A primer on the steps anyone in middle management can/should take to move into the executive ranks at medium to largish companies.

1. M O V I N G O U T O F
M I D D L E M A N A G E M E N T
A P R I M E R B Y @ T YA H M A

2. O V E R V I E W
A G E N D A
1. Jobby-job v Startup
2. The board
3. Leadership
4. Developing your skill-sets
5. Tactics
6. LinkedIn reminders

3. S TA R T U P E X I T S
H O B B Y- J O B S V S TA R T U P
1%8%
91%
FA I L
S U C C E E D
A C Q U I R E D
“How exits have changed in 2012” by Basil Peters
‣ Most startups fail.
‣ This deck isn’t about startups.

4. T H I S I S A B O U T J O B B Y- J O B S
J O B B Y- J O B V S TA R T U P
‣ This deck is about jobs at medium to large companies (75+ employees)
‣ I call these jobby-jobs.

5. G E T T I N G A D V I C E
Y O U R P E R S O N A L A D V I S O RY B O A R D
Y E S , T H I S H A S T H R E E C O M P O N E N T S
‣ There are three types of people who can give you advice
‣ You need mentors, sponsors and advisors
‣ If you don’t have these three groups, you are at a
competitive disadvantage to your peers

6. Y O U R P E R S O N A L A D V I S O RY B O A R D
Y O U
S P O N S O R
‣ Sponsors sit in your organization, but not in your direct reporting line
‣ They keep you in mind for other opportunities in the organization
‣ You want people thinking about opportunities for you even when
you are not in the room
‣ Your boss cannot be your sponsor. (There is a conflict of interest.)
1 . S P O N S O R S

7. 2 . A D V I S O R S
Y O U R P E R S O N A L A D V I S O RY B O A R D
‣ You speak to advisors as the need arises, and usually because they
have specific domain expertise. It is irregularly-timed advice.
‣ They are not mentors
‣ Their advice tends to be not tailored to you, personally.

8. 3 . M E N T O R S
Y O U R P E R S O N A L A D V I S O RY B O A R D
‣ You meet with mentors, over coffee (but not like this, which is weird)
‣ You talk to them every month, for 1-2 hours
‣ They give you advice tailored to you, specifically
‣ You need two, so that you can triangulate your options/approaches

9. 3 . T O O L S O F L E A D E R S H I P
L E A D E R S H I P
‣ There are three main tools of leadership (they follow this slide)
‣ Leadership isn’t telling people what to do, but giving them a model
and framework for success
‣ It also involves truth-telling in palatable ways

10. 1 . S E L F - A WA R E N E S S
L E A D E R S H I P
G O O D A T B A S K E T B A L L , B A D A T H U M I L I T Y
‣ Self-awareness is knowing where you excel and where you
fall short
‣ In the areas where you fall short, hire great people, or
get better in that area, or do both

11. 2 . A C T I N G W I T H I N T E G R I T Y
L E A D E R S H I P
‣ It is not enough to do and say the right thing
‣ You have do so consistently
‣ You have to behave in a manner that is ethical
‣ Leaders are usually beyond reproach (with small exceptions)

12. 3 . S U C C E S S P L AT F O R M S F O R
Y O U R T E A M
L E A D E R S H I P
‣ Leaders reverse the “do as I say!” paradigm to
“how can I support your success?”
‣ There are three components to this paradigmatic reversal

13. A . C L E A R C O M M U N I C AT I O N
L E A D E R S H I P : S U C C E S S P L A T F O R M S
‣ Your staff needs to know about goals, timelines and deadlines
‣ You should presume that when you first communicate this material,
it will be misunderstood
‣ So repeat it in different settings in a non-irritating way (this is hard)

14. B . P R I O R I T Y S E T T I N G
L E A D E R S H I P : S U C C E S S P L A T F O R M S
‣ You can’t do everything
‣ Your staff can’t do everything
‣ Your company can’t do everything
‣ Set priorities and stick to them, using objective, clear-eyed criteria

15. C . T O O L S F O R S U C C E S S
L E A D E R S H I P : S U C C E S S P L A T F O R M S
‣ This is beyond the right equipment
‣ Your team deserves the right inputs
‣ You can’t make pancakes without milk and eggs, for a poor analogy

16. P L O T T I N G Y O U R G R O W T H
S K I L L S E T S
1976 2016

17. The
Product
Owner
Role
Product Owners
sit at the middle
of three legs of
a slightly
unbalanced
stool.
GM
Engineering
UX/Design Business
The General Manager runs the software
product business. “Sports” is an example.
Builds the MVP, runs
operations, maintains the
existing product, and
manages QA.
Business
development, sales
and marketing
The customer experience.
Product Lead

