Give People the Benefit of the Doubt — But Know When to Stop

I used to give people endless chances.
Because that’s what good leaders do, right?
You assume good intent. Ttrust that they’ll figure it out.
You believe that care will turn into accountability.

Sometimes it does.
Most times, it doesn’t.

Over time, I realized that giving the benefit of the doubt is important, but knowing when to stop is leadership.

Here’s how I see it:

First time: A mistake.
Could be lack of clarity, context, or awareness. Coach, don’t correct.

Second time: Still a mistake.
Maybe the message didn’t land clearly. Revisit expectations, provide support, and make it clear.

Third time: A choice.
Now they know. They just chose not to change. 
This is where silence hurts the team more than confrontation.

Fourth time: A habit.
And by now, it’s not their pattern anymore. It’s yours. 
Because what you tolerate, you endorse.

Most founders and CXOs struggle here.
Not because they don’t see what’s happening, but because they’ve built their careers on high ownership and self-drive.
They expect the same from everyone.
And when it doesn’t show up, they take it personally.

The reality is that not everyone carries the same stakes.
You might be fighting for survival; they might just be doing a job.

That’s why your empathy must come with boundaries.
Address things while they’re small.
That’s when you still have the best chance of fixing them.
Wait too long, and it turns into politics, resentment, and damage control.

Give people the benefit of the doubt; Yes.
But give it with awareness, not guilt.

Leadership is about knowing when trust turns into tolerance, rather than about trusting endlessly.

Observe once. Coach twice. Intervene the third time. Decide by the fourth.