Rich and Paul, the co-founders of Aboard (a software product), discuss shipping software. They give advice to better ship products within time estimates. They also provide tips and tricks for better product management.

hey, rich.

Hey Paul.

Are you ready to launch our new software product?

On, I know, and we have a date for it all picked out, and

we, we have a, we have Scope.

We're about to have a big long scoping meeting.

Visit

a board.com.

Sign up for the beta.

So related to that, I saw a tweet that.

Uh, made me think of you.

Oh,

yes.

And it's by a, uh, an engineering lead who goes on Twitter

as artificial Nicks, n I X.

And she wrote the following, and I thought of you immediately After being

a manager in tech for like four years.

Now, I don't understand what everyone is saying about how, how hard it

is to estimate timing for products.

That's tweet one.

Tweet two is My team always ships on time.

Our KRS are always green.

People act like we're superheroes, but we just have our shit together.

So we should talk about this.

. Thank you Nicks Sophie for, um, giving us, uh, a good topic for this podcast.

Let's talk estimation, my friend.

Do you have any good tips or tricks?

I sure do, but it's not what you think.

Okay.

All right.

Let's do it.

There is something really brutal about not.

Being held accountable to someone outside, if I tell you you can pick up your Super

Mario birthday cake on Saturday for your kid's birthday party Saturday afternoon.

As a bakery owner, I should probably have the cake done.

You ruined the birthday.

You ruined the birthday.

That's right.

Don't ruin the birthday.

We should.

We should point out, there's a context here and there's a context for that tweet.

Software products are notoriously late.

Teams deliver, late, consultants deliver late.

Nothing ever lands.

And so one of the reasons people would come to us is they

would finally get their thing.

It would be expensive and it might be less of a thing than they were open for.

Mm-hmm.

But they'd get it.

Yes.

I'm a pilot and for a 7:00 AM J F K New York to Charles Dugal Paris.

Flight.

I have to check in to my airline and be at the airport at 5:00 AM

there's paperwork, there's whatever I have to do.

big checklist,

big checklist, and you know the check the checklist

for the plane and all that.

So I gotta be, I gotta, I'm on the plane at six.

We're gonna get outta there at seven.

I gotta be at the airport at five.

Those are, Very clear external commitments that can things happen.

Can I have kidney stones and be doubled over in pain?

Can the oven

No, but I need to be up by 3 45 and shaving.

Yeah, look, things can happen.

The oven can break.

in, in, uh, at the bakery.

And maybe that kid will have to take a fudgy, the whale

There can be a thunderstorm at the, at the airport or the, the, the

flight attendants can all get covid.

Like, there's all sorts of things happen.

What's really, really hard about, uh, software,

but also other industries.

We always talk about software, but there are other industries that have this

No, there are, there are no other industries.

I have one more, uh, industry that has this challenge.

Um, the book is due,

Oh boy.

Why'd you do this to me, man?

Why'd you have

the article, the article's due and again, course

as bad, but, okay.

Okay.

Well,

the article has an advantage over the book, which is

shorter.

we're going to print, we're going,

The problem with the book is they'll wait.

They'll wait.

And the book, actually, when you turn in the book, it's nine months before the

book actually goes, goes on the shelves.

The article, it might be going up on the web the later that day,

And I think editors have come to understand that you can't pick

up the phone and scream at the writer.

It doesn't work.

Just doesn't

Oh no.

Editors live.

So editors, it's, it's a pure structure of, I, I live this.

Right?

So it's a pure structure of passive aggressiveness and, and manipulation.

So the, first of all, they lie to you about the due date.

And then as you get older and more serious in your career, you, you realize when

you're being lied to and you're like, oh, well then it, it'll be the Thursday after.

That's fine.

More time.

Yeah, yeah, yeah.

You start to figure out the game.

Then they invoke the managing editor and the other editors.

And so that's, it's never them, they never, they're, they

understand that you're an artist.

But the managing editor just can't, they gotta get it in their

I, I think there's a, I think why it's a challenge.

Read the first part of that tweet again, cuz the, it's a two-part tweet.

It's an observation and then a declaration.

Read the observation again

After being a manager in tech for like four years now,

I don't understand what everyone is saying about how hard it is

to estimate timing for products.

Period.

Stop there.

Mm-hmm.

Okay.

What they are really saying is that, uh, the leadership who expect the

product to be done at a certain time.

Refuses to hold everyone accountable to a commitment and tries to simp,

sympathize and empathize with the team and the complexities around it.