18. J O S H E L M A N
C A S E S T U D Y
Design Engineering
Product
Business development
What follows are
self-reported skill-
sets from some of
the top product
people on the
planet. Product
people are cross-
disciplinary. This
provides insight
into areas where
you can improve.
PA R T N E R , V E N T U R E C A P I TA L

19. L I S A G E L O B T E R
C A S E S T U D Y
Design Engineering
Product
Business development
L E A D E R , D I G I TA L E D U C A T I O N

20. M E
C A S E S T U D Y
Design Engineering
Product
Business development
P R O D U C T- F O C U S E D C E O

21. L U K E K N O W L A N D
C A S E S T U D Y
Design Engineering
Product
Business development
H E A D O F P R O D U C T

22. A N G I E H I C K M A N
C A S E S T U D Y
Design Engineering
Product
Business development
H E A D O F P R O D U C T

23. F I V E F O L K S
C A S E S T U D Y
Design Engineering
Product
Business development
Taken as a
whole, the skill-
sets have very
different
shapes. You
can be less-
than-exemplary
in some fields
and excel in
others, but you
should have
competency in
all of them.

24. Y O U
C A S E S T U D Y
Design Engineering
Product
Business development
M A K E A P L A N .

25. N I N E H A B I T S O F
S U C C E S S F U L P E O P L E
TA C T I C S F O R M O V I N G U P
T H I S S E E M S P E D A N T I C , B U T I T M A T T E R S

26. 1 . I N B O X Z E R O
TA C T I C S F O R M O V I N G U P
‣ This is dysfunctional
‣ You can’t run your group
from a mobile device
‣ Put time in your calendar
for email catch up
‣ Unsubscribe from
newsletters and threads
that aren’t valuable with
extreme prejudice

27. 2 . P U N C T U A L I T Y
TA C T I C S F O R M O V I N G U P
‣ Be on time
‣ Start meetings on time
‣ Respect other’s time

28. 3 . O P T I M I S M
TA C T I C S F O R M O V I N G U P
‣ Lucky Charms dude is very optimistic
‣ Optimism is infectious
‣ Most companies in the Valley have a
“no-jerks” rule
‣ Jerks sometimes win, but optimistic
people have better chances of doing so

29. 4 . 1 : 1 S E A C H W E E K
TA C T I C S F O R M O V I N G U P
‣ Each member of your
staff deserves at least
30m with you each week
‣ Items to cover in your 1:1
‣ Status updates
‣ Skill development
‣ Tactical and strategic
questions

30. 5 . S TAT U S R E P O R T S
TA C T I C S F O R M O V I N G U P
‣ After the 1:1s, you can generate status reports
‣ Distribute them widely, even if no one else is doing so
‣ Sharing information is power, hoarding it shows weakness

31. 6 . B E G R A C I O U S
TA C T I C S F O R M O V I N G U P
‣ “Thank you” notes and “your welcomes” will never go out of style

32. 7 . TA K E R E S P O N S I B I L I T Y
TA C T I C S F O R M O V I N G U P
‣ If something goes wrong, communicate that behind closed doors
‣ Take responsibility for the shortcomings of your team and own their
mistakes. You have to help them to be better.
‣ Pass praise down to your team members.

33. 8 . Q U A R T E R LY U P D AT E S
TA C T I C S F O R M O V I N G U P
At least once a
quarter, talk about . . .
‣ Missed
opportunities
‣ Feedback about
your performance
as a leader
‣ Questions and
feedback from your
staff

34. 9 . U S E O K R S T O M A N A G E
TA C T I C S F O R M O V I N G U P
‣ Short for quarterly “Objectives and Key Results,” these are
much more valuable than annual goals and five-year plans
that are usually fiction

35. L I N K E D I N H Y G I E N E
I N B O U N D
‣ Steps to make yourself attractive to your
own hires and outside partners and agencies

36. 1 . M I M I C
Y O U R C V
L I N K E D I N H Y G I E N E
1. Make sure you have a photo
2. Customize your LinkedIn URL
3. Make sure your title reflects your job
4. Don’t connect with anyone you haven’t met
in person or spoken to on the phone
5. Make sure that your summary is crisp

37. 2 . G E T R E C O M M E N D AT I O N S
L I N K E D I N H Y G I E N E

38. 3 . W R I T E A N D P O S T
L I N K E D I N H Y G I E N E
‣ Medium is best for this
‣ Write about your area of expertise
‣ Use your other social channels to amplify and respond

39. T H A N K Y O U , @ T YA H M A
A P R I M E R B Y @ T YA H M A