On April 8th, I attended LeadingEng 2022 New York conference. This visit was my sixth time attending an event organized by LeadDev. My fifth one came earlier the same week, and I’ve written up my notes for StaffPlus 2022 New York too.

This event is the first LeadDev organized affair aimed strictly at Director/VP/CTO level technology leaders. The LeadDev series of events are aimed at any kind of engineering leader. Below I share my notes from the talks. I don’t necessarily agree with everything, but I found all of it interesting. I hope it can give a sense of what LeadingEng is all about. My notes are listed below in chronological order.

Meri Williams, Career vectors - CTO flavors: Mixing & matching skillsets

• Meri’s journey: code, systems, architecture, processes, people, teams, systems of systems
• The jobs of technical leaders, and the skills of those leaders, will be good across different vectors:
  • hands-on, in-depth tech
  • tech strategy
  • delivery (getting stuff done)
  • organizational leadership & management
  • commercial understanding
  • domain depth
• Some, but not all, CTO archetypes:
  • Hands-on, deep technical expert - usually where deep technology IS the product
  • Outward-facing chief technologist - lots of investor relations
  • Architect type roles
  • Combo manager/leader roles - developing and enabling teams with a significant strategic component
  • Organizational leader - some places split this off in VP Engineering peer or report
• The proportion of “general executive” skill set tends to grow with company size & complexity
• Don’t try to make everyone equally generalist - if you try, everyone will become just equally mediocre

Yvette Pasqua, Engineering leadership with a little help from my friends

• Sustainable networking nurtures community, motivation, growth
• Growing your network can feel scary, but we should strive for sustainable and fulfilling
• Tactics to use:
  • Cold email, direct message, LinkedIn
  • Join groups
  • Connect 1:1 at events
• Framework:
  • Step1: what gives you energy? (love to do, doesn’t seem like work, unique ability)
  • Step2: what are your networking options? (coffees, day-time get-togethers, tech meetups)
  • Step3: what problems to solve? (should combine with what gives you energy)

Charity Majors, Great engineers are made by great engineering teams

• False: hire great engineers, and you’ll create a great team
• Accelerate provides a way to measure high performing teams
• When an engineer from a high performing team joins a medium or low performing team, their productivity tends to match the team they join
• A team of all senior engineers is a WEAK team
• A great team is made up of engineers who are ALL curious and motivated and challenged by their work

Krishna Kannan, Aligning teams through allocations

• What happens when you do the wrong thing well?
• When struggling with customer impact, you should look at what you’re doing:
  • Create a balanced plan
  • Work backward to understand the allocation
  • Track alignment frequently
• To make an impact: establish org-wide goals, build team-appropriate plans, reconcile those plans, adjust and align

Nivia Henry, Living in the future: How leading leaders is a lot like time travel

• We have to operate at a different plane of time than our directs: weekly, monthly, quarterly, annually
• Managers of managers are typically at a quarterly/annual timeline
• Managing first-line leaders and senior leaders is different: for example, you have to provide context for business strategy multiple quarters ahead
• The components of a self-optimizing organization:
  • Effective: clear vision and mission, strong skillsets, feedback loops
  • Efficient: role clarity, alignment, speed
  • Enduring: health checks, fast recovery
• Seamless navigation: you need to have a view of how the organization is performing and what is happening in the organization
• Navigational tools: skills map for your team, org dashboard with key metrics

Lara Hogan, Intentional influence

• When we’re trying to convince someone else, it’s effortless if they speak the same language and care about the issue: that’s rarely the case
• Long road: convince them to see your point of view
• Short road: see it from their point of view
• Influence is needed, no matter what title and formal authority you have
• Humans accidentally influence each other constantly: that’s why this session is called intentional influence
• Identify stakeholders, understand whether they are a blocker, an ally, or a decision-maker
• Understand the needs of your stakeholders: belonging, improvement, choice, fairness, predictability, status
• Open questions can help understand the needs of your stakeholders
• Influence is about ideas and finding the right solutions (instead of describing problems): “Our current vacation is outdated” versus “A new vacation policy would help us attract more talent”
• A good tactic is to suggest an experiment, measuring the metrics that your stakeholders would care about

Jason Wong, The tools of culture change

• Peter Drucker, 2006: “Culture eats strategy for breakfast”
• The book “The Changing Culture of a Factory” by Elliott Jaques was written in the 1950s
• Culture is defined by the behaviors we reward and punish
• How We Recognize Engineers by Lara Hogan
• Promotions are the key way to define culture in your organization
• How to give effective feedback
• Deterrence theory: swiftness (how fast you’ll get caught), certainty (how likely), severity
  • Research has shown that swiftness and certainty are way more important than severity

