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Do Repeat Yourself: How to move from Development into Leadership

Luke Stringer
September 05, 2023

Do Repeat Yourself: How to move from Development into Leadership

As a developer moving into a leadership role for the first time it can be can be tough, confusing, and at times overwhelming. This was certainly the case for me. I discovered that the principles I had once followed when building software were no longer effective as a leader. However, after a few years I can confidently say that becoming a leader is one of the most fulfilling things I've done. In this talk you will learn some of the ways to adapt your developer skillset to that of a tech lead, and I will share my observations in making these adjustments myself. We'll look at how the problems you need to solve are suddenly very unfamiliar, with incentives that are often the reverse to what you've been used to. If you've had similar experiences or are considering a move into leadership yourself, this talk is for you. You will leave with an number of effective strategies for becoming a tech lead, while remaining kind to yourself and others.

This talk has been delivered at:
iOSDevUK, September 5th 2023

References from this talk

📕 Books
The One Minute Manager
Leadership and the One Minute Manager
The First 90 Days
The Phoenix Project
Leading Snowflakes

📰 Online Resources
Note Taking During One on Ones
My Manager README

👥 Community
LeadDev
Software Lead Weekly

🗣️ Talks
Becoming an iOS Dev, again by Michał Waśniewski
Next Step: Management? by Leah Vogel

🔨 Tools
Things
Bear
Xmind
Fantastical

Luke Stringer

September 05, 2023
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Transcript

  1. Luke Stringer, @lukestringer90. September 5th 2023. iOSDevUK, Aberystwyth.
    Do Repeat Yourself
    How to move from Development into Leadership

    View Slide

  2. Hi, I’m Luke !
    I’m an iOS Developer from Sheffield
    I work for AND Digital as a Tech Principal
    I go by @lukestringer90 online

    View Slide

  3. Hi, I’m Luke !
    I’m an iOS Developer from Sheffield
    I work for AND Digital as a Tech Principal
    I go by @lukestringer90 online

    View Slide

  4. 1. Developer Life 2. Opportunity to Lead
    3. First Steps
    5. Technical Leadership
    4. People Problems
    6. Communication
    7. You as a Leader
    8. Finding Peace

    View Slide

  5. 1. Developer Life

    View Slide

  6. Individual Contributor
    Clear outcomes
    Code compiles Tests pass
    PRs approved
    Code is merged
    App is released
    App is improved
    1. Developer Life

    View Slide

  7. Individual Contributor
    Clear outcomes
    Code compiles Tests pass
    PRs approved
    Code is merged
    App is released
    App is improved
    1. Developer Life

    View Slide

  8. Course, tutorials, books Side projects
    Code review WWDC content
    Improving your developer skills
    1. Developer Life
    Individual Contributor

    View Slide

  9. 1. Developer Life
    Individual Contributor
    Strong peer group

    View Slide

  10. Challenge
    Skill
    Boredom
    Anxiety
    Flow
    State
    1. Developer Life
    Individual Contributor

    View Slide

  11. Challenge
    Skill
    Boredom
    Anxiety
    Flow
    State
    1. Developer Life
    Individual Contributor
    …foreshadowing

    View Slide

  12. 1. Developer Life

    View Slide

  13. 2. Opportunity to Lead

    View Slide

  14. 2. Opportunity to Lead
    A new role
    Internal promotion

    Your boss leaves

    A new team is created

    Leadership opportunity at a different company

    View Slide

  15. 2. Opportunity to Lead
    Reasons for moving
    Want a new / more challenge

    Bored of just writing code

    Solve problems you have seen as a developer

    More influence

    Avoid regret at not taking the opportunity

    View Slide

  16. (not so good)
    2. Opportunity to Lead
    Reasons for moving
    You are a good developer, so you must
    be a good leader (right?)

    Business thinks you are the only
    person who can lead a team

    It’s the only route for progression and
    promotion

    …ahem… more money

    View Slide

  17. (not so good)
    2. Opportunity to Lead
    Reasons for moving
    You are a good developer, so you must
    be a good leader (right?)

    Business thinks you are the only
    person who can lead a team

    It’s the only route for progression and
    promotion

    …ahem… more money
    Michał Waśniewski

    View Slide

  18. (not so good)
    2. Opportunity to Lead
    Reasons for moving
    You are a good developer, so you must
    be a good leader (right?)

