Episode 35

full
Published on:

3rd Jun 2024

How to Be a Sharper Operator - Wes Kao

There's a set of skills we rely on everyday at work, often without realizing it: how we think about problems, make decisions, market our ideas, manage up, give feedback...they're all part of the operating system of how we interface with the business world.

I’m fascinated by these things both because they have a massive impact on our effectiveness and because they often go unexamined. They’re just part of how we operate. But what if our ways of working are holding us back? What if we could optimize them and radically improve our performance?

Today's guest is a serial entrepreneur, marketer, and operator. These days she focuses on exploring and writing about these "deceivingly basic" topics in one of my favourite newsletters, which reaches more than 250,000 people.

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About Today's Guest

Wes Kao is an entrepreneur, speaker, coach, and advisor who writes at newsletter.weskao.com. She is co-founder of Maven, an edtech company that raised $25M from First Round and Andreessen Horowitz. Previously, she co-founded the altMBA with bestselling author Seth Godin.

https://www.linkedin.com/in/weskao/

Key Topics

  • [00:00] - Introduction
  • [01:28] - Why write about “deceivingly basic” topics
  • [06:56] - Rigorous thinking
  • [10:43] - Building a culture of rigorous thinking
  • [21:10] - Bottom line up front
  • [26:39] - Relationship with your manager
  • [37:23] - Change management
  • [41:32] - Empathy
  • [44:09] - Being a LinkedIn creator

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Transcript
Speaker:

justin-norris_1_05-16-2024_120520:

Welcome to RevOpsFM everyone.

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Today's guest is a marketer, an

entrepreneur, and a writer, Wes Cahill.

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In 2014, she launched Alt MBA

with Seth Godin, which has

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served thousands of students.

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And then she went on to co found

Maven, which is a platform for live.

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Cohort based courses, but I became

familiar with Wes through her weekly

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newsletter at Wes ko That's weskao.

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com Which reaches more than 250

000 readers and if you're not

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already one of them You should

definitely go check it out.

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It is one of my favorites

and Wes touches on marketing.

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She touches on ops She touches on

entrepreneurship But really why I like

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her writing is that she's often dealing

with topics that are kind of a level

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You Deeper than any one functional area.

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She writes about how to think, how to

communicate, how people relate to each

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other in a business context, how to make

decisions, stuff that's really part of the

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core operating system of business life.

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And she brings this clarity of insight and

a keenness of observation to these topics.

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I think no one else writes more

posts that when I see them, I think

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I wish I could have written that.

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So Wes, I am thrilled to have you

on the show today, and I really

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look forward to chatting with you.

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wes-kao_1_05-16-2024_120520:

Thanks, Justin.

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And those were very kind words.

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So thank

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you.

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justin-norris_1_05-16-2024_120520: So.

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I wrote that intro and then I saw on

your website you wrote that you are

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fascinated by topics that are deceivingly

basic, which is essentially a much more

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pithy way of saying what I just said.

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And I thought it was a perfect

description of your subject matter.

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I'm just curious, we can start with why,

why do those subjects appeal to you?

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What draws you to write about that?

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wes-kao_1_05-16-2024_120520: I think

that there are a lot of pieces of advice

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that we see on a daily basis around

management, leadership, being good at

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your job that are too generic and too

Captain Obvious, you know, you read it

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and you're like, Yes, I agree with that.

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Of course.

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I agree with that.

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Like, who would disagree?

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and yet trying to put it into practice.

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There's definitely a gap.

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and so where is that gap?

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clearly it's something between this

abstract theory and the realities of.

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Daily life and real relationships

and real situations at work.

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So, I love topics that are deceivingly

basic because, you might think, oh,

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well, I already understand that, or

there's nothing left to unpack there.

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but very often there is, and I think

that the upside is in understanding,

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on a deeper level, whether it's

the specifics or the concrete

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or the nuances of a situation.

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so I like unpacking that every

week in my newsletter because I

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personally find it fascinating.

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and I love nerding out with other

people who also find it fascinating.

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justin-norris_1_05-16-2024_120520: I'm

sure other people touch on these subjects,

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but don't see a lot of them out there.

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And I, maybe that's why your work is

resonating with a lot of people, because

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It's things that like for me, when I

read it, I'm like, Oh yeah, of course.

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I don't know, use a concrete example.

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You were talking about the power dynamics

of a situation where you're sending

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your like Calendly link to somebody

like it's just things that people

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process in this almost unconscious way.

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And you're kind of teasing that

up and bringing it to the surface

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and, holding it to the light.

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So I just, find that really valuable.

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Is that just sort of a natural,

You make an observation and

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you find it interesting.

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Are you deliberately searching

these situations out?

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wes-kao_1_05-16-2024_120520:

Basically, whenever I catch

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myself thinking something.

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I pause and.

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Ask why and try to think, is

there something beneath that?

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and is my reaction justified?

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So a lot of my posts come from me

asking myself, is my reaction justified?

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and, uh, there's this great

subreddit that's very popular

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called, am I the asshole?

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A I T

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A.

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I don't know if you've heard

of it, but it's amazing.

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So basically people from the internet

submit situations that they're

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dealing with and ask for help

figuring out, there's four options.

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one is you are the asshole.

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Two is the other person is the asshole.

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Three is neither of you are assholes.

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Four is, both of you are assholes.

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And then five is there's

not enough information.

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And so I think about AITA all the

time in my own life, you know?

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So if I get a Calendly, request from

someone who, you sounds a little bit

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too cavalier, a little bit entitled or

demanding, biz dev person in my LinkedIn,

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DMS sliding to the DM saying like,

pick a time here, that feels off to me.

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So when I, get the feeling of like, oh,

like that feels weird, I like to think

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like, wait, am I being unreasonable or

is the other person being unreasonable?

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Or maybe are we both

potentially being unreasonable?

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and I try to think about that,

in a bit more granularity.

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and usually, I like

thinking about both sides.

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So I like thinking about, both, the

person sending that message and the

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person receiving it, because I'm often

that person sending outreach, right?

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Like all of us are, whether it's,

you know, an intro email or, uh,

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DMing someone that you think cool.

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You've been following their work.

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Like we are often on both sides of the

situation, depending on the circumstances.

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So I like putting myself in the

shoes of, both parties, and thinking,

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why might someone have done that?

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Why might it have felt.

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Like the appropriate thing to do

for that person, why might it have

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been reasonable in their mind?

