On how to better understand context and communicate questions

One of the biggest things I have learned in the past three years of running my own company is the importance of having transparency in communication with your employees.

On some days I feel I have lost many a few times in maintaining good communication with my team members, but I try to solve their problem statements as much as I can.


The biggest thing I am learning is people, assume a lot of things without asking the right question.

This is probably how I was five years ago - rash and quick to make assumptions about people and situations.

The truth is that time is the best teacher. With time, I have learned well how to think through situations instead of jumping to conclusions.

Now imagine trying to provide this message to a team of 60+ people.

We are a super-transparent company.

I invite all and any feedback or criticism from my team.

But this cannot be fruitful if people come to me already making up their minds about things.

An example from a recent conversation with one of my employees: “Why are we not spending more time on planning our upcoming project?”

I would instead phrase this as a two-parter- “How much time are we spending on planning? And then if it does warrant, why are we not spending more?”

The context that is lost here is that this was an internal project and the employee only worked part-time on it.

Without context, it was assumed we haven’t been planning too much. Whereas in fact, we had spent nearly three months on designs, planning, BRD, competition analysis, and more.

On providing context

Imagine you are trying to run a 60+ person team. And with more than 15+ projects, everyone can feel they are running in silos.

What’s the best approach here to provide context? Communicate often.

But no matter how much one would like decisions, they will never have the full context to them.

The onus cannot be on one person to provide all information. A team cannot be cohesive and strong if they aren’t seeking the right information.

How does this reflect on you

Early in my career, I was pretty ambitious, but that also meant any decisions I didn’t understand were obviously wrong.

Why I mention this is, that I now take my time. I take a day to respond to important decisions.

I have not taken a single decision since starting the Company without consulting my partners or at least two other people.

With hardwork, one can be the best developer. But context is king. You cannot solve a critical CompSci problem without understanding the background.

“Why was an unoptimized solution committed by someone to the code?” “Why was a shadow variable left around?”

This is a good example from Rails- Rails-test-message-encryptor-test

I wasted several hours finding answers to the above questions, only to realize that having definite context would make it way easier.

Ask the right questions

So, let’s change the narrative from now on! Instead of asking questions like “Why are we doing this?”, let’s ask, “What are we doing first?”

Get supporting information. Ask more, Ask often.

That shows a sign of a person who can lead the team.

Remember, it takes days to understand context, but only one minute to change a single line of code.

Context is King.

This is also the best way you will progress in your career.


It takes a lot of experience in making right conclusions and decisions to view things positively.

I visited my team in India the previous month. My most meaningful discussion was with two of my senior-most employees.

They came prepared with the right questions. They didn’t mince words and stuck to the point.

Once they were addressed, they suggested solutions. Not before.

This shows a sign of leadership.

So, the only take away if any from this post that you do, is, to get more context.

You will make educated decisions.

Is there something that I can learn more from you about this subject? DM me on Twitter- vipulnsward.

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