And so what you end up with is a really snugly dynamic, but no one knows.

Where success is anymore.

And by success I don't mean

business success.

a dynamic where people are all snuggling together.

People assert themselves.

Sure.

Engineers say, no, you don't understand.

I once sold a piece of business, um, and I didn't architect it out.

I didn't go looking at libraries and seeing, but.

In my cursory understanding of technology, I sold the piece of

That's what a salesperson does.

My head of engineering said I need to talk to you as soon as

possible.

Right.

Ah,

And he's like, what you, what you sold isn't possible.

I was like, really?

And then I, I, I sat in a very ignorant place.

I was like, and it wasn't a time constraint, what he was doing.

And, and we worked it out and I was like, why don't you just do it this way?

He's like, is it okay to do it that way?

I'm like, when did it become not okay to do it that way?

Of course you could do it that way.

They don't know anything.

They don't know technology.

Go do it that way.

And we did it and we delivered it and we, it was one of the most

profitable projects we ever worked on.

And so what was going on there?

What was going on There was, uh, the head of engineering, asserting

control and wanting to be in the room.

When we arbi arbitrate, what

is.

You know what, I always think of this as, by the way, the AUR theory of software

development.

There's your title,

title of the podcast.

is.

It's just like this sort of

explain, that.

so there's a, a famous, there are theories of what makes a

movie and what, what art is and where it

Sure.

And so film in particular is really interesting because

there's the concept of the director and is the director the artist

of the movie or is the movie.

A combination of all the efforts involved manifesting together, prob led by the

director.

Mm-hmm.

Mm-hmm.

And so the director and software would be the

product manager in the,

the mm-hmm.

the magazine world would be the, the editor-in-chief,

et cetera, et cetera.

So the Aura theory is that like the director is the artist and everyone else.

Falls, uh, you know, in their wake they are.

And, um, there are other theories and other concepts that say that

no, it, it's actually much more the sum total and that person just

kind of receives all the glory.

So when you talk about the art and, you know, French cinema in the sixties

was very like, There are con, there are spaces where like the director exercised

total control made these little films.

People like Godard or, or, or Vees, you know, not French, but um, where

they, it was really their vision.

And then it's like Steven Spielberg on War of the World has a team of 1500

people and you watch the credit troll.

Is there an Altura behind Mar, you know, Avengers Endgame?

Yeah.

Uh, and so there.

The Arturo theory of software development, is the engineer going,

Yeah,

this possible.

Yeah,

probably French accident.

Smoking a, uh, what, what is the oa?

The, the cigarettes.

How do you pronounce that?

Do you know?

Oh, there's Like

really long

like a French cigarette that's really

It's really long.

Yeah.

I

I think it's G A L O I.

I

let's just say Virginia Slims and get on with

whenever I get, uh, whenever I pronounce anything

French, I get yelled at.

So there we go.

Yell at me.

Um, anyway, so yes, here you are.

The engineer has said it's not possible.

You've said it's possible.

Here's what's counterintuitive today.

What's counterintuitive today.

And today, you know, there's a lot of, um, there's a lot of, um,

sort of pausing before you assert yourself in the workplace and

in a work in a team environment.

There's a lot of like, Don't assert your power, don't be, um, don't

disenfranchise your teammates.

Like there's all that, even if you're the boss, right?

There's like, how do you get people aligned?

How do you inspire people?

Let me, he, let me say something that's gonna sound counter to a lot of

well, well hold on.

The dominant and, and sort of positive assessment of management

is that you should be a servant leader and that you should come in

and you should empower your team.

I never heard that phrase before.

I want you to never say it

servant

leader.

Yeah.

Here's it.

Turns out, it turns out that you will actually have a happier team if you say

to them, when I tell you I want something.

on

a certain date and we can have some dialogue about it.

I need you to take it seriously.

And it's like, okay, wait.

That sounds like a jerk.

You could,

you could see it through that lens.

Uh, you should always be respectful and always have a

dialogue about what's at stake.

But here's the thing, when you do that, There may be a little bit of friction, a

little bit of pushback there, but believe me, down the road, they really want it.

They actually really want it because there is nothing more painful than

spinning and spinning and spinning and trying to do something perfect,

um, and not being able to ship.

People who are great at what they do want leadership.

A, to keep the bullshit out.

That's meaningful.

That's part of being a leader.

And B, clear goals.

That's out of fashion today because that sounds like power or money or

something.

Power Power is out of fashion, but clear goals should not be out of fashion.

Respect your team.

Communicate, have a dialogue.