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And then on the other side, why is that

the person who received it, who felt

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like, Hey, like that felt a little bit

off, why is that person also justified?

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And then what can both

parties do to better translate

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their intent into reality?

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Because I think a lot of times, like when

we're the ones pitching or when we're the

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ones making a request to other people.

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we're not thinking, you know, Hey, I

want to be entitled or Hey, you know,

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I want to come off as someone who

doesn't appreciate other people's time.

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Like no one is thinking that right.

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But yet you still come

across that way sometimes.

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Because your execution didn't take

into account certain nuances, that

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the word choice that you used or,

the posture or assumptions you made

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when you made this outreach, actually

made you seem kind of like a jerk.

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And I always think that, we can

only control our own behavior.

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and so you can complain that,

well, I didn't mean it that way.

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that wasn't my intent.

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you can say that, and go

about living your life.

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Great.

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You do you, or you can realize that, you

know, if the other person is interpreting

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what I'm saying a certain way.

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and they're interpreting it not the way

I want them to, then I have the power

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to adjust the way that I communicate.

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I have the power that I, to

adjust the way that I pitch

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or make a request or whatever.

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and so I'm, trying to always,

decrease the space between.

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Your intent and the, impact and

reality of what the other person

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is actually hearing from you.

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justin-norris_1_05-16-2024_120520: One

of those things that, you've talked

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about a lot is rigorous thinking.

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which again is something that, we have

to think to do everything at work,

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like every decision, every task that

we work on, but it's sort of like

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we're focused on like the tactics or

the strategies or the end results.

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Not even like what's actually happening

on an individual level to produce that.

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Maybe just walk us through a little

bit, like your point of view on

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rigorous thinking, why it's important.

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wes-kao_1_05-16-2024_120520: Rigorous

thinking is having a systematic

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approach to making decisions.

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You know, we hear a lot about the

importance of thinking strategically,

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but I find that the word strategy

gets thrown around so much and you

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know, this person is strategic.

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This person is not, it gets thrown around

so much that it, I think it's lost.

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It's, it's lost.

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Meaning a bit.

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so I like saying rigorous thinking,

because to me, rigorous thinking is,

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sharing your logic and thought process

and rationale behind why you are

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doing something and inviting critique.

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So there's two parts of rigorous thinking.

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First is, asking yourself hard

questions about why are you doing

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this and what's the best way to do it.

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For trying to get from point A to point

B, what are the different steps needed?

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What are the assumptions

that we're making?

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what does success look like?

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And putting a bit of thought up front into

your approach before diving straight in.

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I think sometimes people, push back and

say, well, like I don't have time for

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rigorous thinking, you know, isn't it

all about shipping fast and diving right

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in and iterating learning by doing.

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Do what should I say?

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It's both.

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So you should put a little bit of

thought up front into what you're about

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to do and then jump into doing it.

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And you're going to learn

and iterate, of course.

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but you don't want to burn your

energy making avoidable mistakes.

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So I do think that there are,

better and worse mistakes.

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There's a spectrum.

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There's some things where if you

literally thought about it for 10

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seconds, you would have realized

that this was an obvious risk.

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so you can either, waste your energy

on those, or you can, spend that energy

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iterating, from a higher baseline.

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So that's kind of part one is

putting some thought upfront

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into what you're about to do.

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Part two is.

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The debate culture aspect.

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So, no matter how much thinking

you put up front, there's

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going to be potential holes.

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In the way you're looking at something

because you're looking at it from

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your own singular perspective.

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and, one of the powerful things about

rigorous thinking is encouraging a culture

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of debate where, any idea goes, anyone

at any level can propose an idea and

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make a suggestion, make a recommendation,

but you should be prepared to explain

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your thinking behind that, to advocate

for your idea and to make the business

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case for it and to welcome critique.

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That once you share your idea that other

people are allowed to poke holes and

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ask you about how does this part work,

or I'm not quite sure I agree with this

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assumption, or I feel like you're making

a logical leap getting from here to here.

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and that is very much a

part of rigorous thinking.

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and so, you know, 1 way I suggest.

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Managers and leaders to start

encouraging a culture of rigorous

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thinking is to ask their team members.

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What do you think?

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Give people a chance to think rigorously,

to put, all these questions into

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play for themselves, to feel on the

hook and to feel, skin in the game.

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If you're always the one doing

all the rigorous thinking and then

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structuring, scoping, and shaping a

project before giving it to someone

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for them to execute, they're never

going to have the opportunity to ask

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these hard questions for themselves.

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So you can't be surprised when,

you know, they're not quote

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unquote thinking strategically.

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So it's about.

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really putting the thought up

front, allowing and encouraging

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debate, and then giving your team

a chance to really practice that.

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justin-norris_1_05-16-2024_120520: There's

a lot of companies that have this idea of

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the best idea wins, or, we have a culture

of, they might not use the term rigorous

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thinking, but they aspire to that, or

they have it as one of their values.

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In practice, it doesn't

always work that way.

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ideas get dismissed out of hand.

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Like one person's logic is

superior to another person's logic.

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There's still a lot of

this room for subjectivity.

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how do you address this?

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Is it just a matter of like

organizational commitment?

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Is it a matter of calling it out,

especially when it comes from the

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leadership levels, it often does.

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wes-kao_1_05-16-2024_120520: It definitely

needs to be something that the leadership

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team cares about and believes in.

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I think as an individual in

an organization, you have a

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limited amount of leverage.

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To be able to change things 180 degrees.

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So, it needs to be something that,

your manager cares about, that

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your leadership team cares about.

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and so, you know, usually when I

write, I write for, again, both sides.

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I write for both the direct

reader, who's going to be

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implementing rigorous thinking.

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and, also for the manager or leader

who, sometimes needs to be sold to.

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so with rigorous thinking, for example,

I think this is very beneficial for

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managers and leaders who want their team

members to come to them with better ideas.

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I think a lot of managers, end up feeling

like the bad guy who always has to say no.

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You know, their team is always coming to

them saying, you know, can we try this?

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Or, oh, I think we should do this.

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And if you're always having

to say, no, that's not a

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positive experience for anyone.

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and you're also having to sift

through a lot of bad ideas and you're

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also carrying the full weight of

doing all the strategic thinking.

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So, um, I think, you know, really

thinking about how is this beneficial

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for managers who might want to do

this, and also for team members.

