It was just over a month ago, but it still makes me feel sick. I was presenting an important and sensitive topic to the team, something I’d worked hard to get right. There were two versions of the deck I’d created, and between the stress of the day and a variety of technical difficulties, I found myself presenting the wrong version to the team. The fact that this version and the scenario it described were old and outdated didn’t matter. There it was, for all to see.
The worst part of my mistake was that I wasn’t the only person who was embarrassed by it – the deck I’d accidentally presented had implications for others on the team too. It was not my best hour. In response, I did what a lot of reasonable people would have done in the same situation: I ignored the mistake and hoped it would go away.
Only – surprise! – ignoring the mistake did not make it go away. It was only after I acknowledged the mistake a full week later that the team could get past it. “I made a mistake,” I said, genuinely, “I’m really sorry I did that.”
In response, one of my team members said something that truly amazed me. “I’ve never had a boss apologize to me before,” he said, “that means a lot.” What took me so long?
Sorry seems to be the hardest word
It’s not just Elton John who thinks so. According Renee Garfinkel, Ph.D., in Psychology Today:
Apologizing is difficult because it requires humility. Apologizing temporarily reduces one’s self-esteem. The offender who apologizes yields some power, some control. Having announced their imperfection and error, the offender is now vulnerable. It takes humility to make a sincere apology, and for some people humility is just too uncomfortably close to humiliation.
When we apologize, we acknowledge our “imperfection and error,” which makes us feel weak and vulnerable. But we are imperfect, and we do make errors. There’s nothing weak about it at all. I’d argue that you need self-confidence in order to admit your failures. As Plato said in The Republic:
I am the wisest man alive, for I know one thing, and that is that I know nothing.
I used to wonder at what age I’d be smart enough to stop putting my foot in my mouth, but that was a long time ago. Now I know that age will never come, that I’ll never be that smart. I may not be “the wisest man alive,” but I know I don’t know everything. And if I don’t know everything, sometimes I’m going to get things wrong – and sometimes that will require an apology.
“Sorry” can be overused
The internet is littered with articles describing people who apologize too much. According to Greatist:
If you’re someone who throws out “sorrys” like candy from a parade float, that can be a problem. While on the surface this might seem like a polite habit, overusing any word can devalue it—and more importantly, excessive apologizing can make you look guilty when you haven’t done anything wrong.
While according to Tonic:
Apologies aren’t always helpful—and sometimes they can be excessive. This behavior may stem from anxiety or depression, although research on the topic is scarce. What we do know is that, for some, the urge to say “I’m sorry” for every little thing is involuntary and often has little to do with actual remorse.
According to the Child Mind Institute, this is especially problematic for girls:
Apologizing can be a good thing—a sign that a child is empathetic and has strong social skills. But saying you’re sorry too much can backfire. For instance, when a girl starts a statement by saying, “Sorry, but… ” or “I might be wrong, but …” she may think she’s being polite, but it undermines what she’s about to say. “It says ‘I don’t feel confident in what I’m about to say or my right to say it,’ ” explains Dr. Rachel Busman, a clinical psychologist at the Child Mind Institute.
Got it? The point is not to apologize with abandon. It’s to acknowledge that we genuinely care when our actions hurt people, and to admit that we make mistakes.
Coda
We’re actively hiring at work – we’ve got lots of open roles on my team and lots of great candidates, both internal and external. In an effort to get the word out quickly and get the ball rolling, I rushed a few job descriptions out before checking them with the hiring managers.
Can you guess what happened? Candidates had applied for a job based on a description they’d seen last month, and we were planning to interview them based on a job description we’d updated last week. Not ideal.
As a believer in the Agile Manifesto, I’m committed to welcoming change, to favoring individuals and interactions over processes and tools, and to responding to change over following a plan. I move fast. I break things. My intentions were pure, but this issue was entirely my fault. As I called each of the candidates, letting them know how and why the job they’d applied for had changed and asking them if they still wanted to apply, I made at least one thing clear.
“I’m really sorry about this,” I said, “I made a mistake.”
“No problem,” they responded, “thanks for taking the time to explain what happened. See you next week.”
Like lots of other people on 
Every time I read a management or a self-help book, I find myself saying, “That’s fine, but that wasn’t really the hard thing about the situation.” The hard thing isn’t setting a big hairy audacious goal. The hard thing is laying people off when you miss the big goal. The hard thing isn’t hiring great people. The hard thing is when those “great people” develop a sense of entitlement and start demanding unreasonable things. The hard thing isn’t setting up an organizational chart. The hard thing is getting people to communicate within the organization that you just designed. 
There are all sorts of great ideas contained in 
Lee Zukor 