Here's, here's the irony of all this.

This is one of the trickiest things, and you learn this from pretty senior

execs, is that by being demanding and making hard calls, you are actually

advocating and protecting the careers of the people who work for you.

More than if you empower them to have control when they're not ready.

Yeah.

I,

I have a terrible tell.

when,

when people, when I'm like, so what do you think?

And you say that because you actually want to hear what people's perspective and, uh,

people

wanna be heard.

People want their 2 cents.

And they're telling you about things that can go wrong and you're hearing them out,

and then there you should hear them out.

But there is a point where that dialogue.

You lose your bearings and it overwhelms everything and you've lost which direction

you should even go or where the ending is, and you've lost control of it.

And I have, one of the things I've, one of the skills I've built over the

years is that when someone seems to be taking me away from that goal, And

is taking me on their own adventure.

On some other adventure.

I literally tune them out.

I will nod my, I've learned to like use my neck muscles to nod, but Karen

Carpenter is singing in my head,

why do birds

is it that song

and obnoxious, but it, and it isn't me like

giving them the middle finger.

What it is is me like, Man, these are smart people who are making

sense and they're taking me off.

My bearings bad

and I need to come out of it.

Uh, you know, one of the things that happened is people

are anchored to their disciplines.

Their disciplines are their, their sense of power and control.

And so they advocate for their disciplines.

You're in that meeting and you're running the product and, and sort of

people are like, well, I need this because of this and this is how this

works and this, what happened that was weird in the last few years is.

All the disciplines kind of took their eye off of the product and got into

themselves in a really specific way.

Like

it's, it's a product of just the demands of a job market,

which is softening now, but it was

right.

So it's like,

absolutely impossible to get great talent,

will only use framework X to program.

Oh, well, o.

O, okay.

I will only design this way.

had this project 10 years ago, like, closure was like hot.

Oh yeah.

Closure is a language that's based on lisp.

For the people out there listening who even understand what that sentence means,

they couldn't get logged in done after like four months.

Like, I couldn't log into And so then, then, and I, I've, I've learned just

enough about tech to understand it.

Right?

So I went into GitHub.

Oh, that's not true.

You actually, you know the stack pretty

I know the stack

can

program.

Yes, yes, yes, yes.

So I went into GitHub and I was like, let me see what's going on here.

And I looked at all of it, and then I called you.

I remember I was in front of Brooklyn Borough Hall.

was an awkward one.

And I said, Paul, I need you to do me a favor.

I'm looking at this.

I don't think there's anything in here.

And you're like, okay, I'll call you back in an hour.

You called me back and you're like, there's kind of nothing in

I remember once I did a project and I was the only programmer,

I was the only anything on it.

And I was off on my own and I made every decision and every

decision I made was wrong.

I used the wrong database, the wrong data model, the wrong programming language.

Every, everything I did was wrong and I slept on the floor

to get it done by myself.

Yeah.

And, and I paid the price for, and then later someone came in

and replaced me and about two years later, but I shipped working

software.

Okay.

but you went astray,

I went to Stray, but.

I, I would, and I would, I adopted everything cool before it was

ready, but I shipped the thing.

And what had happened is they had gotten like, oh, you need

this kind of logging database.

And so, and they architected for a world that didn't yet exist, and then

they forgot to build the product.

They built everything around the product.

See, and I thought I was gonna be like estimation.

You'd be like, here's the five estimation points.

You went very meta.

Well,

no, I, I estimations that's a, that's a.

That's a straw man.

See that's the thing.

a straw

so this is the thing you're actually saying, which is that estimation

is usually presented as a set of tips and tricks for how to like define scope.

bullshit.

I'll tell you why it's bullshit.

There's gimme a login and then there's industrial strength SSO two factor off

that sends you a set of 10 codes in case you forget your two factor off.

Estimation is useless without leadership, keeping everyone focused through scope.

If you can't help them say, look, I know you know the best way to do it

in the world, but I need it Friday.

Mm-hmm.

Right.

And that can sound.

That's, that can sting a little.

Well, it also people, it, it's not just sting, people feel that

they're betraying their discipline.

Yes.

And they feel that you as a leader are minimizing their, their

and their value expertise.

Yes,

So how do you get around that?

You get around that three ways.

Okay.

Now we're finally tips and tricks.

Tips and tricks.

First, tell them why.

You're not doing it because you wanna flex.

There's, you are connected to the world.

I hope, unless you're a nonprofit that just makes nonsense software, that

may be, but even then, tell them why.

