Note: I wrote the following note over a year ago, but only recently decided to send it to my newsletter. I’m not sure why I sat on it so long. Your [respectful] thoughts are welcome on Twitter.
Empathy doesn’t always come easy, but it goes a very long way toward building trust with those around you. I’ve seen many well-intentioned people lose the trust of their peers because they fail to communicate with empathy. Perhaps they rush when replying to a message, or they fail to set aside frustration with a decision they believe should have gone a different way. In many cases this is a matter of differently weighed trade offs or a misunderstanding about who is empowered to make a decision. It turns out these things are sometimes unclear.
It’s important to take a step back in moments like these to get a broader view of the situation: try to understand the position the other person is in, their priorities, how they may be weighing trade offs differently from you, whether they have context you don’t, and who should make the decision. Afterward, think about how to move the conversation forward in a way that’s constructive in the short and long term. Be direct, but diplomatic and try to address their concerns directly.
I understand using light gray for the text color here is important to you because it matches our logo, but it’s really important that the contrast is high so people with colorblindness can read it.
This example is intentionally low key — let’s set that aside. We start by showing empathy for our colleague’s point of view. We tell them we understand their concern and attempt to repeat it. This gives them a chance to correct us if there’s a misunderstanding on our part. We then share our proposed decision and the explicit trade offs we’ve made. In the first example above, we posited accessibility was more important than whether text color matches our logo color. Making implicit value judgements about trade offs explicit is key to building understanding.
If we don’t understand the concern then we ask clarifying questions.
I want to make sure I understand your concern. Are you worried about whether the text color matches the logo, or are you generally worried about brand guidelines? Is it something else?
Earlier I said to be “constructive in the short and long term” but what I really mean is if you treat people poorly then they will not want to work with you. If you do this repeatedly then you’ll have a bad reputation and, in turn, your effectiveness will go down over time as more teammates view working with you as a burden.
You might have been told to “disagree and commit” at some point in your career. Knowing when to fold ‘em, as they say (whoever “they” are), is an important tool in maintaining trust long term and maximizing your effectiveness at work. When deciding whether you should disagree and commit you should consider the long and short term ramifications of a decision and whether you’re the person empowered to make the decision. For instance, if the decision is regarding something like the naming of an internal API then arguing until you get your way is going to erode some amount of trust from your teammate(s). Over time situations like this will cause you to be seen as an inflexible person. On the other hand, advocating for something like maintaining or increasing user privacy is likely really important and is worth fighting for.
You might also be asked to consult on a decision. This might come in the form of a friend or colleague asking for advice, or some sort of group setting that’s more formal. It’s important to recognize your place in these situations. Are you being asked to give input or are you the decision maker? It’s important to set your expectations accordingly to avoid disappointment if the designated decision maker makes a decision in conflict with your advice. If you don’t understand the decision then ask what trade offs they made or what additional context and inputs they took into account. Remember that they may weigh trade offs differently from you and that’s okay.
If you’re a decision maker asking others for advice, then set their expectations early. Some people may need you to tell them their input is valuable and appreciated, but you are also taking many inputs into account in some broader scope. These people may also need to be told directly that you may make a decision counter to their recommendation if other inputs need to be weighed more heavily. This approach can help avoid needless escalation and conflict.
Resolving conflict is more difficult if there’s not a well-defined decision maker. For example, consider the case where you and a peer have conflicting viewpoints on a decision and you’re at a stalemate after going through the process. In cases like this it’s helpful to bring in a third party to mediate or break the tie. It might also be helpful to consider whether the decision is reversible. If it is, then it’s easier to disagree and commit to move forward. If it doesn’t work out the team can take its lumps and change course. Most decisions are reversible.
A final note: it’s sometimes quite hard to strike the right balance between directness and respectful tone in text. Try talking to your counterpart face to face or video chat if a conversation goes sideways via text chat. It may remind you both there’s a human on the other side of the discussion.
 It’s important to keep ethics in mind here. If you’re fighting to uphold some ethical boundary then it’s always worth continuing to advocate for your position.