    Business thinks you are the only
    person who can lead a team

    It’s the only route for progression and
    promotion

    …ahem… more money
    Leadership /
    management isn’t
    the only path for
    progression
    Michał Waśniewski

    View Slide

  19. 2. Opportunity to Lead
    Michał Waśniewski
    Becoming an iOS developer, again

    iOSDevUK 2022
    INTERN
    ASSOCIATE
    INDIVIDUAL CONTRIBUTOR
    SENIOR INDIVIDUAL CONTRIBUTOR
    STAFF
    SENIOR STAFF
    PRINCIPAL
    FELLOW
    MANAGER
    SENIOR MANAGER
    DIRECTOR
    VICE PRESIDENT
    SENIOR VICE PRESIDENT
    Leadership /
    management isn’t
    the only path for
    progression

    View Slide

  20. 2. Opportunity to Lead

    View Slide

  21. 3. First Steps

    View Slide

  22. Thrilled at the opportunity …but feelings of being

    an imposter
    Excitement! Anxiety!
    3. First Steps

    View Slide

  23. Thrilled at the opportunity …but feelings of being

    an imposter
    Excitement! Anxiety!
    3. First Steps
    This is totally
    normal

    View Slide

  24. From the business

    From your team

    From yourself
    High expectations
    3. First Steps

    View Slide

  25. From the business

    From your team

    From yourself
    High expectations Be realistic

    You can’t change everything
    right away

    You need to find your feet

    Set expectations accordingly
    3. First Steps

    View Slide

  26. Be realistic

    You can’t change everything
    right away

    You need to find your feet

    Set expectations accordingly
    3. First Steps

    View Slide

  27. You were a peer, now a boss

    People will now look to you for
    answers and direction

    But you are missing information
    and clarity yourself

    Uncertainty and ambiguity

    Unfamiliar Territory
    3. First Steps

    View Slide

  28. You were a peer, now a boss

    People will now look to you for
    answers and direction

    But you are missing information
    and clarity yourself

    Uncertainty and ambiguity

    Unfamiliar Territory The best leaders are
    comfortable being
    themselves

    Get used to uncertainty

    Don’t worry about what you
    cannot control
    3. First Steps

    View Slide

  29. Loss of your peer group
    3. First Steps

    View Slide

  30. Loss of your peer group
    3. First Steps

    View Slide

  31. Loss of your peer group
    3. First Steps
    You now have a
    different peer group

    Technical
    Leadership

    Engineering
    Management

    View Slide

  32. You now have a
    different peer group

    Technical
    Leadership

    Engineering
    Management
    3. First Steps

    View Slide

  33. 3. First Steps

    View Slide

  34. 4. People Problems

    View Slide

  35. 4. People Problems
    What should to ask?

    Sometimes they are
    uncomfortable and
    awkward

    They don’t seem very
    effective
    1-2-1 meetings

    View Slide

  36. 4. People Problems
    What should to ask?

    Sometimes they are
    uncomfortable and
    awkward

    They don’t seem very
    effective
    1-2-1 meetings Ask what they want to discuss

    Also prepare what you want to
    discuss

    Choose the right open vs
    future closed

    Have a few ice breakers /
    prompts

    View Slide

  37. 4. People Problems
    1-2-1 meetings Get to know people

    Not always be about work

    Sometimes people are
    awkward, including you!

    Take notes, so you can track
    progress and effectiveness
    What should to ask?

    Sometimes they are
    uncomfortable and
    awkward

    They don’t seem very
    effective

    View Slide

  38. 4. People Problems
    Get to know people

    Not always be about work

    Sometimes people are
    awkward, including you!

    Take notes, so you can track
    progress and effectiveness

    View Slide

  39. 4. People Problems
    Within your own team

    Between you and your team

    Between your team and
    another

    Between you and the
    business

    Feeling stuck in the middle
    Dealing with conflict

    View Slide

  40. 4. People Problems
    Within your own team

    Between you and your team

    Between your team and
    another

    Between you and the
    business

    Feeling stuck in the middle
    Dealing with conflict Doing the right thing is hard

    Have empathy, and be fair

    Have a plan, but prepare to
    think on your feet

    Ensure you have support;
    confide in other leaders

    View Slide

  41. 4. People Problems
    How do I manage people with
    different skills and seniority?

    Am I spending too much time on
    problems?

    Am I nurturing talent?

    Growing a team

    View Slide

  42. 4. People Problems
    How do I manage people with
    different skills and seniority?

    Am I spending too much time on
    problems?

    Am I nurturing talent?

    Growing a team
    Have confidence in your
    technical skills
    You now have different
    responsibilities, and not
    everyone will understand

    View Slide

  43. 4. People Problems
    How do I manage people with
    different skills and seniority?

    Am I spending too much time on
    problems?

