Top CTO Concerns for 2019

Each year we poll our technology leaders to see what they think are the most pressing issues for the year to come. While recruiting is still the top concern, this year data privacy and regulations topped security. These are the area our members will be focusing on in 2019:

  • Recruiting: attracting talent, building pipelines, hire vs. train, junior vs. senior, non-traditional candidates
  • Cultural integration after an acquisition
  • Retention
  • Data privacy: real and perceived privacy concerns; public perception and regulation
  • Security: information security, IoT, supply chain, social layer
  • Regulations on privacy, transactions, and subscriptions
  • Keeping up with the pace and breadth of change
  • Burnout from a volatile market
  • Velocity
Top CTO Concerns for 2019


Every year we poll our technology leaders to see what they will be focused on. As in years past recruiting and security topped the list. This is we found most pressing for 2018:

  • Recruiting: building education pipelines; attracting talent to Seattle; achieving diversity
  • Securing our data; security as culture
  • EU/UK expansion: privacy and other concerns
  • Big Data: growing data, and maintaining all of it
  • Security and Privacy Regulations: GDPR, but also making public policy that works with the rapid rate of change in security and privacy protection
  • Containers/Microservices/Serverless
  • Regulatory interactions with an unpredictable (unstable) U.S. government
  • Connecting SaaS tools (G Suite, Slack, Concur, Gusto, Smartsheets, Wiki, Jira, …)
  • eCommerce: Amazon has monopolized the marketplace and competes with it’s best marketplace performers

Critical Developer Skills for the Next Five Years

The Seattle CTO Club members chimed in on what they thought were the most important technologies and skills for development teams for the next five years. This is not meant to be a prediction of the future but an insight into what is important now that will remain important in the near term.

  • Containers, Docker, Kubernetes/Mesos
  • Security; threat modeling
  • Deep learning, AI, Machine learning
  • International user experience
  • Remote communication and collaboration
  • Natural user interfaces (voice, gesture, eye track, language)
  • Functional programming (Clojure, Scala, etc.)
  • VR and augemented Reality
Critical Developer Skills for the Next Five Years

Top CTO Concerns for 2017

We ran our annual poll of CTOs and came up with the following list of concerns for 2017.

  • Hiring in a market where tech salaries continue to rise
  • Economic and geopolitical uncertainty
  • Other company’s assaults on personal privacy
  • Large scale bot attacks
  • Data breaches (who’s the next Yahoo?)
  • Infrastructure cyber attacks

The fact the the list is really small this year is an indicator that these three topics are so vastly more important than anything else at this time.

Top CTO Concerns for 2017

Top CTO Concerns for 2016

We polled the members of the Seattle CTO Club to see what they were most concerned about and came up with a list. Topping the list seems to be the question “Are we in a bubble?” and the corollary “Is this the year it is going to pop?”

  • The economy, is this a bubble? Is it tech, oil, credit? How does that affect venture funding, private company valuation, hiring and retention?
  • Employee hiring and retention: for multi-locations team, career paths
  • Cyber-security: compromised systems, data leaks, exposure through partners, ransomware, designing for security
  • Organizational “as a service” transition, modern organizational design given a baseline of CI/CD, microservices, and heavy automation
  • Interaction between engineering and product
  • Will Google make real inroads on AWS business in cloud computing? Is AWS the newest 800-lb gorilla?
  • Business models around open source
  • Most effective way to both operate and contribute to a large open source project
  • Container specifications war: rkt vs docker; OCI
  • Where & how to apply machine learning
  • Physical space design and team productivity
  • Enterprise software alternatives
  • Working with legacy IT organizational structures: cloud versus managed services; outside consulting versus internal innovation
  • Competing with Amazon on delivery
  • Beacons, location awareness, hype
  • Apple Pay, alternate payment systems, slow EMV adoption
  • Building one’s stack and managing technical diversity; is it futile to try to keep the portfolio small?
  • What are the most common reasons startups fail?
  • Is the Agile fad over? If so, what’s next?


