A CTOs Guide to Time Management

To be strategic, CTOs need blocks of time available for deep thinking and collaboration to maintain a standard they hold themselves to. Here's how to secure that time.

Photo by Pawel Czerwinski on Unsplash

Introduction: The Importance of Time Management for CTOs

Time management might seem like a prosaic topic, but for any CTO who aspires to be more strategic, it starts with being in control of one's time.

As I made the case for in an earlier post, the demands on CTOs are at an all-time high:

CTO: The most demanding position in the modern enterprise

With these demands on the CTO and that many CTOs have not been equipped with the skills to manage the many demands on their time. This can happen, especially with CTOs may not be who rose to the role from a purely technical career progression track, which is many of us.

I was reasonable at managing my time in previous roles but the demands of my executive role required me to learn a new set of skills and habits to stay on top of the demands of the role and to enable me to be proactive in the ways you need to be if you wish to be strategic in your approach to the role.

It took me multiple years as a CTO to acquire the knowledge and discipline to be in sufficient control of my time to make time for activities with uncertain pay-offs over long periods of time. The better I got at this, the more proactive I was in all aspects of the role and the more resilient I could be against the events that can quickly rob a CTO of their time or focus.

In this post, I will survey the most important aspects of managing CTOs' time. Reading this post won’t magically make you brilliant at managing your time - finding which ways work best for you and building habits and discipline in maintaining these behaviours takes time. Still, hopefully, it gives you a frame for the things to consider and a set of opportunities to improve your time management you can experiment with.

The Essentials: What Behaviours Are Important for Good Time Management?

Be Wary of Not Having Time For Important Things

I’ve covered the issue of prioritising only over the short term. In this post, I reference the classic comic strip with the cart with square wheels:

Being too busy for important things, such as optimising how you invest your time, maybe because you are trying to be quick in the short term. The consequence is that you will have the same efficiency the next time. This can become a repeating pattern, which is how we get stuck wasting time every week on a range of inefficiencies we were always too busy to correct.

This post is full of opportunities for using your time more efficiently. You will never change your situation if you are too busy to try any of these opportunities or any you have identified. The demands of your role will conspire to make your situation worse, so regular assessment of how healthy your use of time is and opportunities to free more time is a regular investment you will need to make to keep your head above water.

I visualise the compounding impact this can have in this post:

Long term average pace > short term pace

The Folly of Busy-ness

Being busy can make you feel important. Some people boast about their busyness and wear it like a badge of pride. The reality is that being busy is not something to be proud of; it indicates indiscipline. The busier you are, the less time you have available for each thing you do. You also waste time by context-switching between each thing on your list.

If this describes you currently, I suggest shifting your perspective on busyness and avoiding rewarding yourself for being busy. Be aware of that feeling and instead consciously aim to be as in control of your time as you can be. Value downtime and time for thinking are essential for strategic CTOs.

Ask Why Now?

A key question in strategy that can apply to your time management is ‘Why now?’. There should be a good reason to take on something new, now. If it might be the right thing down the track, be disciplined and don’t pursue it until you have the capacity to approach it in a focused way. If there’s not, it’s better to focus on completing what is already on your plate.

Delegate Whenever Possible, Responsibly.

A significant determinant of a CTO’s busyness is their ability to delegate. For CTOs who were previously engineers, the temptation to think through problems in terms of how they would implement them rather than the desired outcome can lead to missed opportunities to delegate work to the full extent possible.

Successful delegation requires being clear on what the person is responsible for (i.e., what their mandate is) and when they should involve the person who has delegated the authority. John Cutler's Mandate Levels concept has been a useful guide for the former, and the Delegation Poker cards are a good reference for the latter. I will share more about this in a future post.

It does not mean abdicating responsibility. If a person is not ready to take on the responsibility or it would be unsafe for them or others to take on the responsibility, you should not put them in that position.

I’ve covered aspects of responsibilities and empowerment here:

Using a game to foster safe and engaging conversations about responsibilities within teams.

Have Good Meeting Practices

A common area where time can leak for executives is in meetings. There’s nothing worse than sitting in a meeting and realising you are not adding any value by being there. Setting some expectations of what the minimum expectation is for meetings and leading by example by upholding those standards will start to build discipline across the team.

Practical meeting standards include:

• Write down the purpose of every meeting. Be specific and avoid weasel words.

• Expect an agenda for every meeting.

• Be clear on who is needed at the meeting and who is optional.

• Provide time constraints for each agenda item.

• Expect preparation before meetings and be clear on when agenda items and pre-read information is to be circulated prior to the meeting.

• Make it possible for meetings to proceed even when some people are not available.

• Be clear on how decisions are made in this forum.

• Don’t accept poor meeting discipline - the more you accept, the more you will experience.