Sometimes you have an externality, like an event or a presentation

that you've, you're scheduling against, but sometimes you don't.

So first, be transparent about why you're, you're, you're making

them take a shorter filthier path

Let me let me make, I'm gonna pause.

So that's number one.

Number one, there's a thing I wanna say that I, I, it's a hard thing to say,

but

I am increasingly convinced as I get older and I see people in their careers

and I talk to people and I mentor people and so on, most people don't

know what business they're they just don't, they, they know their discipline.

They know that they have a kind of a job.

They know that they get a paycheck and they know that they

did okay on the annual review.

you know who, who's like that?

Tax attorneys.

Tax attorneys get like their own wing that looks like a

daycare center at the law firm.

Cause they're so valuable.

so valuable, but they're also so weird and they're so awkward.

A lot of the time

Yeah.

These are, you're, no one goes into tax tax law because they're like,

ah, I'm just having too much sex.

They're not the rainmakers, right?

They're not social.

Some are, I'm not gonna stare, but most are like, they're almost like quant, like

Yeah.

So they're sort of famous in the law firm.

Like who's that guy that never comes out of his

Someone else is worrying about the p and l of the law firm, the

tax expert that really enjoys the problem.

They're not usually the same person who goes to the cocktail parties to,

to be the rainmaker for, for the firm.

So, number one, be transparent about why you're telling them

to take path B instead of path

which might actually mean explaining what business you're in.

Yes, yes.

I, I, I know that sounds awful and reductive, but it's literally like we

have only this much budget and therefore we must prioritize in order to achieve

the goals so we can get more budget.

Half your employees have never thought that way.

That's right.

That's right.

We've had employees tell us, why are you making getting more business?

Yeah.

Why do you keep growing?

They think it's greed and they don't know it's

Well, they they don't realize that all the other business could

go away, because once you hit that state, no one assumes that everything

will just implode on any given day.

is static.

Right.

Well, it, especially with a small startup or an agency.

that's two.

Okay.

One.

One.

That was one.

Let's get the two.

tell 'em why.

Be transparent about why you're putting certain kinds of pressure over our why.

You're saying you need

Mm-hmm.

Mm-hmm.

Are you

that outta thin Air number two, um, is probably the most important

thing and is the hardest thing to pull off, which is if they trust you,

you don't even have to tell them why.

If they trust you and they trust your judgment, And there

is a, a respectful dynamic.

They will get it.

And you don't have to explain it every time,

But that's only earned by shipping.

So you gotta solve the fundamental problem first.

It's only earned by shipping.

It could be earned by you being a great business development person.

It could be a, it could be earned a lot of different

ways.

Yeah.

But that's a kind of shipping,

what you're

earned by delivering what you're

you're essentially saying is this, what you're essentially saying

is, You are amazing at what you do, and we have an amazing team at a board,

like it is really a world class team.

It's like what?

Probably the best team I've ever worked with.

But what we're also saying is, You are a practitioner and a and and as good

as it gets in your bus, in your craft.

I know you don't think I have a craft.

I know you think I put on a shiny suit, but trust me, I'm gonna

go talk to the world about this.

You're gonna do what you're gonna do.

Now I'm talking about our example, but there is.

If people there, it is the, it is the, the, the heart, the pinnacle of being

a leader is that you don't have to put pressure and stress on people to do it.

They believe in you and they trust you to do, to go in a certain

let, let me add one caveat, and this is universal.

Everyone thinks that everyone else's discipline is essentially fraudulent.

O what a cynical way to, it's not close out.

This

Not not our team, our teams, our team has worked together and so on.

But in general, designers are like, ah, engineers and engineers

are like, ah, marketing.

And everyone is like, ah, managers.

And so.

a great way to, I mean, it's a great observation.

It's real,

when you're earning that trust, you have to have, I mean,

look, I've learned all these lessons.

The hard way, trust, building trust with engineers is not like, I understand

how hard it is can can be to write code cuz they'll look at you and

they'll be like, yeah, it's hard.

And that's all they wanna talk about.

You actually have to have a little, it's not fear, it's just the sense

of like, yeah, I know you can get it.

I know you can do it.

Yeah, you can ship this.

I, I see it, I can see part of it, but you can see the whole thing.

And I'm counting on you to take it the rest of the

yes.

It's a, it's a great point.

I'm, I'm oversimplifying it.

You're right.

Everyone is convinced Their own discipline is the most important

It, it's the only thing that matters because without you, if

you sub, if you subtract any of the disciplines, the whole thing does fall

It does.

