You Borked It, Bro

Note: There’s some “coarse language” later in this entry. Since I value realism over other peoples’ comfort, I opted not to censor this entry. However, I did hide the bulk of the entry under a cut just in case. If your workplace filter is hardcore or whatever, you might want to save this one for later.

I've been thinking about the moments where a person's character shines through most strongly. Life is filled with challenges and moments that ask you to make a difficult choice, one that demonstrates exactly who you are as a person. And sometimes, that choice is whether or not you tell someone that they've dropped the ball in a way that means people are genuinely impacted.

It's seriously an art to be able to tell someone that they've messed up. And by "art," I mean "a carefully considered series of checks and balances" because hey guess what you're probably an at-will employee. So, let's talk about how to tell someone they've messed up, and how to figure out if that's something you should do.

The Chosen One

Before you start telling people what they've done wrong and why, you have to figure out if you're the right one to deliver the message in the first place. This is actually pretty damn hard to figure out even for people who are super self-aware and savvy. It's also a role you don't want to find yourself always playing; there's a fine line between someone who keeps management honest and a Negative Neddie.

That said: good management and good leadership should recognize both the value of this information, as well as the motivations for calling out that person.

There are 5 key things you need to ask yourself before you decide to dive in and start telling people they've messed up.

1. Did you witness the moment firsthand? -- Calling someone out on secondhand info is dangerous, in that it can make you look like an idiot. Beyond that, you'll have to do a lot more digging (i.e. your due diligence) in order to determine what actually went down and how it shook out. Remember that the injured parties' verion is the most suspect, and the uninjured parties' version will lack damning details. You're going to be stuck playing Rashomon for too long to make the messaging effective. Furthermore, if you're delivering the message up the ladder then your position is extremely weakened by your absence. When telling a boss/manager/team lead about their misstep, your best (and least vulnerable) position is one of eyewitness.


2. Can you ask the wronged parties for details? -- Just because you saw that some people were made deeply unhappy by someone's unwitting actions doesn't mean you know the entire situation. If you're comfortable with or close enough to the injured parties, ask them what about the situation was frustrating for them and why they felt that way. This is a classic support technique, but it'll come into play later, when you're actually having the conversation with the person in the wrong.


3. Do you have a good working relationship with the person who misstepped? -- This is probably the most important of these questions. If you and this person don't have a solid enough relationship / series of interactions beyond this moment, you could be jeopardizing yourself inadvertently. The more fragile this relationship, the kinder and gentler your approach will have to be. If you and this person are distantly polite to one another or have a really negative relationship, find someone else to deliver the news, especially if they're up the ladder from you. Have someone on their level whom you are close to talk to the other person.


4. Are you doing this for selfish reasons? -- The toughest question to ask yourself is about your own motives for deciding to call someone out on their insensitive behavior. Are you doing this for selfish reasons? By that I mean: are you looking / expecting to gain favor with specific people when you do this? Are you hoping to be rewarded or recognized in some way for doing this? If so, have someone else deliver the message. Your motives will be suspect to others around you, especially if you have a track record of racking up accolades, which could take the power out of your message. If you're not going to be helpful, step aside.


5. Are you ok with having an otherwise positive relationship turn tense for a while? -- Last thing to ask yourself and possibly the second most important. This person isn't going to be happy with you for a little while. Assuming they're a grown-up, they'll quickly realize your intentions aren't to shame or scold, but rather to inform and better them. But this takes longer for some to understand; there's potential for an awkward lull to cloud your relationship as one person digests what you've told them. If you rely on this person too much to have this relationship be temporarily broken, reconsider.

If at any point the answer to one of those questions is NO, then don't call the person out. While I'm not as risk-averse as some, this is a case where you could genuinely take a huge amount of flack for insubordination or attempts to politicize an otherwise functional office environment. Do not turn yourself into the obvious cultural-unfit by being a hero when you don't need to be.

