Executive Operating System: Tracking Personal Initiatives

The tech executives I work with sometimes notice a vacuum when taking on their first senior leadership role. Up till a moment ago, every job they had was focused on delivery, even if at a distance as a team or group manager. They had sprints, deadlines, and so on. Leaders, though, tend (and should) work at a different resolution.

All of a sudden, they are measured by things that are quite high-level.

What happens then is that as the organization grows, executives end up defaulting to a few common patterns of work:

Focusing on the micro: We’ve all seen it, the leader might start getting involved in little details in a specific situation, e.g., trying to push for a particular tech decision in a project. While in some rare cases, it might make sense, it more often means the ICs are being overrun, and the executive is wasting his/her time.

Flailing around it all: Similar to the previous situation, the executive, not knowing what else to do, starts getting involved in everything. This manifests in direct messaging ICs in Slack about the progress of different tasks, dropping into meetings, and so forth. Helicopter-parenting in the corporate world.

Re-org for re-org’s sake: What everyone fears the most after the appointment of a new executive are the constant re-orgs, the mission statement discussions, and values workshops. These all have their place and might be greatly needed, but they are also something people tend to do as they think they should do something.

Pushing in too many directions at once: Leaders should be thinking about ways to improve their organizations. If they see an issue that should be addressed in some manner, like fixing terrible and constant production downtimes, growing turnover, or delivery delays, it’s their job to make sure something gets done to fix it. However, we all know the jokes about the exec that says “do this and that” only to forget about it a second later and never review it again. People learn to ignore these, even if not consciously.

These patterns boil down to not knowing what is it that you do in the company and not knowing how to manage yourself. For the latter, I advise for my technically oriented clients to start treating their initiatives with the same tools they are accustomed to.

The Executive Accountability System

Once you know what you should be spending your attention on and have identified an issue that you think you should help the organization improve on, take them seriously. To do this properly, your system should incorporate a few tools:

Initiatives List: Similar to a list of the different ongoing projects in your organization, you should keep track of the various initiatives that you have started and that are still ongoing. Are you establishing new production quality guidelines? Cross-organization mentoring? A healthier 1:1 process? Whatever it is, you should have it listed so you can track it.

Current and Next Steps: Where does each initiative currently stand? If it is still under your responsibility and hasn’t been assigned a champion (i.e., someone else that takes full ownership of pushing it forward), then it is usually up to you to track it, especially in engineering organizations smaller than 50 people.

Deadlines and Reminders: If you do not measure something, it will not get done or improved. You should always set yourself deadlines or reminders to move on to the next step or review the current situation to assess your progress. Some managers like doing these by merely setting a regularly recurring status meeting, others add items to their task managers. Either way, make sure that you do not leave it to your brain to remind you of everything you should be tracking at the right time. If the Initiatives List is the projects in the “Exec Sprint,” these are the equivalent of the “daily standup” (even though rarely do they need to be daily).

Reviews and Retrospectives: To tie up this “Exec Sprint” that you will be managing for yourself, you should all review the different initiatives that you’ve pushed for.
At some point, things have to be marked as done so you can make room for new initiatives and efforts. Assess how well the change was incorporated, whether it was worth it, and how you could help the next ones be implemented even better. We all have space to grow and learn, and this is where you have to give yourself feedback (or consult your mentor/advisor).

All these together might end up being merely a note and some reminders on your phone, nothing too fancy. Keep in mind that this personal-agile system is intended to propel yourself forward. Without deadlines, you might have change initiatives literally go for years. Without retrospecting, you won’t improve. Without reminders, people will learn you never revisit what you asked them to do, and so ignore it.

Would you be interested in an accompanying guide of how to kickstart change initiatives in your team? Subscribe below to the newsletter and get it once it’s ready.

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