0:00

I wanted to become a CTO and I recognized

0:02

it wasn't just about being the best

0:04

engineer . It wasn't that I could code better

0:07

or faster than others . There were all

0:09

these other skills I would need Leadership

0:12

, networking , negotiating , communication

0:14

, hiring , team building . But

0:17

no one ever taught them to me , so

0:19

I began to work to upskill myself

0:21

. We didn't have great podcasts

0:23

like this back then . It was a lot harder and

0:26

as I did , I realized these

0:28

skills will help everyone . They

0:30

are not just for leaders , not just for managers

0:32

. Everyone down to your summer interns

0:35

can benefit from these skills

0:37

. So I began to upskill my

0:39

team .

0:39

Hello and welcome to Developers

0:42

Journey , the podcast bringing you

0:44

the making of stories of successful

0:46

software developers to help you on

0:48

your upcoming journey . I'm your host

0:50

, Tim Boulgigno . On this episode

0:52

, I receive Marc Hirschberg . Marc

0:55

has launched and developed new ventures

0:57

at startups , Fortune 500 and

1:00

Academia . He's the author

1:02

of the book the Career Toolkit Essential

1:04

Skills for Success that no

1:07

One Told you , and helped

1:09

to start the undergraduate practice opportunities

1:11

program , dubbed MIT's Career

1:13

Success Accelerator , where he still

1:15

teaches annually Formerly

1:18

, a top ranked ballroom dancer and

1:21

among many other activities . He

1:23

also works with many nonprofits , currently

1:25

serving on the board of the Plant A

1:27

Million Corals Foundation . Marc

1:30

, a warm welcome to everyone .

1:33

Well , thank you for having me . It is my

1:35

pleasure to be here .

1:36

Oh , and it's our pleasure to have you here . But

1:38

before we come to your story , I

1:40

want to thank the terrific listeners who

1:43

support the show . Every month , you

1:45

are keeping the DevJourney light

1:47

up . If you would like to join

1:49

this fine crew and help me spend

1:52

more time on finding phenomenal

1:54

guests than editing audio tracks

1:56

, please go to our website

1:58

, devjourneyinfo and

2:00

click on the Support Me on Patreon

2:03

button . Even the smallest contributions

2:05

are giant steps toward a

2:07

sustainable DevJourney journey

2:10

. Thank you , and now

2:12

back to today's guest . So

2:14

, marc , as you know , the show exists

2:17

to help the listeners understand what your story looked

2:19

like and imagine how to shape

2:21

their own future . So , as is

2:23

usual on the show , let's go back to your beginnings . Where

2:26

would you place the start of your DevJourney ?

2:29

The start of my development journey probably

2:32

began at the end of eighth grade . I

2:34

was going into high school . I already

2:36

knew that I wanted to study physics in college

2:39

and go into politics . So

2:41

when we're trying to decide what

2:43

elective for me to take , I'm sitting with my guidance counselor

2:46

and I'm looking and saying well , I

2:48

want to take justice . Justice , that sounds

2:50

like law . That seems very appropriate for where

2:52

I wanted to go . And my guidance counselor

2:54

looked at me and said oh yeah , we're not offering

2:57

that . Next year , pick something else . I

2:59

was caught off guard . I didn't

3:01

have a bad . What do you mean ? The class was listed in the catalog

3:04

. I didn't know what to do and

3:07

my guidance counselor , who didn't really

3:09

provide much value other

3:11

than this one critical moment , said why

3:14

don't I sign you up for computer programming

3:16

one ? I didn't really

3:18

want to do that , but I had no other options

3:20

. I thought , well , I'll come up with something

3:22

. Maybe over the summer I can switch . I'll find something

3:25

else . But never saw anything else I wanted

3:27

, and so I showed up to the class

3:29

. Now I had done a little . I had a programming

3:31

book . I think a few years prior I did some things

3:34

in basic . But

3:36

we did this class and they're teaching us

3:38

basic , more advanced stuff and

3:41

I'm loving it . I would get a programming

3:43

assignment and I would go home and

3:46

right away do the assignment

3:48

. We had a computer at home this was in the 80s

3:50

and I'd code it up and say

3:52

wait , I'm done , I want to do more , I

3:54

can't wait for an extra assignment . So that really

3:57

got me excited . And when I went off to MIT

3:59

I decided to double major in

4:02

physics and in computer science . And

4:04

even though I also minored in political science

4:06

, still thinking I wanted to go into politics , I

4:09

very quickly got turned off from politics

4:11

. So I didn't go further down that path . And

4:13

then as I graduated the 90s , physics

4:16

was , funding was declining , it was the end

4:19

of the Cold War , but software

4:21

was really taking off . This is now the mid 90s

4:23

, and so that put me on that path

4:26

.

4:27

Did you look back at any any time at

4:29

the beginning of this CS 101

4:32

classes saying , well , but I still want to go there

4:34

. I was really love at first sight and

4:36

you never looked back .

4:39

It was both because I do

4:42

love computer science , Even

4:45

though I was not the best of students freshman

4:47

year at MIT and definitely got

4:50

beat up a bit by some of the classes

4:52

but then at the same

4:54

time I love the other stuff . I am so glad

4:56

I studied physics . I wish I had more time

4:58

to do physics . So it was love

5:01

at first sight , but I have a

5:03

harem of interests and I tried

5:05

to spend as much time as I can with

5:07

each of them .

5:08

So how did you choose your path , first

5:11

at MIT , into going into this , this

5:13

computer science major , and then doubling major in physics

5:15

? How did you decide which path to

5:17

take ? I suppose MIT

5:20

, mit's offering is absolutely humongous

5:22

and really huge and you can go anywhere . How

5:25

did you find your path in there ?

5:27

Well , going in I knew I wanted all

5:29

three of those areas . I knew I wanted physics

5:32

. I knew I wanted CS and

5:34

I knew I was interested in politics . I didn't think I

5:36

could fit a third major in , but

5:39

I was able to get that as a minor and through

5:41

some clever planning that actually

5:44

laid the foundation for some of

5:46

what I now teach , I was able to fit

5:48

all three of those into my time

5:50

at MIT .

