Tips for tough conversations
It’s become a cliche to say that navigating difficult conversations is a key part of getting things done in any tech company— or any organization at all. But what makes a conversation difficult? In my experience, engineering leaders I’ve mentored usually identify a few consistent features of a difficult conversational situation:
They want to be direct and efficient: to say just what they mean without euphemism or circumlocution. This is sometimes a personality-based preference, but often comes from a sense of urgency around the message.
They want the message to be effectively received and acted on. They don’t want to feel like they’re shouting into the void: they want people to really listen to what they have to say and act accordingly.
They want to be well-received socially while delivering the message: not to come across as an uncaring jerk or clueless newbie, not to burn bridges for saying something too bluntly.
I’ve given the same advice on how to thread that needle now for many years. My reports and clients have found it useful enough, repeatedly enough, that they’ve started asking me to publish it more widely. So here they are: Nick’s tips for tough conversations.
Above all, recognize that good conversations are hard because trust is hard. Direct, blunt communication with someone you have close mutual trust with is awesome, but that trust is rare and hard to build. The goal is to simultaneously
build the foundation for trust as fast as possible
and get points across effectively while it's still under construction.
Ideally we wouldn't need that foundation in order for the direct approach to work, but in practice we do.
Some of the best strategies for this I've found:
Emphasize up front the most important single thing you would like from someone and the most important reason why you want it. Ideally, state that in terms of a goal you'd like them to help achieve rather than specific steps to achieve it. If you have a stack rank of goals, that's great, but if not, just pick #1. That way, you avoid muddying your message and make efficient use of everyone’s time.
Acknowledge others' point of view and motivations even when you disagree with them. Make an effort (which can feel like making a bit of a show) to demonstrate that you have done the mental exercise of putting yourself in their shoes. This builds trust by demonstrating to others your respect and sympathy for them. It also helps ensure that, when you disagree with them, you respond to their strongest arguments.
Where feasible, get across your points with questions more than answers. Leading or "Socratic" questions, or questions followed by statements about your own experience that motivate/justify your point, are fine and indeed a great teaching tool. But the key is that the questions are not merely rhetorical: it should be clear in the phrasing of a question that you're open to learning something from an unexpected answer. This again demonstrates respect and sympathy and puts people in a better frame of mind to say, "Hm, that's a good question, I hadn't thought of that."
Emphasize future-orientation of questions and goals in particular. If you think a past decision was wrong, and past experience demonstrates it was wrong, try to only say that if it's absolutely necessary to inform the question of what to do next. This is hard to do when you have good reason to believe that big past decisions were in fact terribly wrong. But it’s especially important when you need to get people who had a hand in those decisions on your side!
Have your justificatory data-- with comparative context explaining e.g. why a number is actually big or small-- as close to your fingertips as possible. This is super hard and nearly everybody screws it up sometimes; I certainly do. It is also super frustrating when people ask for data in a way that demonstrates their broader contextual ignorance. Nonetheless, in engineering today, "show me the data!" is a socially approved reflex response, so it's worth thinking ahead about how to handle that response efficiently.
I hope you find these tips useful. If you’d like to have a deeper discussion about how to apply them in your particular situation, you can schedule a free 30 minute intro chat at https://calendly.com/nweininger.
