Three Mistakes That Changed How I Lead (More Than Any Training Ever Did)

Welcome to my newsletter! I'm Dave Anderson, an ex-Amazon Tech Director and GM. I write this newsletter I've called Scarlet Ink, which is a weekly newsletter on tech industry careers and tactical leadership advice.

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Our most powerful learning moments come from our mistakes. Lectures from your manager or parents or teachers might give you some ideas. But those emotional lessons where you made a mistake? Those really sink in.

The reason the below stories are detailed and specific is that they're burned into my memory. Not because they were life-altering in some way. Instead, it's because it was a consequence I cared about, and I knew it was my fault. I'd messed up. I felt the emotional pain of realizing that the consequences were Dave's fault, and I couldn't toss the blame elsewhere. Even a tiny mistake can be seared into your memory if you care enough about the result.

I've been to plenty of leadership training courses. Some of them were pretty good. None of them hold a candle to a memorable mistake.

These stories, as usual, follow my anecdote policy.

Whoops. I repeatedly rescheduled an employee's one-on-one meeting.

Managers will almost inevitably end up with their calendar 100% booked if they're not careful. I regularly went through this cycle. I'd end up with an incredibly busy calendar, and at some point I'd aggressively clean it up.

However, while I was in the middle of a busy cycle, I regularly had meeting conflicts. I'd be double or triple booked for any given time slot.

When an important new meeting was scheduled, I'd have to spend some time moving conflicts. As this was before I had an executive assistant (EA) running my calendar, I had to spend a good amount of my (expensive) time moving conflicts.

This ate up an unfortunate amount of my personal time. Imagine I had a relatively important 5-person meeting at 10am, and then a more critical 25-person meeting dropped on top of it. I had to move that 5-person meeting. I had no openings, and likely those other 4 people didn't have many openings. It was a huge pain. I usually had to create yet more conflicts with that moved meeting.

Of course this all means that you try to move the easiest meetings. The easiest meeting to reschedule will be a one-on-one meeting, as there are only 2 participants.

This employee in particular had a recurring meeting at a popular time slot. Something like 10am on a Monday. That was my first mistake.

As a consequence, their one-on-one meetings for many weeks in a row were rescheduled. I didn't fully cancel them, but they hopped around my calendar like a little bunny.

A few weeks later, we had some performance review cycle, which included employees writing 360 feedback. When I met with my manager to review my 360 feedback, I was pretty shocked that one of my employees was seemingly very upset.

He had written (anonymously) that he was feeling some combination of offended and undervalued because I didn't prioritize his one-on-one meeting.

I begged my manager to tell me who it was, because I felt bad. I wanted to improve things, but "never reschedule a one-on-one for anyone" didn't feel feasible. I needed to know who was impacted.

To be clear, my rescheduling decision wasn't about importance. I didn't cancel his meeting. I simply found it easier to reschedule. And I understand that this employee felt that rescheduling was a sign that his meeting wasn't important, which certainly wasn't my intention. I absolutely didn't want to send that negative signal to my employee.

The reason this slipped by is that as a senior manager, I had many meeting reschedules every single day. I didn't think twice about a meeting moving; it was simply a part of my life. I drove my day off my current calendar, wherever meetings ended up landing. But I understand that someone else's view of their calendar could be different. Regardless of my intentions, the impact was real for that employee, so it mattered.

Thankfully my manager trusted me and told me who it was so that I could get things fixed. I met with the employee, and let him know I heard his concern, and I apologized. I explained the above, that my movement was an attempt at schedule jenga, and was not intended to be a statement about his worth. I explained that his meeting was unfortunately at a popular time for critical organization-wide meetings I had no control over.

So my first move was to change his recurring meeting to a time that was less likely to have conflicts, and I told him that I'd do my best to not reschedule his meeting. On my end, I made an extra mark on my calendar (I used color codes for reasons like this) to help remember that this time slot needed to be protected.

He said he understood, and appreciated that I responded to his feedback, and that I came up with a solution. Thank goodness.

Ok, that's the story. And I think it's filled with valuable lessons. Three distinct things come to mind.

🖊️ Lesson One? Employees aren't all the same. Listen carefully to everyone individually.

When I received this 360 feedback, I was worried. Not just about this employee, but about the general impact my crazy schedule might have had on my team. What if most of my team felt the same way? What if they were all angry at me??

I quickly contacted multiple other employees. I said that I had noticed that I had rescheduled their one-on-ones frequently and that I felt bad. I said that I didn't intend to signal that their meeting wasn't important.

Every single person insisted they hadn't noticed and didn't care. I could feel free to keep rescheduling their meetings.

I'm not saying this to suggest that the other employee was wrong. Instead, my point is that everyone is different. I don't personally care if my meetings are rescheduled. But it was a mistake to assume that everyone felt the same way.

This is true for many situations, and I've been caught in others. Assuming everyone feels the same way is a recipe for disaster. My main learning here is to watch employees's reactions closely. A loud chorus of agreement from a crowd might be hiding a few disagreements. I've regularly caught outlier opinions through 360 reviews, requests for private feedback, etc.