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Who want to do this, and I think

that that's important to think

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about again, both sides, because,

90 percent of managers are

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also direct reports themselves.

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So I think we don't really acknowledge

or talk about this out loud, or

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at least I haven't really seen,

people be explicit about this.

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It's usually here's advice

for managers and leaders.

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Here's advice for direct reports.

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But, unless you're the CEO, the CEO

reports to the board, but, you know, let's

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just say like CEO in an organization.

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So, if you're the CMO, if you're a co

founder, if you're an SVP, you might

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have a big team and they see you as

the boss, but you also have a boss.

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So, really understanding

both sides of that.

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I think makes us better leaders and

managers where we're able to put

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ourselves in the shoes of other people.

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I think as a direct report, you also

realize that all the stuff that you worry

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about with your manager, your manager's

also worried about with their manager.

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So there's a little bit of, I don't know

if it's schoenfreude, but, you know, a

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little bit of, of we're in the same boat

here, that I think is very encouraging.

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justin-norris_1_05-16-2024_120520: Do

you find that rigorous thinking is like

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this capability is sort of just a core

human trait that anybody can develop?

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Or is it something akin to

like, I dunno, creativity.

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Like some people are like, I'm a

creative or like I'm a numbers person.

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Like everyone has it to a degree,

but some people spike higher in

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that part of the chart than others.

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wes-kao_1_05-16-2024_120520:

It's probably both.

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I think that there are some people

who naturally, might see more risks

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and be able to de risk, for example.

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So I would say that I'm naturally a hyper

vigilant person, which has pros and cons.

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So I consider it a strength though,

because my mind just naturally has a

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filter where I'm constantly thinking

what could potentially go wrong.

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And then how can I stack

the deck in my favor?

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towards a favorable outcome, so some

people might not think that way.

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and many times I wish I didn't

think that way because it can be

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kind of hard to turn off sometimes.

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So everyone has their own strengths,

and characteristics, that are often,

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you know, strength and weaknesses

are two sides of the same coin.

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but I think with rigorous thinking

that it is very much a learnable skill.

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So, you know, I have 20 some questions

in my post that you can ask yourself.

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and many times when you see

any one of those questions, you

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immediately have a reaction.

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You immediately have an idea.

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I had a coaching call an

hour ago with a client.

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and, you know, we were talking about

de risking something and, literally

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asking the question of, you know,

what are potential risks here?

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I said, you know, I bet you already

have some that immediately come to mind.

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And he said, yes, I

already know what they are.

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Like, we don't need to talk about that.

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We can move on to the next thing.

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And it was great because.

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It just shows that, sometimes even,

asking yourself a certain question

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or realizing you should think about

something is 80 percent of the

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battle because your subconscious has

already been connecting the dots.

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So, it's more about remembering

to pause and think rigorously,

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and then let yourself kind of

fill in the blanks from there.

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justin-norris_1_05-16-2024_120520: Have

you seen a company, struggle to get here?

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Like what are some of the factors.

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that might lead to, a failure

to implement this sort of thing

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on a broad cultural level.

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wes-kao_1_05-16-2024_120520: One

area where I see leaders sometimes

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fumble is, you know, they say to their

teams, I want you to think rigorously.

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I want you to put more thought

into how this would actually work.

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and I also want you to speak

up to ask clarifying questions.

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So I want us to be really direct.

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And then their, team member comes

to them with a question or with an

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idea, or, wanting to, have thought

partnership and, a sparring session.

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and then the manager either jumps right

in to solve the problem for that person,

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or gives that person a wrist slap and

makes it a negative experience that

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the person shared their point of view.

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I think as humans, as creatures,

we are all very sensitive

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to negative experiences.

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It becomes a black spot in our memory.

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Hey, Justin told me that I should

come to him and share a point of

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view and advocate for my idea.

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I did that.

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And then he said it was stupid

and like said to go back to work.

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if that happens, the chances

that that person is going to

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want to do it again is very low.

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the other thing to keep

in mind is as a leader.

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Your words carry more weight

in the minds of your team.

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That is just fact.

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That is just truth.

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There's a power dynamic there.

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So even when you say something casually or

you know, flippantly, people might think

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that you were really serious about it.

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Right?

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So there's a great Silicon Valley,

episode where I think the, the CEO

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of the Google of the show, I forget

what it's called, but it's like.

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You know, the fake Google says

something very casual, didn't mean it.

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I think he said something

like, we need more honey for

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the bear, something like that.

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And then his team goes off and

spends two weeks trying to dissect

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what he means running around.

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I think they, at one point they

like get a real brown bear, right.

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And something, and he's like, wait, no,

I just meant that, in the kitchenette.

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we ran out of that, the honey

that comes out of the, you

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know, the shape of like a bear.

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Um, and so like that, that's real, right?

335

:

It's funny because it's true.

336

:

and so I think as a leader, you

just have to be cognizant of that.

337

:

and my takeaway from it is that I

want to really celebrate and reward

338

:

the behavior that I want to see.

339

:

if I say, I want you to ask clarifying

questions, I want you to raise your

340

:

hand if you don't understand something.

341

:

I don't want you to suffer in silence.

342

:

If my team member comes

to me and has a question.

343

:

Because they did what I asked,

I'm going to celebrate that.

344

:

I'm going to say, awesome.

345

:

I love that you brought this up.

346

:

Right.

347

:

Even if I think the question is like,

Hmm, maybe not a great question, whatever.

348

:

The broader point that I want to emphasize

is I liked that you brought this up to me.

349

:

I want you to do this again.

350

:

This is great.

351

:

I'm not going to be bad at you.

352

:

So.

353

:

Realizing that you have the power to

shape your culture by celebrating certain

354

:

types of behavior and reinforcing that

over time, that becomes your culture that

355

:

becomes the way that I talk, Justin, that

becomes Justin's leadership style, right?

356

:

over and over that becomes what

it's like to work around here.

357

:

justin-norris_1_05-16-2024_120520: as

you're talking there, I was thinking

358

:

about past experiences that I've had

where a lot of people that end up in

359

:

very senior leadership positions can be

a a little bit off the wall, sometimes a

360

:

little bit zany, a little bit mercurial.

361

:

And, People can form like judgments

and create impressions very quickly.

362

:

And if you're worried about that, like, I

better not go to so and so with this idea,

363

:

I better be careful asking such and such a

question, you know, it's really limiting.

