CTO Wisdom with Charity Majors | Beyond the Program

Jan 7, 2025

CTO Wisdom with Charity Majors | Beyond the Program

Welcome to CTO Wisdom. In this series, we interview technical leaders who have stepped into executive positions.

Today’s guest host, Eric Brooke, speaks with Charity Majors, Co-founder and CTO of honeycomb.io

In today’s episode, they discuss:

  • How Charity’s career started with a music scholarship and led to being a Founder, CEO and CTO.
  • How a love of Command line and firefighting fueled a passion for infrastructure engineering.
  • Navigating ADHD and its impact on building a successful career.
  • The evolution from engineer to successful manager, director, and executive.
  • The value of co-owned decisions and full board transparency at the executive level.
  • And more!

About today’s guest: Charity Majors is the co-founder and CTO of honeycomb.io. She pioneered the concept of modern Observability, drawing on her years of experience building and managing massive distributed systems at Parse (acquired by Facebook), Facebook, and Linden Lab building Second Life. She is the co-author of Observability Engineering and Database Reliability Engineering (O’Reilly). She loves free speech, free software and single malt scotch.

About today’s host: Eric Brooke has a rich and varied leadership career – leading up to 21,000 people and Billions in revenue, throughout 14 countries. In their career, they have been an Executive six times (e.g. President, CEO, CMO, and CTO) and a Board member of multiple organisations. Eric has been a CTO of scaling startups from 0 to 120 engineers. As an adviser and mentor, they have helped multiple other startups scale both in Canada and the US. As well as supporting multiple startup incubators such as 1871 in Chicago and TechStars.

Sign-Up for the Weekly hatchpad Newsletter: https://www.myhatchpad.com/newsletter/

Transcript
Eric Brooke:

Hey, listeners, Tim Winkler here, your host of The Pair Program.

2

:

We've got exciting news introducing our

latest partner series beyond the program.

3

:

In these special episodes, we're passing

the mic to some of our savvy former

4

:

guests who are returning as guest hosts.

5

:

Get ready for unfiltered

conversations, exclusive insights,

6

:

and unexpected twist as our alumni

pair up with their chosen guest.

7

:

Each guest host is a trailblazing

expert in a unique technical field.

8

:

Think data, product management,

and engineering, all with a keen

9

:

focus on startups and career growth.

10

:

Look out for these bonus episodes

dropping every other week,

11

:

bridging the gaps between our

traditional pair program episodes.

12

:

So buckle up and get ready to

venture beyond the program.

13

:

Enjoy.

14

:

Welcome to CTO Wisdom.

15

:

My name is Eric Brooke.

16

:

This series, we'll talk to leaders

of technology at organizations.

17

:

We'll understand their career, what

was successful and what was not,

18

:

and what they learned along the way.

19

:

We'll also look at what the

tech market is doing today.

20

:

We'll understand where they gather

their intelligence so they can grow

21

:

and scale with their organizations.

22

:

Hi, my name is Eric Brooke

and welcome to CTO Wisdom.

23

:

Today, with us, we have Charity, and

Charity, give us your elevator pitch.

24

:

Charity Majors: Hi, uh, my

name is Charity, I'm the co

25

:

founder and CTO of Honeycomb.

26

:

io, which is, I would say we were

the original observability company.

27

:

Uh, we make observability for software

engineers, um, and it's really about,

28

:

you know, helping to accelerate those

feedback loops that sit at the heart of

29

:

every high performing engineering team.

30

:

Eric Brooke: Awesome.

31

:

So how did you get started in technology?

32

:

What was like, what was your journey

to kind of like coding your first

33

:

line of code or building something?

34

:

What was the thing that

really sparked for you?

35

:

Charity Majors: Yeah, I grew

up in the backwoods of Idaho.

36

:

Very rural.

37

:

I didn't have a computer until I

went to college, um, and I went

38

:

to college on a music scholarship.

39

:

But when I got to school, I realized

that all of the people who got

40

:

their music degrees were still

hanging around the music department

41

:

and working very low wage jobs.

42

:

And I was like, dude, I grew up poor.

43

:

I do not want to be a poor adult.

44

:

And that's when I found computers.

45

:

Um, and I was really taken

by the Unix command line.

46

:

I've always liked words and the, the

command line is just so expressive

47

:

that I found it fascinating.

48

:

So I'm sure that my first line

of code was a bash script.

49

:

Eric Brooke: Oh, great.

50

:

Um, okay.

51

:

So when did you, um, tell us about

your first kind of foray into kind

52

:

of like being paid for kind of

like the work that you were doing?

53

:

Charity Majors: Yeah.

54

:

In, in college.

55

:

I mean, I'm old enough that

back then they actually paid me

56

:

to run the university systems.

57

:

I was assistant men for the CS department,

the best dad department, and then the

58

:

university as a whole, they gave me root.

59

:

I don't think they do that these

days, but back then they gave me root.

60

:

And I, and I parlayed that into a job

at the local web development shop.

61

:

And then by the time I was 18, 19,

I got recruited to come down to San

62

:

Francisco and I've been here ever since.

63

:

Eric Brooke: Awesome.

64

:

Um, so tell us through your career,

like kind of maybe highlight some

65

:

moments before you got to management.

66

:

And then obviously we want to

dig in a little bit about your

67

:

first foray into management.

68

:

Charity Majors: Yeah, you

know, I feel so lucky that I

69

:

got into tech when I did when.

70

:

You know, hiring standards were low,

and if you were curious, interested,

71

:

you know, they could find a job for you.

72

:

You know, the world has changed a lot.

73

:

Uh, I've been watching my little sister

try to find engineering jobs, and I just

74

:

feel so lucky that I got it when I did.