Top CTO Concerns for 2016

Top Things CTO’s are Focused on in 2015

We polled our membership at our January meeting and discussed further on the list. Here are the things that Seattle-area CTO’s said they are going to be looking at in 2015:

  • Cyber security (DDoS protection; in-store POS security)
  • Containers and deployment
  • Minimal OS / Core OS
  • Microservices (what does that really mean and how do they work in practice?)
  • Networking (the data kind)
  • Office layout
  • Data storage and analytics (still not a solved problem; how do you really count quickly at scale?)
  • Women in tech
  • Interviewing for passion
  • Fingerprint checkout for mobile
  • Data retention policies for big data
  • Interaction between engineering and product
  • Streaming compute for big data
Top Things CTO’s are Focused on in 2015

Burnout and deadlines

Yesterday, Ruben Ortega came and led an interesting discussion on burnout, deadlines, death marches, physiology, culture and more. We had a great talk, including our own experiences with burnout and lots of deep information about it. Here are some notes:

  • Nearly all of us had some personal experience with burnout; in some cases with physical and health-related effects.
  • Despite all the literature (all the way back to Mythical Man Month or even Deming) and popularity of agile practices, burnout still happens.
  • Slogging through a hellish time and coming out successful in the end makes us feel good and makes for good stories; in fact that’s the root of most of our myths and entertainment.
  • People who regularly overwork themselves develop physical impulses to continue to produce neuropeptides that encourage them to continue to overwork. This can take years of dedicated work to change and can be akin to countering addiction.
  • Startups often include periods of over work at the beginning
    • In fact “startup” implies this in a way that “small business” doesn’t
    • This creates an early culture of overwork and, if you want to change that, may mean major cultural shift early in the company (i.e. replacing much of the staff)
    • While tech startups are often started by engineers who want to work with the best engineers they know (and therefore hire them); if a startup will require a lot of work up front (because time is critical) then this argues strongly for contractors
  • In a business whether you choose to overwork people or have “work-life balance” is a business decision
    • If you are looking for an early exit and value profit over people then you might choose to overwork people to increase short-term gain
    • If you are interested in a long-term investment, then investing in people (and not burning them out) is clearly better
    • However, this was a rhetorical discussion as we all prefered long-term investments in people.


Burnout and deadlines

June Meeting Recap

Our discussion revolved around “How to manage technical people when you are less technical or no longer as technically involved” as well as how to get less technically involved to do more mangement. It was an intimate discussion, but here are some sailient points:

  • Struggles included:
    • Learning when to keep your hands in and when to step out and trust your staff
    • Keeping the trust your technical folks have in your decisions and knowing which horse to back
    • Showing that your work is also valuable when you aren’t able to connect over the technical work
    • Working with devs who get sidetracked on projects
  • Share what you do with your team (share status reports). This way your direct reports understand the value (and amount) of work you do. Show how the work you do (administrative and management work) allows them to do what they do best (technical work).
  • Trust your technical leads to make the right choices.
  • Consider workflow management like kanban for tracking ‘technical debt’ or ‘ideals’ — this allows the team to manage their own vision of the product’s direction. The actual work to be done should managed through a separate set of stories in scrum/lean or whatever you use across the company or group.
  • Set stricter tasks for reports who are off-target; suggest “when you’ve completed this goal [that’s needed immediately], then other work can be done.”
  • Look at alignment — are your reports doing other work because that’s what they really want to do? Consider new job responsibilities/position.
  • Ask reports, “What decisions have you made? What are the consequences of those?” Discuss their personal motivations.
  • A key trait is the ability to influence others and to build consensus. One-on-one coffee conversations can be great for this.
June Meeting Recap

March Meeting Recap

At our monthly meeting Sarah Novotny (of Blue Gecko.) talked briefly about the Velocity Summit – a meeting of IT management leaders to discuss the topics to be presented at O’Reilly’s Velocity Conference in June. This sparked an interesting conversation about the future directions of IT within and for technical organizations. In particular we had a fairly long discussion on the state of and future of cloud computing – hype vs. reality, etc.

Following that we spent an hour reviewing some of the open organizational questions. The feedback from members present aligned strongly with the thoughts that John Helm and I had already put to paper, which was validating. There is a need for this organization, at least for a good number of technology leaders in Seattle area. There is excitement about keeping it active and flourishing. Mostly we all agreed that it needs to be an active, engaged forum that builds on peer support and collaboration. I’ll put details on the list for discussion.

March Meeting Recap