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.

cto-culture-technology-operations


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 LinkedIn and Medium.

3-5-7 Meeting Format for Weekly Staff Meetings

If you are the manager of a team of people at your job, here is a format we suggest for running your staff meetings. We call it the 3-5-7 format because of its convention of giving 3 to 5 minutes per person to answer 7 questions. This system assumes that you have fewer than ten direct reports so that you can complete such a staff meeting in under one hour.

The purpose of a staff meeting need not be to get status reports. If you have excellent collaboration tools at work where statuses, issues and risks are already documented, that’s preferable. Some companies like Automattic (WordPress) make great use of internal blogs for communication. However, face-to-face meetings are continue to be useful because our brains have evolved being wired for being most effective in face-to-face conversations for several things.

An in-person (or via video conference) discussion structured around these questions is likely to be effective in finding solutions, building a more collaborative team and keeping everyone on the same page.

Here are the seven questions we suggest you request each attendee to come prepared to answer.

  1. What did we (you and the team reporting in to you) do over the past week?
  2. What did you learn over the past week?
  3. What do we (you and the team reporting in to you) plan to do over the next week?
  4. What issues are we (you and the team reporting in to you) facing now or are likely to face in the future?
  5. What do you suggest are our countermeasures to address those issues?
  6. What do you need help with from the rest of us in this meeting?
  7. Is there anything non-work-related that you’d like to share?

Each person may answer the seven questions the order of their choice and may also combine the answers to multiple questions. The only requirement is that all seven areas be answered in a focused, efficient, and effective narrative lasting between three to five minutes.

Some of this advice is based on management experiences shared by Don Kiefer in an operations management class he teaches at MIT’s Sloan School of Business.

Posted Signs for Productive Meetings

You can post these slides as signs in your meeting rooms and offices or include them at the start of your presentations. You can also open the original Google Slides document to print or leave comments.

Suggested Template For Requesting a Meeting

Every time someone calls a meeting, they should consider using this simple template.

[ meeting-invitation-template begins ]

The desired outcome of this meeting is:

  • e.g. Come to agreement on solution for issue X
  • e.g. Make a decision about Y.
  • e.g. Share announcements about topic Z.
  • e.g. Continue to grow a good working relationship with each other by socializing in person.

Note: Explain what this meeting is meant to accomplish, instead of providing a description of the meeting. Focus on the desired result of the meeting. A meeting should accomplish one or more of three things:

  1. Solve problem(s)
  2. Make decision(s)
  3. Share knowledgeand agree to act on it and/or make it a practice
    • Knowledge, as in: data –leads-to–> information –leads-to–> knowledge –leads-to–> practice

You should come to this meeting because:

  • e.g. You are likely to have input into potential solutions for issue X
  • e.g. You are one of the folks who has a viewpoint on what decision to make regarding Y.
  • e.g. It would benefit you from hearing the announcements in this meeting.
  • e.g. This is your opportunity to ask questions about topic Z.

Note: Give the attendees at least one good reason to attend. Sometimes attendees have no idea why they are invited to this meeting. Don’t be seen as a waster of others’ time.

The guidelines for participating in this meeting are:

  • e.g. Please come prepared having read the document about ChaosMonkey.
  • e.g. Laptops & mobile communication devices are considered contraband during this meeting. If it is critical for you to have a computer during this meeting, bring a desktop computer :-)

Note: Set the expectations of the participations.

[ meeting-invitation-template ends ]

Further Reading & Thoughts:

Templates for Replying to Meeting Requests & Polite Ways to Decline Meetings

By default, we should only attend meetings where we are active participants, not passive attendees with not much to contribute to the desired outcome of the meeting. There are some exceptions to this like training sessions, educational presentations or others where the purpose for attendees is to learn something.

When I receive a meeting request, I often reply with the following text.

May I please request the following information in advance of this meeting? It will enable me to prepare, participate and be productive in the meeting.

  1. What do you recommend I should prepare in advance of this meeting?
  2. What decisions do we need to make at this meeting?
  3. What problems do we need to solve at this meeting?