75

:

Um, but I really, you know, as someone

who, I did not, I'm a serial dropout,

76

:

I've never graduated from anything.

77

:

Uh, I, I really kind of made a career

specialty of being sort of the first,

78

:

Infrastructure engineer to join a group

of software engineers, the startup, just

79

:

when they're starting to get customers,

things are starting to get real.

80

:

And helping them sort of grow

up and make reliable systems.

81

:

And I, and I really, I

love being an engineer.

82

:

I really, I really enjoyed that.

83

:

Eric Brooke: So you, when you,

you, you had a love for Unix,

84

:

and then you obviously kind

of went into infrastructure.

85

:

What was it that was kind of like about

infrastructure that really interested you?

86

:

Charity Majors: Oh, the fires,

the firefighting for sure.

87

:

So I got my ADHD diagnosis in

:

88

:

life make a lot more sense now.

89

:

Like I tried being a straight

up software engineer a couple of

90

:

times and I always got so bored.

91

:

You're sitting down.

92

:

You're like, OK, I know

what I'm building today.

93

:

I know what I'm building tomorrow.

94

:

And.

95

:

Next week and next month and

months after and it's just like

96

:

my brain just like goes off.

97

:

Uh, and for better or for worse, there

are always fires to fight in ops in SRE,

98

:

you know, things are, I have never been

more calm than when everything is on fire.

99

:

Everyone's freaking out.

100

:

And I just like, I hit my groove that

that is the best time to be alive in my

101

:

mind, which is not an uncommon story.

102

:

When you get to know folks in the SRE

community, like There's a lot of us who

103

:

are like, ah, I found a way to focus.

104

:

Life hacks.

105

:

Fires.

106

:

Eric Brooke: Um, do you mind

talking a little bit about how

107

:

you think ADHD has helped you or

hindered you in your career journey?

108

:

Like, what are the things

that you've learned from it?

109

:

Charity Majors: Yeah, you know, I wish

I had realized earlier that there was,

110

:

I just thought it was really weird, you

know, I was homeschooled my whole life.

111

:

I didn't really experience

traditional schooling.

112

:

So I kind of just thought that I didn't

develop the right habits or I always

113

:

struggled with the sleep schedule.

114

:

I always struggled with, you know,

and, and so after starting Honeycomb in

115

::

CEO for a while and my life stopped

116

:

functioning like my everything just

went to hell And in retrospect, I now

117

:

understand that as an engineer One tool

and I used the hell out of that tool.

118

:

The tool is hyper focused, right?

119

:

But I got interested in something I

would never Dive into a hole and I would

120

:

not emerge until I had figured it out,

whether it was hours or days later, you

121

:

know, and that tool got me a long way.

122

:

And then when I became CEO, you

don't get to use that tool, you know?

123

:

And I, I'm not a structured person.

124

:

I'm not a predictable person.

125

:

I'm not a person and I'm not

someone who can just like.

126

:

muster through on willpower.

127

:

You know, like my co founder,

Christine, who structured people who

128

:

can be like, at 10, 20 in the morning

tomorrow, I will sit down at my desk

129

:

and I will write an essay on X, Y, Z.

130

:

And then I will be, I can't do that.

131

:

I need fuel or I literally can't focus.

132

:

Um, and so like a lot of my picking

fights on the internet and the

133

:

public acts of aggression over

the years, I think just been.

134

:

Attributable to trying to bomb my

brain with adrenaline so that I could

135

:

concentrate on something, but as CEO,

I realized that if I had been awake for

136

:

at least 30 hours or so, things kind of

slow down and I could force myself to

137

:

do boring things like expense reports.

138

:

So I just basically for three or four

years, I ran on no sleep, like sleeping

139

:

every two or three days was the only

way I could get myself to force myself

140

:

to, which did not mean I was doing a

good job on any of it, but I could sort

141

:

of, you know, so like, it's, you know,

I, I, I am very grateful for, um, the

142

:

patience that the world has had with me

and sort of figuring out my plumbing.

143

:

And I hope that.

144

:

I hope kids get to figure it out a

lot sooner than I did, because tools,

145

:

medication, God bless drugs, they are

the best thing that ever happened to me.

146

:

Even having a regular schedule, getting

up every day, like delivering his

147

:

promise, like, it's, it's night and day.

148

:

Eric Brooke: I really appreciate you

sharing that, and I think also you've

149

:

shown that even with that diagnosis,

that you have been successful, and it

150

:

shouldn't hinder or push people away.

151

:

And having that diagnosis

has really helped you.

152

:

Charity Majors: Yeah, 100%.

153

:

I mean, tech has long been a

haven for neurodiverse folks.

154

:

You know, there are a lot of ways

in which it plays to our strengths.

155

:

Just that sort of, you're a dog with a

bone, you're curious, you're interested.

156

:

If you can learn to like, align

your curiosity and your interest

157

:

with things that the world

needs, it's a, it's a superpower.

158

:

Eric Brooke: Yeah, I concur.

159

:

Um, so you've traveled a journey.

160

:

Um, you've been like, so you did

a kind of like an icy role and

161

:

individual contributor role for a

while when you first got to management.

162

:

Like, what were the things

that you had to learn?

163

:

Charity Majors: Oh, no, I think

I've learned so much more about

164

:

being a manager since I stopped

being an engineering manager.

165

:

You know, like I think in the moment I

was very reactive and very just sort of

166

:

territorial and kind of, you know, I had

just gone through this acquisition by

167

:

Facebook and I wasn't very happy about it.

168

:

I don't think I was, I wasn't really

a team player in a lot of ways.

169

:

And in retrospect, a lot of these

things make a lot more sense to me.