364

:

like you said, you're

not going to do that.

365

:

wes-kao_1_05-16-2024_120520: and I

think again, really thinking about what

366

:

is within our control is useful here.

367

:

So with a manager and leader, I would say.

368

:

you should expect to repeat yourself more

often than, you think you will have to.

369

:

very often I hear, you know, a CEO will

say to everyone or their leadership team.

370

:

I said this 20 times, how are

people not getting it And then the

371

:

leadership team will say, I think you

said that once, maybe max twice max.

372

:

And then the rest of the team will

say, wait, you said that at all.

373

:

Like you said that even once,

so there's a little bit of

374

:

telephone where things get lost.

375

:

And so as a leader, I think setting your

own expectations to not get frustrated

376

:

that you'll have to repeat yourself.

377

:

And then second, that, to be mindful

of, am I celebrating what I want to see?

378

:

I'd keep those two in mind.

379

:

but then as a direct report, as a team

member, I think it's also important

380

:

to think what's within my control.

381

:

and if you realize that, you know,

CEOs can be mercurial creatures,

382

:

and have their idiosyncrasies.

383

:

well, what's your takeaway from that?

384

:

And my takeaway is that, you should

confirm understanding and, feel a

385

:

sense of ownership for making sure you

get what you need from that person.

386

:

So they should do their part to

communicate, et cetera, but you also

387

:

need to make sure you get what you need.

388

:

and I think actually senior leaders

are, best at managing up many junior

389

:

people think, Oh, at a certain point,

I won't have to manage up anymore.

390

:

but actually senior leaders are

best at dealing with CEOs who are

391

:

sometimes scatterbrained are sometimes.

392

:

little bit Kurt who don't necessarily,

think of the other point of view

393

:

or who say random things, right?

394

:

senior leaders know that

they need to parse out.

395

:

What do you actually mean here?

396

:

that they need to confirm that,

this is what I'm about to do, or

397

:

this is the priority here, right?

398

:

So they're constantly managing

up, and, realizing that it's your

399

:

responsibility to get what you need to

do a great job, not to expect people to.

400

:

lay out everything for you

really neatly, really clearly.

401

:

when both people, try their, do

their part, I think that's when

402

:

a really great manager direct

report relationship happens.

403

:

justin-norris_1_05-16-2024_120520: So

we've kind of come into the subject of,

404

:

communication and I know you've written

dozens of posts on this, so it's like

405

:

a big, big subject, and something that

a lot of people, frankly, I think just

406

:

struggle with, like they are under

optimized with their communication.

407

:

and they suffer

professionally as a result.

408

:

So if you had to think of like the

top things that someone should work

409

:

on or implement to just improve

in this area, what would they be?

410

:

Yeah.

411

:

wes-kao_1_05-16-2024_120520: The first

thing is probably a concept in the

412

:

military called bottom line upfront.

413

:

Bluff, B L U F, the person that

you are communicating to might

414

:

be coming out of a meeting.

415

:

They might be task switching.

416

:

they might have a surface level

understanding only of what it is

417

:

that you're doing, or they might

not be thinking about it as much.

418

:

So for ourselves, our work is a hundred

percent of the pie for your manager.

419

:

However, your work might be 10%.

420

:

Of what they think about on a daily

basis because they have six other

421

:

direct reports and their own IC work and

managing up to their boss's priorities.

422

:

So when you just shoot something over

without thinking about the right amount

423

:

of context that that person needs, you

can end up creating a lot of back and

424

:

forth, which wastes a lot of time, a lot

of effort, a lot of energy, and is just

425

:

frustrating and annoying for everyone.

426

:

and so when you put the bottom line

up front, you are super clear with.

427

:

What it is that you are asserting,

whether it's a recommendation,

428

:

a question, an action item,

and then putting context below.

429

:

So the way that I adapt bluff in,

let's say a Slack message is putting

430

:

the main point up front, and then

saying context colon, and then I

431

:

might have paragraphs of context.

432

:

So what you do there is you

are giving your reader agency.

433

:

To either read only the bottom line.

434

:

If they get it, great, they can move on.

435

:

Or if they have questions about

how you got there, they can

436

:

read the rest of the context.

437

:

And I think the reason this is important

is because, there are some pieces of

438

:

communication where you can't simply

quote, unquote, be concise, right?

439

:

Because usually people are like,

oh, we'll just make it shorter.

440

:

and that's not always practical because

the, Thought process and your rationale

441

:

behind what it is that you're saying

might be actually just as important,

442

:

if not more important than the final

bottom line that you came up with.

443

:

the bolder, the claim, or the more

controversial claim, the more you

444

:

need to back it up, the more you need

to support what it is that you're

445

:

saying and convince the other person.

446

:

So sometimes you do need that, real

estate to describe why it is it.

447

:

You got to where you got to.

448

:

So, putting the main point and then

context below I found is a super useful

449

:

way, to separate out what it is that

you're saying and, be more concise, but

450

:

also comprehensive at the same time.

451

:

justin-norris_1_05-16-2024_120520:

There's a similar kind of idea called the

452

:

pyramid principle came out of McKinsey.

453

:

We have a lot of ex

McKinsey folks where I work.

454

:

So it's like one of the things

we try to practice at my company.

455

:

It's such a transformational principle.

456

:

Like just reorient, like rather than

like blah, blah, blah, blah, blah.

457

:

So like, all right.

458

:

And then there's this thing I

want you to know or decide or do.

459

:

just starting with that bottom line and

it really changes how you're perceived,

460

:

not only is it clear for the other person,

but you just like, you seem sharper, you

461

:

seem more professional, more competent.

462

:

why don't more people do this?

463

:

wes-kao_1_05-16-2024_120520: because they

don't realize that it's actually doing

464

:

multiple cognitive steps at the same time.

465

:

when you are trying to be concise in

real time, the reason that it's hard

466

:

is because You're usually describing

something for the first time, right?

467

:

If you're in conversation talking

about something, you're talking

468

:

in a stream of conscious you're

trying to assess the importance.

469

:

of various things that you're

saying, as you are saying them.

470

:

And so therefore that's where you

get situations where it's, blah,

471

:

blah, blah, blah, blah, blah, blah.

472

:

This important thing, super

buried in the middle, blah, blah,

473

:

blah, blah, blah, blah, blah.

474

:

Right.

475

:

Because you're like, you're

thinking as you are speaking.