We need everybody.

Everybody.

It's a team,

It's just, it's humans are very, very funny.

Okay, so that's 0.2.

Yeah.

Uh,

0.3.

Did you have a 0.3 or did you just like the number

No, no, I have it

have a Okay.

I have a 0.3.

Um, you can't do this all the time.

You can't do it all the time.

You have to exhale.

You have to let them exhale.

Sometimes you'll be like,

wait, you mean let the schedule slip?

No.

What you have to do is you gotta, you want your thing by Friday?

Get it by Friday.

But the following week, when you see a practitioner who is just

hangar in a fold out new librarian, you kind of gotta let 'em do it.

You gotta let them.

Oh yeah.

No little cognitive treats are very important.

They are, no, it's like Absolutely try

by way.

It's not just letting them kind of, you gotta give people a sense of autonomy.

Yes.

And you do that, you

the boot on the neck the whole time.

NPM installed dog biscuit is what you just

Look related to that.

Also, even when they come outta the other side, you ask them to do

something, they're, it's not the proudest moment cuz it's the junkies

login they've ever put together.

You say, look, I really appreciate what you guys did here.

It looks great.

Right?

You gotta make them feel good even about the stuff

Have an after eight mint.

Um, no, but this is real.

Like if, if a designer says, I need, uh, can I think about it and

come back to you with some ideas?

You can't.

Every, sometimes you're gonna say, I look yes, but tomorrow, like sometimes you're

gonna put the pressure on and be like, look, I, I, you do whatever you want.

I need it by Friday.

Other, you gotta have some other times where you let

the engineer do the refactor.

You let the designer think bigger thoughts.

You gotta let them exhale because.

Especially if they're good, cuz if they're good, it, it's a huge part of who they are

and they are not assembly line workers.

know what we're getting to at the end, at the end here, and I.

Let me, let me take a breath and articulate this.

People are loyal to their disciplines in their careers, and one of the,

one of the jobs of shipping a product is actually getting people to come

off of Discipline Island and come to Product Island and focus on the

to Pragmatism

Yes, but Pragmatism Island, Is actually a dangerous place for people to

spend all their time because then they, they lose the, the sort of rootedness

and the connection to the things that they care about and the matter to them.

And actually they don't charge their batteries up to bring good

ideas back to product island.

You gotta let 'em come out and come back

so there's an oscillation, and this is

interesting.

to

I call it exhaling, I call it, it's like breathing.

right.

It's a sine wave.

You're going, sometimes they, we all gotta get on a product island and sometimes

we go back to discipline island and do the things that we love and care about

and we think are really fun and then we gotta bring those to the other place.

It's import export all the time.

I learned something on Product Island and I learned that the big

idea I thought I had was a bad one.

Nobody liked

it.

Nobody liked it, the users didn't care.

So I'm gonna take that back to Discipline Island and I'm gonna internalize it

along with all the other work I do.

Uh, let, let's end it with a bonus tip.

All.

If you're in a Fortune 1000 company and they have absolutely no sense and all

they see is like billions of dollars flowing through the windows, they're

always on discipline island for years.

Oh.

Discipline Island is where they live.

And in fact, you know what they do?

What, what you do in a Fortune 1000 is you go shopping for new disciplines.

You know?

Hey, how about content architecture?

Yeah.

Right?

Or, or information.

Um, I don't know.

talked about this, by the way.

There was a previous podcast, you should listen to all of our podcasts, but

there's a previous one, where're, like why can't big companies ever do anything?

Uh, and that's this, right?

They are only on

discipline.

They're on discipline island.

And when, and to get everyone on a product island is, is a thing of fear.

So, uh, alright, rich.

Well, if people want to get in touch, what do they do?

They hit us up at hello@zdiford.com.

Uh, we're also on all the popular podcast networks and apps and whatnot.

Um, give us five stars when you can.

We're Zdi Ford on Twitter

Mm-hmm.

zdi.

Z I a d e f o r d.

I'm Lebanese, that's the ziti part.

And who Spon?

Yeah.

I'm for it.

I'm for, it's the Irish part who sponsors

This podcast and probably a lot of the future

ones sponsored by a board.

A board is a killer new tool that's coming out in May of 2023 in case

you're listening to this five years from

Mm-hmm.

Um, that, uh, lets you organize your passions on

the web, beautiful apps coming, and mobile apps and whatnot.

So check it out@aboard.com.

We love it.

We love it now.

Um, okay, let's get back to work.