People & Culture

Stride Tech Talk: Jon Williams on Guidance and Strategic Roadmaps

This month, CEO Debbie Madden talks with Jon Williams, Fractional CTO about CTO guidance and strategic roadmaps.

As an advisor to NYC CTOs and tech teams, you see under the hood inside many teams. What are the top 2 things that CTOs seek outside guidance for?

First, you don't have to have the CTO title to be functioning like a CTO. I am currently a consultant, yet call myself a CTO. To answer the question, the top two things are:

  • How to help keep their technology teams as productive as possible.
  • Find out what other companies & teams are doing with technology.


Why do you think these are the top 2 most requested things?

Team productivity

This is really how a CTO is measured by her company. I don't call it managing, it todays world we are beyond that. Tech team members are also seeking guidance on how to be more productive, both individually and as a team. This is in the DNA of being a developer. I think communication and process tools are always a big focus, and I am seeing many CTOs no longer mandate technology but let individual teams choose.

What others are doing

This is key to staying abreast of technology trends. For example, should we be focusing on NoSQL? What about MVC Javascript? Mobile? This can all be learned by talking to and meeting with other CTOs and technology teams to gauge where others are in the process, and when is the right time include this on the CTO's technology roadmap.


What advice to you have for folks looking to improve tech/biz team alignment?

My #1 recommendation is: Include business teams in the Agile process. Have the business attend stand-ups, sprint reviews, and maybe even sprint retrospectives. I had a great experience with a business team where we ran an all-day Lean Coffee meeting (, prior to launch. We got feedback that this was one of the most productive all-day meetings the business had ever attended, and the business team also got some insight into how we run Agile projects.

My #2 recommendation is shoulder surfing. I've seen the most amazing ideas come out of tech team members watching end users using the tools they developed.


You talk a lot about strategic roadmaps for tech teams? Are they are useful tool for all tech teams, no matter how big or small?

Yes, whether big or small. Strategic Roadmaps are a critical communication tool for the CTO in her communication with

  1. Tech teams
  2. Business executives

By sharing your roadmap with the tech team, it allows them to understand that a larger vision is at hand, and they can therefore focus on the tasks at end (i.e. next sprints), knowing you will include them on future roadmap discussions.


By sharing roadmap with executives, they'll know you have a long-term vision in hand while the teams focus on short-term deliverables. This protects the tech teams from having to be in the middle of this conversation, I believe it's the CTOs role. I've seen many tech teams overly-focused on strategy/roadmaps, and not deliver in the short term.


How do you suggest a team or tech leader get started with a strategic roadmap?

This is a difficult question, and I've seen tech leaders approach it different ways. While a product backlog is a useful tool / list for starting a roadmap, I don't see it the end product.


My approach is

  1. Get the list of business objectives from executives by quarter
  2. Draw out a 2 to 3 year delivery roadmap by quarter, as a discussion tool with business executives to gauge priorities.

The CTO can then keep this strategic roadmap as a discussion tool for planning, rather than as a firm schedule for epic / quarterly planning. One comment I always make to executives is that 'distant objects appear closer than the are', meaning that the further it is out on the roadmap, the fuzzy it is.


For those that already have a strategic roadmap, what are 1 or 2 tweaks you suggest to improve their usefulness?

  1. While this takes a lot of work, I am an advocate of 'versioning' the Roadmap every quarter, to show what has changed / moved / delayed, or been pushed earlier.
  2. Even if you don't know how you will execute a goal or project, add it to the Roadmap. This gives you a discussion point with all teams
  3. Share you strategic roadmap privately with other CTOs for input / advice



About Jon Williams

Jon works as a “Fractional CTO”, assisting clients with technology change and growth. With more than 25 years experience developing, deploying and managing technology solutions for companies, Jon has been involved in many of the technology innovations of the digital era. As a strategist and CTO, Jon has enabled companies such as Kaplan, NBC/Universal, Experian CheetahMail, Time Warner, Grey Healthcare, and others to translate their business needs into technology applications and successful product launches. Jon specializes in architecture, turnarounds, and building effective teams and processes.


Jon co-founded the New York CTO Club, non-profit professional organization for 100+ technology leaders, now in its 15th year, who meet monthly to share insights and support each other.