Insights and Opinions

Turbo-charging your CTO

How do we raise the level of technical education, discourse, and requirements in the Internet companies that we build?

Start at the top – with the CEO and CTO.  To improve communication between these two leaders, CEOs should address the following issues:

  • Clarify your expectations of your CTO.
  • Learn how you can best support your CTO.
  • Implement measures to improve the CTO's teams' goals.
  • Have a plan in place to handle your CTO's departure and replacement.

What if the CTO is hit by a truck and becomes incapacitated?

This is one of a company's Worst Case Scenarios. It's also the nicest way to bring up the subject when speaking with a potentially cantankerous (read: underperforming) CTO.

At a minimum, to survive this life-threatening-or-not event, CEOs must have the following:

  • A secured master list of accounts with passwords for every service that touches the technical platform
  • Source code and data ownership (access and download capabilities)
  • Economic ownership of source code, data, and all system and vendor accounts
  • A schedule of recurring costs
  • Documentation - as much as they can get!

This is simply CTO 101. Other than the documentation, if a CEO is missing any of the above items, they must resolve the situation immediately! I often say, “You are a heartbeat away from being locked out of your own business.”

CEOs and CTOs can improve their working relationship.

In practically every situation, the CEO and CTO come from very different backgrounds, specifically their academic upbringing, and usually have very different personality traits. Good CEOs and CTOs lead by example, so it is a good idea for both parties to spend time focusing on understanding their gaps in knowledge and understanding of the other. The CEO needs to make sure that the CTO can ‘make the business case' for technical projects, for example, and vice versa, the CEO must be able to ask questions of the CTO and technical team and look for consistency in explanations.

Trust is a core issue, and building up trust takes a lot of work from both sides. Sometimes, a CEO (or CTO) may need to call out ‘dream time' when talking about future features and possibilities. I know CEOs who answered “Yes!” to the question, “When your CTO says you have a good idea, do you think it will then be built?” Alternatively, there are CTOs who will go ahead and build everything the CEO says. Neither is a good situation, as they are based on personal assumptions.

One recurring ‘Management 101' failure of startup CEOs and CTOs is setting metrics and measuring themselves. It is never okay for a CTO not to make estimates. It is not okay for a CTO to have lots of missed deliverables, while refusing to be measured. It is not okay for a CEO to accept either of the aforementioned statements or situations! Cross-functional education is a key component of the CEO/CTO relationship. If they aren't measuring themselves, they must start doing it together until they get really good at it.  A first step is to start measuring downtime, which can be lost revenue, customer acquisition cost, organizational cost, and so on. Metrics are also one of the key ways for them to ‘keep each other honest' and help build trust.

Tools are not used often enough.

This one continues to personally bum me out, as I see it all the time. Startups need three required systems in order to manage themselves effectively:

  • Product Management for managing product features, releases, and major areas of the business
    • Really good for business and creative types and the executive team
    • Examples: Trello and Pivotal Tracker
  • Project Management for managing development (lots of detail and lots of tasks)
    • Really good for developers and analytical types. Not so good for business and creative types
    • Examples: Basecamp, Unfuddle, FogBugz, and Redmine
  • Knowledge Management (Intranet/Wiki) for managing a company's accumulated knowledge (specifications, client processes, employee onboarding, and countless other things)

    • Really good for everybody
    • Examples: Wiki, Google Sites, Intranet software

These are all easy to use tools, provided the team uses them every day. Typically, they should use a separate tool for each of these jobs. It is possible to have one tool do two things (like Product and Project Management or Project and Knowledge Management) but it requires having people who really know how to use the tools per the company's process.

The ongoing education of the CTO.

This falls into two areas: Training and mentoring.

  • Training consists of leveling up the technical leader's technical and business skills (sometimes called the skill and managerial tracks). Schools, targeted meetups, and hackathons are good venues for improving a CTO's technical skills. To build up a CTO's managerial and business skills, CEOs can consider having the CTO lead hackathons, speak at technology events, or lead a guild in a video game.
  • Mentoring (as in getting the CTO a Mentor) is probably one of the easiest ways a CEO can help a CTO grow outside his or her own boundaries.  This is a very successful tactic, and not employed often enough.

Begin implementing now

These strategies and tactics can make a quick and dramatic difference in the quality of a technology team's performance, the smoothness of business operations, and the long-term excellence of the CTO.  Start now.

John Shiple is a technology consultant to CEOs. His work brings forth new products, optimizes business processes, lowers operating costs, and enables operational scalability.  He architects award-winning technologies that scale businesses while concurrently building, training, and mentoring development teams.  You can reach him at