Leading a team when you've never had a boss

I manage 12 people across two offices. I’ve never had a boss. Never watched someone else run a team or sat through a single performance review.

When we needed to scale Ken, I was terrified this would be a problem. How do you manage people when you’ve never seen what good management looks like? When you have zero reference point for what you’re supposed to do? It turns out some of my worries were valid. Most weren’t.

Here’s what I’ve figured out.

I thought not having traditional job experience would hurt me. Like I wouldn't know how to talk to people professionally. Or I'd miss some obvious thing that everyone who's had a boss just knows instinctively.

I was completely wrong. You see, management in a startup isn't about knowing corporate norms or following some playbook. It's way simpler than that. Can you communicate clearly? Can you tell people what needs to happen and why? Can you treat them like actual humans? That's basically it.

What I realized is that people who've been managed before aren't automatically better at managing. Some learned terrible habits from bad bosses. Others just copied what they saw without thinking about whether it actually worked.

Not having a model meant I had to figure out what made sense for us. No "this is how it's always been done." Your team isn't like anyone else's team anyway. So copying someone else's management style probably wouldn't work. You don't need corporate experience to manage a startup well. You just need to communicate clearly and treat people like humans.

This was the actual hard part. When you've been managed, you know what you liked and what you didn't. You have examples. A bad boss taught you what not to do. A good boss showed you what works. I had nothing. So I had to figure it out by watching what happened. If something broke, I'd reverse engineer why. If something worked, I'd try to repeat it.

Early on I thought managing meant being available all the time, answering every question immediately, and solving every problem myself. That didn't scale. Then I swung too far the other way. Delegated everything and disappeared. That also didn't work.

I eventually landed on a hybrid model. Monday to Friday I'm very active. I aim for inbox zero and respond to everything quickly. Then Friday to Sunday I'm basically unreachable. I only reply to messages when they are almost too important to ignore.

Make sure people know what they're working on. Remove blockers when they're stuck. Check in regularly but don't hover. But I only found that balance by trying things and seeing what broke.

When you've never been managed, you don't have shortcuts. You experiment and pay attention to what actually works for your team. There's no universal playbook. You have to build your own.

I learned this one the hard way. I can build something in a few hours that takes the team a week. I’m impatient and I want things done yesterday. It always felt faster to just do it myself. So I just kept doing everything myself. We went from 3 people to 16 in four months and I was still personally involved in everything.

I became the bottleneck. Everything broke. Processes collapsed, people would finish tasks and just sit there waiting because I hadn’t told them what to do next. That’s when it hit me. If you don’t delegate, you cap the entire company at what one person can handle.

But here’s the thing. The tension doesn’t go away. Delegation still feels slow. People who move at my speed are rare, and even if I found them, expecting everyone to operate like that isn’t realistic. So I had to accept the trade-off. Delegate and scale, or stay fast and stay small. There’s no third option.

Now I delegate even when it feels slow. Because staying involved in everything feels fast but actually stops growth.

Last month, I gave someone on my team a 30% raise. When I told him, he said the timing was perfect. Turns out he was moving to a new place, so he needed the cash. His sister was also graduating and he planned on covering the celebration. He's also the one supporting his family.

I had no idea about any of this. He never mentioned it. He just showed up and did great work for two months.

Early on I assumed people knew they were doing well because I wasn't complaining. Wrong. Good people don't pitch you on why they deserve recognition. They just do the work. If you wait for them to ask, you've already waited too long.

Performance reviews have their place. But if someone's crushing it right now, act on it immediately. Don't wait for December to recognize work that's happening in June.

When you've never been managed, you don't know how demotivating it is when great work goes unrecognized. You have to learn this by paying attention to who stays and who leaves.

I'm still figuring out how to give feedback well. When to be direct, when to be gentle. How much detail people actually want. But I learned that recognizing great work can't wait for scheduled reviews.

We write a lot of email copy for clients. My copywriter was drowning in work, so I figured we needed to hire another one. Posted the job. Started interviewing. Then I got so busy I couldn’t even manage the hiring. It just died.

But the problem kept bugging me. So I looked closer at what was actually slowing him down. Turns out he was spending most of his time on repetitive stuff that could be automated. So instead of hiring, I built an AI agent that helps him write faster. Same quality. Actually better in most cases. Few weeks later he had tons of free time. We didn’t need another person. We needed to understand what he actually needed to succeed.

When you’ve never been managed, you don’t have a model for this. Your instinct is “too much work means we need more people.” Sometimes that’s true. But sometimes your team just needs better tools, clearer processes, or fewer blockers.

When you've never been managed, you don't know what a reasonable ramp time looks like. I'd hire someone and expect them to be productive week one. Maybe month one. But that's not realistic.

People need to learn your systems, understand your context, figure out how you think and that doesn't happen instantly. I'm impatient by nature so waiting for someone to ramp up felt like wasted time. But that patience is necessary. Even hiring the right person takes time to pay off.

From 2020 to 2025 I couldn't scale any business I touched because I expected everyone to operate like me immediately. Everything depended on me because I didn't give people enough time to actually learn. Now we're at 12 people and the team handles stuff I used to do myself.

But getting here required accepting that people need time to ramp. You can't shortcut that. Hiring wrong costs months and thousands of dollars. But even hiring right requires patience.

We’re at 12 people and things are working. I expect we’ll hit another breaking point around 25 people and I’ll have to figure out the next level. But that’s the job when you’re learning this from scratch. The team you build matters more than any code you write.

Cristian Frunze - Founder @Ken AI