Swati Vauthrin, An Eng Leaders Intro on Understanding “the Business”

• EBIDTA: Earnings Before Interest, Taxes, Depreciation, and Amortization
• Revenue is the money generated from normal business operations; it’s essentially how your company makes money
• Cost Center: a department or function within an organization that does not directly add to profit
• P&L (profits and loss): shows a company’s revenue minus expenses for running the business
• Budget: an estimation of revenue and expenses over a specified future period
• Imposter Syndrome is sometimes worse when learning about “the Business”

Camille Fournier, Building aligned strategies

• You’re stuck in the middle between your team and people that want stuff from you
• Strategic communication: create understanding, drive agreement, build trust
  • Storytelling with SAR (Situation, Action, Result)
• Strategic execution: keep your org aligned and focused, identify problems early, develop leadership
  • Leadership meetings: heavily participatory, don’t over-structure, not just your direct reports
  • Update meetings: scheduled, reporting on results, opportunity to shine
• Strategic planning: time-based (yearly down to quarterly), broad view with top-down elements, provides information to answer the “whys”
  • Good outputs require good inputs
  • Creates shared understanding: agreement on where we are, where we need to go, understanding of risks
  • Narrative objectives, measurable indicators: 3-5 objectives, 3-5 measures per objective
  • Inputs: current state of things (headcount, maintenance overhead, existing projects), variety of perspectives, a retrospective of what happened over the last cycle

Michael Winslow, Getting buy-in for your transformation strategy

• Why a transformation is needed:
  • in response to a crisis
  • customer needs are changing
  • the technical landscape is changing
  • outpacing the competition
  • time-saving / operational efficiency
• Identify a strategy type:
  • compete: gaining an advantage over competitors
  • survive & thrive: gaining an advantage over a changing landscape
  • self disruption: gaining an advantage over our former selves
• Demonstrate due diligence:
  • Have other people attempted this change previously?
  • Have you incorporated learnings from previous attempts?
  • Are there champions you can recruit from these teams?
  • Have you identified the “network” you’ll need to influence?
• Come up with our vision
• Distribution & the financials

Lee Matos Jr, Everyone can contribute: Make it so!

• Have your Support Team contribute code
• Blockers:
  • Support teams don’t have read-access to code
  • Support teams don’t have write-access to docs
• Start with visibility/transparency/access
• Well-defined code review workflow is key (InnerSourcing)
• Product engineers focus on product, support engineers focus on bugs

Chad Carlson, Examples are hard: Prioritizing developer experience

• Platform.sh takes care of your infrastructure — from hosting and technology to global deployment and support - so you’re free to explore new ideas

Laura Thomson, The places you’ll go: how to keep learning in leadership

• You need to “keep current,” but you have no time to focus
• Why: make strategic technical decisions, know what to fund, maintain credibility, get a job, stay motivated
• Challenges: you don’t know where to start or what to learn, you don’t have time between meetings
• Sometimes, it’s easier to learn a brand new thing than remember how to do things you used to know: relearning old skills can feel alien
• Learning new skills and becoming a generalist support systems thinking, and that’s the job of a senior manager
• Specialization is for insects
• How to learn: warm the cache, use your ears, train yourself to learn in sprints
• Tips: listen to people at work and what they are excited about, try learning about an area you know nothing about, embrace your dilettante

Maria Gutierrez, Healthy and effective leadership teams

• Problems: misaligned priorities, duplication of work, a huge waste of effort, blocked from shipping, performance concerns, teams frustration
• The Advantage by Patrick Lencioni and the summary of the organizational health model from the book
• Your first team is the team of your peers: for a CTO, the peer executives are their first team
• The first team of engineering directors could include other R&D leaders (product, design)
• What gets in the way of a strong leadership team: visibility, time, access
• Five Dysfunctions of a Team by Patrick Lencioni
• Thanks for the Feedback by Douglas Stone & Sheila Heen
• Cadence of meetings: daily check-in, weekly tactical, monthly strategic, quarterly off-site review

Phil Calçado, Don’t try this at home. How to practice self-improvement as a senior leader

• The higher in the org chart you are, the less time/patience/experience your own manager will have to coach you
• People hate being jerked around as leadership “learns more”
• First-level managers make sure the team’s delivery machine works to the expectation
• Senior managers do whatever is needed in the current stage
• Figure out what your boss thinks you should be doing
• Think of your role as discrete parts
• Think of management books the same as design pattern books
• Favor internal peers for networking
• Technical skills become relevant again when you land in senior management roles
  • When you’re a first-level manager, you’re surrounded by technical people - that’s not the case when you’re a manager of managers