476

:

that's super important to recognize.

477

:

as an issue, because otherwise

everyone knows they should be concise.

478

:

Like, why isn't everyone

just concise then?

479

:

Like if it were that easy, right?

480

:

So I think we need to realize

like, what is the root problem?

481

:

And I think the root problem is we're

trying to do too many things at once.

482

:

So this is why when you are drafting

a message, often the last few

483

:

sentences you pull up to the top.

484

:

Well, why is that?

485

:

Because you realize what you were

really trying to say as you got

486

:

near to the end, as you yourself

clarified your own thinking.

487

:

So, when you're speaking in real time, it

can be a little bit harder to do, which is

488

:

why I highly recommend for folks to Take

a moment to prepare, especially if they're

489

:

presenting something, especially if you

know you're going to get certain obvious

490

:

questions to take a moment to think

about how you want to answer something.

491

:

because in my experience, it's

extremely difficult to do that in

492

:

real time for something that you are

talking about for the first time.

493

:

if you've talked about something.

494

:

Often, or we've talked about it

before it becomes a lot easier, right?

495

:

So we all have stories that we've told

dozens of times and you know, every

496

:

beat to that story, you know, when

people are going to laugh, you know,

497

:

when people are going to gasp, you

know, when people are going to hold

498

:

their breath because you've told the

story a bunch of times you've figured

499

:

out what is the core arc of that story.

500

:

But in normal conversation with

your coworkers, your boss in a

501

:

meeting, that's just not the case.

502

:

So the only way I found around that is.

503

:

Taking a few moments to prepare,

so you can clarify your own

504

:

thinking a bit beforehand.

505

:

justin-norris_1_05-16-2024_120520:

Totally.

506

:

And we've touched a little bit

on, this concept of managing up.

507

:

Maybe we can dive a bit deeper into that

and that specific type of communication.

508

:

The first thing that strikes me when

I think about this is the, true, like

509

:

weirdness of the relationship, like the,

manager employee relationship, because

510

:

it's like, are they there to help you?

511

:

Are they there to make you perform?

512

:

Are they there to like supervise you

and punish you when you do wrong?

513

:

And there's like an element.

514

:

Of all of this going on, what's

the right way for someone to

515

:

conceptualize this relationship in

order to get the most out of it?

516

:

wes-kao_1_05-16-2024_120520: You mentioned

a bunch of things that a manager might do.

517

:

I would say the answer

is D, all of the above.

518

:

And I think that's why the relationship

is so complex and can Create anxiety.

519

:

I think on both sides.

520

:

I think there are very few Dynamics in

our lives where someone, is both there to

521

:

support and guide you but also is there

to evaluate you and has the power to

522

:

cut off The way you make a living Right.

523

:

So the stakes are relatively high.

524

:

I posted about this on LinkedIn

and a bunch of people were like,

525

:

well, it's kind of like the parent

child relationship in some ways.

526

:

I disagree with that.

527

:

first it's kind of weird and

infantilizing and paternalistic.

528

:

but the other thing is, once you become

an adult, most people opt in to have,

529

:

you know, an ongoing relationship with

their parents and and there's a spectrum

530

:

you can have as a little contact with

your parents as you want to, or as

531

:

much as you want to, and having less

contact doesn't mean that you can't

532

:

pay your mortgage or pay your bills.

533

:

Right.

534

:

and so, you know, the power dynamic

there is different once you're an adult.

535

:

so yeah, I think it's a, a

very, unique relationship.

536

:

I'm still processing, you know,

what are really the takeaways there?

537

:

Because I think first, just

acknowledging that it's kind of

538

:

a weird situation is, is useful.

539

:

for me, it's useful because I've

definitely spent, nights not being

540

:

able to fall asleep, being anxious.

541

:

Because of something that happened with

my manager, I think many of us have,

542

:

it's almost, encompassing to a certain

degree that, if your relationship

543

:

with your manager is rocky and you are

worried about being let go, or you're

544

:

worried about what they're thinking

of you, it's almost like you can't

545

:

really focus on anything else, right?

546

:

It's, effectively an existential

threat to your psyche.

547

:

you know, many times I've

beaten myself up over that.

548

:

That why can't I just let it go?

549

:

Why can't I just care less?

550

:

and I think acknowledging that no,

like there's a reason why you care

551

:

so much and why this feels so heavy,

that in itself removes that judgment.

552

:

So you at least stop spending energy

judging yourself, and can kind of

553

:

focus on, on the problem at hand

and see it with a bit more clarity.

554

:

So I think that's one piece.

555

:

I think the other piece is

that, you know, I think a lot

556

:

about, information asymmetry.

557

:

in this situation, and there's

this weird thing where you both

558

:

the manager and direct for it

want to be honest with each other.

559

:

but there are some things where you can't

really be that honest, on both sides.

560

:

and I think that that's a weird line

to tread, and that requires judgment.

561

:

this is where savviness comes into play.

562

:

because if you share where you're

struggling, but you share it in a way

563

:

where you act like a quivering bowl of

jello that has no, internal fortitude, it

564

:

does not inspire trust in your manager.

565

:

To give you bigger projects or, to

trust you to handle certain things.

566

:

Right.

567

:

so, so that's kind of awkward.

568

:

you know, at the same time, people think

like, oh, well, my manager has all the

569

:

power, The power dynamic is, one such

that the firing direction goes one way.

570

:

And that is true.

571

:

but that's also again, too

simplistic because many

572

:

managers feedback to their team.

573

:

why would you worry if you had

all the power, why would you worry

574

:

about telling so and so that they're

doing a shitty job at this thing?

575

:

Right.

576

:

It's because you're afraid

they're going to rage quit on you.

577

:

And you don't want that to happen.

578

:

You're going to have

to backfill this role.

579

:

It's going to take three to six months.

580

:

you're going to look like a bad manager.

581

:

So to your manager, you're going

to look incompetent and they're

582

:

not going to want to give you more

head count or more responsibility.

583

:

So actually managers are just

as worried as direct reports.

584

:

They're just worried

about different things.

585

:

in some ways.

586

:

Managers have more at stake, different

stuff at stake, let's say, because, the

587

:

higher you climb, the further you fall.

588

:

And so they're trying to

protect what they've built their

589

:

reputation as a leader, and, if,

their team members are unhappy.

590

:

And unproductive that

doesn't reflect well on that.

591

:

Right.

