minutes. That’s not leadership. That’s micromanagement dressed up as data.

Instead, I focused on defining clear KPIs. I wanted people to know exactly what was expected, when it was due, and what good looked like. Then I gave them space to deliver. If the work was solid and the deadlines were met, I didn’t care if they did it in a hoodie at home or at a coffee shop downtown.

People want to be measured by what they produce, not by how often they tap their keyboard. And from a tech perspective, it’s smarter too. Monitoring software adds noise, causes friction, and doesn’t tell the full story. Results do.

Feedback and Check-Ins Build Momentum

When I managed remote teams, one thing that made a big difference was having regular check-ins. Not just to track tasks, but to stay connected and catch things before they became problems. Sometimes we’d talk through blockers, other times it was just a quick gut-check on how things were going.

Those conversations helped build trust and motivation. I’ve found that people actually want more feedback than they say. When you're working remotely, feedback becomes one of the few ways to really gauge how you're doing.

It also helps people feel seen. And when people feel seen, they show up stronger.

Hybrid Gave Me Perspective on Remote Work

Back at the transportation company, everything went remote during the early stages of the pandemic. When things opened up, we had the option to return in a hybrid setup. I chose to go in often, not because I had to, but because I liked the environment.

There’s something about being around other people that helps me focus. For those of us who are neurodivergent, this is often called body doubling. It means just having someone else nearby — even if they’re not working on the same thing — helps you stay on track.

In a remote world, I’ve recreated this by staying on a video call with someone else while we work. We might not even talk much. But having that presence helps keep the gears turning. It’s a reminder that you’re not doing it alone.

Remote Work Isn’t for Everyone, But It Works for Some

Here’s the thing. Not everyone thrives in a remote setup. And that’s okay. Some people need the routine, the separation of work and home, the face-to-face energy. Others feel completely at home working from wherever they’re most comfortable.

The important part is recognizing that one approach won’t work for everyone. In my experience, the best way to figure it out is to look at the results. If someone is thriving remotely, hitting their KPIs, collaborating well, and staying engaged, let them run. Forcing them into an office just because it's the traditional way of doing things doesn’t make sense.

And if someone struggles with remote work, that’s not a failure. It’s just information. Maybe they need more structure. Maybe hybrid is the right fit. The goal isn’t to create a perfect system. It’s to create the right conditions for each person to succeed.

Let the Results Lead the Way

One of the biggest benefits of remote work is access to a wider talent pool. You’re not hiring based on who lives nearby. You’re hiring based on skill, mindset, and fit. But to make the most of that opportunity, companies need to shift their mindset too.

Performance should lead the way. The numbers, the outcomes, the feedback from teammates, that’s what tells the real story. Not how active someone looks online or how quickly they respond to a ping.

Remote work works, but only when there’s trust, clarity, and communication. The same goes for hybrid. The key is knowing your people, looking at the data, and being open to adjusting as you go.

These past few years have shown me that people can do incredible work when given the right tools and trust. It’s not about where the work gets done. It’s about how we set people up to do their best work, wherever they are.