CTO Agenda

Many tech leaders tell me they feel adrift. Instead of deciding where they’d like to go today, they are shoved here and there based on whatever issues the day brings. In what feels like a nod to Douglas Adams’s writing, they are leaders being led by their calendars and interruptions. You can take the lead by deciding your agenda and proactively choosing how to invest your time.

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Flipping the Calendar

The starting point for this change, as I often go through it with my clients, is to be reminded that the calendar is supposed to serve you. Instead of being a mechanism that makes it surprisingly easy to hand out your precious time, use it to shape your most important resource—your time.

Start by considering what an ideal week should look like in your organization. It’ll be different for you, the managers, and the ICs. Will every week look like this ideal week? Hah! However, many strategists have realized a significant portion of success is having taken the time to create a plan, even if that plan ends up evolving routinely. Having a thought-out expectation of how people spend their time will aid in measuring people’s productivity as well as simply making them more aware of choices.

So, take the time to decide what your personal calendar should look like, even if it will take a while to get there. Do the same exercise with your managers. Now, what does a good executive agenda contain?

Agenda Suggestions

You can copy these suggestions as-is, or cherry-pick whatever matches your preferences. These are all based on doing this exercise with many leaders over the years, and suggestions that have been field-tested by readers of my | books.

Weekly (or close to it):

  • Regular 1:1s with your direct reports, CEO, and peers.
  • Skip-level 1:1s: These won’t be with everyone every week, but you should have a few slots routinely for rotating everyone.
  • Ceremonies: Instead of accepting all those recurring events on your calendar, think about which ones make sense from scratch.
  • Leadership blocks: Time for yourself to think, make plans, learn, review. This is your leadership ‘deliberate practice.’
  • Office hours: Dedicated time for people to freely approach you. Encourage people to use it for non-urgent matters, reducing the interruptions you get regularly.

Every 2–3 months:

  • Quarterly goals: I regularly talk to executives, even CEOs, who are caught by surprise that yet another quarter is ending. Put regular reminders to kickstart the review and planning process so you don’t regularly do it late or in a rush. Set goals for the organization, but also for yourself—otherwise you won’t grow as fast as you ought to.
  • Calendar check: Sort of like we’re going through here. Things will change, and it makes sense to reconsider how your time is being spent.
  • Coaching objectives: Similar to setting personal goals, have the same for everyone in your org. People should make tangible progress every quarter or so, as opposed to assessing their progress once a year for performance reviews.
  • Org health: Statistics, quality metrics, happiness reports. Check how well your team is doing and if there are any trends worth noting before things are on fire.
  • Processes and similar: The different ceremonies and processes at play are your organization’s operating system. Review whether things still make sense or if they need to change. Similarly, update procedures such as onboarding materials.
  • Impact retrospectives: Make sure that what your team is doing is actually moving the needle, and communicate it to them. See here.
  • Intermissions: Regularly make time for real innovation, not just hackathons that look good on social. An introduction to intermissions is here, and you can grab the sample chapter of my book that explains this at length here.

Making it Happen

Equipped with those things, it’s time to put pen to paper or invites to the calendar. I’ve covered how to do a calendar reset on the podcast, but essentially it’s like a good ol’ defrag. Group things, and create blocks to reduce context switches. Put in place recurring invites so you don’t forget things. Have recurring events that take up time, so people can’t fill up your week easily.

Make the calendar serve you, and you’ll make time to grow as a leader. If you cannot think of what you should do to grow, get help. Good luck!