How to be a CTO: Lessons from LeadingEng 2022

Recently I was lucky enough to attend LeadingEng London, here’s what I learned.

LeadingEng is a new conference aimed at VP/Director/CTO level engineering leaders by the organisers of LeadDev.

With a more intimate setting & audience, we were seated at tables with people from organisations of a similar size/area, encouraged to talk throughout the day between a single-track of interactive workshops and talks.

The material throughout was genuinely brilliant, even if some was beyond what I’m doing today, and I walked away having learned a lot. As a reference and to help digest the material of the day, I’ve written up just some of my takeaways, grouping them by the major themes: Culture & Relationships, Strategy & Prioritisation and Personal Development.

Culture & Relationships

Healthy culture and relationships are the foundation of everything we do, and without them, we won’t execute effectively. As leaders how do we cultivate culture & relationships that thrive?

Dolapo Falola spoke about how culture isn’t just what we say, it’s how we act and how people behave. Healthy, inclusive culture promotes growth and improves business outcomes, toxic culture slows results and makes people leave:

  • Our assumptions and our written values might not represent our real culture. Surveys and representative groups can give us a real, objective view.
  • Resolving the tension between written and real/”felt” culture will help, as ultimately our role as leaders is to model & reward the behaviour we want to see.
  • Between hiring people who add to our culture, and changing the structure & membership of our teams, we can positively influence culture.

Lara Hogan ran a workshop on organisational influence, highlighting the importance of positivity, framing & empathy. Regardless of where we sit in our organisation, we make change happen through influence. Can we approach it more mindfully?

  • Builders not haters: We need a mindset shift! Being problem-oriented feels like we’re returning from a negative state to a baseline; which demoralises & encourages resistance. Influence is about ideas, so we should reframe problems as opportunities, solutions & winnable experiments.

    • e.g. Problem: Our disaster-recovery plan is flawed because it’s expensive & stresses staff out.
    • e.g. Opportunity: By rethinking these details in our disaster-recovery plan, we’ll improve staff-wellbeing & reduce costs.
  • Know what matters: We will still encounter resistance, so we need to understand who we’re trying to influence and what’s important to them. Broadly we encounter allies, blockers and/or decision-makers; All of whom have their own needs which we must practice empathy to discover and address: We can consider these in advance of a proposal.

  • Experiment & Iterate: Okay, we’ve successfully pitched a positively-framed experiment, backed by data. But that doesn’t mean that we’re there yet! We should gather feedback early and often, and be prepared to change course with our change if any flaws arise.

Maria Gutierrez showed the importance of healthy leadership teams and gave practical advice about improving the health of your team at any level. When things aren’t working you see misaligned priorities, duplication of work and frustrated teams. For Maria, the crux was a 48-hour incident many years and jobs ago. But the outcome was positive!

  • In her current role, her team made a concerted effort to get to know each other, their varied working styles, etc. aligning on mission, vision & priorities. Patrick Lencioni, in The Advantage, talks about our first team being that of our peers: Horizontal, not vertical. i.e. For a Director, this is their cross-functional leadership team of other directors (e.g. Product, Design, Delivery).
  • Lencioni presents a four-step discipline for effective teams: Build a cohesive leadership team, create clarity, over-communicate clarity & reinforce clarity. The Five Dysfunctions of a Team, also by Lencioni, presents a model for measuring this effectiveness: Trust, Conflict, Commitment, Accountability & Results.
  • By meeting regularly (from 1:1s through to off-sites), assessing themselves against this model, and presenting a unified front the whole leadership team is credible and successful, making us credible and successful too!

Kat Kuhl pointed out that the move from managing individuals to managing managers (or, managers of managers) at first is a challenging step: We must resist helicopter-managing/micro-managing as it disempowers and demotivates our manager-reports. Instead, we should focus on the actions that drive the most impact across all our teams:

  • Managing managers means giving them a destination (vision) & letting them lead their teams towards it. Engaging the help of our manager-reports we build vision by talking to everybody to assess our situation and challenges. Communicate 2-4 major pain points and measures to remedy them, delegating full ownership to our manager-reports in delivering on these.
  • Along the way, support your manager-reports by helping them develop their skills through coaching and asking questions more often than we offer solutions/tactics. Share as much of your context (as we tend to have more visibility into the company) as is useful, e.g. constraints. Vitally, we also ensure that they have clarity on our expectations and outcomes.
  • The real magic happens when we encourage our manager-reports to collaborate with and teach each other: What skills can they share? How can you best encourage that? You’re also building future organisational leaders, so help them get into the habit of collaborating sooner than later.