592

:

So I think, understanding the psychology

of your manager and what they're

593

:

worried about, is useful because a, it

helps you better, add value to them.

594

:

And better understand their world.

595

:

but B it also helps you

understand your leverage.

596

:

and I think that is useful, especially

if you are in a function that's

597

:

quite important or have skills

that are difficult to replace.

598

:

You are less fungible.

599

:

there are some ICs that are actually,

I would say more valuable than

600

:

their managers, more difficult

to replace than their managers.

601

:

and so you see these managers kind of.

602

:

Catering around that person or the skip

level, telling the manager, it's fine.

603

:

Just make it work, right?

604

:

Because that person has more leverage.

605

:

So in any situation, I think

it's useful to understand what

606

:

is the leverage that I have?

607

:

What is the leverage that

the other person has?

608

:

and to some people, this may feel

a little bit Machiavellian, but

609

:

I think it's, it's practical.

610

:

It's practical.

611

:

It's good for you.

612

:

you don't have to be, weird about it,

it's simply looking at a situation

613

:

with clear eyes so that you can

figure out what's the best course of

614

:

action that is going to likely get

me to the outcome that I want to get.

615

:

because if you miscalculate your leverage

or you don't think about your leverage at

616

:

all, this is where you get into trouble.

617

:

This is where you overstep or where you,

take a risk that, you're not aware of.

618

:

what could, possibly go wrong

or, or the thing goes wrong.

619

:

And that's not an acceptable

thing for you, right?

620

:

you want to take risks where if it

doesn't work, you are okay with that.

621

:

and that requires you to understand your

leverage and the other person's leverage.

622

:

justin-norris_1_05-16-2024_120520: So

given the like complex dynamics that

623

:

you've just described and how we should

think about optimizing the relationship

624

:

with this person, there's sort of

a spectrum I've observed on the one

625

:

hand, almost like you can infantilize

yourself where you just go to the boss

626

:

and you're like, tell me what to do.

627

:

Or.

628

:

You know, if you have a problem, you

just kind of lay it all out on them and

629

:

just push all your problems upwards.

630

:

And obviously, as a manager,

that's very challenging, can

631

:

be frustrating to deal with.

632

:

There's an opposite extreme, I find,

where you just like keep this wall up.

633

:

And like, I'm performer.

634

:

I don't have any problems.

635

:

Everything's fine.

636

:

Like you just want to look good

for your boss and you don't, and

637

:

so you don't get enough feedback.

638

:

You don't collaborate with them enough.

639

:

Cause you're always just want to

seem like you're on top of it.

640

:

And, probably that's not the

healthy place to be either.

641

:

how do you like thread that needle of

showing that you're competent, but at

642

:

the same time being like vulnerable,

but not too much and getting feedback

643

:

in the right way and collaborating,

but in the right way, that problem.

644

:

wes-kao_1_05-16-2024_120520: I was

definitely that person that you described

645

:

that had a wall up that wanted at

all costs to seem competent, to show

646

:

that I was independent, that I can

handle this, you know, give me more.

647

:

And I think a lot of high

performers fall in this bucket.

648

:

lot of high performers, I would say,

have a high pain threshold, where you can

649

:

deal with a lot of bullshit and a lot of

struggle, and still kind of seem okay.

650

:

So this is, I think,

definitely a strength.

651

:

but it's also, there's

a shadow side to that.

652

:

There's a weakness.

653

:

Um, You know, it can be a weakness

too, because, it's not sustainable.

654

:

First of all, you know, eventually

cracks start to show you know,

655

:

start to feel burned out,

misunderstood, resentful, big one.

656

:

I definitely held things in and

then felt resentful of other people.

657

:

so first it's not

sustainable for yourself.

658

:

but second, you also don't.

659

:

fully take advantage of having a

good manager that you can learn from.

660

:

when you try to keep it all in yourself.

661

:

that's something that

took me years to learn.

662

:

I actually, you know, had the

revelation one day that my manager

663

:

is actually here to support me too.

664

:

Wow.

665

:

Weird, right?

666

:

Like before I was so hyper

focused on the evaluation piece.

667

:

does take judgment to thread that needle.

668

:

probably the simplest framework

that I have for threading that

669

:

needle is, bringing up challenges.

670

:

In a way that make me seem competent,

but also objectively show where

671

:

I'm having challenges or where I

feel that there's a bottleneck.

672

:

So, it's all the same problem per

se, but the way that you express

673

:

it and the way that you bring

it up makes a huge difference.

674

:

So to your point, you know, you

can just lay it all, verbal vomit

675

:

on them and complain and say,

like, this is all really hard.

676

:

I don't know what to do.

677

:

I feel stuck.

678

:

Yeah.

679

:

that's one way, you know, and

that makes you seem more junior.

680

:

the senior person has all

those same problems too.

681

:

They're just framing it in a

more organized way that makes

682

:

them look more competent, right?

683

:

So, framing up what the problem

is, what you've tried so far,

684

:

where you would like support.

685

:

Very simple.

686

:

If you do that and you use bottom line

up front bluff, you make it very clear

687

:

that you have attempted to solve this.

688

:

And those attempts have

been rooted in logic.

689

:

Common sense.

690

:

and you make it really clear

how your boss can help you.

691

:

and when you frame it that way, you are

able to get the support that you need.

692

:

but you also seem like a competent

person who has your shit together.

693

:

justin-norris_1_05-16-2024_120520: It

just reminded me of a post that you had

694

:

written about being clear about the sort

of feedback you want I think we've all had

695

:

that experience of like I don't want to

share this with my boss because I'm just

696

:

gonna get back like A ton of commentary

on things that aren't even finished yet or

697

:

aren't even ready for feedback and so we

hold ourselves back and it's really simple

698

:

framing of like I want feedback on the

big picture I want feedback on XYZ It's

699

:

that little extra level of, of thought

about how you approach that person that

700

:

actually makes it easier for them as well.

701

:

wes-kao_1_05-16-2024_120520: It

totally makes it easier for them.

702

:

Your boss does not want to spend an

hour giving you detailed feedback.

703

:

If you wanted a 10 minute initial.

704

:

Reaction from them, making sure that

you were going in the right direction.

705

:

So you really need to

help people help you.

706

:

you.

707

:

can't expect them to read your mind.

708

:

and when you send someone something

for feedback, again, think about

709

:

de risking and, the obvious ways

something could go wrong, right?