For me, when I called out Zach, I had two extra advantages: (1) Zach and I were reasonably similar in temperament, meaning I could read his reactions because they'd align with my own; (2) I'd developed enough of a rapport with him to be aware that I had one trump card, one big "get out of jail free" pass when it came to him. Were there times later when I wished I still had it? Maybe, but I used it on behalf of colleagues whose situation was more immediate and I don't regret it.

Break It to Them Gently

There's definitely a right way and a wrong way to do this. I'm going to talk about how you can tell someone you believe they've borked a situation without embarrassing or hurting them.

1. Speak to them privately. -- Don't call them out in front of a large crowd (unless you super just don't care anymore) because anything you say is going to be tainted by intensely negative feelings of embarrassment and self-consciousness. Pull them into an office, walk around the block with them, go grab coffee, whatever you feel comfortable doing with them that puts you both on even footing. Don't talk in their office or in yours; talk in a conference room. Don't speak in your preferred cafe or their favorite lunch spot; pick a new, neutral ground. When I called out Zach, I did it on a walk we occasionally took together to our respective transportation options. I made sure to time our departure so that we left together, and I let him lead the conversation until I found an opening.


2. Be specific. -- If you're going to deliver news that's hurtful no matter how you slice it (because, listen, people take their work personally, and being told they've failed those around them is always going to be an ugly truth) then you have to deliver it like it's ripping off a bandaid. No cotton candy puffery around it; tell them what they did wrong, who it affected, why it was hurtful, and how they can fix it. Cover the reporter's checklist when you're telling a person they've messed up. Don't qualify these statements; be direct and keep your sentences simple. "You fucked it up because you didn't include them in the conversation. It's your responsibility as team lead to make sure the right people are involved with the meetings they need to be a part of. You didn't do that here."
   
   The most important part here is to offer a solution if they don't come up with one on their own. In my case, Zach understood that he needed to talk to the injured parties and get them on the same page with what was happening and why. The part that I think really made it hit home for him was when I said, "You said that how we do reflects on you. Well, the other way is true, too. You should have known better, Zach."
   
   Which leads into my next point:


3. Know what approach to take. -- With Zach, a certain amount of directness and an addition of calling his work into question did the trick. But I didn't expect the depth of his reaction, and I apologized for being hurtful the next day. I knew how to approach this with him because I knew him well enough to guess. The same approach (including the parental "I'm disappointed in you" line) isn't going to work on everyone and could, in reality, backfire spectacularly. Don't lose the directness, but know what to emphasize in your conversation with them: logical arguments, emotional appeals, or a questioning of their values. For Zach, a purely emotional approach would have tanked; I went with logical and emphasized how his actions compromised his own values (and by extension, his self-image) inadvertently.


4. Follow-up with everyone. -- The hardest part of this process is the follow-up. You're going to have to check in with this person eventually and make sure that they aren't a seething ball of anger towards you, though hopefully they shouldn't be. If they are upset, let them explain why they are upset with you. It's a learning opportunity; chances are, one of you will have to do this for the other later on, because we all bork it at one point or another.
   
   But it's not enough to follow up with the person who dropped the ball; check in with the injured parties as well, make sure they when the reconciliation happens, they get what they need out of it.


5. Keep this to yourself. -- Presumably, you've been discreet (and maybe even discrete? I don't know your life) up until this point. Stay that way; don't brag, don't tell people that you've used whatever pull you had to help them out, don't shout your triumph from the rooftops. For one, this is a pretty sensitive topic for the person who was inadvertently hurtful. For another, hello Tackyville, population you. If you're doing this for the right reasons, the lack of recognition won't chafe.

The key to telling someone they fucked up is to do it one-on-one, be direct, and cover all the big questions. The other stuff -- following up, keeping your mouth shut -- are courtesies that speak more to your professionalism and class rather than necessities in the process.

In my case, I stepped in because I was the best person to do so. I respected (still do, honestly) Zach; over time I came to understand that he respected me (still does) just as much. I think that's the reason I felt brave enough to say something. I think, also, that because I was stepping in for others' sakes, it was clear my motivations weren’t selfish.

Regardless, being the person who keeps someone, especially someone reasonably influential in the company, honest and aware of the impact of their own behavior, can make you invaluable.