3 Rules of Hard Conversations
I remember my first hard work-related conversation. To set the scene, it was the late 90s and I regularly wore Gap overalls and Tretorn sneakers to the office while rocking a pixie haircut dyed Raggedy Ann red and a pair of glasses perched on my little nose on a face still somewhat childishly round. I was just past drinking age, and had just graduated from a PR-writing job to a real copywriting job at my very first agency.
The ECD at said shop was a notorious hard ass. He didn't really want me in his department but was short staffed and I had people on my side, so he was already predisposed to give me a hard time. To make matters worse, I had so many questions, about everything. Including the brief I was given. Who was this for, why would they care, what kinds of things did they need, etc. (Shocking that I ended up a strategist, yeah?) It was implied that I was paid to write and not ask questions, but I girded my proverbial loins before the next creative review and went in with a few options and a bunch of questions, because it felt like the right thing to do in order to get to better work.
I was told that maybe I didn't understand what my job was, and that if I couldn't figure it out perhaps I should find a new one.
Oof.
You never forget your first one.
I've had a number of really awkward, strained, panic-inducing conversations in the 20ish years since that first one. I've had them with clients (like the time I had to fire one for being abusive to our team), I've had them with direct reports (like the time I had to confront someone who had accepted a job on my team, hoping it would land her an immediate job on someone else's), I've had them with bosses (like the guy who thought it was cute I wanted to be paid more), and really there are just so many.
I've said before on this blog that I've been incredibly lucky to have excellent mentors throughout my career, and they've definitely taught me a thing or two about having tough conversations. And some of it is just living it, and trial and error, and storming into a conversation that goes sideways and suddenly realizing what a horrible error you've made!
Here are three things I've learned along the way:
You've gotta have the hard conversation. (Caveat: Unless it's unsafe for you to talk to the person causing you grief/panic/anger, in which case you probably have to have a hard conversation with someone else.) There are two types of hard conversations: the ones you have because someone has caused you pain, and the ones that are centered on uncomfortable topics. In either case, you just need to do it. The longer you put it off, the worse it will be, the more your resentment will build, the more chances the person has to upset you again, the longer you go without the raise, etc. I have seen people leave jobs they love rather than have hard conversations. That's nuts! I'm not telling you anything you don't already know here. Yes, you have to do it.
Hone your point of view. Do not go into a hard conversation unprepared. What is the outcome you're hoping for, and what are the most important points for you to make? Getting tight on what you what to say can be grounding. I also wouldn't rule out rehearsing what you want to say — even role playing with a trusted friend or mentor! — so you have it in your bones when your hands are shaking, your guts are clenching, and you want to run out of the room. P.S. I've sometimes found myself having hard conversations before I'm ready, which is less than ideal. Over the years I've gotten better about asking for time to think things through. Try this: "I'd like to think through how I feel about this, can we chat more tomorrow?"
Be prepared for any outcome. In my experience, most hard conversations are only hard for the first five minutes or so. Once someone has started the ball rolling and everyone's cards are on the table, the feeling is usually relief. Satisfaction even. But there are definitely times things won't go your way. For instance, your boss telling you that if you don't like something, perhaps it's time for you to move on. (Thanks, Bob, you jerk.) So, while you're prepping the things you want to say and the thing(s) you want to ask for, also prep for what you will do if you don't get what you want. Are you willing to resign? Will you have to escalate the situation? Who will you escalate to? Are you willing to compromise? To what extent? Again, knowing how you'll respond to different outcomes will give you more confidence in the room.
Back in 1998 I decided being a copywriter wasn't for me. I mean, it wasn't. I'm not built for it, but I think back to that horrible conversation and how I sort of froze, backed out of the room, and then cried in the nap room (anyone remember those?). I hate how it cemented an impression of what workplace conflict would be. For a long time I was willing to just keep my head down and my mouth shut, which caused all sorts of different problems.
Having hard conversations will never not suck. I had one last week, and I still got that gross feeling in the pit of my stomach and sweaty palms. My voice was embarrassingly shaky for a sentence or two. But it does get easier to plan for them, to identify the root cause of the anxiety or the most important points of debate, to know what you need from the conversation and to ask for it.
// Image by Christin Hume