3 Roles of a CTO: Culture. Technology. Operations.

This is a guide for CTOs, VPs of Software Engineering and other technology managers responsible for a software engineering organization. The purpose of this checklist is to help the CTO cover the areas of culture, technology and operations in their teams. It is presented in the form of a memo to direct reports.

Dear Tech Management Team Colleagues,

For those of you who have weekly 1:1 meetings with me, this template is a guide for our regular discussions. I value your experience, so please feel free to suggest making this format even better. I’d like us to cover three major areas on a regular basis.

1. Culture
2. Technology
3. Operations

Each of these three major areas is further divided into three sub-categories containing a list of items to consider reviewing.

The first time you see this list, it may seem too long to review in a 30 minute meeting. This is a guideline to structure our conversations. You are not expected to discuss each one of these at every meeting. This checklist will help us review things that are relevant at the time. Managers have successfully used this checklist to review pertinent items in less than 30 minutes.

Tip: Here is one way to effectively use this. Let us both spend 5 to 10 minutes to read this checklist in advance of each of our regular 1:1 meetings. We can even use the first 5 minutes of our meeting to read it. Then we will both have a good idea of which items are relevant for the next discussion from our perspectives.

Culture “people, behaviors & teamwork”

Relationships

1. How well are your team members collaborating with each other?
2. …with their colleagues in other tech teams?
3. …with their stakeholders, customers and executives?
4. Are there any tensions that I need to be aware of?
5. Advocacy: What should we do to be better understood, respected, and appreciated by our stakeholders, customers and executives and vice versa?
6. Anything in this area that you are waiting on or need from me?
7. Is there anything non-work-related that you’d like to share?

Retention

1. Are the people in your teams happy with their work? How is team morale?
2. Is the work intellectually challenging?
3. Are they learning new things and getting better at existing skills?
4. Do they feel they are making a positive impact?
5. Are we taking good care of them?
6. Are we proactively providing feedback, coaching, and training?
7. Is anyone considering leaving that you know of?
8. Has anyone given notice?
9. Is there anything related to retention that you are waiting on or need from me?

Recruiting

1. Are you feeling a staffing shortage this week?
2. Are we thinking ahead and planning for capacity, skills and having some slack for flexibility?
3. How many open positions do you have in your team this week? How long have they been open?
4. What are you doing for recruiting?
5. Is there anything related to recruiting that you are waiting on or need from me?

Technology “engineering, infrastructure & innovation”

Architecture

1. What new technologies, platforms, products and APIs are we evaluating?
2. …implementing?
3. …decommissioning?
4. …consolidating?
5. …releasing as open source or making public?

Integration

1. What are we doing to support integrations across teams?
2. Are you facing any challenges integrations across teams?

DevOps

1. In what areas are we implementing temporary hacks?
2. How are your apps and platforms doing with respect to their goals in Performance & Scalability?
3. …Reliability?
4. …Security?
5. …Test Coverage?
6. …Technical Debt?
7. …On calls and P1s?
8. How are the integrations, process and relationships between the development, infrastructure and security folks?

Operations “projects, sustainability & recycling”

Work

1. Are there any projects at risk?
2. Are there any changes to a) due dates, and/or b) delivery dates?
3. What did we a) accomplish, and b) work on over the past week?
4. What do we plan to do over the next week?
5. What projects/work can we decommission?
6. What was your budget forecast? How are we doing with respect to it? Any budget issues?
7. Did we recently say “no” to a stakeholder or executive’s project request (or say something would be very hard to do) that I should know about?
8. … any that we said “yes” to that I should know about? :-)
9. Did we give any estimates that I should know about?
10. What can I do to help? What do you need from me?

Learn

1. What did we learn from the past week?
2. Are we sharing these learnings with others who’d benefit from them?
3. Did we do any retrospectives? What changes are we making based on retrospectives?
4. Are there any process changes that you recommend? … for both outside and inside of your teams.
5. How can I help?

Challenges

1. What issues are we facing now or are likely to face in the future?
2. What prioritization problems are we facing?
3. What do you suggest are our countermeasures to address those issues?
4. How can I and/or others help and support you or remove obstacles from your path?

Mixing it up

To prevent our weekly discussions from feeling too structured and getting stale, I suggest mixing it up a bit. Let us try this format for 3 out of every 4 of our regular 1:1s and keep 1 meeting free-form.

We can also break monotony by switching the locations of these meetings and having some of these discussions walking about.

Why discuss this in a meeting and not ask for this information in a weekly status report?

… because no one likes to write a status report, but everyone likes to talk :-)

Let us take a test and learn approach with this and adjust as we go along.

Thank you in advance for your help with this.

This article is mirrored at my blog and Medium.

You can find my work on the Web at rajiv.com and via Twitter @rajivpant