5:51

Wow , is that normal

5:53

to have two majors and a minor in undergrad

5:56

?

5:57

It was not very common back then

5:59

. Normally you'd have a major , maybe

6:01

a major and a minor . Double majors

6:03

were pretty rare . I believe these

6:05

days it's become a lot more common for people

6:08

to dual major or do

6:10

a major with multiple minors . So

6:12

it's become the trend and in fact , one

6:14

thing we saw at MIT and I suspect is

6:17

true at other schools we would

6:19

have students that'll past maybe 10

6:21

, 20 years would study computer science

6:24

but also biology because they were interested

6:26

in biotech , and MIT

6:29

would see these trends and then would create these special

6:31

subdivisions

6:33

within , for example , in computer science . You

6:35

can now subspecialize in biotech

6:38

, you're still getting a CS degree or EECS

6:41

, but with a biotech

6:43

focus , and so they were recognizing

6:45

this Interesting . Call

6:48

it maybe not an overlap so much as

6:50

a conjunction , and

6:52

when I really think about where opportunity

6:55

lies , this was true in

6:57

the 90s . I think it's still true today . It's

6:59

not necessarily within a discipline , but

7:01

when you go cross discipline , usually

7:04

that's much more virgin territory and leads

7:06

to a lot more opportunity .

7:09

Much more conjunctions or synergies

7:11

than adding

7:13

to think that I have nothing to do with one another

7:15

and falling into a crack . It's really

7:17

adding up in the middle . There's something new

7:20

that emerges and where there's way

7:22

less , let's

7:25

say , offering in terms of

7:27

demand and offering

7:29

, there's way less people that have the

7:31

skills to really strive in there

7:33

, and so you can have your niche

7:35

there . Well , very cool . What did

7:37

you have in mind for the

7:39

mark that was coming out of his

7:42

MIT degree as double major and

7:44

minor ? What did you picture your first

7:46

and second and third jobs would be ?

7:50

Once I recognized I wasn't going to go into

7:52

physics , I said , okay , I'm doing computer science

7:54

. I thought I'd be a software engineer

7:56

. Well , I first spent a year doing research

7:59

at MIT for a professor . I

8:02

do like academia , I do like pure research

8:04

. But then I just said , okay , I'll

8:06

be a computer programmer . And I

8:08

found a job . At

8:10

this time I didn't have a lot of direction . I

8:13

knew I didn't want to work for big tech

8:15

, and back then big tech was Microsoft

8:17

and IBM . Modern big tech

8:19

mostly didn't exist . I

8:22

knew I didn't want to work for Wall Street . I

8:24

knew I didn't want to go into

8:26

consulting . Those were three big

8:28

industries that pulled from MIT and

8:31

I wound up at this tiny company

8:33

. They called it a startup . I

8:35

hadn't heard that term before . I

8:37

said , okay , fine , small tech

8:40

company , let me do this . And I was

8:42

very lucky that I had a really

8:44

good manager and some really good peers from

8:47

whom I learned a lot , because I thought

8:49

, well , I've got a degree from MIT , I know a lot

8:51

, I'm a smart guy , and I didn't know

8:53

how much . I didn't know . But

8:56

it was during

8:58

that time they started to grow and

9:00

I had a very pivotal moment a

9:02

couple years into that job . My

9:05

CTO called me into his office one day and

9:07

said listen , this might come as a surprise to you

9:09

or maybe not , but I'm

9:11

leaving the company and I'm going to start

9:14

my own . I'm taking some people with me and

9:16

you should come too . Now

9:18

, this was a surprise to me . It should not have been

9:21

, because I noticed a lot more closed door meetings

9:23

with the senior team , not just there once

9:25

a week meeting . There is definitely something going on

9:27

and I didn't have

9:29

the mindfulness to think

9:31

, hey , what's going on ? I should figure

9:34

out . Could this impact me ? I just

9:36

sat there and happily coded and

9:38

when he offered me this new job

9:40

, all of a sudden I had a choice , because

9:42

I thought , well , I'm at this job , I'm happy , I like

9:44

the people , I'm making good money I

9:46

never even thought should I consider something

9:48

else ? So once he gave me this new job

9:51

offer so well , now I have two choices

9:53

. I need to figure out

9:55

what is the right next step . So

9:58

I have to prepare the jobs and then quickly

10:00

start to think about my long term future

10:02

. I was a competitive chess player as

10:04

a kid , so I never think one move

10:06

ahead , I think multiple moves ahead . It's

10:08

not just this next job ? What's

10:10

this setting me up for ? Five

10:13

, 10 , 20 years down the road , I

10:15

realized I had more than two job offers , because

10:18

this was a dot com era in Boston , so

10:20

I'm not limited to just these two . Let me look around

10:23

, and that's when I really

10:25

started to be more proactive in my career . Where

10:27

am I trying to go and how am I going to get there

10:29

?

10:30

I want to come back to that situation , or awareness

10:33

, understanding what's happening around you

10:35

, because I've seen that a couple times

10:37

already , people who are

10:39

so in

10:41

their work , in the

10:43

tasks that they were given , they don't

10:45

realize first and foremost and I'm not thinking

10:47

about about next steps and everything they don't realize

10:50

how what they're creating fits

10:52

in the big picture . They don't realize

10:54

how the big picture is constructing

10:57

around them and how sometimes

10:59

people go around them to to get something

11:02

and and and understand how they

11:04

fit into this . And this is this has been

11:06

one of the key

11:08

areas I poke at during

11:10

interviews is understanding . Did you get the

11:13

whole picture ? Did you get why you were

11:15

there and why you were doing this and how it

11:17

fit in the whole picture ? And then that would , of

11:19

course , as you said , fit as well in understanding

11:22

what's happening around you . Is there a meeting you're

11:24

not invited to where there seems to be something

11:26

important happening ? And maybe you should pay attention to

11:28

that , and it really pays

11:30

to becoming more senior to start

11:33

understanding this understanding or

11:36

the situation around you . I have

11:38

no better word to put that .

