Why Isn't Hard Convo Flowing in Your Company?
How to encourage these difficult conversations
As leaders, we daydream about our teams constantly offering feedback to each other — the kind of feedback that leads to real changes in behavior, fosters growth, and ignites a virtuous cycle unlocking the limitless potential of our teams and our company.
Sounds pretty great, doesn't it?
You can measure your own growth by how many challenging conversations you’ve had. These interactions nudge us out of our comfortable spots and encourage new ideas and approaches, and we absolutely want the same for everyone around us.
Realistically, though…
Most companies are miles away from this kind of feedback culture, despite what their mission statement says. Because, well, hard conversations are hard.
No one wakes up thinking, "I can't wait to have a hard chat today".
Most of us are not trained for it.
When things go south, it scares us away from trying again.
And most of the time, we’re not great at handling feedback, either.
So, what's your job as a leader?
You have to work on creating the right environment and tools for this. Feedback loops require commitment. Whatever you're doing now, double it. Once that sticks, double it again.
One of my fav ideas is feedback on feedback. Create these systems and keep up-leveling it. Iterate on it. You want to encourage it, measure it, and make sure people are not putting it off.
Our natural inclination to avoid hard conversations will hold fast, but you want to foster an environment where people want to close the loop, so they can move on to their next idea or task.
A way to think about this in engineering teams is to:
crush the latency on hard feedback
Who should be having these?
Of course, these can happen between any two people. I touch upon crucial conversations in my earlier post here. But here are the opportunities between people that should be happening on a repeat, on a schedule, and in a way that can’t be avoided.
you and your manager
you and your directs
you and your cross functional peers
you and yourself (yay! to being hard on yourself)
What should be discussed?
That’s highly variable based on your employees and your organization, but you can at least get to the baseline that drives productive conversations:
Harvard Business Review, suggests that rather than relying on a feedback hierarchy, managers should consider a partnership model that distributes power and increases two-way conversation with their employees – a.k.a “window gazing” vs. “mirror holding.”
And then, Gallup data suggest that when employees agree they received "meaningful feedback" in the past week, they are almost 4X more likely than other employees to be engaged at work.
Personally, I lean on crushing the latency on both positive and negative feedback.
If I know my feedback may not land, then I work on how best to land it but not at the cost of reducing its latency. I don’t get it right every time but I have to keep reminding myself that it always feels worse in my brain.
Asking more of leaders
Sheryl Sandberg (Meta COO when I was there) would always ask her team, “When was the last time you had a hard conversation?” She pushed this relentlessly at company meetings and trainings, and it gave folks the green light to actually dive in and ask each other about it.
It’s a great question to ask prospective employers and has become one of my go-to's. I remember asking an entire executive team before joining, as well as everyone I talked to when starting a new role. You’ll learn a lot about how leaders and organizations deal with feedback, as well as what they care about most.
Hard conversation topics are nuanced and require a lot of practice and preparation, see how it is like peeling an onion for me, to make sure you’re having the desired impact. Hopefully, these insights help, and over time, it gets easier. It's not just a process, it's a culture, one that sets expectations right and helps embrace growth and open communication.
In your next time team meeting, ask folks to:
Raise their hands if they had a hard conversation in the last month
Make sure you are having them too, and crush that latency when you do.
Ty for reading! Vivek.
PS: Caveat of don’t be a jerk during hard chats is assumed and applies and is not tolerated.

