utsinha's blog

I write about product marketing, startups and music.

I have often been told that I need to work on my assertiveness. Multiple managers have shared this feedback with me. Often, more than once. It is admirable consistency albeit in a short 6 year career spent in 3 different companies.

I used to have a tough time unpacking this comment.

In fact, the day I began writing this draft (to expand on a recent Tweet thread), I got into a very involved argument with another friend about assertiveness. I realized that there could be a lot of other people that struggle with this feedback.

I wanted to share some advice that have helped me figure this out.

First of all, know that most feedback is subjective!

I am reminded of the meme/original quote from George Carlin -

Have you ever noticed that anybody driving slower than you is an idiot, and anyone going faster than you is a maniac?

I think assertiveness is a bit like that.

It took me a long time to understand that this feedback was subjective.

It depended both on my behavior, and the other person's experiences with me.

To some, I came across as thoughtful but confident. To others, I came across as not assertive enough.

Know that this feedback isn't about you as a person, but more about how you come across in specific contexts.

When are you not comfortable saying no?

Reflect back on how many times were you pushed into doing something against your wishes or your best judgement.

I found this as a useful marker to identify contexts in which I was not assertive enough.

Identifying the contexts in which you seem to be lacking assertiveness is a seemingly obvious, but often underrated exercise in the middle of all the self-doubt cloud.

Be generous with your opinion, and your reasons

My assertiveness related issues were mostly work-related. I rarely had problems saying no in personal or social situations. (I am sure you can tell I am not very popular with friends or family!)

For a long time, I put this lack of assertiveness to me lacking seniority or the right qualification to make a decision or even share my opinion on a particular topic. I may have been right some times, but I was also wrong on many occasions. I could also trace it back to a fear of being proven wrong.

I started testing my opinion and my reasons and assumptions for my opinion. First with myself. And then later with the group.

My self-examination did one of two things. It either increased my conviction in my opinion/decision, or helped me understand what I didn't know enough about. (Or when my reasons were driven by ego more than logic, because let's face it – we are humans.)

If you can test your opinions with yourself, you would be more confident sharing it with the group. Also share your own reasons. And be okay admitting what you don't know enough about. If you are a chronic self-doubter like me, share your caveats if it makes you comfortable.

Assertiveness isn't dominance.

The last thing I will leave you with is that assertiveness doesn't mean getting your way all the time. That is bullying.

The whole point of assertiveness is that you get to air your opinions. That's the low-hanging fruit you should aim for.

People will agree with you when they see reason. If you are in a group setting, and you are able to convince key stakeholders, they will push your decision through for the final decision.

Lastly, because you have tested your opinions and reasons privately, you are also generally more comfortable than others in taking back your opinion if you realize it was misinformed, or because you lacked specific context.