11:41

It's funny you struggle with the words because

11:43

this is all covered in chapter two of my book

11:46

, titled working effect

11:48

, and that's probably my least favorite

11:50

title . I could not come up with a better

11:52

title for that chapter because

11:54

it encompasses all the things you're talking about . It's

11:57

not your work itself , it's

11:59

not writing code or if you're an accounting

12:01

doing financial reports , it's

12:03

all the other stuff . Now that includes corporate

12:05

culture and corporate politics , which

12:07

we get caught up in whether we want to be or

12:09

not . It's understanding . How

12:12

are you delivering value ? Most

12:14

people couldn't tell you who their

12:16

customers are . They might have a list , but

12:19

they couldn't say well , our customers tend to be

12:21

mid-market industrial supply

12:23

companies . They don't know

12:25

who their customers' customers are

12:27

. They don't understand how to add

12:29

value , and I always teach

12:31

my students and in all the other work I

12:34

do If you don't know how

12:36

you're adding value , then it's harder

12:38

to add more value , which is how

12:40

you get ahead , how you get raises and promotions

12:42

by delivering more value . But you're doing

12:44

it without a map . So

12:47

understand the business that

12:49

you're in . Understand who are your customers

12:51

. Now , it might be an internal customer , it

12:53

might be the other groups . Adding this button

12:55

helps the sales team . Okay

12:57

, how does it help the sales team ? It could be an external

13:00

customer , but understand your customer's

13:02

customer , how doing this creates

13:05

value for them . To create value to their customers

13:07

, understand your industry

13:09

. When I do monthly meetings

13:12

with my team , we'll go over

13:14

, okay , what's happening and let's do some big

13:16

picture updates . But I will

13:18

make sure to talk about here's what's happening

13:20

in other departments . People

13:22

often bring in another department head the

13:25

CFO , head of sales

13:27

, cmo say can you

13:29

come talk to my team ? We're going to spend 20

13:31

minutes of this meeting . You give updates

13:33

from your department . Help them understand what's

13:35

happening . But even if your

13:38

manager doesn't do this , here's

13:41

something that kills me . Most people cannot

13:43

name the coworkers

13:45

around them . Oh , there's

13:48

some woman . She sits 30

13:50

feet from me . I think she's in finance

13:52

. I think her name is Sarah , but

13:54

that's about all I know in finance . I guess I don't

13:56

know . She does stuff with checks . They

13:59

don't know . You're saying 30 feet from this person

14:01

for a year . So go out

14:03

, meet your coworkers , talk

14:05

to them , meet them for coffee to

14:08

say , hey , I'm trying to learn more about the

14:10

different aspects of the company . Can we just grab coffee

14:12

? Tell me about your job ? What do you do here , you're

14:15

going to learn so much and you will be much more

14:17

effective because you have a better

14:19

understanding of your role

14:22

and how it fits into the business and

14:24

your industry .

14:26

And I'm cringing because

14:28

I'm in a 100% remote

14:30

company and so there's no really

14:32

way to see this person 30

14:34

feet away from you . She is somewhere

14:37

on Slack and you just don't see her . And

14:39

so you have to be explicit about this

14:41

. You have to be poking at

14:43

different , different persons you don't know and say

14:45

, hey , random person , I have never met

14:47

you , let's talk .

14:49

I'm going to recommend . I rarely recommend

14:51

third party tools , but I'm going to recommend

14:54

two . There was a company called Donutai

14:57

. I remember when they were

14:59

pitching they were looking for angel funding

15:01

. I saw the pitch . I liked the idea . I

15:03

just didn't believe in the size of the market

15:06

. It didn't seem defensible . And it's

15:08

not because a friend of mine wrote a competitor

15:10

called SUP . Sup , as

15:12

in what's up , they are both

15:15

plugins to Slack which , given

15:17

the technical audience , I suspect most people are

15:19

using Slack and what it does

15:21

. It just creates these random pairings

15:23

. So this week I'm going to get noticed

15:25

that , hey , you and I are supposed to get together

15:27

for coffee . It can be done in person

15:29

, it can be done virtually , and it

15:31

just says , Okay , you're gonna meet and mark

15:34

, you take the initiative and I'll just Slack . You say , Okay

15:36

, hey , we're supposed to meet , Let me know when you're free . And

15:38

that's a good way to really just

15:40

create some of that water cooler

15:43

conversation that you don't always get when

15:45

you're virtual .

15:46

Absolutely , and smiling because we're using Donut . It's

15:50

exactly this . It's really exactly creating

15:53

those , those serendipitous

15:55

, serendipitous meetings , just

15:57

because you don't have the opportunity

15:59

otherwise . That's very important

16:02

. Okay , let's , let's go back to

16:04

that CTO grabbing you and

16:06

telling you hey , common born and shit

16:08

. Did you say yes ?

16:11

I looked at his company , I

16:13

looked at my current company and

16:15

, as I mentioned , I realized there were more than two

16:17

options , because this was the end of this was 1999

16:20

in Boston , the end of the dot com error . We

16:22

didn't know was the end of it , but there were so

16:24

many opportunities and I realized where

16:27

I wanted to go . I wanted to become a

16:29

CTO , and it wasn't

16:31

just about being a better developer . Both

16:33

of these companies were going

16:35

to continue me , primarily

16:38

in my individual contributor

16:40

skills . I'd be doing more

16:42

coding and maybe more advanced coding , but

16:44

I wanted to get more into project management

16:47

and start working on other skills . So

16:49

I looked for an opportunity that would take

16:52

me down that path and that's where I went . Did

16:54

you feel ?

16:54

ready for leaving IC

16:57

behind you and going for something else ?

