How to Be a Good Boss

I started, grew and sold a blogging business (think online magazines).

After many years of running and growing this business on my own, I built a small team of full-time and part-time employees and contractors.

When I sold the business, my team was understandably anxious about the transition.

What would the new bosses be like? What if their work life changed for the worse?

But they agreed to stay on board and give the new owners a chance.


Out of respect and loyalty to me and the business.

I feel a little embarrassed even writing that. It’s flattering and humbling.

I never thought of myself as a good boss. In fact, I’m pretty sure I’m a bad manager. I hate meetings, I’m unorganized, and I tend to want to be friends with my employees (which is apparently a bad idea).

And yet, my team members have been incredibly loyal over the years, and they were almost certain that any new boss would make their lives less enjoyable.

How many people hate their jobs?

I recently heard that some companies are monitoring and tracking their employees’ activity because they don’t trust them to work hard enough from home.

On one hand, this makes sense: if someone hates their job (which many do), they’ll slack off and get away with as much as possible.

There’s even a whole subreddit dedicated to being “overemployed” (secretly holding down multiple full-time jobs). 

On the other hand, this sort of mistrust is sort of creepy.

Employees don’t respect their employers. Employers don’t trust their employees.

How did we get here?

How can a boss avoid this increasingly common dynamic?

I think, for the most part, having employees who like their job and their boss, and who feel like they’re being treated fairly, don’t need to be monitored. 

They’ll self-regulate. They’ll feel bad for slacking off.

This isn’t always true. Some people will take advantage of any situation, even if they like you (the boss).

But most people won’t.

Granted, I’m speaking from the point of view of a guy who’s run a very small company (less than a million annual revenue and only a handful of employees).

I’m sure things are different when you run a big company with hundreds or thousands of employees.

But, I’ve also been an employee in several companies. I’ve been a small cog in a big wheel. I’ve had great bosses and managers, and not so great ones. I’ve had hands-off “long leash” leaders and micro-managers.

And I was a boss for a few years, both to full time employees and (many) part-time contractors.

Here are seven things I’ve learned about being a good boss.

1. Let employees work wherever, whenever they want to

As long as they’re getting the job done, you should let your employees do pretty much whatever they want.

This means working whenever, from wherever, getting more money when they ask for it (within reason), taking time off when they want it, and changing their role as needed.

If your business model allows for this, I think it’s the way to go.

2. Give them more money when they ask for it

Of course, you can’t lose money on an employee. But if you can afford it, you should pay them what they think they’re worth.

When a freelance writer, for example, asks for a rate increase, I almost always say yes.

If they want a new arrangement (say a fixed monthly fee instead of a per-word rate), I always say yes.

When a part-time contractor wants to increase their level of effort, I say yes.

Now, if someone asks for an unusually large bump, it needs to be justified. Is their role or level of effort changing?

And if you can’t afford it, you can’t afford it.

But don’t just say no out of principle. Hear them out, then try to come to some sort of agreement so they feel fairly compensated (and so they feel good about their own financial situation).

3. Let people customize their role

The worst kind of employee is one who:

A) Doesn’t need the job (i.e., no kids and modest lifestyle)


B) Is bored with their responsibilities

If A is true, but B is not, they’ll stick around because they’re clearly not in it just for the money.

If B is true, but A is not, they’ll work hard to avoid losing their much-needed income.

But if A and B are both true?

They’re probably keeping an eye out for other opportunities, or considering moving to northern Italy to become a violin maker’s apprentice.

The best kind of employee is one who:

A) Feels fairly compensated


B) Enjoys their work

B is more important. Money often isn’t enough to keep someone who hates the day-to-day reality of their job.

On the other hand, if someone loves what they do, they’ll often accept less money than they could make elsewhere. This is definitely true for me!

So I regularly asked my employees and contractors how they were doing, how they felt about their work, if they were bored, and if they were interested in learning about other parts of the business or changing up their roles.

Oftentimes, they weren’t really looking for change. Or maybe they wanted to test the waters with a new type of task, just to see if they liked it.

Maybe they wanted to take an online class to dive deeper into something they were already doing.