170

:

Um, but the things that I, you know,

I mean, I think that the first thing

171

:

that every new manager has to figure

out is, is, is just like, You know, you

172

:

became a senior engineer, presumably,

and which means you learned to have,

173

:

have, know how to trust your own

judgment or know when to trust your

174

:

own judgment and when not to, right?

175

:

And when you become a manager, I mean, the

first jarring fact is that you no longer

176

:

know when to trust your judgment or not.

177

:

You might be doing well, you might

not be, you're probably going to

178

:

feel like shit no matter what, right?

179

:

You never get to go home at the end of

the day, feeling like, yes, I did it, I

180

:

built it, I figured it out, I fixed it.

181

:

Achievement unlocked.

182

:

You know, you don't get

that feeling like, as a man.

183

:

Over the years, you learn

to look for those moments.

184

:

They're, they're a bit more muted.

185

:

They're, they're more unpredictable.

186

:

They're more, it's more like someone will

come to you and be like, Hey, that thing

187

:

you did for me three years ago was great.

188

:

And you're like, Oh, that does feel good.

189

:

You know, but it's not like the

dopamine hits that you get as an

190

:

engineer where you're solving puzzles

all day or you just leave work

191

:

feeling just like high on life, right?

192

:

It's not like that.

193

:

So I feel like the first big adjustment

of every new manager is just like,

194

:

you're kind of like you're a beginner.

195

:

You're a beginner again.

196

:

You don't know when or where to

trust your judgment and you don't

197

:

know where to find your joy.

198

:

Eric Brooke: So, yeah, I

concur with all of that.

199

:

It is, you go from competence

to incompetence and it

200

:

doesn't feel comfortable.

201

:

Um, so what were the things that

you would tell now a new manager?

202

:

Here's the one thing you should focus on.

203

:

I know it's very individual, it's

context driven, but what are the

204

:

things that you ask them, like

a new manager, to focus on now?

205

:

Charity Majors: Oh, well, that's a slip.

206

:

You started off asking, what would you

ask your, your past self, which is a

207

:

very, I would tell my past self, if you

don't feel like you could with your whole

208

:

heart or most of your heart represent

the company, you shouldn't be a manager.

209

:

I never felt like I could

represent Facebook as a manager.

210

:

And so I was at odds with the system

kind of fine for an IC in a lot of ways.

211

:

It is not fine for a manager.

212

:

If you can't do that.

213

:

You should take yourself out of that

role ethically, like practically,

214

:

pragmatically, like the idea of managers

as shit umbrellas, that is a flawed model.

215

:

It is not good for you.

216

:

It's not good for them.

217

:

It's not good for the company.

218

:

It's not good for anyone.

219

:

If you're in a place where you feel like

that's your only option, you should.

220

:

Get the hell out of there, you know, at

Facebook, I should have been an engineer.

221

:

I should have rested, invested.

222

:

I should have done my part.

223

:

So I could have checked out at the end

of the day, gone home, been with my

224

:

sweetie, gone out with friends, you know,

and as a manager, you can't do that.

225

:

You know, you take a home with you.

226

:

So much of it is emotional labor.

227

:

You take a home with you.

228

:

And which means that you have to, your job

is to represent the company to your team.

229

:

And if you don't think you

can do that, you can't.

230

:

Don't take the job.

231

:

What I, what I tell new managers now,

like who I think by and large at our

232

:

company, I don't think have that sort

of like tug of war of wills inside

233

:

of them is much more just like, Oh

God, I think some of the best advice

234

:

I ever heard was from Simon Willison.

235

:

He was like, you know, if you're, if

you're a new manager or, or if you're

236

:

not sure if you're a good manager or

not, you know, you can be 90 percent

237

:

of a good manager just by asking

yourself, What would a good manager do?

238

:

Just like, you know, whoever's in

your mental model is a good man,

239

:

just like, what would they do?

240

:

And just do that thing.

241

:

Because like, so much of it is just like

being basic human being, following the

242

:

rules, explaining things to people, you

know, it's not like heroic sin glory and

243

:

all that stuff that you can, you can get

a long way by just like trying to be a

244

:

basic, good human being and manager and

investing in yourself, you know, not

245

:

resting, you know, you're not an expert.

246

:

Slip into beginner mind, ask

questions, open up, be curious, be

247

:

creative, you know, take advantage

of the time for what it is.

248

:

Like the final 10 percent of

being an excellent manager

249

:

is like a lifelong quest.

250

:

So you're not going to

get there overnight.

251

:

You're not going to get there

in the first few years, right?

252

:

And so just like be fine with that.

253

:

Eric Brooke: Yeah, thank you.

254

:

Um, so moving up the kind of

the ladder or, um, is, um, like

255

:

coming to a director where you're

kind of managing other managers.

256

:

Do you have any thoughts about that?

257

:

Or did you learn anything in that part

of your journey where you're managing

258

:

managers but not managing ICs as much now?

259

:

Charity Majors: You know, I think

this is an under, under understood.

260

:

Um, I think a lot of folks have this

idea that being a director, director

261

:

is like being a super manager or

a super senior manager, but it's

262

:

not, it's a whole different role.

263

:

And the Delta between management and being

a director is at least as big as the Delta

264

:

between being an IC and being a manager.

265

:

Now, this is not to say this is true

everywhere because, uh, titles get

266

:

very undisciplined, especially in

startups and people are called directors

267

:

and they do all kinds of things.

268

:

But like my mental model of real

directors is directors run the company.

269

:

They're the ones that are responsible

for taking the strategy, the decisions

270

:

that are being made about resources

by VPs and C levels, and making

271

:

it actually work on the ground.

272

:

So they're responsible for like the

heartbeat of the company, right?

273

:

Making sure that things are high

functioning, that the wheels are

274

:

turning, that people are performing

up to spec, that bad performers are

275

:

getting, holding managers accountable.