17:01

It depends on when

17:03

you're asking me that , because at the time

17:06

I would have said yes . Today

17:09

I would have said maybe

17:12

. And what I mean is there's

17:14

a famous expression in the land

17:16

of the blind the one I'd man as king . I

17:20

currently did not have more than one eye

17:22

open , but that was one more than most

17:24

of the other people , because at this time we

17:27

were so desperate for coders

17:30

If you just knew

17:32

how to use a computer . I remember I had a . There

17:34

was a recruiter who tried to pitch me a QA person

17:37

, and I asked about her background . I said , well

17:39

, she knows how to turn on and use a computer

17:41

. Now , my standard was a little higher

17:43

than that , but yeah , that

17:46

was a level when he could pitch people , because in 1999

17:48

, such demand and such a shortage

17:51

that you could sell people that way . So

17:53

, having even a few more years

17:55

of experience , I had a lot

17:58

more to offer . For the record

18:00

, I was also a competitive ballroom dancer and

18:02

I know a lot about the ballroom dancing world . If

18:04

you go into a ballroom dance studio and

18:06

you say , oh hi , we're here to

18:09

take some classes or learn for a wedding

18:11

, chances are , the person

18:13

teaching you is not some world

18:15

class champion . It's someone

18:17

who may have only learned to dance six

18:20

or 12 months before me

18:23

and the other competitors . We

18:25

could I and the other competitors we

18:27

could run circles around this person , but

18:29

this person was sufficiently ahead

18:31

of the wedding couple that he was fine

18:33

teaching them Absolutely . So really

18:36

, you just need someone who's just a little bit

18:38

better than you and you are adding value

18:40

. So I think I still had a long way to go

18:42

, but I was still . I

18:45

had enough to add value at the time .

18:47

Okay , I want to flip

18:49

it around and and wrongly reformulate

18:51

it , just to see how you react when

18:54

you say back then yes , maybe now

18:56

maybe I'm also hearing

18:58

the naivety of the youth

19:00

saying , yes , of course

19:02

, I'm ready for that and now

19:04

, in hindsight , thinking , well

19:07

, actually wasn't , but it

19:09

was sufficient .

19:11

I still didn't know all the

19:13

things I didn't know . I remember

19:15

, for example , I was talking with one of the

19:17

founders and we're talking about the project

19:20

we had . Most of our developers

19:22

were either just to have college

19:24

or some of them had dropped out to

19:26

do a startup . And I remember

19:29

we're talking about timelines and

19:31

one of the founders said well , we're just

19:33

going to ask them to give their estimates , because

19:36

if they give an estimate then of

19:38

course they have to hold

19:40

themselves accountable towards it . I get

19:42

like we as managers can't tell them what to do because

19:44

we might not get it right . But if they say it

19:46

, well , then they've got to complete it . And

19:49

I remember thinking that doesn't sound right

19:51

, like there's still some problems

19:53

by couldn't articulate . Estimates

19:56

are hard and even if you ask them to do it , it doesn't

19:58

magically mean they can complete it by

20:01

then , yet have the vocabulary , the

20:03

mental models sufficiently fleshed out to articulate

20:05

it . My gut was going in the right direction

20:07

, but I still didn't have as much experience

20:10

as I would have liked

20:12

if I had hired me in that role

20:14

.

20:15

I hear you . I hear you . So how did

20:17

that work out ? Did you find a CTO position

20:19

? Did you manage to get some

20:22

experience on your belt and really step into this

20:24

direction ?

20:25

Well , in that job . Now we technically

20:27

had a CTO who is the 22

20:30

year old college dropout co-founder

20:32

, who to this day I don't

20:34

know what exactly he did . I

20:36

had the entire engineering team reporting

20:38

to me . I then

20:40

had I don't

20:42

know if you'd call it foresight or not

20:45

quite sure what term I said . You know , at a certain point

20:48

I am realizing

20:50

I might be not the best person

20:52

for this . I think I'm doing a good job , but there

20:55

must be better people , more experienced

20:57

people , and if we bring in one of those

20:59

, I could learn from him . We

21:02

brought in a guy who had decades of experience

21:05

at IBM and I watched

21:07

him make a whole bunch of just dumb

21:09

mistakes . He probably knew more

21:12

about business than me . He knew a lot less

21:14

about managing people than I did

21:16

, and I looked

21:18

back at the time and think I should not have

21:20

brought this guy in because he did not know more

21:22

than me and it became very frustrating

21:24

watching him make some dumb decisions

21:27

that he knew . You know , this is how big

21:29

companies work and this is how I've done it for

21:31

years , and it was very frustrating

21:33

watching that , causing me to eventually leave . But

21:35

after that I then started going

21:37

into other senior positions

21:39

, vp level positions and then CTO

21:41

positions .

21:43

And regretted any of that compared

21:46

to staying in IC , I mean .

21:50

No , I think I went down the right path

21:52

. I do miss some

21:55

IC work . The analogy I always use

21:57

is Legos , something that

21:59

I suspect nearly every one of your

22:01

audience has played with at some point

22:03

. So ask yourself

22:06

this question why did

22:08

you stop playing with Legos ? And

22:10

if you need to pause the podcast , take

22:12

a minute before you hear my answer . Think about

22:14

why you may have stopped playing with Legos . The

22:17

answer for myself and

22:20

for many people is that it gets

22:22

repetitive . I had built

22:24

a number of spaceships . I fly them

22:26

around the room and I take them apart . I build another spaceship

22:28

, but spaceship 63

22:30

looks a lot like spaceships one

22:32

to 62 . And at a certain point

22:34

you want different challenges . I

22:37

like coding , but I was getting tired of okay

22:39

and we're going to build another user system . Make

22:42

sure users have these attributes on , don't forget the

22:44

logging and build all this , and

22:46

back then we didn't even have the libraries

22:48

we have today . But still , if you think

22:50

about your code , we know it's

22:53

that 80-20 rule 20%

22:55

is the core code and the 80% is the defensive

22:57

coding around it , and

22:59

that gets very repetitive . What

23:01

I like about the people side

23:04

of the business and that's managing

23:06

people or the business strategy . It's

23:09

always going to be different and every

23:11

rule has an exception , so it's a harder

23:13

set of problems . Just as I moved

23:15

on from the Legos to a more complex

23:17

type of play activity

23:19

, I wanted to move on to a more

23:21

complex set of challenges , because

23:24

that's right for me . That's not right for everyone

23:26

. So I'm glad

23:28

I am where I am . I do wish

23:30

I had X hours a

23:32

week to keep coding . The bigger

23:34

challenge it's not that I can't carve out the time , but it's that

23:36

I can't always keep up with the latest

23:39

software .