Strategy & Prioritisation

As Kat’s talk points out, people increasingly look to us for long-term, big-picture direction & prioritisation. How do we do that?

Camille Fournier spoke about creating strategic alignment by being consistent & getting the fundamentals right. By involving others (especially individual contributors) in all of these tools, we build trust and establish a future bench of leaders!

  • Strategic Communication: Getting this right creates understanding, drives agreement and builds trust. A good step is communicating outwards with everyone regularly about recent wins and challenges. When structuring updates, tell stories with the SAR framework (Situation, Action, Result) and pass them through the “So what?” test so it’s relevant to your audience.
  • Strategic Execution: Regularly meet with teams to report on their progress & results and avoid unnecessary drift. These meetings create accountability within teams, and a chance to celebrate success & develop leadership outside of your immediate circle, so avoid sending negative signals by rescheduling.
  • Strategic Planning: Yearly down to quarterly, leadership regroup to answer the “whys” of strategy and to ensure a shared understanding of our position & where we’re going. Create narrative-driven objectives & measures (eg OKRs, KPIs), aiming for 3-5 objectives including 3-5 measures each. Seek good inputs (Our current state, a retrospective of the last cycle, from a variety of perspectives) to create good outputs (objectives/measures, costs & shared understanding!)

Anna Shipman ran through how to create, revise & review a strategy by recounting the stories of two similar major website launches. The core premise of Good Strategy/Bad Strategy states that Strategy is Diagnosis, Vision & a Plan - how did these two teams apply that?

  • Diagnosis: You need to be clear about where you are starting. originally was a monolith which was difficult to support and work on, so a new team iterated on a new microservice-based replacement called Next which launched in 2016. Years later: the technical direction had lost clarity, teams weren’t clear on purpose or ownership and there were areas of the codebase which grew intimidating. The Diagnosis? These were’s difficult teenage years.
  • Vision: This is where we want to go. Launching something new is a very clear vision, as, for example, the launch date drives prioritisation. A new vision may be the same, or, may include new details (e.g. Citymapper expanding beyond London moved from “Save Londoners from London” to “Make cities simpler”). The Vision for’s difficult teenage years? Without another costly rebuild, improve what’s already there: No next Next.
  • Plan: A coherent series of actions that get us to the new vision. We should prioritise the highest leverage actions. In this example, the teams began communicating decisions with technical design documents, established teams with fixed product-aligned ownership & strategically rebuilt the most intimidating area of the codebase (a shared front-end library) with something modular, well-documented & well-tested. The outcome? Clearer clarity, purpose & ownership.

Smruti Patel posed the difficult question: With fixed resources: Maker vs. seller, the myth of fungible engineers & rapid-scaling challenges; prioritisation is hard. So, how do we give teams and individuals agency, autonomy and accountability, whilst ensuring they’re working on the right thing for our organisation and users?

  • Instead of top-down or bottom-up, with the SPADE decision framework, we do both! Starting top-down with leadership providing Setting & People as context, or the “why” and “who”. Setting includes What, Where & Why.

    • To provide “What?” we evaluate the current situation, using RICE to prioritise.
    • To provide “When?” we use SWOT.
    • To provide “Who?” we ask “Who are the users, stakeholders & teams this impacts?”.
  • Next, with this context teams work bottom-up to form Alternatives, proposing the “What”. Teams first do discovery, reframing the challenge based on their constraints and using techniques like 5-whys and MECE to understand the space. Next, they evaluate their options & trade-offs, forming ideas (w/ trade-offs/etc) which are our Alternatives.

  • Finally, together we review, to Decide & Explain. We review the options, decide on what trade-offs we accept, and from there make our decision. To drive clarity, focus & progress we communicate it clearly and widely!

