Welcome entrepreneurs. I’m so glad you’re here.

Some big news in my world this week. I’m excited to announce that I’ll be collaborating with OnDeck, the world’s #1 community for ambitious people of all stripes (and a good bet at what a top University looks like in 50 years), to launch the first ever On Deck Scale program. Through this program we will help 80-top founders from around the world (Series Seed—Series D+; average raised ~ $20m) to grow into their full potential as leaders and human beings, and scale world-changing, life-giving companies in the process.

I’ll be serving as one of three seasoned executive coaches dedicated to supporting founders throughout the program, both in one-on-one coaching and group facilitation. I believe deeply in the OnDeck vision to help people grow in community, and when I heard they were doing a program for scale-up founders, partnering just made perfect sense (I’ll talk about the incredibly serendipitous series of events that brought us together in another post). I am stoked to be a part of this program, which I have a feeling will be a rock in the pond of startup culture a la Y-Combinator back in the late 2000’s.

If you’re currently scaling a company and want to learn more or apply to the program, reply to this email or check out the link above.

That out of the way, this week’s essay is a reflection on how important self-awareness is to leaders (there’s more data supporting this than even I expected), as well as a deep analysis on how much harder self-awareness is to develop for leaders than “regular-folk.”

Important topics, so let’s dive in.

The paradox of self-awareness in leadership

For companies to succeed, they need self-aware leaders.  But the deck is stacked against leaders developing that self-awareness.  

That’s what Daniel Goleman found, in his book The New Leaders.  Daniel quoted research into what distinguished the leadership of a number of highly-successful US healthcare companies from the least successful ones (based on return on equity, share price over a 10-year period). He found that self-delusion was associated with poor performance, and self-awareness with company success:

Tellingly, the CEOs from the poorest performing companies gave themselves the highest ratings on seven of the ten leadership abilities. But the pattern reversed when it came to how their subordinates rated them: they gave these CEOs low ratings on the very same abilities. On the other hand, subordinates saw the CEOs of the best performing companies as demonstrating all ten of these leadership abilities most often.

In separate research, Goleman also found that the more senior the managers, the more likely they were to inflate their own ratings, saying: “Those at the highest levels had the least accurate view of how they acted with others.”

Let’s recap that research, because it’s important.

1. Self-awareness (measured by the alignment between how you see yourself and how others see you) is critical to your success in leadership. It’s the dashboard by which you educatedly adapt your leadership to get the most out of your people, and drive successful outcomes in a changing marketplace.

2. But the more senior you are, the more difficult self-awareness becomes.

For entrepreneurs, particularly those in the CEO seat, success depends on overcoming these four obstacles to self-awareness:

1. You don’t look - Lack of Self-Reflection

2. You don’t ask - Fear of Feedback

3. You don’t listen - Ineffective Listening

4. You don’t interpret - Contextual Interpretation

“We cannot change what we are not aware of. And what we are aware of, we cannot help but change.” — Sheryl Sandberg

Barrier One: Lack of Self-Reflection

You don’t look.

Running a company is all-encompassing. Many leaders wake up every day at 100mph, consumed by marketing, sales and product-market fit, never considering the impact of their personality or leadership style on the results they get. They don’t know that those things are malleable, so they don’t bother looking at them. Their leadership style is behind the “subject/object wall,” meaning it’s just “who they are.”

These are what is called “unconscious leaders.”

About 80-85% of leaders are in the realm of Unconscious leadership, which is the world of managing and directing. The English verb “manage” literally comes from the Italian “maneggiare” (to handle, especially tools or a horse). So, these are your managers, who treat their employees as resources (literally, horses) to be directed and optimized.

To illustrate the difference:

• Conscious leadership: my tendency to argue a point to the death comes from my ego’s need to feel like the smartest guy in the room, and is something that, when I catch it in time, I can simply choose to not indulge (and therefore to not suffer the interpersonal consequences of an argument).

• Unconscious leadership: it’s just my personality, and my employees need to adapt.

The vast majority of leaders fail because it doesn’t occur to them to look critically at their leadership style. They only see the work to do “out there,” and barrel through it ever more urgently, regardless of results or feedback.

Barrier Two: Fear of Feedback

You don’t ask.

Of the leaders who are conscious (meaning for our purposes today that they are looking actively at their leadership style, and aware that they can adapt it to change their results), many still sub-optimize their results because they don’t ask for feedback.  Why?  Mostly because they’re scared of the answer.

The good ol’ willful-ignorance approach.