23:40

I know that problem . I'm trying to cover Legos

23:42

hidden behind me .

23:46

I have some as well on other shelves , but

23:48

I don't spend a lot of time taking them

23:50

apart and putting them back together to play with them . Many

23:52

of us have on our shelves but we're not actually

23:54

playing with them .

23:55

You don't know what you're missing . Yeah

23:58

, I totally agree . The

24:00

people problem is really what

24:02

attracted me at some point as well , saying , well

24:04

, I did a lot of consultancy and

24:07

saw the same patterns and say , ok

24:09

, that's where we are on the journey

24:11

. Ok , now we're going to have this problem , and now

24:13

we're going to have that problem . Now we're going to start scaling

24:16

and we're going to have that problem . And again and

24:18

again and again , you see the same patterns and the same problem

24:20

. On the technical side , at some point

24:22

it becomes a bit dull and

24:25

says , hey , let's see what's happening

24:27

on the people side , and every case

24:29

is different , and this podcast

24:31

is an example as well . This is Joe 280

24:33

, and no story has been

24:35

twice the same . It's always different

24:37

, there's always something different , and so throw

24:40

a bunch of people in the same room and you

24:42

have a synergy that you've never seen before and

24:44

you have something that's completely unique again , and

24:46

I love this puzzle . I really love this puzzle as

24:48

well .

24:49

Before we start recording , you and I were talking

24:51

and you mentioned the book the Mythical

24:54

man Month , which is a fantastic book

24:56

. Now , half of the book is gold

24:58

, like the Mythical man Month , and if you haven't

25:00

read it , you probably find the article

25:02

online . The article that's the title of the

25:04

book . Half of it is very dated

25:06

. He talks about documentation by Grafiche

25:09

. Just go , okay , that's . It's interesting

25:11

from a historical perspective but

25:13

very out of date . But another

25:16

book I would put at that level is

25:19

People Wear by Tom

25:21

DeMarco and Timothy Lister , and the thesis of People

25:23

Wear is that most software

25:25

projects fail not

25:27

due to technological reasons but

25:30

sociological reasons . It's

25:32

that we didn't communicate well . It's

25:34

that we had too many changes

25:37

during the thing . It's not that , oh , we needed more

25:39

PhDs to get this done . It

25:41

wasn't technically too

25:43

complex , it was all

25:45

the people issues that made it really hard

25:47

. There's not a line of code in the book

25:49

. It is still one of the best books on

25:51

software or management in general that

25:53

I've read .

25:54

Indeed , indeed , and that's actually been the

25:56

way I describe my job

25:59

to non-technical people . It's

26:01

basically well , throw 200

26:04

engineers in a room and make them work

26:06

together , and I'm here to help . That

26:08

Usually it's enough

26:10

for people to say , oh , I see

26:12

, and

26:16

that's indeed a People Wear is fantastic

26:18

. I really recommend it as well . And

26:21

that's what we've seen recently with Conway's Law and

26:23

Reverse Conway's Law , with books

26:25

talking about one or the other meaning how do

26:27

you design your software to influence the

26:30

organizational structures and

26:32

vice versa , how the organizational structures

26:35

influence the way your software is built , and

26:37

this is really a balance you have

26:39

to keep , and both of them are going to influence

26:41

the other , and if you veer too hard

26:43

on one , then the other one is going to become

26:46

a problem , and then vice versa . So really

26:48

you cannot leave this out . This

26:50

is so important .

26:52

I would actually very

26:54

actively think about who is sitting

26:56

where . Back when we were in physical offices

26:58

five days a week , we'd move into

27:00

new office . I think , how do I want to lay

27:03

out this office , these teams

27:05

? Because you have your organizational

27:07

structure , but even just physically , who

27:09

is near whom impacts

27:11

your communication flow and

27:14

what happens . And in fact

27:16

, I encourage managers really , when

27:18

you think about modern management , it

27:20

is about managing information flow

27:22

. It's about making sure the right

27:24

people have the right conversations

27:26

at the right time . If

27:29

you can do that , then

27:31

you're going to be an effective manager

27:33

. Now that might happen because we have

27:36

a weekly check-in meeting or after this happens

27:38

you need to send an email to the team . But

27:40

also happens because you put these people

27:42

near each other whether they're physically

27:44

near each other or their teams that have

27:46

regular coordination meetings . You're going

27:48

to enhance the chances of

27:51

having those right conversations with the right

27:53

people at the right time .

27:56

And add the remote variable on top of

27:58

that , that becomes an interesting

28:00

puzzle .

28:02

Well , that's where you have to be more explicit , because

28:04

we don't have that water cooler

28:06

conversation . We're not both getting coffee at

28:08

the same time . We can

28:10

use tools like Donut to

28:12

facilitate that . Or we can just

28:14

be more explicit and just say we're

28:16

going to have maybe more check-in

28:18

meetings , or it's more important that you send

28:21

this email when this happens to give an update

28:23

. As long as we think about and manage

28:26

that information flow , we can do it formally or informally

28:28

. And when you think about a team that

28:30

might be four people saying in

28:32

a room together , you don't need a lot of formal

28:35

meetings because the information flow is natural

28:37

when you have 40 people . That's where

28:39

we need the structure . Likewise , when

28:41

we're even just four people , but in

28:44

different time zones , we just need to add

28:46

a little more structure to foster that communications

28:48

.

