Dear 26ixty: Corporately Clueless

Welcome to Dear 26ixty — a new column where I take your questions, dilemmas, and chaotic situations and answer them the only way I know how: honestly, from experience, and like a friend sitting on the couch with you having a deep, late-night talk. Have something on your mind? DM me. I’ll do my best ♡

Dear 26ixty,

At work I got a direct report (I’m the manager) who is super shy and quiet and the rest of the team is complaining he’s not contributing to problem-solving, etc. And it’s gonna become a bigger deal if we don‘t fix it.

How do I bring it up without making him feel awkward and self-conscious?

— vine boom

---

Dear Vine Boom,

Fifteen year old me sat around a Harkness table — a large oval, twenty students all talking over one and another, trying to sound more pretentiously intellectual than the next — absolutely terrified to open my mouth. So when you asked me this, Vine Boom, I knew exactly who your direct report was.

I wasn’t confident in myself at that time, and who is at fifteen? The only true place I felt confident was when I was penning my thoughts to paper, where I could process, realize, and articulate what I wanted to say. Of course, it also didn’t help that I was the scholarship kid at the fancy, private all-girls school. There was already a sense that I was an outcast, and I can still see the smirks of the more fortunate girls in the back of my mind.

A decade later, I still remember this one particular day like the back of my hand. There was maybe five minutes left of class, right before the lunch bell. The teacher told everyone to stop and started calling out five of our names one-by-one, asking us to stand. I stood standing alongside four other girls, us looking at each other in total fear. The teacher commented how we had not participated in the discussion and that the class would not be dismissed until we each said something. In that moment, I had completely forgotten everything about the book we were reading. The only thing I was focused on was the fact that I had to say something — cheeks red, hands sweating, body trembling. And I would constantly beat myself up for it, asking myself what was so wrong with me that I can’t just speak. From that moment forth, I absolutely dreaded going into that class and for a moment, even resented writing because of that.

After graduating college, I had reconnected with some of those girls separately who happened to be apart of that humiliation, and we ended up discussing it. I found that what we all had in common: we never forgot that moment, it hindered our confidence, and we were all equally hard on ourselves for not participating in the first place. It’s not that we didn’t want to, we were all just painfully shy.

---

But on the contrary, I also had a chemistry teacher, who never once singled me out or asked me to participate more. And the only thing I loved more than writing was coffee — which she knew, and would sometimes send me e-mails through our school network of caffeine molecule related jokes and memes. One time when we had to choose an element to do a project on and I chose lithium, I remember her looking at me in my Hot Topic band tees and immediately asking, “Evanescence or Nirvana?” Both.

Before I realized it, we had an unspoken deal almost where whenever we had our monthly presentations in front of the class — something I absolutely dreaded — she always had me first on the list to present. There was something about me knowing in advance that I’d be the first to go and then it would be over with that gave me so much more relief and confidence. Compared to other classes where I’d sit waiting for my turn, not even focused on the presentations ahead of me because I was so scared to do my own.

I excelled in that chemistry class and it was my favorite that year, even though I had never been that into science. Halfway through the year, I was regularly raising my hand, asking questions, and participating like a functioning-non-anxiety-ridden student for the first time in my life. And it was genuinely because the teacher had fostered such a safe and positive experience for me to do so.

---

When I started at my first job years later, I was still very shy, but not to the point of hands-trembling anymore. Just very quiet, smiles and nods, not really offering my opinion, much like your direct. But since getting to know the team through time, holiday parties, and bowling hang-outs, I regularly joked around with my team and felt comfortable voicing my thoughts and concerns — like a time when I felt I was the only one doing all of our side work. Something I wouldn’t have been able to self-advocate for had it not just been through time and low stakes moments where nobody is performing for anyone. So if there’s any way to build in something like that, even something small like a pizza party, it’s worth it.

---

And this is all to say, Vine Boom, that I have been on both ends of your problem — the one who was doing too much and the one who wasn’t doing enough. I know firsthand how frustrating it can be to do all the work, but I also know how hard it can be to just open up sometimes.

I can tell you’re a good manager by the fact that you asked how you can bring this up without embarrassing him, or making him feel self-conscious. From an introvert’s perspective, having that talk with him privately instead of humiliating him in front of his peers is definitely the first step, but I suspect you already knew that. If he really is that introverted, odds are he probably knows he needs to speaking up more, and he might already be hard on himself about it.

So while you need to have a discussion with him, maybe don’t emphasize on the fact that’s he shy and just slip it in while trying to connect with him a little more. The more comfortable he feels around you, the easier it’ll be for him to speak up. Not to say you have to become his new best friend, but fostering some sort of professional relationship where he knows that you’re his boss, but also that you still genuinely care about him and his growth — and I can tell you do.

Do you know of any of his interests — a particular band, or game, or something he’s mentioned before? Maybe just ask him how his weekend was, try to relate to him personally, and casually slip in the part about participation. I think it’s all about the approach: if it seems like a lecture or he’s in trouble, he might take it harder, but if it’s a friendly conversation with a tiny bit of constructive criticism, I bet he’ll leave that meeting feeling more positive and confident.

Or maybe you don’t even need to bring up the shyness at first. Maybe just have a small talk with him and then ask “Hey, what did you think of (insert something from the last meeting)?” And when he tells you privately his idea, really just encourage him and hype it up. Verbally affirm that he has good ideas that are worth sharing. Maybe if you’re able to email him some notes on the meeting beforehand so he has a moment to think and prepare what he could say.

The chemistry teacher never made me feel like my silence was a problem to be fixed. She just made me feel safe enough that I eventually fixed it myself. I think that’s all he needs from you — and something tells me you already know how to do that.