• Make introducing new work contingent on finishing or killing existing work.

• Expect meetings to be minuted. Even better are meetings where notes are taken where everyone can see them, so clarifications can be immediate. Absentees can catch up on what they missed.

• Make the meetings in the organisation accessible and discoverable. It should be easy for anyone to know how to approach decisions that are outside their responsibilities.

• Prioritise and measure decision velocity - once a decision is identified as needed, measure the lead time until it is resolved.

These meeting practices are beneficial for protecting everyone’s time level and the playing field for different personality types and reducing the ambiguity of resolving issues that may be preventing them from making progress. It's common for people in organisations to waste a lot of time puzzling over how to get problems resolved, which might eventually require the CTO to spend time-solving that issue. Instead, if people know which forums or people they can engage with to get problems resolved quickly independently of the CTO, it will prevent you from spending unnecessary time.

This is an expanded aspect of delegation. If your team has a model for how everyday decisions are made, it further reinforces the responsibilities of individuals and groups and helps everyone navigate the system more easily. Many organisations have no real theory on how decisions are to be made leaving most decisions to be a completely novel exercise where significant time is spent trying to work out who and where it will be addressed.

Prioritisation & Focus

CTOs face many demands and have almost infinite opportunities. It’s easy to hear about new problems or solutions and follow them, creating a new commitment to your time.

The ability to say no and the discipline to stick to your current focus are critical for a CTO. To say no, you need a clear view of how and why you prioritise things, which is clear to you, your team, and anyone who depends on your services.

Some people use prioritisation frameworks to align with their stakeholders. It’s not a terrible way to start, to bring everyone to the table, and to help bring about change if previously you were being pulled in many directions by different groups only concerned with their priorities. A prioritisation framework, such as one that scores each opportunity on standard criteria, can give them a predictable and seemingly fair playing field for how work will be prioritised.

However, I don’t recommend using a prioritisation framework for the long term. Ceding over prioritisation to a formula is an inferior approach that can diminish your impact on the organisation.

A better frame of reference for prioritisation is to be clear on the outcomes that represent the success of your role, your team, and your organisation. You can use a small number of outcomes you are focused on as a filter, which helps you identify what you say yes and no to (or, at least, not now). You might complement this with principles that help you quickly identify ways to sequence where you apply your preciously finite amount of focus.

For example, a principle I used when choosing where to start a new software effort was ‘front-to-back’, so if we were presented with the choice of backend effort or frontend, we would usually start with the user experience and mock out the backend. The reasoning is that if we learned things about what the users needed, it may significantly change how the backend functions. If we started in the reverse order, we may be up for significant rework later, more time wasted.

The Basics of Personal Time Management

Blocking time

A strategic CTO needs time for deep work. That might be time to draft a plan or analyse a problem to review a proposal closely or to appropriate due diligence for engaging a critical vendor on one of a whole range of things that have the potential to be high-impact contributions.

You may be familiar with the idea that no matter how much storage we have, software or possessions will expand to fill the space available. The same is true for calendars. If you have a lot of free time visible in your calendar, people will book that time.

It's, of course, important for CTOs to be available, but you can be intentional about how you approach this. For instance, I used a combination of the following:

• Advertising ‘office hours’ where people can visit you during an allotted time.

• Organising periodic ‘skip-level’ meetings, both 1:1 and group meetings - sometimes open-ended and more often with a focus.

• Hot desking, allowing you to spend time with different groups within the organisation.

• Participating in social activities—I regularly joined the after-work table tennis, indoor soccer, and various other activities, which gave me many serendipitous opportunities to get to know more people well and hear different perspectives.

Weekly Calendar Review

Do you find yourself in meetings that don’t feel like the best use of your time or your time dominated by activities that don’t align with your priorities?
A weekly calendar review is a very simple discipline but a great foundation for getting on top of your schedule.

This involves reviewing your calendar at the start of the week—I did this every Sunday evening for about 15 minutes.

I was looking for several things:

• Was I the best representative to attend the meetings I was invited to?

• Were there blocks of contiguous time for me to deep work?

• Were there opportunities to adjust the schedule to increase the number or length of contiguous blocks of time for deep work?

A regular review of your time use also enables you to reflect on what is working and what is not and decide on the next improvement you can make. Only some things you experiment with will work out. Persisting with what is working and cutting what isn’t helps keep things lean and not wasting time with things that aren’t helping you.

Advanced: How To Be Even More Proactive with Time

I have covered some more advanced topics for paid subscribers, which helped me significantly protect my precious time.

• If Possible, Get an Administrative Assistant for Diary Support

  • Meeting plan

• Advanced: How To Be Even More Proactive with Time

  • Calendar Architecture

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