Trying to be a nice boss nearly killed my startup

megakim

megakim

Regular Member
Jr. VIP
Joined
Feb 27, 2025
Messages
325
Reaction score
116
I started out thinking being everyone’s friend would make us crush it as a team. I said yes to every little thing, avoided tough convos, and kept handing out second chances when people messed up. The chill vibe felt right for a while but it didn’t take long for things to unravel. Stuff stopped getting done, deadlines slid, and the best people either got burned out or bounced.

The real slap in the face was losing a major client because a project totally dropped. I wanted to blame the team but I’d set the tone that nothing was really urgent and nobody would be called out. The business took a hit and suddenly being the cool boss just looked clueless.

That’s when I finally snapped out of it. Let some people go, set clear rules, and gave real feedback even when it was uncomfortable. At first it was awkward and kinda stressful but the vibe shifted way faster than I thought. The team shrank but the people who stayed got way more invested and results actually started showing up again.

Lesson: you can treat people well and still hold the bar.
 
Advertise on BHW
You have to remember that the boss is always an asshole. No matter what you do, that's just the way it is.
I think people should look at how cool the boss is. That does matter more.
If you are a cool boss, then the team will work better.
 
I've been there myself.
Once expectations become optional, it gets really hard to get things back on track.
 
megakim said:
I started out thinking being everyone’s friend would make us crush it as a team. I said yes to every little thing, avoided tough convos, and kept handing out second chances when people messed up. The chill vibe felt right for a while but it didn’t take long for things to unravel. Stuff stopped getting done, deadlines slid, and the best people either got burned out or bounced.

The real slap in the face was losing a major client because a project totally dropped. I wanted to blame the team but I’d set the tone that nothing was really urgent and nobody would be called out. The business took a hit and suddenly being the cool boss just looked clueless.

That’s when I finally snapped out of it. Let some people go, set clear rules, and gave real feedback even when it was uncomfortable. At first it was awkward and kinda stressful but the vibe shifted way faster than I thought. The team shrank but the people who stayed got way more invested and results actually started showing up again.

Lesson: you can treat people well and still hold the bar.
Click to expand...
Discipline is essential in the workplace.
 
That’s a lesson a lot of founders learn the hard way, being respected matters more than being liked.
 
Not to be a d!ck, but this is a story old as time itself. It never works.

Never mistake business as anything other than business. There's a difference between being fair & providing a relaxed work atmosphere; and being a doormat and systemically running your own business into the ground...
 
I made the same mistake too when running a digital marketing agency some years back. Burnt my capital trying to be friends with employees and making sure they got everything they asked me for - I thought making them comfortable would improve efficiency, I was wrong. They got lazy, kept making unnecessary demands, and regular tasks took longer to deliver because ofc the boss would "understand" even if they under-deliver.
 
Great share! Being a leader means finding the right balance between empathy and execution.
 
Business is business. You can never please everyone. With this said, you have to be clear that the ultimate goal of a boss is to fight a successful war and enjoy the fruits with the team. It is not to create a kindergarten for those who want to shirk the responsibilities.
 
megakim said:
I started out thinking being everyone’s friend would make us crush it as a team. I said yes to every little thing, avoided tough convos, and kept handing out second chances when people messed up. The chill vibe felt right for a while but it didn’t take long for things to unravel. Stuff stopped getting done, deadlines slid, and the best people either got burned out or bounced.

The real slap in the face was losing a major client because a project totally dropped. I wanted to blame the team but I’d set the tone that nothing was really urgent and nobody would be called out. The business took a hit and suddenly being the cool boss just looked clueless.

That’s when I finally snapped out of it. Let some people go, set clear rules, and gave real feedback even when it was uncomfortable. At first it was awkward and kinda stressful but the vibe shifted way faster than I thought. The team shrank but the people who stayed got way more invested and results actually started showing up again.

Lesson: you can treat people well and still hold the bar.
Click to expand...
leadership is not always about ensuring that all members are comfortable with each other. there needs to be trust as well as accountability in a good team. the toughest fedback can be the one that makes the greatest difference. it is always better to be fair, establish expectations nd nip issues in the bud.
 
Great share really appreciate your input. I was also in business and unfortunately a business was failing because of the cool atitude?
 
Who knows if this cat spammer is saying something remotely true, all the time posting random threads and never engaging with them again, probably another fiction story to farm likes
 
megakim said:
I started out thinking being everyone’s friend would make us crush it as a team. I said yes to every little thing, avoided tough convos, and kept handing out second chances when people messed up. The chill vibe felt right for a while but it didn’t take long for things to unravel. Stuff stopped getting done, deadlines slid, and the best people either got burned out or bounced.

The real slap in the face was losing a major client because a project totally dropped. I wanted to blame the team but I’d set the tone that nothing was really urgent and nobody would be called out. The business took a hit and suddenly being the cool boss just looked clueless.

That’s when I finally snapped out of it. Let some people go, set clear rules, and gave real feedback even when it was uncomfortable. At first it was awkward and kinda stressful but the vibe shifted way faster than I thought. The team shrank but the people who stayed got way more invested and results actually started showing up again.

Lesson: you can treat people well and still hold the bar.
Click to expand...
The desire to be good to everyone often turns into a trap that harms both the business and the team itself.
We always learn from our mistakes
 
megakim said:
That’s when I finally snapped out of it. Let some people go, set clear rules, and gave real feedback even when it was uncomfortable. At first it was awkward and kinda stressful
Click to expand...

That's the way to go. Gotta be professional in the business. You're there investing time, health and money to make a living, not to make friends.

Of course, outside the business you should be nice to them, just make it clear business is business, but when you step outside the company, you should probably have social occasions, a BBQ, a light hearted event and so on. Just keep it clear what the mission is during work hours
 
Since my first business many years ago, i always told to anyone i hired that i'd keep then while they could keep the cash coming. Always paid way above the average wage and always gave bonus. But always based on cashflow. Had to let go of a lot of people, but i always kept the best, and all my business always run smoothly
 
megakim said:
I started out thinking being everyone’s friend would make us crush it as a team. I said yes to every little thing, avoided tough convos, and kept handing out second chances when people messed up. The chill vibe felt right for a while but it didn’t take long for things to unravel. Stuff stopped getting done, deadlines slid, and the best people either got burned out or bounced.

The real slap in the face was losing a major client because a project totally dropped. I wanted to blame the team but I’d set the tone that nothing was really urgent and nobody would be called out. The business took a hit and suddenly being the cool boss just looked clueless.

That’s when I finally snapped out of it. Let some people go, set clear rules, and gave real feedback even when it was uncomfortable. At first it was awkward and kinda stressful but the vibe shifted way faster than I thought. The team shrank but the people who stayed got way more invested and results actually started showing up again.

Lesson: you can treat people well and still hold the bar.
Click to expand...
tbh this is a common founder mistake. being friendly is gud, but clear expectations nd accountability are what keep gud people from getting frustrated.
 
Advertise on BHW
You must log in or register to reply here.
Sign up now!

Main Menu

Home Main Forum List Black Hat SEO White Hat SEO BHW Newbie Guide Blogging Black Hat Tools Social Media Downloads

Marketplace

Account Selling Content / Copywriting EBooks / Methods Hosting Misc Proxies For Sale SEO - Link building SEO - Packages Social Media Social Media - Panels Web Design More

Making Money

Affiliate Programs Hire a Freelancer IM Journeys Making Money Pay Per Click Site Flipping Want to Buy

BlackHat World

Dispute Resolution Forum Suggestions & Feedback Introductions Lounge
Back
Top