276

:

Making sure that the communication

patterns are scaling.

277

:

Looking for, you know, it's

a socio technical machine.

278

:

That's never working perfectly.

279

:

And, and it's, it's the job of directors

to like, it's a lot of abstract thinking.

280

:

It's a lot of relationship building.

281

:

It's a lot of incremental, you

know, work, but it's so important.

282

:

And I feel like, you know, I'm actually

like kind of, I may be writing a series

283

:

on this and on our blog or something.

284

:

Cause I feel like even lots of really

great engineering managers don't actually

285

:

really understand what it is that Upper

levels are looking for in people that

286

:

they want to promote to be a director, you

know, and another aspect that I feel like

287

:

a lot of folks don't really grapple with

is that I feel like making career goals

288

:

in tech is kind of like a fool's errand.

289

:

I think that the best thing you can

really do is like always be learning,

290

:

be curious, be creative, be following,

be aware of what you're enjoying and

291

:

be open to opportunities because all

of the interesting opportunities I've

292

:

ever gotten that were changed my life.

293

:

I was not expecting.

294

:

I was, I was not gunning for them.

295

:

But I was in a position where

I was able to take advantage

296

:

of them when they popped up.

297

:

And I think that tech is so fast,

you know, every step up the ladder

298

:

that you go, there's at least an

order of magnitude fewer openings.

299

:

Which is the way it should be, right?

300

:

So you can't always predict.

301

:

You can try and put yourself in

line to have a good shot at being

302

:

tapped for a director, but you

can't always predict where those

303

:

opportunities are going to open up.

304

:

Uh, so like, I think that like, you

know, building a career where you're

305

:

happy where you are, and you'll

be happy if you don't move up to

306

:

the next level is super important.

307

:

Uh, and I think it is the people who are,

who manage to find that joy, who tend to

308

:

be tapped to do the next level of stuff.

309

:

Eric Brooke: Yeah, I concur.

310

:

Um, so let's move up to exec level.

311

:

Um, and so like either VP of

it and kind of like engineering

312

:

or CTO role, cause obviously it

differs in many different places.

313

:

What would you say is the.

314

:

the magnitude or the changes

that you really have to kind of

315

:

like encompass at that point.

316

:

I have

317

:

Charity Majors: this thing that I keep

chewing over lately, which is just

318

:

like, out of all the C level roles in

the world, CTO is the least formed.

319

:

It's the, it's the only one that there

isn't really a, a predictable pattern for.

320

:

CTOs are all over the freaking map.

321

:

Some of them are ICs, some of them

are, Managers, some of them run orgs,

322

:

some of them encompass product and

design, some of them don't, some of them

323

:

are, you know, some of them are like

extrovert, they're all over the map.

324

:

And when it comes to like VPs,

I feel like engineering VPs have

325

:

historically been sort of like

the junior members at the table.

326

:

Like they are not quite

the top tier execs.

327

:

Consistently, and I think that a lot

of this is because The whole philosophy

328

:

of having a high functioning exec

team is that you co own and understand

329

:

decisions that you make organizationally.

330

:

So, like, the whole exec team needs

to understand, okay, this is our

331

:

marketing strategy for the year.

332

:

Yes, we sign off on this.

333

:

We own this together.

334

:

You know, and I feel like people really

struggle to do that with engineering.

335

:

Some of this is the fault of Other execs

who don't think that they need to learn

336

:

as much about what makes good engineering

orgs as they do about P& L statements.

337

:

Some of this is historically the

fact of engineering orgs who don't

338

:

really try to convert their work

into like the terms of the business,

339

:

but there's been this big gap.

340

:

And I do feel like the end of the

zero interest rate era is forcing

341

:

us to start to close that gap.

342

:

And I think it's painful and

awkward and uncomfortable for us.

343

:

And I think it is so.

344

:

healthy.

345

:

Eric Brooke: I wonder sometimes if we

were to take like one area like delivery,

346

:

who is responsible for delivery?

347

:

Is it product engineering?

348

:

Um, what are the factors

that come into that?

349

:

How predictable is software engineering

in terms of like taking the SAS model

350

:

as opposed to gen AI model for a second?

351

:

Um, and that kind of like when you

look at sales, they often have like

352

:

a high level of predictability, not

always because it's very much macro

353

:

economic driven a large degree.

354

:

What are your thoughts about like,

how do we actually improve our

355

:

performance in terms of delivery?

356

:

Because that's usually what

the exec care about from us.

357

:

Like, are you and your team going

to be able to do this on time?

358

:

If time is a factor, time is

359

:

Charity Majors: always a factor.

360

:

Yeah.

361

:

Yeah.

362

:

You know, I feel like

there are so many aspects.

363

:

There is a higher level of

unpredictability and engineering

364

:

than in sales full stop.

365

:

Um, but that doesn't mean that we can't.

366

:

That we can't get much better at

pointing at a place and saying, that's

367

:

where we're going, getting updates

along the way about how we're going

368

:

at getting there, and trying to

arrive there roughly on time, right?

369

:

I think that like, anytime there's a big

shakeup in your org, whether it's a hiring

370

:

growth spurt, or a leadership change, or

a re org or whatever, it takes time to

371

:

like, you have to relearn all over again.

372

:

Uh, but like, if we aren't focused

on that consistently, we aren't going

373

:

to, we aren't going to like, Level up.

374

:

Um, I think I think there are a lot

of really interesting that there

375

:

are a lot of new startups out there

that are kind of focused on giving.

376

:

Engineering leaders visibility into

their team without using that punitively

377

:

and without using it necessarily.

378

:

There's always a story behind it, right?

379

:

Maybe this is what good tends to look

like in terms of like number of PRs, etc.

