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.