Cancelling One on Ones

As a company grows one on ones are critical, show me a manager who doesn’t schedule regular one on one’s with her direct reports and I’ll show you a bad manager.  I am a BIG student of one on one cadence, questions, etc because I suck at them.  I’ve done them because I realize their importance, but I’m not good at structured systems.

Here are some of my favorite reads on one on ones:

As a growing company you’ll find yourself wearing many hats that don’t involve your people, manager, consultant, financial analyst, etc, and as such you will feel the pull of those multiple hats at some point, and something will have to give somewhere.  Your other option is to not do regular one on ones, and watch your people feel under-invested in, so what’s a gal to do when she feels the stretch of having to wear multiple hats and do one on ones with her direct reports?

I have always had regular one on one’s scheduled, I have struggled with the format, but I’ve tried to make sure they were all scheduled. I started realizing an issue, even though I had cadence for my one on ones, the other hats often resulted in me cancelling or rescheduling them.

My other hats were mostly travel, visiting clients, etc. I tried to do my one on ones from hotels, but when you are in a time zone 6 hours off of HQ, you don’t want to have your managers waking up at 5AM for their one one one. When I did get back to the office for the rescheduled one on ones, my days were so packed that I would not be well prepared for them them less effective than I would like, and my team would have liked.

So what is a manager to do?  Data is the key.

My recommendation is to keep track of cancelled one on ones, they are going to happen sometimes, that is OK.  If it occasionally, use something like a trello board, I update mine every 7-14 days for my one on one’s with my manager, Crystal.  In that way even if we have to cancel I can still keep her looped in.

However if you are finding yourself canceling or rescheduling frequently, stop! Here are some steps you can take to address this:

  • Talk. Create a comfort level between you and your direct reports on rescheduling (do this as a group, so they agree together vs you creating individual cadence for each person, I have found separate systems for separate people is a sure fire way to fail at scaling. Remind them that you are pulled in multiple directions, and that spending time with them matters to you.
  • Be inclusive. Make your direct reports part of the solution. This is time set aside for them, so they should help to develop the solution.
  • Set Boundaries. Make the goal to mutually walk out of this conversation with a promise, maybe its “I’ll make 80% of our scheduled one on ones next quarter”
  • Plan to fail. Decide that if you dip below the agreed upon % of attended one on ones for more than “X” months in a row (or some level you are all comfortable with), be open to restructuring your team, adding in another manager, or step aside all together and focus on the other areas that you must.

Where I failed was on having hard numbers (data) and communicating this was a concern to the team. I was looking at my cancelled meetings on my calendar and kept track, but never communicated that I was looking at this to my team.

I found that I was rescheduling approximately 30% of my one on one’s. Of my many hats, one required a lot of travel and a lot of client meetings that were happening while I was supposed to be doing one on ones.  That was a big part of why I realized that as the company grew, it was only going to get “worse” with demands on my time traveling, speaking, funding people’s ideas in labs - etc - so we have a director of SEO who will have higher availability & accountability to my former direct reports. Not to mention, a different approach to tackling the problems I faced.  At this point all my direct reports worked with me so long, that they kinda knew how I’d approach things, getting a new manager will help them learn new ways to tackle issue. So that is an upside as well.

How many one on one’s have you cancelled or rescheduled? Is it too many or just right? Only you will know, but communicate that its an issue early and often.


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Wil Reynolds
Wil Reynolds
CEO & Vice President