Awareness, skill, or will - why you should have more kind, uncomfortable conversations:

I grew up a conflict-avoidant person. The hardest part of my day-to-day job is stepping in when a teammate is missing the mark. It’s tough because the right thing to do is to have an immediately uncomfortable conversation with that person. But what if my words make them feel bad? What if I’m wrong, and they know it, and I end up looking like a jerk? What if I reach out, but they hate me anyway and start giving me the cold shoulder at the office?

Despite the discomfort, intervening and having hard conversations is the most crucial part of my role. By leaning into these uncomfortable moments, I’ve learned two things: first, people rarely react angrily after tough conversations; and second, to my surprise, folks feel more cared for afterward, not less.

So why is it important to address issues immediately? When someone fails to deliver on the job, it’s typically a problem of awareness, skill, or will. They either aren’t aware they’re not meeting expectations, they are aware but lack the expertise to execute, or they are aware and can do the job but choose not to.

Let me share an example. Once, a teammate was consistently missing deadlines. Instead of assuming they were uncommitted or bad at engineering, I brought it up in a one-on-one. It turned out (as is so often the case) that they were unaware that their delays were impacting the team’s progress and that there were even noticeable delays in the first place. After our talk, they adjusted their workflow, and the issue was resolved. They’re now perceived teamwide as a better engineer.

Addressing a teammate’s lack of skill or motivation is a challenging task that can’t be solved overnight. However, most issues stem from a lack of awareness, which is the quickest to resolve. It just requires a swift, albeit uncomfortable, conversation. Pull the teammate aside, step into a room or hop on a call, and express—genuinely and from a place of care—that they’re missing the mark. You’re not there to tell them how to improve or that they should be doing better. Instead, you want to help them understand that there’s a gap in the first place.

Now, it’s possible you’re mistaken. Maybe they’re actually doing great, and you just don’t see it. But giving negative feedback is uncomfortable enough that people almost always under-communicate rather than over-communicate. By the time it’s noticeable enough that you’re considering a chat, your intuition is probably onto something. Maybe they’ve heard it before—that’s okay. You’re adding a second independent data point that can help build deeper awareness.

The key to building awareness is to always act from a place of kindness. Point out the issue, but underscore the honest truth that you care about your teammate and wouldn’t be saying something if you didn’t. Only close friends, mentors, and loved ones tell hard truths privately face-to-face; true jerks just insult and criticize behind others’ backs. You don’t have to be a manager—you just need to be someone who cares about your team. When done right, I’ve been surprised to be thanked by folks for having a tough conversation.