380

:

But like there's always

going to be outliers.

381

:

Some of them will be outliers because they

are outlier individuals who Excessively

382

:

helping the team, you know, move faster.

383

:

Sometimes they're outlet, but it's always

the starting point for a question, right?

384

:

And I think that our fear of being tracked

of having our, I mean, it's, I always

385

:

forget the name of the law, but the law

that once you're once you're tracking

386

:

something, people will start to like adapt

their behavior to deliver that metric

387

:

instead of, you know, is a real thing.

388

:

And so I think you really have

to be careful with this data.

389

:

You have to emphasize to people that yeah.

390

:

You know, first, you're

not looking at one metric.

391

:

If you look at one metric or two or

three, they're going to get game.

392

:

But if you're looking at the

broad Basket of behaviors, right?

393

:

Things will start to, and if you're

using them as the starting point

394

:

of the conversation, I think they

are, there's leading indicators

395

:

and trailing indicators, right?

396

:

And whether or not we hit our

deliverables on time, it's always

397

:

going to be a trail indicator.

398

:

So a big part of the battle is looking

for leading indicators that we can start

399

:

to use to find these things before it's.

400

:

Oh, shit.

401

:

We said we were going to ship today

and it's been, you know, a month, two

402

:

months, three months, but nobody knows it.

403

:

You know, that's what degrades

trust, not missing by a week,

404

:

not, you know, that sort of thing.

405

:

Eric Brooke: Yeah.

406

:

Concur.

407

:

Okay.

408

:

So, um,

409

:

when we look going forward, we talked

a little bit about your career and

410

:

that you moved through a honeycomb

and you were the CEO for a while.

411

:

Now that you're the CTO, um, I guess like

when you think about it, what is success

412

:

and how, what has helped you be Always

413

:

Charity Majors: many

414

:

people are different.

415

:

And that's why I feel like It always

starts with self awareness, uh, and

416

:

just trying to be conscious of who

you are, how, you know, your, your

417

:

own, your own responses to things,

uh, your impact on other people.

418

:

Uh, I have not had an easy few years,

and I feel like I've finally gotten

419

:

to a good place, but like, I think a

certain amount of, uh, stubbornness

420

:

and tenacity is also necessary.

421

:

Um, I, I feel like it's sort of

the nature, blessing, the curse of

422

:

leadership positions that everybody

kind of thinks that they want to be one.

423

:

You don't really know if you like

it or not until you've done it.

424

:

Um, and after this, oh my God,

my dearest wish after this is to

425

:

go be a staff engineer someplace.

426

:

I just want to sit in the corner

and write code and have it be

427

:

someone else's problem for a while.

428

:

But I feel very grateful for the time

that I get to be in the seat and do

429

:

this thing for as long as it lasts.

430

:

Eric Brooke: And so what were the things

that help you in that, around you?

431

:

Um, yeah.

432

:

Charity Majors: Uh, journaling, um,

writing, uh, I used to do Twitter

433

:

a lot and it was really helpful for

me in sort of working out external

434

:

messaging as well as working out

what I thought and felt about things.

435

:

Um, I don't do it as much anymore.

436

:

There's just too many places.

437

:

There's like, what, Macedon, Blue Sky,

and Twitter, and LinkedIn, and there's

438

:

just too many, and I can't keep track.

439

:

Um, but like, writing has helped me

sort of externalize what's inside

440

:

my head, and look at it from a

new angle, and get feedback on it,

441

:

and it's been invaluable to me.

442

:

Um, I do not really, a lot of the

standard advice like mentors and

443

:

classes just really don't work for me.

444

:

I have a lot of problems with authority,

and anybody who I, this is not anyone

445

:

else's problem, it's my problem, but

anyone who I perceive as trying to set

446

:

themselves above me, I automatically

lash out at, which is not, not great.

447

:

So, I consider everyone my peer,

whether they're an intern, or a student.

448

:

Or like fucking Elon Musk or

everyone's my peer, right?

449

:

That's just how I make

my way through the world.

450

:

And realizing that about myself

was a very healthy thing.

451

:

I don't mind if other people

think of me as a mentor.

452

:

That doesn't bother me at all.

453

:

They're still my peer to me, right?

454

:

So like I said, I think a lot of it is

just about understanding your internal.

455

:

Because when you're in IC, you have,

you have much more of the luxury of

456

:

not having to be on all the time.

457

:

It's okay.

458

:

Your mistake, the higher up you go, the

more Your internal struggles become,

459

:

it's so easy for them to be externalized

and become other people's problems.

460

:

And if there's one thing that I

really can't abide, it's people in

461

:

positions of leadership who make their

problems everyone else's problems.

462

:

It's so irresponsible.

463

:

It's not okay.

464

:

People do it all over the

place and it's hard not to.

465

:

So I feel like, you know, the

thing about you need to apply

466

:

your own oxygen mask before you

can use it on others is so real.

467

:

Eric Brooke: I really love that analogy.

468

:

That's a really good one.

469

:

Um, is there a problem that

you're looking into and trying

470

:

to figure out at this time?

471

:

Charity Majors: Yeah, um,

I have just, uh, taken over

472

:

responsibility for our AI strategy.

473

:

This is probably the most boring and

predictable answer in the world, but,

474

:

um, I am excited about it because,

you know, I, I, I'm excited because

475

:

I think part of what brings companies

to Honeycomb as customers is our

476

:

reputation for engineering excellence.

477

:

You know, I think we've, we've really

tried hard throughout our entire history

478

:

to share what we've learned about what

makes for high performing teams, what

479

:

makes for predictable, consistent software

delivery, what makes for happy team.

480

:

Um, it's what's made it easy for us to

recruit, even when, you know, in the days

481

:

when everyone's, you know, fighting for

engineers, and it's, and it's brought

482

:

a lot of customers to us because they

trust what we say about the future.

