90 Day Plan for a CTO in a New Job

This is a checklist for a new CTO, head of Product, or leader in a similar role starting in a new job. It is meant to kickstart continuous improvement in your product engineering organization. I encourage you to take a scientific test and learn approach to everything you do. You should customize this template based on your own experiences over time. If you find it helpful, please feel welcome to send me additions and improvements to this list.

Repeat the following seven steps iteratively to make incremental and continuous improvements.

1. Understand your job. Learn the organization and industry you are in.

  1. Make a list of the areas you are responsible for. These are likely to include:
    1. Technology: Software Engineering, Infrastructure Engineering, DevOps, Cyber Security, Systems Operations, Application Support
    2. Product: Product Management, Project Management, User Experience, User Interface Design
    3. Data: Data Science, Data Engineering, Data Visualization
  2. Review what it takes to be an effective Chief Technology & Product Officer.
  3. Create a mind map of culture, technology, and operations parts of your CTO job.
  4. Meet customers, executives, stakeholders, colleagues, and team members.
  5. Connect with a network of your peers outside your organization.
  6. Get feedback.
  7. Collect, compile, and synthesize information into knowledge.
  8. Check: How are we doing in relation to our existing metrics for success?
  9. Identify common themes, patterns, and problems.
  10. Consider retaining the services of an executive coach.

2. Define and revise measurements for success.

  1. List metrics for the success of the company as viewed by shareholders.
  2. Prioritize metrics for the success of the teams you manage and how they relate to the metrics for the success of the whole organization.
  3. Determine: What metrics are no longer a priority?
  4. Determine: What new metrics do we need to add?

3. Articulate your vision and strategy.

  1. Clearly communicate it to customers, executives, stakeholders, colleagues, and team members. On a regular basis.
  2. Meet regularly with your team members, peers, executives, stakeholders, customers, partners, and vendors. Human relationships and face to face communications (when feasible) are essential.
  3. Host regular 1:1 meetings with your direct reports, at least once a week. team members
  4. Host regular all-hands meetings and communications. Monthly all-hands for staff less than ~100 people depending on space. Quarterly all-hands for staff more than ~100 people, depending on space. Encourage your departments to hold regular all-hands meetings of their own.
  5. Host regular social, relationship building events and activities. For example, a monthly celebration event to mention professional and personal milestones that people want to share.
  6. Implement processes to have productive business meetings.

4. Organize people for success.

  1. Reorganize teams and redeploy people.
    1. Ensure that your organizational structure factors in products, stakeholders, and career growth needs of your team members.
    2. Here is an example of a technology team organization for media companies.
  2. Reinvigorate people.
    1. Implement managerial and technical career tracks.
    2. Standardize titles while still retaining flexibility, and fun.
    3. Consider that career pathways are not linear.
  3. Recruit talent.
    1. When feasible, interview people by putting them to work.

5. Build culture.

  1. Align team members towards common good, shared goals.
  2. Ask team members how they are doing. Are they happy in their jobs? Are their jobs exciting, challenging, and rewarding?
  3. Solicit advice, including leadership advice from your colleagues, regardless of their level or experience. You can learn important leadership lessons from people who report to you. This also encourages your colleagues to become leaders.
  4. Remember to thank people when they deserve it.
  5. Implement a performance evaluation and career development system.
  6. Build and maintain a cohesive leadership team. Make it well known that internal rivalries are strongly discouraged and not tolerated.
  7. Encourage good life/work balance, including a sensible vacation policy.
  8. Experiment with ideas to keep the workplace interesting.

6. Revise processes for success & delivery, and suitable for the environment and the times.

  1. Create checklists to help you do your job better (like this one itself). These checklists will also help your colleagues. Encourage others to collaborate on checklists and share them.
    1. Here is a sample one I made about reviewing managed services contracts
    2. and another one for dealing with outages.
  2. Encourage a culture of sharing best practices, like simple personal productivity tips.
  3. Design evaluation scorecards and criteria to justify, prioritize, and classify projects.
  4. Ensure that your project portfolio management system and your people role definitions factor in the need to regularly evaluate and decommission projects and products that don’t make sense to continue.

7. Upgrade technologies.

  1. Pay off technical debt [external link]and continue performance enhancements.
    1. App, site, and service reliability
    2. Automation (QA, deployments, support, etc.)
    3. Performance
    4. Security (e.g. start down the path to HTTPS)
  2. Make each team increasingly autonomous and self-sufficient while enabling collaboration and economies of scale.
    1. For example, by moving to a microservices model, using tools such as Docker, hosted on a cloud service provider (AWS).