Thank you in advance,

Time Management Tip: When you receive an invite for a meeting at work where you believe you may not add much value, reply to the invite with a polite message like:

Thank you for inviting me to this meeting. It seems from the subject, agenda, and attendees list that I’m not a required participant for this meeting. If I’m mistaken and my presence is required in this meeting, please accept my apologies and let me know that I should attend.

This is preferable to ignoring the meeting invite or declining without comment that may come across as rude.

To save time, you can save the above templates as text snippets to be inserted via a keyboard shortcut/macro or in a place from where you can quickly and easily copy and paste.

Discussion about declining meetings: https://plus.google.com/107443707510532643538/posts/inUkYy1Ufg7

When to have and when not to schedule meetings

Companies should, by default, avoid scheduling meetings that start before 10am or end after 5pm. If an employee comes to the office at 8am on some days, it is often to use the two hours of the morning before meetings to catch up and/or get a head start on the day. Meetings that start before 10am are often harmful overall since they put the attendees in reactive catch up mode for the rest of the day. Similarly, meetings that go on beyond 5pm (or worse, start after 5pm) take away valuable time from employees that they use to absorb information and events of the day, catch up with replying to email and get ready for the next work day.

i.e. Companies should consider any time outside the 10am to 5pm window to be not available for meetings and definitely not any weekly recurring meetings.

Preferably, employees who are ‘makers’ should have one 4-hour continuous block of time each day when they are free from meetings. (‘Makers’ differentiated from ‘Managers’)

50/25 Meeting Format

If you manage a team, value your team members time and want to improve productivity at your workplace with a simple change, consider implementing the 50/25 Meeting Recommendation that some companies are embracing. You can communicate something like the following to your team:

Dear Colleagues,

We deeply value your time, your productivity and your comfort at the workplace. As a part of our initiative to make your workday more productive, less hectic and better manageable, we recommend a 50/25 meeting format. It is simple concept: As much as possible, let us take all our meetings that are 1-hour long and shorten them to 50 minutes. For our meetings that are half-hour long, let us limit them to 25 minutes.

You will find that a 50 minute meeting will accomplish no less than a 60 minute meeting did and a 25 minute meeting will be as productive as a 30 minute one was. In fact, by having clear 50 minute and 25 minute deadlines, our meetings are likely to be better focused, on topic and more attentive. (For example: Since you will have time after the meeting to check email, there is likely to be less temptation to check emails during the meeting itself.)

The extra 10 and 5 minutes will give you valuable time back that could be used for many useful activities: Getting in the frame of mind for the next meeting or task; checking your messages to see if there is something urgent that needs your attention; or simply taking a bio break.

Please note that this not a mandate, but a recommendation. We realize that you may not be able to do this for every meeting. What we ask is that you consider doing this for meetings that you organize or can influence. As a result, we will make our great work culture even better, less stressful and even fun.

Further Reading & Thoughts:

  • NYTimes article about Larry Page, Google’s founder and new CEO instituting the same 50/25 meeting recommendation at Google:
  • http://www.nytimes.com/2011/11/10/technology/googles-chief-works-to-trim-a-bloated-ship.html?pagewanted=all
  • If a meeting accomplishes all its goals in even less than the 50 or 25 minutes, please, by all means end the meeting even sooner.
  • We suggest that you do book the full hour or half hour in the calendar even as you implement the above so that others don’t schedule over the “10 minutes left over” in your calendar.

Thank you for considering this,

[Signature]

A discussion about this 50/25 Meeting Format: https://plus.google.com/107443707510532643538/posts/AtYgnmbhtqc

Using Laptops or Smartphones in Meetings

You might think that no one is noticing when you are using your phone if you try to hide it below the table surface, but you’d be mistaken. It is like picking your nose: Your being oblivious of others doesn’t make you invisible to them. Photo Credit: Brad Kagawa

Using smartphones — or worse, laptops — during in-person meetings diminishes productivity, is disrespectful to others and decreases your brainpower. Yes, scientific evidence indicates that multitasking makes people less intelligent.1

When you are  doing something unrelated on your phone or laptop in inappropriate situations (e.g. during business meetings), you lose out because you become oblivious to the environment, people, and subtleties around you.