483

:

And up until now we really haven't said

much about AI and I think that's starting,

484

:

starting, it's about to start to hurt us.

485

:

And it's time for us to start

talking about where we think the

486

:

future of AI fits into the world

and how people should be preparing

487

:

for it, how they should be hiring

for it, how they should be building.

488

:

So over the next few months.

489

:

Um, we are not only starting to build

some things internally that use AI that

490

:

I'm really excited about that I can't

really talk about, but also we're planning

491

:

to put out a drumbeat of material.

492

:

It's just engineers talking to

engineers about how to apply.

493

:

Good software engineering

principles to non deterministic

494

:

systems, which is something that

nobody's really figured out.

495

:

You know, there's all of

this hot air and thought.

496

:

I hate that term thought leadership.

497

:

It gives me hives, but all these

people just like thinking out loud

498

:

all over the place about how great

or how bad everything's going to be.

499

:

And I'm so irritated with that.

500

:

I just want to hear engineers talking

day in the life of the engineer.

501

:

How, how am I using this for good?

502

:

How's it screwing with me?

503

:

How can we make some progress here?

504

:

Uh, and my hope is that we can earn

some credibility with folks who are

505

:

using LLMs and building models in

the way that we already have people

506

:

who are just built writing code.

507

:

Eric Brooke: Yeah, it's

a fascinating space.

508

:

It feels like an industrial revolution

and like, realistically, every

509

:

CTO is going to have AI as part

of their journey going forward.

510

:

It's some

511

:

Charity Majors: combination of industrial

revolution and giant fucking bubble

512

:

and nobody really knows what the

percentage is yet in some sense It's

513

:

very clearly like a trillion dollar

solution looking for a trillion dollar

514

:

problem, which we haven't found yet We

found a lot and that my friend can't

515

:

quirk who works at honeycomb it I should

attribute that but I would say that

516

:

it Stuck with you like that's so true.

517

:

Lots of little like ten million

dollar problem Maybe a million

518

:

dollar problems, you know Well, you

know, I probably, no, not so much.

519

:

So how much of it, how much of

each is it going to be like TBD?

520

:

Eric Brooke: Yeah.

521

:

Yeah.

522

:

Concur.

523

:

Um, I also want to point out that I

found, um, I'm going to be careful

524

:

of the word because I don't want

to give you hives, but like some

525

:

of your articles and blog posts are

excellently written and have definitely

526

:

helped me think farther and wider.

527

:

So I definitely recommend

our viewers check out your

528

:

blog because it's very good.

529

:

Okay, moving on.

530

:

Um, what's it like?

531

:

You talked a little bit earlier

about working in the exec and it's a

532

:

lot about, you know, as a business,

we're like the one team and our

533

:

job is to kind of align on that.

534

:

What are the things in hindsight

you would say that could prepare

535

:

someone for their first exec role?

536

:

Charity Majors: Oh, that's

a really good point.

537

:

I think that for engineers in particular,

you need to understand how this works.

538

:

You need to be curious about the business.

539

:

You need to, you know, I think we get so

deep into tech for the sake of tech and

540

:

even tech, tech's affecting the business,

but just like, like when I started

541

:

Honeycomb, I did not know the difference

between sales and marketing, much less

542

:

demand gen versus product marketing.

543

:

You know, I didn't, I had never

heard the term product market fit.

544

:

I didn't know that categories existed, you

know, and I was phenomenally ill prepared

545

:

and it was very hard to recover from.

546

:

And I think that You know, if, if you

want to lead engineering or you really

547

:

need to learn about how, um, and most

engineers don't, uh, and, and there's a,

548

:

there's this kind of ingrained snobbery

that a lot of us have, you know, Silicon

549

:

Valley is infamous for thinking that

engineers can do everyone else's job.

550

:

You know, and while I would, I would

still hold, I think an engineering

551

:

background prepares you for that.

552

:

Incredibly well for a range of

careers, only a few of which

553

:

involve writing code all day.

554

:

It teaches you how to think and

debug and it gives you this really,

555

:

you know, and having a technical

orientation where you can trust

556

:

your own judgment to some extent.

557

:

It's just like it's

currency in this world.

558

:

Uh, but you have to care as much

about the business as you do about

559

:

technology in order to be pretty exact.

560

:

Another thing I would say is that,

you know, a thing that I think that In

561

:

order to co own, you know, each other's

decisions, I, there was a, there was

562

:

a moment when Honeycomb, I think, kind

of crested a thing that we had been,

563

:

where we had been messing up for a

long time without realizing, where we

564

:

were just like nodding, going, yeah,

that sounds reasonable, and moving on.

565

:

And when we started going, no way.

566

:

What exactly do you mean by that?

567

:

Wait, are we using the word

enterprise to mean the same thing?

568

:

You know, just like digging in to

make sure that what's in our head?

569

:

Because otherwise you're

going to be surprised, right?

570

:

And, and being able to like early

detect those areas of misalignment.

571

:

My friend, Emily Nakashima, who's

our VP of engineering, wrote two of

572

:

the best blog posts I've ever read

on becoming a VP of engineering.

573

:

And she talked about how creating

alignment It's a buzzy, buzzwordy

574

:

sounding thing, but it's like

so much of what the job is.

575

:

Just making sure what is in people's

heads is not just the same words,

576

:

but the same concepts, the same

ideas, the same priorities, the

577

:

same, you know, learning to get you

that spidey sense when something is

578

:

not on the same page, you know, and

how to resolve it is so critical.

579

:

Eric Brooke: I remember when traveling

my first journey with domain driven

580

:

design, and one of the things it

talks about is ubiquitous language.