Regardless, I think just knowing they weren’t stuck doing the same things week after week helped them feel at ease.

They weren’t scared to let me know if they felt burnt out on a certain task, or if they were bored of another one.

I never had anyone leave because they didn’t like their job. In fact, I only ever had one person leave. She was a freelance designer who decided to go back to school, and she left on good terms.

Check in with your people. Make sure they’re happy with the actual work, not just the compensation.

4. No more than one meeting per week

Meetings suck. No one likes meetings.

Except for extroverts, I guess, but they’re weird. They’re always claiming to be introverted, even though they clearly love being around people and can’t bear to be alone in a room with their own thoughts, forced to deal with their crushing insecurities and growing sense of existential dread (a mundane, even pleasant scenario for us actual introverts).

And most meetings are pointless. Any meeting that starts with, “Let’s go around the room and…” is pointless.

When I was running my blogging business, I had one 1-on-1 meeting per week with each key employee. These were phone calls, not video. They lasted one hour.

There were no group meetings unless we really needed one.

We used email and Trello (and sometimes texting) for most of our communications.

It worked perfectly, and my team members appreciated the fact that 90% of the time, they were left alone to do their actual work, not stuck in meetings all week like most other people their age.

When in doubt, cancel the meeting. Question the necessity of any standing meetings. Consider whether or not everyone needs to be there (they probably don’t).

5. Be available

Let your people call or text you whenever. It doesn’t mean you have to respond immediately.

You shouldn’t respond immediately. To anyone, really. Except for your wife. That’s urgent. She just put a fresh gallon of milk in her shopping card and needs to know if there’s already some in the fridge.

But your employees shouldn’t have trouble getting a hold of you, and they shouldn’t be worried that they might be bothering you.

5. Don’t tell them to work hard

No one wants to hear this. If they respect you and are a good fit for the job, they’ll push themselves as hard as they need to.

No matter how much you love your business and how hard you work for it, you can’t expect anyone else to care as much as you do. Why should they?

And that’s why when employers or job descriptions say things like:

“Work hard, play hard”


“We don’t take ourselves seriously, but we take our work VERY seriously.”

It’s just cringe (and maybe even a red flag for potential employees). It’s certainly not convincing anyone to choose your company over some other company.

I always told my employees and contractors the exact opposite:

We’re not curing cancer here. Our work isn’t that important. No one is going to die if we make a mistake or miss a (self-imposed) deadline.

Me, to my team

Don’t get me wrong: I kept the bar high for the type of work we were doing — producing and publishing men’s fashion and lifestyle content.

I wanted everyone involved to feel proud of their work. I wanted them to feel like our content was better than our competitors (which it usually was). I wanted to feel that way too!

But I didn’t pretend like we were involved in some sort of higher mission. People see right through this stuff.

It’s like when an apparel brand claims to be “creating a more sustainable future for the planet” or some nonsense. You’re just selling clothes. Try to make good clothes and treat your customers well, but don’t get all high and mighty on us.

I think my team members appreciated the honesty and pragmatism.

7. Be their friend

Last but not least controversial, you should be friends with the people who work for you.

You spend a lot of time with the people in your work life: your employees, contractors, colleagues and superiors.

Like as much time as you spend with your significant other and family. Maybe more!

You know them well. Let them get to know you too. Tell them what’s going on in your life. Be vulnerable. Be friends.

It’s okay.

Yes, it’ll be hard if you have to let them go. It’ll be awkward if they want to go work somewhere else.

But those situations will be uncomfortable no matter what. It won’t be worse if you’re friends. Unless you did them dirty, in which case you weren’t a very good friend.

I’m not saying you should go into business with friends. That’s different (although not always a bad idea).

I’m saying to be friends with the people you work with, or for, or who work for you.

These things worked for me 🤷🏻‍♂️

I don’t know what it’s like to manage 100+ people in a big company with a bunch of legal policies and layers of management and red tape.

But for a small business with a flat org chart, these tips helped create a pleasant work culture in which my employees and contractors enjoyed working for me.

If I were to build another team – which is unlikely – I’d do it the same way.