However, there are a few situations where it makes good sense to use a laptop or smartphone during in-person meetings.

  • When you are the designated note-taker for this meeting.
    • Taking notes on a computer or smartphone saves time, and is more accurate than taking paper notes and digitizing them later.
    • Notes on paper can’t be searched easily, pile up as clutter and are less environmentally friendly.
    • It is more secure than taking notes on paper that can be forgotten and read by others who should not have access to the information.
    • Meeting notes and action items can be automatically saved in real time and shared quickly after the meeting.
    • There should be only one person taking notes during a meeting. If it is a negotiation between two opposing sides, then there should be no more than one note-taker per side.
  • When you need to quickly look something up that is relevant to the discussion and is either necessary or helpful to the meeting in progress.
  • Entering action items that come up during the meeting into your to-do-list so that you can focus on the meeting. This is useful for people who use the GTD system with a tool like OmniFocus.
  • Quickly and discreetly asking a question, or sharing an opinion or information over instant message without disturbing others in the meeting.
  • The distractions on the device could be managed if the user is disciplined and remains focussed on the meeting, perhaps even using the laptop to participate more actively in the meeting. After all, even a person using pen and paper can be distracted doodling or daydreaming.
  • This is the digital age.

Tip: When you bring a laptop to a group meeting or one-on-one meeting, each time respectfully explain to the others beforehand that you will use the laptop for taking notes and recording action items in your to do list only. Inform them that you will be focusing attention on the discussion and that the laptop is simply your digital notepad.

There are also many reasons against using laptops or smartphones during meetings:

  • It comes across as disrespectful to some other meeting attendees, especially those with traditional styles of working.
  • The laptop screen creates a “wall” between you and the people sitting across you.
  • The laptop does make it easy to get distracted into reading your email or other online activities. (A tablet like the iPad that lies flat on the table like a writing pad does not have this problem.)

Tip: At the start of your meeting, announce that if anyone needs to use their phone or laptop, they should step out of the room, use their device outside and return when done. This way, attendees have the freedom and won’t feel constrained.

In most situations, the drawbacks of using a laptop or smartphone during an in-person meeting far outweigh the benefits.

Tip: Provide a mobile phone charging area in your meeting rooms to encourage attendees to put away their mobile phones and participate.

What do you think? Here is link to a related discussion about using laptops, smartphones and other communications devices in meetings.

(Updated: 2014 July 26)

  1. The High Cost of Multitasking: http://blog.fuze.com/the-high-cost-of-multitasking-infographic/  []

Maker’s Schedule (For Managers Too)

The following memo from a department head to staff is an example of how to implement a productive maker’s schedule at your workplace. This approach recommends starting with baby steps, evaluating results and making changes accordingly.

Comic strip from XKCD

Dear Colleagues in the Technology, Project Management and Product Teams,

Executive Summary:1

We are implementing a maker’s schedule starting this Friday May 31st which means developers will have from 12 noon onwards on Fridays to focus exclusively on writing code, with no meetings or other interruptions. (This also applies to other contributors besides developers. For more information, see details below.) The goal of this is to increase productivity, creativity and job satisfaction. This practice is based on science and employed by other successful organizations. We request your understanding, your support, and your help in making Friday afternoons meeting-free.

The Details:

We are implementing a maker’s schedule system starting Friday May 31, 2013. What is it? A maker’s schedule is calendar scheduling system that gives a group of people a continuous multi-hour block of time to focus on their work with minimal productivity diminishing things like distractions, context switching or frequent interruptions.

The word maker in this context often refers to people like software engineers, designers, testers, systems engineers, infrastructure engineers, documentation authors, editors or anyone else making something. What they are making could be software code, documentation or a configured server. It need not even be technical work. Managers also do the work of making: writing a memo, editing a budget spreadsheet or creating a slide presentation, for example.2

The human brain has evolved in a way that creative work, innovation and productivity are maximized when a person is able to focus and work on one task at a time for multiple hours. It takes several minutes, often half an hour or longer to get in the flow state of mind that results in peak performance at work. Hourlong or half-hour long meetings peppered throughout the day with breaks in between supposedly to do productive work result in low quality work, cause stress, and lead to unhappiness.