28:49

Mm-hmm , I like the way you're putting it . You're

28:52

not advocating for more or not

28:54

advocating for faster , but

28:56

you're just saying adding structure , which

28:58

really is dependent on the context . I

29:01

, for instance , have a base camp in mind

29:03

which we've heard a lot , and

29:05

they really advocate for slower communication

29:08

, more thoughtful communication

29:10

, probably not answering like a chat

29:12

, but really answering . Let's answer tomorrow

29:14

with all the information and

29:17

not on an article , but almost really

29:19

with the thinking process , as if the

29:22

person afterwards won't be able to reach me

29:24

, to reach out and add

29:26

some or ask some more question , and really

29:28

will have only this article to work with . And

29:30

this really brings a different way

29:32

of working and for them that is the right thing

29:35

. For a different company it would be a different

29:37

set of constraints and maybe

29:39

it would need some faster communication

29:41

, but really have to find out what this chemistry

29:44

for your organization is and

29:46

really tell you that structure for what

29:49

you need .

29:50

That's exactly right . When we think about processes

29:53

and we can think about waterfall versus

29:55

agile and agile is great

29:57

in many cases there are also certain

29:59

cases where you do want waterfall

30:01

. I remember reading for the

30:04

US Space Shuttle , which is now retired

30:06

, it would take them six months to

30:08

change a line of code . Any

30:11

of our businesses would die . But

30:13

you think about and say literally

30:15

billions of dollars and lives

30:17

at stake . I'm

30:19

okay with them going really slow and

30:21

being very careful in a very unforgiving

30:24

environment , so that flow is right

30:26

for them . And when you think

30:28

about what these project management

30:31

techniques are , they're really

30:33

about the information flow , whether

30:35

it's we can't move to the next stage

30:37

until this one has had all the checks , or

30:40

just we need to rapidly communicate

30:42

information in a daily standup and

30:44

then do quick changes to get quick feedback

30:46

in a scrum . So

30:49

really it's saying what is that information

30:51

flow and flexibility that we need ? Is

30:53

it slow , steady , fully

30:56

thought out , accurate information versus

30:58

the other extreme , quick , dynamic information

31:01

? And of course there's all sorts of in between

31:03

and it's not just that one dimension .

31:06

No , it is not , and that's what makes the

31:09

work of organization crafting

31:11

so hard . You have to understand

31:13

the right levers and not

31:15

pull them all at the same time , and understand how one

31:18

maybe feeds into the other

31:20

and you can get a reinforcing

31:22

loop at some point and get too much of the goodness

31:25

you wanted to have and break stuff . So

31:27

this is a fun puzzle . I'd

31:30

like to twist the discussion a little bit

31:33

. So obviously , as a manager

31:35

, or as a manager of manager , as somebody in the leadership

31:40

of a company , you probably accompanied

31:42

a lot of people and really did

31:45

some mentoring I wouldn't say teaching

31:47

, but mentoring and really guiding people

31:50

. At what time did you decide to formalize

31:53

this and go back to MIT and teach

31:55

for real ?

31:57

Pretty early on , so

32:00

early in my career , I mentioned how I knew I wanted

32:02

to get into more of the people side . I

32:04

wanted to become a CTO and I recognized

32:07

it wasn't just about being the best engineer

32:09

. It wasn't that I could code better or

32:11

faster than others . There were all these other skills

32:14

I would need leadership

32:17

, networking , negotiating , communication

32:19

, hiring , team building , team building but

32:21

no one ever taught them to me . So

32:23

I began to work to upscale myself

32:26

. We didn't have great podcasts

32:28

like this back then . It was a lot harder and

32:30

as I did , I realized these

32:32

skills will help everyone . They

32:34

are not just for leaders , not just for managers

32:37

. Everyone , down to your summer interns

32:39

can benefit from these skills

32:41

. So I began to upscale my

32:43

team and as I was

32:45

doing that , mit had

32:48

gotten similar feedback . Companies were saying

32:50

these are the skills we want to see , not

32:52

just in engineers , not just in college grads

32:55

. Universally we look for these skills

32:57

and they're very hard to find . So

32:59

MIT was pointing together a program to

33:01

address this . When I heard about

33:03

it through my network , I said

33:05

, okay , well , maybe MIT

33:08

could use some of what I've built . I reached out to

33:10

the person who was starting up this program . I said I've

33:12

got some content , I'm happy to give it to you . I

33:15

thought that would be it One and done , here you go , best

33:17

of luck . But instead he said

33:19

hold on , can you stay

33:21

and maybe help us build a little

33:24

more content ? Okay , sure

33:26

, spend some time , this could be fun . So

33:28

we were building out some additional training and

33:31

as we were doing it , what he told me years later

33:33

is he recognized . I brought

33:35

a different dimension . Now we have

33:37

a number of amazing professors school

33:39

of engineering , sloan , school of Management

33:42

. These are literally the top

33:44

people in the world , but

33:46

they're very academic . They don't spend a

33:48

lot of time in industry . They

33:51

said you're bringing this industry perspective

33:53

. That I think is unique . We

33:55

should bring in more people

33:57

like you to bring in that perspective . So we went out . We

34:00

found a bunch of other folks and

34:02

created this program that's co-taught

34:04

. We have the professors , because we need

34:06

to get academic credit and that requires

34:09

professors , but then also practitioners

34:11

like myself co-teaching

34:13

the students . And this was

34:16

2001,

34:18

. 2002 is what we heard

34:20

. So I have been teaching there for decades and

34:23

it was only the last few years where I said I

34:25

know this is helpful to not

34:27

just engineers , to everyone . How

34:29

can we reach a larger audience ? I was trying to push MIT

34:32

to put this stuff online . For

34:34

various reasons that didn't happen , so

34:37

I thought I'd write up notes , and what I thought

34:39

was going to be 10 or 20 pages of notes expanded

34:42

and suddenly became a 270

34:44

page book .

