The Looking Glass: 2 Motivations and No Truths

Dear Readers,

This week’s tidbits:

  1. The 2 Flavors of Motivation
  2. Why It’s Hard to Diagnose Ineffective Executives Quickly
  3. Why There is No Absolute Truth
  4. If you don’t have a job right now
  5. From the Archives: the Meta-Conversation

For subscribers:

  1. Subscriber mailbag: How to advance in a company where your managers are scared of your power, knowledge, and drive without dimming your light?
  2. Hiring for the 0→1 startup phase
  3. A Juicy Problem

Thank you for all the recent subscribers, especially your lovely notes and shares!

As a reminder, buy a subscription (which is like getting me a fancy coffee per month) to encourage my writing and help me hire someone to properly edit and manage this publication regularly!

The Looking Glass is a reader-supported publication.

We are motivated to do hard things for two reasons:

  1. Eliminating a negative feeling. I better put in the hours so I don’t get fired. I better work out so I’m not flabbier than my friends. I better study so I don’t flunk the test. I better contribute so the group doesn’t kick me out.
  2. Loving something beyond ourselves. I spend hours shuttling around my kids. I volunteer my free time for my community. I burn the midnight oil for our team’s mission. I put it all on the table in the pursuit of human greatness.

The former is the default state.

But let us strive to inhabit the latter — that exuberant, beautiful, oh-so-rare mindspace.

Most of us typically judge if someone is competent on whether they speak knowledgeably and confidently.

This signal is not reliable for executives because the vast majority of them have mastered speaking well.

Furthermore, the boss of the executive — the CEO — typically isn’t a good judge of the exec’s day to day impact. This is both because 1) the CEO doesn’t have the time to go deep and 2) they aren’t expert in the exec’s domain (an engineering founder does not typically know sales well.) They can only tell the executive is ineffective after results fail to materialize, but by that point it has already been months.

The people who are most qualified to judge an executive’s day-to-day competence are the exec’s best reports. A good engineer can usually tell how technical their CTO boss is, for example, just like a good designer can tell how excellent of a design eye the head of design has. They can also assess the caliber of talent this person is able to recruit. However, many of them often don’t sound the alarm for ineffective executives because they don’t know exactly what it means for the exec to be doing a good job. Sure the new CTO isn’t that technical, but maybe it’s fine that she’s not.

Thus, this is the conundrum: the CEO knows the expectations of the exec’s role, but is not qualified to judge if they are meeting it in their day-to-day; the reports are most qualified to judge if they are meeting it, but don’t know the expectations.

There are two paths out of this conundrum. The more labor-intensive path is the CEO becoming more expert in and spending more time in the exec’s domain.

The easier path is for CEOs and reports to share the same picture of what success looks like for the new exec, and to have a short feedback loop between them of how the that person is doing.

There are two questions every single human will always always always have some subjective opinion on:

  1. What are we trying to improve?
  2. On what time frame should we judge our success in improving it?

If you don’t have a job right now, take a snowy white piece of paper and fill it to the brim.

Imagine yourself at 80. When you look back on your life, what do you imagine you will take the most pride in?

Look at your life now. What do you need to realize that vision?

Look at your last chapter. In what ways are you better because of that time?

Celebrate how you’ve changed and grown. Appreciate who you are today. And choose who you want to be in the future.

This page is your reflection in the mirror.

Chapters begin and end, but you, the protagonist, gets to choose where your story goes next.

Read the full article on Medium here.

Have you ever struggled to make a certain conversation productive?

Maybe you’d like to give your coworker critical feedback that he definitely needs to hear, but you can’t bear to do it because you know he’ll immediately ball up like a porcupine and shoot quills at you while defending himself to the death.

Maybe it’s discussing your upcoming wedding plans with your mom because you can’t agree on whether your second cousin twice removed (and other family in that relationship sphere) should be invited, so the conversation always ends the same way, with you threatening to elope and your mom calling you the ungrateful black sheep of the family.

Maybe it’s you and your team not being able to discuss any problem without it entering a spiraling swirl of negativity, as if everyone were engaged in a competition to one-up each other on describing how f-ed up everything is.

In those situations, it seems like you just can’t win. Every time you get together to try and make progress, you just go around in circles, feeling more and more frustrated and dejected. You start to dread having to talk to this person (or group of people). Eventually, you stop trying, so the relationship devolves into active avoidance.

It doesn’t have to be this way!

Introducing a handy tool that can cut through those repeated cycles of tearing your hair out…

Have you seen the movie Inception, where Leo suggests it’s time to go into the next layer of a dream when they’re already in a dream?

It’s getting out of the dream you’re in, and zooming one level up. It’s taking a few steps back to have a conversation about the conversation.

When you make room to have a conversation about the conversation, it can help you break out of the patterns that got your conversation stuck in the first place…

Read the rest of the article on Medium

Read more



Building Sundial. Former Product Design VP @ FB. Author of The Making of a Manager Find me @joulee. I love people, nuance, and systems.

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Julie Zhuo

Building Sundial. Former Product Design VP @ FB. Author of The Making of a Manager Find me @joulee. I love people, nuance, and systems.