One way to do better quality work, get more done and be happier in your job is to divide your day into two halves. Get all your meetings, emails and administrative tasks done in the first half and spend the entire second half of the day doing enjoyable creative work that puts you in the flow state of mind. You will leave the office less stressed, more satisfied and happier each day.

If you are interested in learning more about the maker’s schedule concept, the article titled Maker’s Schedule, Manager’s Schedule by Paul Graham is a good introduction.

Below are the answers to some frequently asked questions.

Q: Who does this policy apply to?
A: This applies to all makers as listed above, especially all engineers and quality assurance staff, people who spend the majority of their time writing, designing or implementing software code, systems or designs. This also extends to those in management roles who’d like to use this time to do maker’s work.  At this time, we are not applying this policy to employees with special employment contracts like guild or unionized employees.

Q: When will we have maker’s hours?
A: Fridays after 12 noon, i.e. the latter half of all Fridays going forward until further notice.

Q: Does this mean I can go home early on Fridays?
A: No. This is not a summer hours policy. This is meant to be uninterrupted software engineering and development time. It does not change anything about when you are expected to be in the office. The prior agreed upon schedules you have with the company will continue.

Q: Why Fridays and why only Friday afternoons?
A: We analyzed our organization’s current meetings schedule and found that Friday afternoon is the period where there are least meetings and those meetings can be rescheduled with least impact. We are starting the pilot program with Friday afternoons. After some months of evaluating the results, we may extend it, keep it the same or cancel it. Until Further notice, this policy applies only to Friday afternoons.

Q: Does this mean I only get Friday afternoons to write code?
A: No :-) What this means is that we must all do our best to not organize, nor attend meetings on Friday afternoons so that time is exclusively reserved for writing code, building systems and doing other maker’s work. You are expected to do maker’s work every business day and to manage your own schedule to block off enough time to do that on others day the same way you already do.

Q: What about production emergencies? Can I get called into an emergency meeting to deal with a critical production emergency?
A: Yes. Production emergencies qualify among the rare exceptions.

Q: What about meetings between makers? For example, between two software engineers.
A: That is a slippery slope. We are strongly discouraging meetings on Friday afternoons in this policy, but we are not the meeting police and are not going to ban all meetings, especially if all the attendees have a strong desire to meet. We trust you to use your best judgement and lean towards not holding meetings on Friday afternoons unless you determine you have a good reason to make an exception to this policy. Our suggestion is this: Pair programming is encouraged. Working sessions are ok, assuming that in the entire working session multiple makers are making something together. However having staff meetings at this time is not a good idea. Nor is it a good time to have your weekly 1-on-1 with your manager. Remember your manager is likely to be using this time to do their own maker’s work. So on the question of can developers hold a meeting with just developers at this time, ask yourself why. What is the meeting for? Is it a working session where each of you will make something together? If yes, that’s likely fine. If not, schedule it for another time.

Q: What should I do when someone invites me to a meeting on Friday afternoon and I plan to observe the maker’s schedule and write code at that time?
A: Please always be respectful, courteous and friendly while declining meetings. Use your discretion and common sense. If the meeting request comes from someone it may not be wise to decline, consult with your boss. In many cases, you can politely, respectfully and nicely point the meeting requester to this policy at http://www.rajiv.com/blog/2013/05/24/makers-schedule-for-managers-too/ and suggest or request another time. Letting your collaborators know about this policy in advance will also help.

  1. Thanks to David Perpich for suggesting this executive summary. []
  2. Since processing email has become such an information overload problem, distraction and waste of time these days, we hesitate to classify doing email as productive maker’s work. If you don’t have the unproductive bad habit of checking your email every 15 minutes and instead you process your email during a few blocks of time a day, you may consider email productive work too. []

Productive Business Meetings

Here are some suggestions for making business meetings more productive, efficient and effective.

Based on readers’ feedback, I have split this article into the following separate blog posts.

(Updated May 29, 2014.)