From the same study:

Psychologists have a lot of theories about why people are so sensitive to hearing about their own imperfections. One is that they associate feedback with the critical comments received in their younger years from parents and teachers. Whatever the cause of our discomfort, most of us have to train ourselves to seek feedback and listen carefully when we hear it. Absent that training, the very threat of critical feedback often leads us to practice destructive, maladaptive behaviors that negatively affect not only our work but the overall health of our organizations. 

The easiest way to get great feedback

Asking for feedback doesn’t have to mean a commissioned 360-degree review. It can be as simple as asking a handful of people who know you well (I suggest about eight people, both professional and personal) to give you honest feedback on how you show up in the world.

The following simple questions are a great way to get started (you can also add your own):

• In what ways do you think I am already effective?

• In what ways do you think I am less effective?

• What could I do to improve my relationship with you?

• What would be the one piece of advice you would give me about how to improve my effectiveness?

• What do my actions say about my values? What drives me?

I’ve yet to meet a leader who wasn’t impacted by the results.

Barrier Three: Ineffective Listening

“Sometimes when you get an idea in your head, it’s impossible to talk to you about anything else.  You don’t listen even when you’re wrong.”

You don’t listen.

This was a real piece of feedback I was given, and I still remember the sensation that went with it.  A jolt of fear, followed by rage, which finally settled into righteous indignation. The giver was misguided.  He didn’t get it. 

Needless to say, the conversation following wasn’t exactly productive, and I missed a chance to improve my effectiveness by evolving my leadership style.  What also happened, but might not be as obvious, is that the giver never gave me the gift of his feedback again.  

A leader’s reaction to feedback is the prime variable in whether or not they continue to receive feedback. Listen, and people will keep helping you grow. Don’t, and you’ll soon live in a bubble of people who tell you what they think you want to hear.

Early on in my career as a CEO (although after the incident above), I was fortunate to hire a Senior VP with decades of experience working in the C-suite. He pointed out to me how difficult it already was for people around me to give me constructive criticism, and the risk they took in doing so given my control over their paychecks. Most importantly, he showed me the impact my reaction had on their willingness to do so. Thanks to his wonderful risk (itself a pretty meta example of the concept), I saw how natural, how incredibly easy it would be for me to get isolated in my position, and with his help started to do the hard work of making it easy to tell me the bad news.

Said simply, self-aware leaders go out of their way to make it easy, and non-threatening, to give it to them straight. But make no mistake about it, this requires work.

Barrier Four: Contextual Interpretation

You don’t interpret.

Even if you embrace the feedback you’re getting from the people around you as the gift it is, it’s also important to consider context. There are two main contextual considerations to keep in mind:

1. The distorting effect of your role/title

A client I worked with, the founder/CEO of a tech company, told me a story once that perfectly illustrated the invisible bubble in which CEOs live. After grabbing his food at the company holiday party, he approached the long, bench table at which his team sat. As he began to make his way to sit in one of the few gaps available on the far end of the table, he cracked a joke without thinking about it, saying, “hey, can you all just scootch down a bit?” Haha.

You can guess what happened. About 30 teammates, all at once, dutifully moved their trays of food down the table, sitting close to one another to open up a seat at the end of the table. With a flippant joke, in five seconds all his employees were cramped and he had his choice of the head of either row, the conversation carrying on without missing a beat. My client, himself quite self-aware, was shocked.

And when he told me this story, I started to question the dozens of times that my team had complimented me on my wardrobe.

We don’t like to admit it, (we all prefer to think that we are simply popular and have good fashion sense), but the reality is that most people go out of their way to please their boss. As a leader it’s important to remember this (it’s difficult if not impossible to change), so you can properly interpret any feedback you get. If you think you’re the exception to this, think again. The question is not whether you live in a bubble, but whether you’re aware of the bubble, and compensating for it in your interpretation.

This is why having a channel for anonymous feedback, although scary, is also so powerful.

2. Your own inner wisdom

After walking through the key challenges to developing self-awareness as a leader, now seems like the right time for an important caveat:

Feedback is not instruction to change.

It’s easy, especially given how much work it takes to solicit objective feedback from the people in your life, to automatically take any negative feedback we receive to heart. But not all feedback is created equal. You have to do your own analysis of that feedback, comparing it to what you believe is true about yourself and what your company needs, in order to develop a solid goal & plan for growth.

Your own leadership journey, like your mission and company values, is on the very short list of things you can’t fully delegate to your team.

—

Self-awareness, the alignment between how you see yourself and how others see you, is the raw material by which top leaders learn how to adapt themselves to the goals they want to achieve. It’s incredibly difficult to develop self-awareness as a leader, and even more difficult to maintain it through the inevitable changes implicit in growing a company.

But a growing body of research says it’s worth the effort.