It was years ago, but I remember it well. I’d been at my company for less than six months, and had spent a good deal of that time trying to figure out how the Product and Engineering team could deliver an enormous system that had been promised to a large client 18 months ago anywhere near on time. The team and I had spent hundreds of hours meeting with the customers, understanding their requirements, discussing system architecture, estimating our work, and building the foundation, but we were at a loss. If each of our engineers worked hundred-hour-weeks for the next five months, we’d still be late.
My boss, who had closed the deal, is one of the smartest, hardest working people I’ve ever known, but he could be scary. Much of his career has been spent willing impossible things to happen and then working tirelessly to make them possible. I dreaded telling him that the project would be late, and since I was relatively new in my role, I sought advice from other members of the Executive team. “I wouldn’t do that,” our VP of Engineering said, “it’s going to make him angry, and it’s going to make you look bad.” “Avoid that discussion at all costs,” our CFO told me, “find a way to deliver.” But I’d done the math, and there was no way. I had to let him know.
At our next touchbase, I approached the conversation with my boss cautiously. “We’re going to be late,” I said, “by at least six months.” It was not a situation where we could force people to work more. There were more hours of work to do than there were hours remaining on the calendar. I’d push the team as hard as I could to deliver quickly, but we needed to start resetting expectations with the client. I knew it was terrible, but we had no choice.
I don’t remember all the things my boss said, but I remember the overall message: we were in this situation because the team didn’t fully appreciate the commitment they’d made, because they weren’t wiling to put in the work, and because I wasn’t pushing them hard enough.
“Everyone warned me not to tell you this,” I said, “but whether or not you want to hear it – or are able to hear it – doesn’t change the situation we’re in. The only thing it changes is what we do about it. If we’re going to work together,” I continued, “I need to be able to tell you these things. I need your help.”
It would be a gross oversimplification to say that everything changed in that moment, or that my boss suddenly accepted what I was telling him without asking lots of hard questions, pushing back, and fighting like hell to stay on schedule. He did all those things, and he was right to do them. But from that day on, we were a team, in it together. And what more could I want from one of the smartest, hardest working people I know?
Clear communication and active listening are good too
Communicating clearly and listening actively are critically important skills, both at work and in the rest of our lives. This post isn’t about either of those things. This post is about why leaders need to listen to their people specifically when they don’t want to hear what they’re saying. When the news is bad.
I could write endlessly about how our inability to face facts that don’t align with our preconceived notions is hurting our relationships and our country, or about how social media creates an echo chamber that threatens to destroy democracy and the world. Fortunately, lots of books and articles on these subjects already exist, saving me an enormous amount of time and energy. 😉 Instead, here are a few thoughts on why listening to the things we don’t want to hear makes us better, more effective leaders.
Reason 1: It Helps Us Build Better Teams
Several years ago, I wrote about Google’s Project Aristotle and the importance of psychological safety at work. People who are free to communicate openly, without fear of criticism or attack, are more likely to tell you what’s really happening. They’re also more likely to take chances.
Blameless postmortems, which Google describes as those that “focus on identifying the contributing causes of the incident without indicting any individual or team for bad or inappropriate behavior,” get at the same thing: when people can openly discuss issues without fear of being berated or losing their jobs, they can be less afraid, more truthful, and more creative.
Reason 2: It Builds Trust
Relatedly, have you ever tried to trust someone who only wanted some the facts? How confident can you be that, when things get tough, your boss – who only has half the story – will have your back? Trust requires openness, and openness requires listening to the things we don’t want to hear and responding in open, helpful ways.
Reason 3: It Makes Us Smarter
The conversation I had with my boss provided the perfect entry point for lots of gnarly, detailed conversations about the business and how my team worked. Through those, I learned more about my company’s sales process and the seasonality of our business, which helped me get better at planning our work. And my boss learned more about the system limitations and people issues I was dealing with. This information made each of us smarter, and – as a result – better at our jobs.
Reason 4: It Makes Us Proactive, Not Reactive
There are very few good surprises at work – even bonuses generally come on a schedule. Typical work surprises involve things like projects being late, expenses being too high, and people leaving. I can’t think of a situation in which I wish I had less to time to understand an issue, formulate a plan, and react appropriately. Can you?
Lots of surprises happen because employees are afraid to share bad news. Which leads me to my next point…
Reason 5: It’s Probably Something We’ll Have to Have to Deal With Eventually
Some problems go away with time. Most don’t. On the morning of March 11, 2020, I told our division leader that I’d been reading up on Covid-19 and I thought we were going to have to go to remote work sooner than we’d expected. He angrily dismissed my concerns and sent me away. Four hours later, corporate headquarters shut us down. The lesson is clear: if you don’t deal with it now, someone else might deal with it for you later.
Reason 6: It Makes Us Part of the Solution
You know who the team turns to when things go south? People who genuinely want to help. When my teams tell me something’s gone wrong, my first question isn’t “how did this happen?” but “how can I help?” (We’ll have time for the blameless postmortem later.)
What Do You Think?
Those are a few of my thoughts. Now I’d like to hear some of yours. Does my experience match yours? Do you disagree? Have you ever had a boss who was great at receiving bad news? What did they do that made them great?
And what about you? How do you respond when somebody tells you something you don’t want to hear? I’d love to know.
When I arrived at a new job several years ago, things were looking good. Work/life balance favored life, the dress code was non-existent, and employees were on track to get bonuses yet again. Our website was usually up, returns were usually down, and customers were generally pleased.
There are all sorts of great ideas contained in 
Lee Zukor 