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

Transcript

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

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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
   

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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
   

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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
   

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5. 1. Developer Life
   

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

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

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

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9. 1. Developer Life
   Individual Contributor
   Strong peer group
   

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

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

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12. 1. Developer Life
    

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13. 2. Opportunity to Lead
    

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14. 2. Opportunity to Lead
    A new role
    Internal promotion
    
    Your boss leaves
    
    A new team is created
    
    Leadership opportunity at a different company
    

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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
    

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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
    

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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
    

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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
    

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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
    

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20. 2. Opportunity to Lead
    

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21. 3. First Steps
    

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22. Thrilled at the opportunity …but feelings of being
    
    an imposter
    Excitement! Anxiety!
    3. First Steps
    

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23. Thrilled at the opportunity …but feelings of being
    
    an imposter
    Excitement! Anxiety!
    3. First Steps
    This is totally
    normal
    

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24. From the business
    
    From your team
    
    From yourself
    High expectations
    3. First Steps
    

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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
    

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26. Be realistic
    
    You can’t change everything
    right away
    
    You need to find your feet
    
    Set expectations accordingly
    3. First Steps
    

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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
    

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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
    

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29. Loss of your peer group
    3. First Steps
    

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30. Loss of your peer group
    3. First Steps
    

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31. Loss of your peer group
    3. First Steps
    You now have a
    different peer group
    
    Technical
    Leadership
    
    Engineering
    Management
    

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32. You now have a
    different peer group
    
    Technical
    Leadership
    
    Engineering
    Management
    3. First Steps
    

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33. 3. First Steps
    

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34. 4. People Problems
    

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35. 4. People Problems
    What should to ask?
    
    Sometimes they are
    uncomfortable and
    awkward
    
    They don’t seem very
    effective
    1-2-1 meetings
    

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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
    

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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
    

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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
    

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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
    

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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
    

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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
    

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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
    

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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
    

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44. 4. People Problems
    From The One Minute Manager
    
    "Goals Begin Behaviours

    Consequences Maintain
    Behaviours”
    

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45. 4. People Problems
    

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46. 5. Technical Leadership
    

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47. Loss of your technical chops
    5. Technical Leadership
    

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48. Loss of your technical chops
    5. Technical Leadership
    

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

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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
    

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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
    

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

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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
    

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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
    

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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
    

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56. 5. Technical Leadership
    

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57. 6. Communication
    

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

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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
    

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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”
    

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61. 6. Communication
    Making people care
    about non-tech issues
    
    Policy changes
    
    Important but
    uninteresting news
    Talking non-tech to techies
    

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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”
    

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

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64. You are the “glue”
    
    Be consistent
    
    Adapt your message
    as needed
    …to non-techies
    …to techies
    Talking
    6. Communication
    

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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
    

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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?!
    

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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
    

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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
    

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69. 6. Communication
    

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70. 7. You as a Leader
    

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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
    

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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
    

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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
    

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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
    

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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
    

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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
    

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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
    

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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
    

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79. 7. You as a Leader
    

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80. 8. Finding Peace
    

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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
    

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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
    

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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
    

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84. Have fun!
    

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85. 8. Finding Peace
    

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86. The Future…
    

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87. The Future
    Talk about your experience
    
    Help create a Leadership Pathway
    
    Mentor others
    
    Create a Manager README
    

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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
    

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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
    

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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
    

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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
    
    • luke@stringer.dev
    

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

    View Slide