    Am I nurturing talent?
    Growing a team
    You are no longer
    building software, you
    are building a team

    Do not neglect rising
    stars

    View Slide

  44. 4. People Problems
    From The One Minute Manager

    "Goals Begin Behaviours

    Consequences Maintain
    Behaviours”

    View Slide

  45. 4. People Problems

    View Slide

  46. 5. Technical Leadership

    View Slide

  47. Loss of your technical chops
    5. Technical Leadership

    View Slide

  48. Loss of your technical chops
    5. Technical Leadership

    View Slide

  49. Loss of your technical chops
    5. Technical Leadership
    Leah Vogel

    View Slide

  50. Loss of your technical chops
    5. Technical Leadership
    You don’t have to 100% lose them

    Not hands on, but hands warm,
    development

    Take yourself out of the critical path

    Work on bugs, experiments, code
    review
    Leah Vogel

    View Slide

  51. 5. Technical Leadership
    Loss of your technical chops
    Watch WWDC

    Attend conferences, meetups

    Discuss code with devs

    Keep an area of expertise;
    Provisioning, Git, CI/CD, Regex

    View Slide

  52. 5. Technical Leadership
    Use the maker calendar
    Switch between “Manager” and “Maker” modes

    View Slide

  53. 5. Technical Leadership
    Loss of your technical chops Trust your team

    Your ignorance is now a super
    power to ask stupid questions

    Normalise for juniors or introverts

    Builds a shared understanding

    View Slide

  54. 5. Technical Leadership
    I don’t have time to keep
    up to date

    I’m getting rusty

    My technical opinions
    won’t be respected
    Being technical enough

    View Slide

  55. 5. Technical Leadership
    I don’t have time to keep
    up to date

    I’m getting rusty

    My technical opinions
    won’t be respected
    Being technical enough
    Accept others will know more,
    seek their help and they will
    appreciate it

    Identify, measure and prioritise
    risks

    Stand up for tech debt

    Champion broader engineering
    principles

    View Slide

  56. 5. Technical Leadership

    View Slide

  57. 6. Communication

    View Slide

  58. …to non-techies
    …to techies
    Talking
    6. Communication

    View Slide

  59. 6. Communication
    Giving the right level of
    detail

    Making people care
    about tech issues

    Getting buy-in from
    non-technical
    stakeholders
    Talking tech to non-techies

    View Slide

  60. 6. Communication
    Giving the right level of
    detail

    Making people care
    about tech issues

    Getting buy-in from
    non-technical
    stakeholders
    Talking tech to non-techies
    Make it tangible; money, time,
    reputation, customer satisfaction,
    speed

    Back it up with data and precedent

    Employ metaphors, diagrams,
    presentations

    You are the voice of “tech”

    View Slide

  61. 6. Communication
    Making people care
    about non-tech issues

    Policy changes

    Important but
    uninteresting news
    Talking non-tech to techies

    View Slide

  62. 6. Communication
    Making people care
    about non-tech issues

    Policy changes

    Important but
    uninteresting news
    Talking non-tech to techies Explain the effects, now and into
    the future

    Use same language as wider
    company communications

    Be clear and honest

    You are the voice of “the business”

    View Slide

  63. …to non-techies
    …to techies
    Talking
    6. Communication

    View Slide

  64. You are the “glue”

    Be consistent

    Adapt your message
    as needed
    …to non-techies
    …to techies
    Talking
    6. Communication

    View Slide

  65. 6. Communication
    Why are my changes not
    embedded?

    Why am I misunderstood?

    Why do people forget
    what I’ve said?

    Why must I repeat myself?

    Being effective

    View Slide

  66. 6. Communication
    Why are my changes not
    embedded?

    Why am I misunderstood?

    Why do people forget
    what I’ve said?

    Why must I repeat myself?

    Being effective
    Have you understood and
    remembered everything
    your boss has told you?!

    View Slide

  67. 6. Communication
    Why are my changes not
    embedded?

    Why am I misunderstood?

    Why do people forget
    what I’ve said?

    Why must I repeat myself?

    Being effective
    Do Repeat Yourself

    Be forgiving to others and
    yourself

    Grab people’s attention

    Inject some personality with
    emojis, memes, gifs

    View Slide

  68. 6. Communication
    Why are my changes not
    embedded?

    Why am I misunderstood?

    Why do people forget
    what I’ve said?

    Why must I repeat myself?

