Two icons with a green person inside a white circle - with the word me under one and the word you under the other one.

The Most Important Self-Awareness Question You Will Ever Ask

5 min read

There isn’t much debate about the importance of self-awareness. It is critical for personal growth, healthy teams and leadership development.

But what if your approach to measuring self-awareness is incomplete?

The most accurate measure of self-awareness isn’t your understanding of yourself, or how it compares to the perspective of others. The best indicator of self-awareness is your prediction of how others see you, compared to how they actually see you.[1]

Asking a Better Question

To make the self-awareness journey practical you need a better question. One that gets to the intersection of internal and external self-awareness. It’s the most important self-awareness question you will ever ask.

What is it like on the other side of me?

Internal self-awareness is necessary but not sufficient when answering this question. You must go beyond a robust understanding of yourself, exploring the nature of the relationship and the nature of the interaction.

For example, if I’m having a conversation with my wife (the nature of the relationship) about buying a house (the nature of the interaction) it will be very different from a conversation about what to do on a date night, or volunteering for a service project.

The nature of the relationship and interaction make this self-awareness question more specific.

What is it like for this person in this situation on the other side of me?

Asking this question is helpful in every relationship, including the workplace. If the person on the other side of me is a direct report, and we are meeting to discuss their performance in the last quarter, the interaction is different from a meeting to talk about a new project, or a promotion, or offering feedback about a presentation they made to the executive team that I don’t think went well.

Of course, the interaction flips on its head if the person on the other side of me is the chairman of the board, the biggest customer or donor. Each of these relationships can have a variety of different interactions.

I’ve spent a lot of time reflecting on my Identity Profile, the unique combination of my personality, strengths, skills, gifts/values and passions.[2] I know I’m a quick verbal processor, self-confident, strategic, opinionated, get to the point, and decisive with a bias for action. Empathy is number 29 out of my all-34 Clifton Strengths Report. All this (which is only part of the picture) explains why I can come across as intimidating, forceful, even combative.

Power distance is an amplifier for the nature of the relationship, and it goes both ways. It’s a factor when an executive meets with a direct report, or a board chair with a senior executive, regardless of the nature of the interaction.

But That’s Not What I Meant

The reality is most of us are not very good at describing what it’s like on the other side of ourselves. Here’s why. I know what my motives are, and they color my perception of how my words and actions should be received. I have information that is invisible to others (my motives) and I can’t help but include that information in my calculation of how my actions should be interpreted.

Pat Lencioni talks about feedback he received from his wife and team related to a “face” he makes in response to situations where he feels frustrated and confused. To Pat, the face (which he doesn’t realize he is making) means he doesn’t understand something and wants more information. To others, it means he thinks they “should be flogged for their stupidity.”

Motive matters. But it isn’t readily available to the people on the other side of me. Even those I care about, and know me well.

Asking an Even Better Question

Reflecting on how a specific person in a specific situation will experience “me” is a powerful way to combine internal and external self-awareness. But there’s an even better version of this question.

What do I want it to be like on the other side of me?

It’s just as important to make this question personal and situational.

What do I want it to be like for this person in this situation on the other side of me?

Push yourself to articulate, in writing, what you want the other person to believe and how you want them to feel on the other side of you when the interaction is over. What would you want them to say about you and the interaction to others?

For example, imagine you are meeting with a direct report to give feedback on a specific project. Your notes might include:

I want this person to know I’m for them, I believe in them, they can trust me, I’m committed to helping them grow, I have high expectations for them because I believe they can rise to them. We value excellence and preparation. I want them to feel cared for and supported.

Then ask yourself, what aspects of your Identity Profile (personality, strengths, skills, gifts/values, passions) will you need to leverage to pull this off (the balcony — you at your best)? What aspects of your Identity Profile will you need to moderate to pull this off (the basement — your shadow side)?

Have a Visual Walk Through

Engage in a thought experiment where you are on the other side of you. Visualize yourself having this conversation in a way that produces the outcomes you have listed.

Think about the aspects of your conversation that are most likely to trigger an emotional response. Remember, emotions are to self-awareness what alcohol is to a driver. A little bit can impair judgment, making us less rational. How will you navigate the sensitive topics in a manner that ensures the outcomes you have listed?

Developing the ability to understand how others experience you and moderating your interaction based on this information is the most important metric of self-awareness. It is simple, difficult and worth the effort.

It will make life better, for everyone, on the other side of you.

[1] 7. S. N. Taylor, “Redefining Leader Self-Awareness by Integrating the Second Component of Self-Awareness,” Journal of Leadership Studies 3, no. 4 (2010): 57–68; S. N. Taylor, “Student Self-Assessment and Multisource Feedback Assessment: Exploring Benefits, Limitations, and Remedies,” Journal of Management Education 38, no. 3 (2014): 359–383.

[2] For more information about the Identity Profile Self-Awareness Tool (IPSAT) visit

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