581

:

I'm using the same words

across the organization.

582

:

And I remember asking each of the exec

at that time, what is revenue to you?

583

:

And every answer was different.

584

:

And that really highlighted to me like,

Oh, how much conflict and extra things

585

:

do we create because we're using words?

586

:

Charity Majors: Yes.

587

:

Eric Brooke: Yes.

588

:

Okay, cool.

589

:

What does an interaction with a board

look like from your perspective?

590

:

Like, what, could you demystify that

a little bit for people that don't

591

:

Charity Majors: know?

592

:

This is something that is near

and dear to my heart, and it's

593

:

something that I think that a lot

of mythologizing goes on around.

594

:

So Honeycomb, we've actually done

something, I think we're the first

595

:

company in America to do this.

596

:

We have an employee, a voting employee

board member on our board of directors.

597

:

We've had this in place for three

years, and part of their role is to

598

:

attend all the board meetings, even the

closed sessions, and then they present

599

:

the board deck that we present to the

board back to the company in the next,

600

:

all hands, and they talk about what

they saw, what they heard, and I think

601

:

a lot of people expected this, this

position to be one of like employee

602

:

advocacy, or, or that there would be

like a Opportunities for the employee

603

:

board member to speak or something.

604

:

People don't realize that that's not

what boards talk about or care about.

605

:

Um, they talk about numbers, sales

numbers, sales efficiency, you

606

:

know, how much, what's your zero

cash date, marketing numbers.

607

:

You know, they do a certain amount

of debugging, like slightly closer,

608

:

but like it's all, I don't even

talk in board members, in board

609

:

meetings, hardly ever, right?

610

:

It's really head of sales, the

head of marketing, COO, CEO.

611

:

And they're talking, they're talking

about things that are not what

612

:

employees care about for the most part.

613

:

You know, things like,

you know, how's my rap?

614

:

I mean, I'm overstating a tiny

bit, but like the kinds of things

615

:

that like, I think employees

think boards will talk about.

616

:

So, honestly, like, I've been doing

a little bit of a tour to be like,

617

:

what has been the impact of this

experiment and everyone, a lot of

618

:

folks have said, you know, what I

think I've learned from this is that

619

:

I don't care about this information.

620

:

It's not, I would be okay if this

experiment went away because I found out

621

:

that it's really boring and I don't want

to think about all this stuff, but I tune

622

:

out during the updates and I'm like, okay.

623

:

Thank you for your honesty.

624

:

I do think that like there's a, there's

a subset of folks, primarily people

625

:

who are aspiring to upper management

for whom it is really interesting.

626

:

There's a lot of details that are

honestly pretty dull if you, if you

627

:

aren't like thinking about that or

caring about all the time and it

628

:

can be very anxiety producing too.

629

:

So it's, it's, I used to operate

from the principle that, you know,

630

:

full transparency on everything.

631

:

That's what builds trust.

632

:

And.

633

:

In theory, I still agree, but I also

have come to respect that it's so easy

634

:

to just drown people in details that

it makes it hard for the things that

635

:

really matter to just stand out and

land as hard as they need to with them.

636

:

So I'm still kind of trying to figure

out how to thread that, you know, to give

637

:

people enough information that like, I

fully 100 percent believes that like,

638

:

if you're an employee, you have a right

to understand how the company is doing.

639

:

When are we going to run out of money?

640

:

What's our strategy?

641

:

How are we, you know, but I also.

642

:

I've come to respect that not

everyone wants to know all that stuff.

643

:

And so, yeah, I don't know.

644

:

It's an interesting, it's interesting.

645

:

It's an interesting sort

of like needle to thread.

646

:

Eric Brooke: Yeah.

647

:

Thank you for sharing that.

648

:

Um, in

649

:

Charity Majors: I mean, obviously

everybody is like AI, AI, AI, and I'm

650

:

already getting so cynical about it

because it's like just because you

651

:

put AI that doesn't make it better.

652

:

Honestly, I think I can say with some

confidence, if you can compute the

653

:

answer, you should compute the answer.

654

:

Because if you can computer it, it's

going to be a better, faster, cheaper,

655

:

and more reliable answer than anything.

656

:

An AI answer is a guess.

657

:

You know, and guesses aren't better.

658

:

There are some problems for which this

is like the only answer or an easier or

659

:

faster answer, but like for, you know,

it's so frustrating to me right now.

660

:

Cause I'm looking at the

observability industry and people

661

:

are just like, dashboards with AI.

662

:

And it's like, yeah, but that's

because you didn't collect the context.

663

:

You can't calculate the answer.

664

:

So you're guessing the answer.

665

:

That's not.

666

:

A plus, that's not a good thing, you

know, and I think that, you know, so

667

:

much money is chasing all of the AI

promises right now that it's inevitable,

668

:

but I think there's already a well

earned, well, a sink of cynicism

669

:

that's sinking in across the industry

and I am pretty irritated with it.

670

:

Is there

671

:

Eric Brooke: anything outside of AI

that you're seeing at the moment?

672

:

I mean, yeah.

673

:

I

674

:

Charity Majors: mean, I think

it's a really interesting time.

675

:

You know,

676

:

there were a few years there

where, you know, there was such

677

:

hot competition for talent.

678

:

It turns out everyone was overhiring.

679

:

You know, and, and now I think that

I think that I think the move towards

680

:

efficiency is a good thing for like it's

a little bit pain growth is fun, right?

681

:

It's fun.

682

:

It's hot, you know, but like, it's

not always healthy and growth for the

683

:

sake of growth is not a good thing.

684

:

And I think that all it's

learning to talk about are.

685

:

Our work and the language of the

business and actually justify it in

686

:

terms of real needs that we're really

solving in a competitive way is really,

687

:

really good thing for all of us.