34:46

Which is great for you , I guess .

34:48

Hopefully helpful to the world , because

34:51

that's my goal is trying to help

34:53

more people develop these skills . I really want to

34:55

see people maximize their

34:57

professional efficacy Indeed indeed

34:59

.

35:00

Way better way to put it . How

35:02

have you seen this program evolve

35:05

in those 20 years ?

35:09

It's . We've evolved , we've learned a lot about

35:11

teaching these skills . It's

35:13

very interesting because this

35:16

is not first of all these skills . It's not how

35:18

we learn programming or other skills

35:20

when you think back to what you're learning . You

35:23

learned history by having a professor say here are

35:25

the important dates . You learn

35:27

coding by okay , here's how memory

35:29

works , here's computer architecture , here's

35:32

one . If then statement does Right , then

35:34

I say okay , I get , and then we

35:36

just go and regurgitate

35:38

the answer . But that's not how

35:40

these skills work . These skills are more

35:42

akin to learning sports . I

35:45

can teach you the rules to a game in

35:47

30 minutes , but it's going to take

35:49

you years to get good

35:51

at . It requires drills and

35:54

scrimmage games and coaching and reflection

35:56

, and that's the approach that we take

35:58

here . So we

36:00

start off doing that . But even coaching

36:02

if you ask , for example , a

36:05

soccer coach or a football coach , what

36:07

they're coaching was like year one versus year

36:09

10 of their career . Like I say

36:11

, I've learned a lot more about how to be a

36:13

coach and I think over the past few decades we

36:16

learned a lot about how best to

36:18

engage the students , what type of activities

36:20

work . We've tweaked the activities to make

36:23

them more likely

36:25

to get the educational goals

36:27

we're trying to achieve , and

36:30

so we've done . I'd say the core still

36:32

works , but we've definitely done a lot of

36:34

tweaks along the way and we've added modules

36:36

and taken modules out , based

36:38

on a number of factors .

36:41

Again , wrong reformulation . To be sure I understood

36:43

what you described is it's

36:45

basically tweaking the form but

36:47

not really tweaking the content . It's

36:50

saying , well , this form didn't really

36:52

fit that context , or maybe we discovered a

36:54

different way to bring it out , but

36:56

the content remained the same

36:58

over 20 years . Is it what you meant

37:01

?

37:02

Yes and no . The content has changed in that

37:04

we've said we're going to drop this module

37:06

and that content and we're going to add a different

37:08

module with different content , just

37:11

because , if you think about the skills

37:13

we're trying to teach these skills

37:15

, you can do a semester-long class on just

37:17

one skill , yeah , and

37:20

we're trying to cram it all into a reduced

37:22

program . So we're just

37:24

giving them a little sample of

37:27

each and just at times you might say let's

37:29

do this , not that , but any given

37:31

module whether this is a leadership module

37:33

, this is a negotiation module how

37:36

we structure it , the way

37:38

we approach it , the actual

37:41

exercise itself might change

37:43

up based on our experience

37:45

and feedback . For example , in

37:48

certain activities we want

37:50

students to fail . They

37:53

do better , they learn better once they fail

37:55

. There's another activity where

37:57

we try to get a 50-50 split . These

38:00

are a lot of role-playing activities and

38:02

at the end we want half the students to make one

38:04

choice and have to make the other . If they're

38:06

all making one choice , whether it's

38:08

right or wrong , it feels like

38:10

, ok , we push them too much in

38:12

that direction . When we get that 50-50

38:14

split , then we can have a real discussion

38:17

before we tell them how this all plays out . Why

38:20

did you think that way ? Oh , I never thought about

38:22

the point you're bringing up and that

38:24

brings out a richer experience

38:26

. So those are types of tweaks

38:28

that we do .

38:30

What is the target audience of this class

38:33

? Is this really a freshman , 18

38:35

years old , coming just out of high school , or

38:37

more , at the end of

38:39

their undergraduate studies ?

38:42

The class I've been teaching is

38:44

for MIT sophomores . We

38:46

have created sister

38:48

programs that go into the junior

38:50

and senior year for typically

38:53

a smaller cohort of students . We hit a wide

38:55

range of hundreds of students each year . Those

38:58

then get down into the tens of students

39:00

and now we're looking at expanding

39:02

. I've been asking for years to expand to graduate

39:05

students , which I think we're finally starting

39:07

to do this academic year

39:09

, 2023 , 2024 , possibly

39:12

next year .

39:13

Did you expect a difference in

39:15

maturity and life experience

39:18

and that this different

39:20

, this life experience would affect the

39:22

way people embrace

39:24

the content or maybe react to the content

39:26

?

39:28

I don't think life experience from

39:31

a few years , from college versus

39:33

college and grad school or sophomore to

39:35

senior I don't think it impacts

39:38

them that

39:40

much . What I'm finding is

39:42

a bigger causality

39:44

of how people

39:47

engage with this content . First

39:49

it's just some natural inclination . We

39:51

just see the bell curve of some students say

39:53

I really want to learn this . Others

39:56

show up and well , I hear you give

39:58

free food so I'm doing it . A

40:00

friend told me to do it . Some just

40:02

like well , I guess I'm here and I'm getting credit

40:04

, but they're not really engaged . And you just

40:06

see people , their level of engagement

40:09

, of interest and how well they take to it . Standard

40:12

bell curve . I will say

40:14

, having now taught for a few decades , I

40:16

have definitely seen generational trends

40:18

in how people approach this and

40:21

their interest to certain things . So

40:23

that's probably a bigger macro

40:26

factor than just

40:28

are you 19 versus 21

40:30

when you're doing this ?

