The CTO Questions: 10 questions that help you gauge the current state of your tech operations

Ever heard this conversation play out?

Manager 1: “We should adopt scaling framework Y.”
Manager 2: “But scaling framework Y doesn’t have a recipe for baking cookies. So we need to do X.”
Manager 3: “Whut? You’re both wrong. We have Agile teams. We’re good!”

In fact, each statement above can be wrong. So the question is, how would you know?

As a coach, it never ceases to surprise me how often management teams lack a shared understanding of their current state of tech operations. If members of a leadership team do not share a common understanding of the current state, it’s easy to fall into the traps of process religion (“my tool is better than yours”), or status quo bias (“why change? From my perspective, everything seems just fine”), or just sheer complacency, “I don’t need to improve, they do”. One piece of solid advice, the last thing you want to do as the leader is to be oblivious to the current state of affairs.

My preferred method of learning the current state is to always start with an “outside-in” view. Assume your operations are a black box and look at the output first, then delve into how the cogs operate inside. Answering these 10 questions helps you do that:

Value oriented

  • Do we create innovations that give us unique marked advantages? How many per year?
  • What is our lead time from idea to delivery? From idea to customer value? Sample data from 2-3 projects.
  • What is our ROI profile? Do we invest first, work long and hard for months and years and hope to reap the business benefits later? Or do we deliver value continuously? Typically Agile?
  • Do we have the development capacity to take on all the good business opportunities that present themselves? What opportunities have we let slip by?

Quality oriented

  • How often can we do releases with quality that include a cross-section of our tech stack?
  • How often do we have slippage on big projects? How much slippage?
  • What proportion of support to business features is clogging up our development pipeline?

Engagement and operations indicators

  • How many projects are there running in parallel in our organization right now? Do we allow skilled people to work with focus?
  • Do we regularly work overtime to meet deadlines?
  • Do we have high personnel turnover for people in coordinating positions?

Of course, you don’t need to answer all the questions above. But getting the facts on the table is the key to building a shared understanding of where you are at, so the management team can start to pull in the same direction when improving.

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