Personal Development

As we grow more senior our continued development becomes more challenging: We’re further away from technology, our managers are less involved in our day-to-day and may be non-technical. (Or, might be us.) How do we continue to grow?

Kevin Goldsmith suggested that by borrowing the ideas which make the most sense, we develop a deliberate personal development practice. To start we can:

  • Regularly block out distraction-free time for personal development, at least 1 full day every quarter. Inspired by Bill Gates, Kevin does a personal-strategy offsite bolstered by resources he’s picked up over the years.
  • Form a sort of “personal advisory board” composed of trusted peers with whom we may be vulnerable. Consider looking at peer groups, especially the local ones. Maybe not the general-purpose or paid networking communities.
  • Intentionally curate our career moves: Instead of pursuing the most interesting thing, or staying somewhere too long, we should seek to move into roles that align with our objectives in which we grow & which set us up for the next thing.

Meri Williams walked us through mapping our skill levels and desired skill levels, across separate vectors: Hands-on tech, Tech-strategy, Delivery, Organisational-leadership, Commercial & Domain-expertise.

  • Plotted hexagonally, the resulting diagrams look like snowflakes. Conveniently no two people or job roles are the same, and nobody is a true generalist: Difference is good - don’t try to make everybody equally generalist, this isn’t Pokémon!
  • Are there any gaps which are essential to doing your job well? Are there any others which surprise you? These are where you can focus your time, either developing yourself or collaborating more.
  • With your newfound power to quickly visualise the skills of people & roles, you can now do the same exercise, for example, with your reports or to evaluate/clarify different job roles across your organisation.

Allan Leinwand talked about staying credible as a technical leader and how to sharpen our technical skills when we are far removed from the technology we oversee:

  • Make the time to read & follow technical literature: Books, code, etc.
  • Keep coding, but not in production: Whilst being careful about power dynamics - Embark on side-projects, look at technical contributions & participate in hackathons. While you could do this outside of work, doing it at work grants offers an additional advantage: By using the exact same tech stack and tools as your software engineers, you better understand your organisational context.
  • “Don’t [try to be] the smartest person in the room; Hire smart people” — Hire and trust great people, ensuring that they’re empowered to work out the details: You will learn from them. And, if you can, find both internal and external advisors to support you with decisions.

Tramale Turner points out that one of our best sources of continued development & of new opportunities is through our professional network, so some tips on how to make the most of it:

  • While networking skills are one thing, quite often we set out without a clear purpose: You’d like your connections to be meaningful if they can be. Try setting out with an end-state in mind, and working backwards, looking for someone who can help you get there.
  • Before expecting something from someone you’ve just met - if possible try to benefit them first. It sets a great early impression & will make your connection more meaningful.
  • If you’re not meeting the right people, you may be looking in the wrong place: If you can’t change the people around you, change the people around you.

My Takeaways

While things get harder as we grow more senior, our opportunities to make a positive impact increase dramatically - but only if we create the right conditions for people. That means:

  • Modelling the culture we want to see, empowering our people & making changes to resolve the tension between written & practised culture.
  • Including modelling a positive approach to our work: Opportunities, experiments & outcomes bring people together across functions; Problems divide us.
  • Being highly aligned as a leadership team and generously sharing our (sometimes broader) context, as much is helpful.

Forming a bigger picture in the form of strategy is the next piece of the puzzle, and it’s an ongoing process:

  • Engaging and consulting our people helps us form a coherent picture & diagnosis. (This too is context, by the way!)
  • That lets us work with our teams, including our first team of cross-functional peers, to craft a vision: Supporting our teams both with growth & to better drive business outcomes.
  • We lead by communicating our progress via stories and course-correcting as we go, intentionally creating room for everybody to shine.

Lastly, we are responsible for our development and must be intentional about finding opportunities to grow and learn, including (as events like LeadingEng do) by sharing our experiences with our peers:

  • It’s important to make regular distraction-free time to personally reflect and review our progress.
  • By finding and labelling them, we can be methodical about addressing our controlling weaknesses.
  • For advice and support at any level, we can lean on our peers (and find new ones), both internal and external.

Special thanks to Anna Shipman for the invite and to Alice Bartlett for proofing this post!

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© Alex Wilson 2024