40:31

OK , that could be an episode in

40:34

itself , just talking about that bell curve and how

40:36

it devolved over years . But

40:38

unfortunately we're at the end of our time box and

40:41

I want to go back to one of

40:43

the things , or one

40:45

key moment I think in the interview is when you describe

40:48

leaving individual contribution

40:50

and going into management . This

40:52

hell , yeah , I'm ready for that . If

40:56

you had an advice for people exactly

40:58

at that stage of their career saying

41:00

, well , I've seen those problems and I

41:02

see again and again and again , I think I'm ready

41:04

for the rest . How do

41:06

I step into this direction ? How do

41:08

I really make

41:11

the right moves to be on the right track

41:13

into going there ? Do you have an advice for them ?

41:16

I mean you have two pieces of advice . The

41:18

first is that you

41:21

have to embrace these

41:23

other skills , Because when

41:25

you're an individual contributor , you

41:27

start out , you solve a certain type of problem and

41:30

when you do well , they say we're advancing you

41:32

and now you solve a bigger version of that problem

41:34

and yet an even bigger version , and

41:36

you're typically doubling down

41:38

on your technical skills . I'm

41:40

using technical , not necessarily coding . Again , it could

41:43

be marketing or finance , but it's

41:45

that domain skill that you are

41:47

using over and over . You're just wielding

41:49

a bigger hammer To

41:51

get to those higher levels . It's

41:54

not about that domain skill , it's

41:56

about all the other skills . It

41:59

is about negotiating

42:01

and hiring and team building and

42:03

managing and leading . And

42:06

the big challenge you have to rely more on those

42:08

skills . And the big challenge

42:10

is you've probably succeeded by

42:12

just being bigger , better

42:14

, faster , but now that

42:16

you're a manager you can't do

42:18

it and we see a lot of managers burn out from that

42:21

hero . Ok , the team's

42:23

flowing , I'm just going to jump in , I'm going to pull the all

42:25

nighter , I'm going to get it done . And you might

42:27

be able to do that in your first role or

42:29

do it from time to time , but as you

42:31

get more and more people . You can't just pick

42:34

up more load . Your ability

42:36

to complete , to

42:39

achieve , to deliver value is

42:41

no longer what you can carry in your hands

42:43

. It's your ability to get the team

42:45

to do that , and that's a very different type of challenge

42:48

than what you've had before . So

42:50

we've basically been rewarding you for a certain

42:52

type of activity and all

42:54

of a sudden we just change the rules of the game when

42:57

you become a manager , and so that's where you often

43:00

get tripped up and that's where you have to say

43:02

it's no longer my technical skills , yes

43:04

, you're going to need those , but

43:06

all of a sudden these other skills really come

43:09

into play a lot more .

43:11

Amen to that . This is so important to realize

43:13

and understand , otherwise , you're

43:15

going for the wall directly . Mark

43:18

, this has been a fantastic discussion

43:20

. Thank you so much . It was really enjoyable .

43:23

Well , thanks again for having me on the show .

43:25

It was my pleasure . Where could

43:27

the listeners reach out and could use

43:29

this question with you ?

43:31

I'm going to give you two websites . The

43:33

first is my book's website , thecareertoolkitbookcom

43:36

, and there you can learn more about

43:38

the book . You can follow me on social media

43:41

. You can get in touch with me if you have questions . I

43:43

put out new articles every week and I have

43:45

a whole page of free resources

43:47

. I have nothing to sell . Technically

43:50

, you have to buy the book for if you want

43:52

the book , but everything else it's free . I don't even care

43:54

about getting your email because I'm not trying to sell you anything

43:56

else . We have the career

43:58

questions . You should be asking yourself Questions

44:01

to ask during an interview to figure out is

44:03

this the right company fit for you ? We

44:06

have questions to ask when you're hiring

44:08

to make sure you're thinking the right way about hiring

44:10

. We've got links to all sorts of other resources

44:13

, again all free , and all of

44:15

this at thecareertoolkitbookcom

44:17

. The second website is

44:19

because so often you read a book

44:21

like mine , say this is great , but

44:24

then you forget . Where do you read those networking

44:26

tips ? Sitting at home ? Where do you need

44:29

them Two months later at the conference

44:31

? We want to put

44:33

those tips in your pocket and again , it's all

44:35

completely free . We created the

44:37

BrainBump app , so if you go to

44:39

brainbumpappcom . You

44:41

can follow links to the app stores to download

44:43

the free app . It has all

44:45

the tips for my book . If you went through with a highlighter

44:47

, this is what you would highlight

44:50

. We don't even check that you bought the book . You

44:52

get this all for free . But you also

44:54

have tips from other books , career

44:56

books , management books , sales books

44:58

, tips from podcasts , tips from blogs

45:01

, tips from other sources , with an ever-growing

45:04

list . So you have them all right in your pocket and

45:06

you can either pull it up as you need it as

45:08

you're going into that conference , pull up

45:10

those networking tips , or you can

45:13

set for a daily reminder . If

45:15

you're a new manager , 9 AM each

45:17

day , just get one of those tips . You don't have to open

45:20

the app , just pops up . You say , all right

45:22

, I remember we're supposed to do this Great

45:24

swipe , but that's going to help

45:26

you remember it and have it

45:28

in the forefront of your mind as you go through

45:30

your day . So that's the BrainBump app

45:32

, completely free . Brainbumpappcom

45:35

.

45:37

And if you didn't get that scroll down

45:39

, it will be in the show notes . Just

45:41

click on it . Goodness , I

45:43

can promise you Anything else .

45:46

That's everything , Marc . Thank you so

45:48

much .

45:49

Thanks again , and this has been another

45:52

episode of Dev . First Journey with each other

45:54

next week Bye-bye . Thanks

45:57

a lot for tuning in . I hope

45:59

you have enjoyed this week's episode . If

46:02

you like the show , please share , rate

46:04

and review . It helps more

46:06

listeners discover those stories

46:09

. You can find the links to all

46:11

the platforms the show appears on on

46:13

our website devjourneyinfo

46:15

. Subscribe

46:18

. Talk

46:20

to you soon .