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How a Chief of Staff can break the cycle of working with outdated processes

June 27, 2023 Kathryn Montbriand

I fell into a trap that affects many CEOs and executives: there is a problem with your operating system, but the mental energy required to address it is too much.

So you do nothing and live with a degraded system.


Recently I was struggling with my writing habits and content calendar.

I changed directions on a few projects but was still relying on my old ‘operating system’ to schedule writing and publishing.

The process didn’t fit my needs any longer.

The reminders became an annoyance. Each time the ‘wrong’ notification came up, I was annoyed and thought: I should really sit down and update this.

And yet….I tolerated it for a while. A long while.


Why did I avoid fixing it?

Because I knew there was a big mental lift to get to the other side.

  • First, investigate and document the current system 

  • Then, identify the needs of the new system

  • Next change the system and build new habits 

  • Get used to the new patterns and system 

  • Finally, once I have some info on what is working, iterate to the final version

I would rather struggle with a system that didn’t work than open the hood and do all this thinking, rethinking, and habit-changing.


How often does this happen in business? How many times do we kick the can down the road and decide that future us will solve the problem?

We know the current system isn’t working. But, it’s a THING, and changing it would mean unwinding a whole lot of other things so maybe it’s actually not worth it to do this month or this quarter.


Finally, I took a page from my own playbook and said: enough’s enough.

I spent the time unwinding and rewinding this spool of yarn. I went through all the steps: Assess the need, look at the current system, reconfigure, set up the process, etc.

Now I’m testing it. It isn’t perfect, but it is much better than the outdated system that was annoying me every week!

If you’re facing an operating rhythm problems and could use a Chief of Staff to get you unstuck, drop me a note or schedule a consultation.

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