Thank you for reading this and for sending me suggestions to make this list even more helpful to others.

This article is mirrored on LinkedIn. It is a part of the ctobook series of articles related to #culture, #technology, and #operations: three critical part of a Chief Technology & Product Officer’s job.

Rajit Gulati, Vice President, Enterprise Products Engineering at BlackBerry

Rajit Gulati shared this recommendation for Rajiv on Apr 15, 2016 via LinkedIn:

I was reporting to Rajiv at COXnet and developed deep admiration for him ever since. He is the type of executive who ensures that the team gets all the credit for successes under his leadership and takes it upon himself to advance careers of each individual in his team. He has this calming influence when everyone is under pressure and is extremely innovative in suggesting product solutions thinking out of the box. I always look forward to opportunities to interact and learn from Rajiv.

As Senior Manager, Software Engineering at COXnet (now Cox Media Group), Rajit Gulati reported to Rajiv.

Mark Thompson, President & Chief Executive Officer, The New York Times Company

Mark Thompson wrote this recommendation for Rajiv on April 13, 2016:

Rajiv is a very strong digital executive with rock solid credentials in both engineering and product, but with great creative flair. At The New York Times, he was a real magnet for talent and built a very strong team. He also showed an exceptional ability to work closely and empathetically with our own journalistic and design creative elite.

Mark Thompson

As President & Chief Executive Officer at The New York Times Company, Mark Thompson indirectly managed Rajiv.

Matthew Bischoff, Mobile Product and Engineering Lead

Matthew Bischoff shared this recommendation for Rajiv on Apr 10, 2016 via LinkedIn:

Rajiv is an incredible leader of technical organizations. His ability at The Times to zoom in and solve small problems one on one with a single engineer without losing focus of the entire team’s goals was unparalleled and the teams he helped build have remained strong long after he stepped away. I can count on one hand the number of people I’d want running my engineering organization and Rajiv is definitely among them.

As Senior iOS Software Engineer at The New York Times, Matthew reported to Rajiv. Matthew subsequently became Product Manager and iOS Engineering Manager at Tumblr before becoming Partner at Lickability, a boutique mobile mobile product development firm.

Leon Shklar, Managing Director at BNY Mellon

Leon Shklar shared this recommendation for Rajiv on Apr 10, 2016 via LinkedIn:

Rajiv played an important role in transforming the technology organization at The New York Times, He succeeded in attracting new talent and made a major contribution to creating a balance between product, editorial, and technology organizations. Rajiv promoted transparency, never set hidden agendas, and was a recognized “force for good” in the organization.

As Vice President of Technology for Ecommerce, Digital Subscriptions, and Marketing at The New York Times, Leon reported to Rajiv.

Hackathon: Impact Journalism in New York

On April 8-9 2016, the Global Editors Network (GEN), The Huffington Post and Change.org will gather the best media innovators in New York for a two-day Editors Lab focused on developing innovative news prototypes.

Theme

Impact Journalism: How can news organizations develop innovative and interactive ways to create impact by connecting audiences with issues they care about?

Jury

Further information at the source: http://www.globaleditorsnetwork.org/programmes/editors-lab/the-huffington-post-and-changeorg-editors-lab/

Robert Larson, Core News Product Manager at Bloomberg

Robert Larson shared this recommendation for Rajiv on Apr 9, 2016 via LinkedIn:

I had the pleasure of working with Rajiv at The New York Times for many years and think very highly of him and the work he did there. Under Rajiv’s leadership and with the team he built there, NYT became a far more innovative company. It also became a more attractive place for engineers to work. Rajiv focused as much on improving the culture of the team as on the technologies they were developing. Recruitment and the quality of the new hires increased. On a personal level, I valued the advice and counsel Rajiv provided as a colleague.

As Vice President, Search Products at The New York Times, Robert worked with Rajiv.

Information for Technologists Interested in Learning about Artificial Intelligence

These days, artificial intelligence is gaining a lot of attention in mainstream media. This is a topic that I’ve been passionate about for many years, and a number of fellow technologists have asked me where they can learn about AI.

I have posted a shared Google Document for people with a background in technology and software engineering wanting to learn about AI. Topics include artificial intelligence, machine learning, deep learning, artificial neural networks, reinforcement learning and other concepts. I plan to keep this document updated as I come across interesting AI related articles, new developments, and sources of information.

The document is for technologists who are interested in learning about the basics of AI and related technologies. You need some background in technology and software engineering to delve into AI. However, some of the information I’ve linked to is of general interest.