    Being effective Take your time; clarity is
    paramount

    Connect what you are saying
    to a larger narrative or
    strategy

    Use all forums & tools;
    1-2-1s, team meetings,
    Slack, email etc

    View Slide

  69. 6. Communication

    View Slide

  70. 7. You as a Leader

    View Slide

  71. 7. You as a Leader
    Tracking many different,
    sometimes unrelated, projects

    Urgent vs important
    prioritisations

    Remembering yours and others
    actions, and the deadlines

    Dealing with context switching
    Being organised

    View Slide

  72. 7. You as a Leader
    Tracking many different,
    sometimes unrelated, projects

    Urgent vs important
    prioritisations

    Remembering yours and others
    actions, and the deadlines

    Dealing with context switching
    Being organised Find a tool or process that
    works for you

    I use;

    • Hand written notes

    • Four colour pen

    • Things for todos

    • Bear for .md typed notes

    • XMind for mind mapping

    View Slide

  73. Use a mind map (notepad,
    whiteboard, digital) to get
    stuff out of your head

    Create connections and
    areas of similarities

    Turn these into actions
    7. You as a Leader

    View Slide

  74. 7. You as a Leader
    Tracking many different,
    sometimes unrelated, projects

    Urgent vs important
    prioritisations

    Remembering yours and others
    actions

    Dealing with context switching
    Being organised
    Spend time curating and
    refactoring your calendar

    Look ahead to make sure
    you are prepared

    Get good with your app of
    choice; I use Fantastical

    View Slide

  75. 7. You as a Leader
    Tracking many different,
    sometimes unrelated, projects

    Urgent vs important
    prioritisations

    Remembering yours and others
    actions

    Dealing with context switching
    Being organised Manage your context
    switching

    Book time in with yourself
    to do your work

    Mute Slack, email etc for
    Flow State work

    Use a Pomodoro timer

    View Slide

  76. 7. You as a Leader
    Doing “people stuff” is draining

    When to be cautious vs acting swiftly

    Perfectionism in my work

    Everyone needs me, and there is no
    time for my work
    Feeling overwhelmed

    View Slide

  77. 7. You as a Leader
    Doing “people stuff” is draining

    When to be cautious vs acting swiftly

    Perfectionism in my work

    Everyone needs me, and there is no
    time for my work
    Feeling overwhelmed Don’t do back to back
    1-2-1s

    Learn from your
    mistakes, but realise
    inaction is also an
    action

    Use an MVP
    approach, and iterate

    View Slide

  78. 7. You as a Leader
    Doing “people stuff” is draining

    When to be cautious vs acting swiftly

    Perfectionism in my work

    Everyone needs me, and there is no
    time for my work
    Feeling overwhelmed Practise and be kind
    to yourself

    Say No and be clear
    on what your priorities
    are

    Find the right work-life
    balance

    View Slide

  79. 7. You as a Leader

    View Slide

  80. 8. Finding Peace

    View Slide

  81. 8. Finding Peace
    For your team to be
    effective, you need
    to be effective
    You need space to think,
    and find your flow state
    Protect your time
    Say No

    No Agenda?
    Then No Attenda
    Be selfish

    View Slide

  82. 8. Finding Peace
    You cannot just watch a
    video / read a book on
    leadership, you have to do it
    Building people and teams is
    hard, but hugely rewarding
    Your feedback loop
    is slower, so give
    yourself time
    Be realistic
    A leader’s role is
    diverse, evolving and
    multifaceted

    View Slide

  83. 8. Finding Peace
    Talk about wellbeing,
    and normalise it
    Recognise you are a
    team contributor, and
    this adds immense value
    Be the role model
    you would want
    yourself
    Be kind
    Find a way to switch
    off from work

    View Slide

  84. Have fun!

    View Slide

  85. 8. Finding Peace

    View Slide

  86. The Future…

    View Slide

  87. The Future
    Talk about your experience

    Help create a Leadership Pathway

    Mentor others

    Create a Manager README

    View Slide

  88. The Future
    Talk about your experience

    Help create a Leadership Pathway

    Mentor others

    Create a Manager README

    Or…

    Start the cycle again

    Go back to being a developer

    View Slide

  89. The Future
    1. Developer Life
    Talk about your experience

    Help create a Leadership Pathway

    Mentor others

    Create a Manager README

    Or…

    Start the cycle again

    Go back to being a developer

    View Slide

  90. 1. Developer Life 2. Opportunity to Lead
    3. First Steps
    5. Technical Leadership
    4. People Problems
    6. Communication
    7. You as a Leader
    8. Finding Peace

    View Slide

  91. " Books

    • The One Minute Manager

    • Leadership and the One Minute Manager

    • The First 90 Days

    • The Phoenix Project

    • Leading Snowflakes

    # Online Resources
    • Note Taking During One on Ones
    • My Manager README
    $ Community

    • LeadDev

    • Software Lead Weekly

    % Talks

    • Becoming an iOS Dev, again
    by Michał Waśniewski

    • Next Step: Management? 

    by Leah Vogel

    & Tools

    • Things

    • Bear

    • Xmind

    • Fantastical

    Contact

    • lukestringer90 online

    • stringer.dev

    [email protected]

    View Slide

  92. Luke Stringer, @lukestringer90. September 5th 2023. iOSDevUK, Aberystwyth.
    Do Repeat Yourself
    How to move from Development into Leadership

    View Slide