710

:

If I send this to you, One obvious

thing that could go wrong is you

711

:

give me a bunch of line edits when

really I wanted, directional feedback.

712

:

and so when you realize that

you can then take action on it,

713

:

you can then clarify the kind of

feedback that you're looking for.

714

:

when you're worried about something,

think about what can I do or say

715

:

to minimize that from happening.

716

:

And often it's so simple, you already

know you want a high level reaction.

717

:

So just tell the person that

718

:

justin-norris_1_05-16-2024_120520:

Want to touch on a subject that,

719

:

even I, almost hate the phrase cause

it feels like some sort of like

720

:

government bureaucratic process and

the phrase is change management.

721

:

I don't know how we could

have come up with a more like

722

:

wes-kao_1_05-16-2024_120520:

I'm already asleep.

723

:

Just kidding.

724

:

justin-norris_1_05-16-2024_120520: way.

725

:

Yeah, way of describing it, but it's

when you are in the position, as many,

726

:

people who are revenue operators listen

to the show are, or really any, any

727

:

leader let's say of like needing to

get people to do something different.

728

:

Like I have a plan, I have an idea,

I want you to change your behavior or

729

:

I want you to start doing something.

730

:

and it is so hard.

731

:

to do that because you, either

get ignored, you get resistance,

732

:

you get pushback, you give up.

733

:

What about this?

734

:

good ideas fail because of this.

735

:

what have you seen work?

736

:

Well, any techniques, any

strategies in this area?

737

:

wes-kao_1_05-16-2024_120520: I think

one of the biggest areas to start

738

:

with is to realize the first principle

that, um, Almost everything at work

739

:

boils down to getting people to

do the thing you want them to do.

740

:

That applies internally and externally.

741

:

externally it's customers, leads,

prospects, investors, the press,

742

:

It's all these external people that

you want them to click, download,

743

:

upgrade, sign up, fill out this form

to do a demo, whatever it might be.

744

:

You, want people to do something.

745

:

internally, it's Managing up to your boss.

746

:

You want certain things from your boss.

747

:

You want certain things

from your direct support.

748

:

you want your team to act a certain way.

749

:

so it all boils down to getting people

to do the thing you want them to do.

750

:

So what flows from that?

751

:

I think studying sales, studying

psychology, understanding,

752

:

behavioral economics.

753

:

Those are all really.

754

:

Simple foundational topics that I think

every leader should at least do some basic

755

:

reading on, marketing your ideas, right?

756

:

Building hype for your ideas.

757

:

that's one piece.

758

:

The second is, I like thinking

about aligning my idea, through the

759

:

lens of what's, what's relevant.

760

:

Interesting, valuable, relevant,

and useful for the other person.

761

:

So often when we have an idea, we

look at it from our point of view.

762

:

Why is it interesting,

relevant, and useful for me?

763

:

It is obviously useful for me

because I'm asking you to do it.

764

:

So like, that's kind of a, the

baseline, I don't need to necessarily.

765

:

Explain from that view because

it's baked in, why I'm asking

766

:

you to do something, right?

767

:

you really need to put yourself in

the shoes of the other person and

768

:

think about what would make this

exciting for that other person.

769

:

and I have a really simple example,

that a newsletter reader, replied to my

770

:

article called how to get an enthusiastic

yes, where I essentially write about,

771

:

this process of, framing things

through the lens of the other person.

772

:

and you were saying that.

773

:

He wanted to get out of a work trip.

774

:

There was this, work event,

his boss wanted him to go.

775

:

He felt like it was kind of stupid and

useless and he doesn't like to travel.

776

:

and instead of saying, Hey boss, I think

this is stupid and useless and I don't

777

:

like to travel, which would not go over

well, it would make you seem selfish and

778

:

like you're not a team player, right?

779

:

instead of saying that he thought.

780

:

What if I put this framework

into practice and thought

781

:

about what my boss cares about?

782

:

And so he ended up writing his boss

an email and said, Hey boss, you know,

783

:

you want me to go with this event?

784

:

I have these three projects

that I think are more important

785

:

to get across the finish line.

786

:

And I'd like to focus on these

because you've shared that, you

787

:

know, these were the priority.

788

:

I'm happy to go to the event, but

wanted to mention so that we can

789

:

align on what the priority is.

790

:

And his manager came back to

him and said, Oh, totally.

791

:

You should skip that event.

792

:

You should definitely

focus on these areas.

793

:

Beautiful.

794

:

so simple.

795

:

So beautiful.

796

:

I love it.

797

:

Right?

798

:

Same, situation, what he chose to

share and how he chose to frame the

799

:

situation, made all the difference.

800

:

And in fact, because he framed

it the way that he did, he

801

:

actually seems more strategic.

802

:

wow.

803

:

Like you're thinking about

what's best for the business.

804

:

You're thinking about not

wasting time going to an event.

805

:

You don't need to be at, you're thinking

about how can I be most effective

806

:

in my work to add the most value?

807

:

So he got what he wanted

and He seems like, an even

808

:

better employee because of it.

809

:

So it makes a huge difference

framing things through the

810

:

perspective of the other person.

811

:

justin-norris_1_05-16-2024_120520:

And so much of that just boils

812

:

down to empathy, which is something

that you've written about before.

813

:

In the sense of being able to put

yourself into the mind of that person,

814

:

understand the world, you know, through

their eyes, understand their priorities.

815

:

wes-kao_1_05-16-2024_120520: have,

a love hate relationship with the

816

:

word empathy because I feel like

people usually use empathy to

817

:

mean, understanding, being kind,

818

:

being soft, like.

819

:

justin-norris_1_05-16-2024_120520: I feel

820

:

wes-kao_1_05-16-2024_120520:

Feeling for you.

821

:

Yeah.

822

:

Like it's very much like.

823

:

obviously there's, a definition

of the word, but it's, it's also

824

:

like, in what context is it used in?

825

:

And it's usually used in the

context of like, you should

826

:

be more understanding to me.

827

:

Like, I want you to be more

empathetic to my situation.

828

:

and, one level further, like maybe

like not be so demanding of me, but

829

:

I think that managers and leaders.

830

:

The core of your job is to confront,

is to confront problems, confront

831

:

people, confront, situations, and

you have to be able to confront.

832

:

I have a post coming up called Positive

Confrontation that's all about how

833

:

can you be really direct with people.

