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Mistakes I made as a founder / leader / manager

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I assumed that if I kept repeating that I have an open door policy and people should feel free to come and share their feedback, they will.

They didn't.

I mistook my ease to share, as everyone's willingness to do the same.
I assumed that if I didn't share feedback on a regular basis, people will assume that everything is fine.

They didn't.

I made the mistake of thinking that feedback is to be given only when things go wrong.
I assumed that people can see through my decisions and the rationale behind them.

They couldn't.

I forgot that I measure myself through my thoughts, but people measure me through my actions.
I assumed that if I sugar coat what I didn't like about their way of working, they will feel less hurt.

They were left confused.

I mistook being nice as being helpful. Being clear and direct is more important than being nice.
I assumed that if I said something needs to be done, it will get done, because everyone nodded.

It didn't get done.

I made the path clear. But I did a poor job of assigning roles that people had to play. So everyone agreed to the path. But they didn't know what to do!
I assumed that if I speak the most, there will be a lot more clarity.

There wasn't.

When I spoke, I stopped listening. And when I stopped listening, I was only repeating what I already knew. Not what I should know.
I assumed that we are all new age and age-old biases do not exist in our minds.

They do exist!

If we had to fix the gender ratio, we had to focus on it.
If we had to be inclusive, we had to focus on it.
Assuming we are "not like the others", is not how biases are fixed.
I assumed just because someone is good at their work, they will become good managers.

They necessarily don't.

Managing one self is easy. Managing people isn't. It requires training to be able to teach/coach/mentor someone else what you know inside of you.
I assumed that once we raised money, everything will be fixed.

Everything wasn't fixed.

Raising money was not the end. It was the start.
I should have celebrated less and reflected more.
I assumed that marketing was the only reason potential customers did not know of us.

That wasn't true.

Customers did not know of us because we hadn't yet built something that they wanted.
And marketing was never going to solve for that.
I assumed that conviction, perseverance and tenacity alone will make us successful.

It didn't.

The market played a much bigger role than I imagined. It didn't care about these things. It cared about how big it was and whether we built for that, or what we thought it should be.
I assumed everyone is equal and everyone's vote counts.

It doesn't.

Everyone comes with their strengths. And their votes should be in accordance to their strengths and not just their presence.
I assumed that building a powerful culture will make us win.

It didn't.

Culture will hold things together when in shit. But it wouldn't help you grow.
I assumed that being forever calm is the best thing I can be, as a leader.

Not always true.

Being a wartime leader in the early days of a startup is more important than being a peacetime leader.
Being paranoid helps, early on.
I thought we should get there faster. Whatever it takes.

Bad idea!

This is a marathon. Not a sprint.
It doesn't matter who gets to 100m first, or who is faster. What matters is who has the stamina to keep running. This will take time!
I thought that no one wants to be led. Everyone wants to do their own thing, so let them.

Not true.

99% people want to be led. They want to be told what to do, and then they will go on to do their best.
They want to be led. Not managed.
I felt that money is not a big motivating factor for people. It becomes normal after a point.

So wrong!

Money is still very important for a lot of us.
Because we grew up in the absence of it.
I felt that if I have to change my decisions frequently, people will understand why.

They won't.

Frequent changes leave people scared.
They expect stability.
And if I couldn't offer it, I shouldn't have spoken about it.
I assumed people will be ok if we lay them off and find them another job.

No!

Laying people off is rarely about the job.
It is about their self respect.
I assumed that old timers should never be asked to leave, because they helped us when we needed them the most.

Wrong!

People who got us thus far needn't be the one who will take us ahead.
Realizing them and making them realize the same, was super hard!
Over the past decade, I have had the privilege and the honor of leading exceptional women and men.

They inspired me, challenged me, helped me grow

And so often I feel they deserved better, than to have a leader who was learning on the job.
I gained at their expense.
The toughest aspect of leadership is realizing how your inadequacy as a leader affects so many people who assumed you were capable all through.

It is the curse of leadership.

And yet, I wish this curse on everyone.
For it is then that we truly experience the power of leadership
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