How well do you know yourself?

Why self-awareness at work just might be the most underrated, overlooked element of a successful leader.

A few months ago, I asked Ben Congleton, CEO of Olark, what he wished he’d learned earlier as a leader. No, he didn’t mention learning a new business development hack, nor did he talk about the importance of hiring well. Rather, what Ben wishes he’d learned earlier was how to improve his self-awareness as a leader.

Self-awareness, really? After considering it for a moment, I caught myself nodding vigorously at his answer. How true!

In my head, I recalled all the moments I’ve personally lacked self-awareness as a leader: When I micromanaged someone yet had no idea, when I argued against a new idea because of my own bias… The list goes on. Each time, I’d shot myself in the foot.

The more I thought about it, the more I realized: Self-awareness at work just might be the most underrated, overlooked element of a successful leader.

Here’s why…

Why self-awareness is crucial for leaders

Fundamentally, self-awareness is about understanding your own mental state. It’s knowing about yourself: When are you energized? When are you in a bad mood? Where are you strong in, and where are you weak? What are you tendencies, your biases, and your leanings toward? What might your blindspots be?

This self-knowledge is irreplaceable. Without self-awareness, you can’t make informed decisions. You don’t know if you’re getting in your own way — if a strong irrational personal bias or misguided mental model is shaping your view on things.

Self-awareness is also critical as a leader because it means that you can build healthier relationships with your employees. Ben himself admits how his lack of self-awareness kept him from resolving an employee conflict as well as he’d like. He recalls:

“I remember there was one point where I was trying to resolve a conflict between two employees, and I just was like my head was somewhere else, my head was just like ‘This is the last thing on my to-do list, I just need to get this done, and then I can hop on a plane and go see my family.’”

Lastly, self-awareness is important for your growth and personal development as a leader. You can’t improve as a leader if you don’t know what to improve in. You have to see the current state of yourself clearly if you want to make any progress in getting better as a leader.

With self-awareness being so important, what are the ways you can actually improve your self-awareness in leadership?

How to improve your self-awareness as a leader

Assume positive intent.

One thing that Ben tries to keep in mind to improve his self-awareness as a leader is to assume good faith. When you feel yourself getting defensive and are not in a good mental state to receive feedback, stop and recognize it.Understand that the source of your resistance to what the other person is saying may be your poor assumption of the other person’s intention. You think they’re out to get you, or have ulterior motives. So assuming positive intent is a first step to bringing a sense of self-awareness to the situation: You may not being hearing things for what they are because you’re misreading the other person’s intention.

Hold up a mirror to yourself and your decisions.

Self-awareness naturally includes assessing yourself for your own mental models, biases, strengths and shortcomings, and the gaps in your perception of reality. Something that Peter Drucker, the well-known management expert, has recommended is: “Whenever you make a decision or take a key decision, write down what you expect will happen. Nine or 12 months later, compare the results with what you expected.” Warren Buffet, in fact, practices a version of this with his investment decisions. This active reflection process helps create a deeper understanding for yourself. And by reflecting on your decisions and the outcomes, you can reach a more objective understanding of what’s working for you as a leader, and what’s not.

It’s not all about you.

Self-awareness isn’t just about reflecting inward, and delving into what you’re personally feeling. You have to understand what’s going on with the other person, as well. How might what’s happening at home or something that a family member is struggling with be affecting her performance? Does this person have preferences and reactions drastically different from your own? Don’t assume that this person wants to be treated the way you want to be treated. Embracing this nuance that everyone is not like you is a cornerstone of self-awareness as a leader. It’s not all about you — you must seek out to understand others’ perspectives.

Ask your team the tough questions.

If you really want to become self-aware, there are few better ways to accomplish this than asking your team. This means asking questions that you may be even hesitant to know the answer to. For instance, try asking, “When’s the last time something I did or said frustrated you?” Or, ask, “When’s the last time you felt unsupported as a member of the team?” When you defer to them to shed light on your tendencies, not only will you get helpful information to give you greater self-awareness, but you show them a willingness to become better as a leader. That, in itself, helps strengthen your bond with the rest of your team. Not sure exactly what to ask your team? Try a few of these questions to uncover your leadership blindspots.

Find an accountability partner.

For Ben, the most effective way for him to develop greater self-awareness as a leader was to hire an executive coach. For Ben, this was helpful for two reasons: (1) It created an accountability partner for him, helping him put into the practice the things he wanted to improve, and (2) it forced him to have a time to reflect every week, causing him to set aside time to deliberately to become more self-aware. Without this third-party intervening to keep Ben actively focusing on his own self-awareness, he doubts he would have made the same progress he did as a leader. Now, I’m not saying you need to go out and hire an executive coach tomorrow. Rather, a third-party serving as an accountability partner could be a friend, mentor, spouse or anyone outside the company. You simply need a buddy to help make sure you’re walking the walk when it comes to becoming more self-aware.


I’m so grateful that Ben admitted that self-awareness was his greatest leadership lesson. It was the reminder I needed to double-down on my own personal self-awareness. Without self-awareness, we fly blind as leaders. Choosing to know ourselves is truly our first step to becoming a better leader.


Claire is the CEO of Know Your Team – software that helps you become a better manager. Her company was spun-out of Basecamp back in 2014. If you were interested, you can read more of Claire’s writing on leadership on the Know Your Team blog.