834

:

But also be really reasonable or

be perceived as really reasonable.

835

:

that's definitely a skill.

836

:

There's a lot of people who are super

direct who confront, and it turns into

837

:

conflict and like, that's not great.

838

:

No, one's happy about that.

839

:

It takes a lot of emotional

labor on both sides to resolve.

840

:

but there are ways where you can

confront where your team members actually

841

:

appreciate you for confronting them.

842

:

That they actually get value

from you confronting them.

843

:

They appreciate you for keeping

them on the hook, for asking

844

:

them to put skin in the game.

845

:

and that's ultimately what

you want to do as a leader.

846

:

and so, you know, with empathy, that's

part of it because You need to be able

847

:

to understand the other person to be

able to cater to them and, and speak to

848

:

them and, figure out how to get the best

from them and change their behavior.

849

:

but I think about empathy

very much through a pragmatic

850

:

lens, as a means to an end.

851

:

I guess that's the best way to put it.

852

:

I see it as a means to an end,

which again can sound a little bit

853

:

Machiavellian, but this is work.

854

:

Right?

855

:

This is, this is work here, you

know, with your family, just be

856

:

empathetic for the sake of it.

857

:

Great.

858

:

Right?

859

:

But at work, I think it's useful to see

it as a means to an end, and the end is

860

:

to do better work together, to create

more value for the organization together.

861

:

and in order to be able to do that,

we need to empathize with each

862

:

other enough so we can communicate

and frame things, so that it's easy

863

:

for the other person to understand.

864

:

It's exciting for them to take action on,

but I see it all as a means to an end.

865

:

I think the problem is when people see it

as an end in and of itself, that is where

866

:

I have a little bit of a, challenge with

that, because it's often used to justify.

867

:

Lower standards, I think.

868

:

justin-norris_1_05-16-2024_120520: I

think we have time for probably just

869

:

one question and I wanted to take it

in a totally different direction and

870

:

just talk to you about your work on

LinkedIn, which has obviously been a huge

871

:

platform for you to get your ideas out.

872

:

I see, you know, pretty much

every one of your posts gets

873

:

hundreds and hundreds of reactions.

874

:

And it's a short form of writing

and it can often lend itself

875

:

to, these very almost formulaic

caricatured forms of writing.

876

:

And you don't go in for that and

yet you still are really getting

877

:

a very strong response from the

audience, which is fantastic to see.

878

:

I'm curious how you think about,

this platform, your approach.

879

:

Are you being strategic in any particular

way or are you just putting your ideas

880

:

out there and seeing what flows from them?

881

:

wes-kao_1_05-16-2024_120520:

great question.

882

:

I think if you are a leader that wants

to start sharing content, you need to

883

:

be mindful of who you're modeling after.

884

:

because there's a lot of different

archetypes I would say, on LinkedIn.

885

:

there are, there are many archetypes

in general, in the world, but on

886

:

LinkedIn, you really see that.

887

:

and so if you're, modeling and

learning and copying from a certain

888

:

kind of archetype, you're giving

certain signals to your audience.

889

:

So there's a certain style

of writing on LinkedIn, which

890

:

is one sentence paragraphs.

891

:

And the thinking behind that

is, it's very skimmable.

892

:

It's fun to read.

893

:

but the downside is it also

looks a little bit spammy.

894

:

and creators who are a little bit

spammy do that plus other things.

895

:

in the way that they share on LinkedIn.

896

:

and readers are very good at

pattern matching as humans.

897

:

We naturally pattern match.

898

:

So in a split second, when you

see a certain kind of post,

899

:

you're already thinking, Oh, it's,

it's probably that kind of post.

900

:

on the other hand, you see people share on

LinkedIn where they're writing paragraphs.

901

:

and you might think, well,

no one reads paragraphs.

902

:

You know, you have to make it skim.

903

:

Well, you know, most

people read on mobile.

904

:

the act of writing in a paragraph

is also a signal and you are

905

:

attracting a certain kind of person.

906

:

You're tracking the kind of person who

has the attention span to read paragraphs.

907

:

and you are showing that you are

the kind of person who doesn't care.

908

:

About, pandering to the algorithm.

909

:

so with everything that you do,

there's a trade off and there's

910

:

a signal that you're giving.

911

:

and so if you choose to share in a

way that is more thoughtful, sometimes

912

:

the reach just isn't as good.

913

:

That's just the nature of,

being on social platforms.

914

:

You know, there are many times

where I can think of a juicier

915

:

hook for what I want to write.

916

:

I can make it sound more extreme.

917

:

I can make it sound more controversial.

918

:

I can sound angrier.

919

:

and that will all get more

clicks, and more views.

920

:

But do I want to do that?

921

:

Not really.

922

:

Do I want to engage with people

who react to stuff like that?

923

:

And what kind of conversation

are we going to have?

924

:

You know, in the comments from that,

not ones that I'm that excited about,

925

:

and so thinking about the kind of

person you want to reach, the kind of

926

:

conversations you want to have, the

signals you want to put out into the world

927

:

about the kind of person you are, those

are all super helpful to think about.

928

:

And I don't think enough

people think about that.

929

:

I think most people look

up LinkedIn algorithm.

930

:

Tips and follow advice, like post

three to five times a week, post at

931

:

the same time every day, comment on

10 to 15 other people's posts, there's

932

:

a lot of advice like that out there.

933

:

and I think the more useful thing

is to think about, what kind of

934

:

person am I, what kind of person

do I want people to think I am?

935

:

and what kind of people

do I want to attract?

936

:

and then to look for a couple

of people that you admire that

937

:

are doing that style of posting.

938

:

And then look at what they do.

939

:

that's a much better starting point.

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About the Podcast

RevOps FM
Thinking out loud about RevOps and go-to-market strategy.
This podcast is your weekly masterclass on becoming a better revenue operator. We challenge conventional wisdom and dig into what actually works for building predictable revenue at scale.

For show notes and extra resources, visit https://revops.fm/show

Key topics include: marketing technology, sales technology, marketing operations, sales operations, process optimization, team structure, planning, reporting, forecasting, workflow automation, and GTM strategy.

About your host

Profile picture for Justin Norris

Justin Norris

Justin has over 15 years as a marketing, operations, and GTM professional.

He's worked almost exclusively at startups, including a successful exit. As an operations consultant, he's been a trusted partner to numerous SaaS "unicorns" and Fortune 500s.