688

:

I feel like, you know, engineers

are the engine of modern

689

:

businesses, the innovation engine.

690

:

You know, we push, we push markets

forward, we push technology forward,

691

:

we push, we push companies forward.

692

:

And.

693

:

We're too expensive to be, to just be

put in the corner or in a closet and

694

:

given tasks, given tickets, right?

695

:

Smart companies are inviting and

encouraging you to come above the

696

:

value line so that our creativity and

our problem solving is being used to

697

:

address, you know, at the very, at the

very top level, what are we building?

698

:

Why are we building it?

699

:

Who are we building it for?

700

:

Um, and so.

701

:

You know, I feel like engineers who feel

like they're being taken for granted and

702

:

treated like, you know, little monkeys,

take a ticket, find, find new jobs.

703

:

They exist.

704

:

Eric Brooke: Thanks, Charity.

705

:

Um, in terms of like your entire career,

we talked a little bit about what's helped

706

:

you grow and what's helped you scale.

707

:

And you've talked about the

writing and how important it is.

708

:

Um, it's, and I definitely appreciate,

as I mentioned, your blogs.

709

:

Um, it's kind of like having an

RFC out in the wild and it's like,

710

:

oh, wow, look at this thinking.

711

:

It's kind of interesting.

712

:

Are there other things that you?

713

:

like have helped you along the journey.

714

:

Um, and I know we've kind of like

covered some of them, but I just

715

:

want to give you a bit of space in

terms of What's helped you scale?

716

:

Charity Majors: Therapy.

717

:

Eric Brooke: Very good answer.

718

:

Charity Majors: I think therapy is, if

you are in charge of other people, I think

719

:

therapy is an investment in yourself that

everyone, everyone should do, you know.

720

:

I've tried a lot of things.

721

:

I've tried, you know, having coaches.

722

:

I've tried, I read a lot,

some might say compulsively.

723

:

I, I think I find a lot of value in

reading about things that are not about

724

:

technology, like books about ethics and

religion and just sort of like practices.

725

:

I think there's a lot of wisdom there that

is not just of the moment, life hacks,

726

:

you know, but is a little bit deeper.

727

:

And I think that as some of us,

you know, I really love what Will

728

:

Larson says about how we have,

each of us has a 40 year career.

729

:

I think it really changes how,

we can be so like, like little

730

:

mice, you know, just darting from

moment to moment, year to year.

731

:

But like you have a 40 year career.

732

:

How do you think about

the arc of that time?

733

:

And whereas the first 10

years, I think for everyone is.

734

:

learning and soaking up and

just like upskilling like crazy.

735

:

Like after that, I think that

once you get some power, what

736

:

are you going to do with it?

737

:

You know, what is the legacy

that you want to leave?

738

:

Like you want to have

an impact on the people.

739

:

I was just talking to this guy, I won't

name him, but like he's an exec and he

740

:

was talking about the place that he works

and how he got kind of disillusioned

741

:

with some other They're living up

to their own values, but instead of

742

:

just quitting, he was like, well, I'm

already kind of mentally out the door.

743

:

Why don't I see what happens if I

stick around for a few months and

744

:

just try to hold people accountable

on the board, my peers, you know, the

745

:

rest, the rest of the execs, the other

folks, just what happens if I try to

746

:

hold up a mirror and go, is this how

you, and I was just, I got chills.

747

:

I was like, what is the point of power?

748

:

If you just perpetuate.

749

:

whatever got you here, right?

750

:

Can't we do better for each other?

751

:

And I think zooming out and looking at

the arc of history and looking at, you

752

:

know, people who have been thinking about

ethics and morality and the good life,

753

:

you know, for longer than technology

has been around can be really grounding.

754

:

for sharing

755

:

Eric Brooke: that.

756

:

Last question.

757

:

What do you do for fun, Charity?

758

:

Charity Majors: You know, during

the pandemic, uh, actually just

759

:

a year, year and a half ago, I

got cats and This is so cliche.

760

:

I grew up on a farm where we had

lots of animals, but we ended up

761

:

eating most of them eventually, so we

never really like bonded with them.

762

:

Uh, but having cats that like to snuggle

with me, I've always struggled with sleep

763

:

schedules and like a regular, you know,

and it has been, it has been wonderful.

764

:

I look forward every evening

to laying down with those cats.

765

:

fuzzy little fuckers and just

like petting them and falling

766

:

asleep and it's in this charity.

767

:

Eric Brooke: It's been awesome having you

and describing your journey and some of

768

:

the wisdom that you've learned from it

and your openness about your experiences.

769

:

I really appreciate it.

770

:

Thank you.

771

:

Thanks

772

:

Charity Majors: for having me.

773

:

It's been a great, great fun for me to

774

:

Eric Brooke: calling all

startup technologists.

775

:

podcast, but don't know where to start?

776

:

Well, here's your chance to shine.

777

:

We're thrilled to introduce Beyond the

Program, our exclusive mini series,

778

:

and we want you to be a part of it.

779

:

As tech leaders and mentors, you'll

get the exclusive opportunity to

780

:

become a guest host right here

on The Pair Program podcast.

781

:

Share your expertise, insights,

and stories with our audience of

782

:

startup focused technologists.

783

:

Excited?

784

:

We knew you would be.

785

:

To be considered, head over to myhatchpad.

786

:

com backslash contribute.

787

:

Fill out a brief form

and submit it our way.

788

:

Let's co create something

amazing together.

789

:

Don't miss this chance to elevate your

voice and expand your personal brand.

790

:

Visit myhatchpad.

791

:

com backslash contribute.

LET’S DISCUSS YOUR HIRING NEEDS

Build a custom hiring solution to grow your product, data, and
engineering teams.