Overcoming Shyness in Remote Teams

Content Marketer
9 min read

This morning, I found myself rewriting a reply to my colleague for the fourth time before pressing send.

That’s how it goes with almost every email or Slack message I send to colleagues or customers. I fear a typo going unnoticed, or that no one will understand me, or that none of my team members would want to pause and speak to me about an article. Such patterns of thinking have often led me to remain silent instead of asking important questions. They have made me pause and doubt my ideas, even downplay my achievements at work.

This is a problem because the spoils often go to the brave at work.

In remote teams, speaking up about the progress of your work and sharing results is even more important—as you don't have in-office visibility to fall back on, e.g., casual conversations, peering over your colleague's shoulder, or walking over to your boss' desk!

At my last job, I watched as the people hired on the same day as I got promoted and led their own teams. Their advantage was that they were vocal in every meeting and present in every Slack thread. I learned that my work would not always speak for me; sometimes, I had to be the one with the megaphone.

In an async remote culture, there's an even greater responsibility to communicating well as you don't have the crutch of a "status meeting" to keep everyone informed. The onus is on you.

Working async remote at Float gives me the freedom to schedule meetings at convenient times and places (like my favorite library).

How my shyness manifests at my work

Shyness affects everyone differently. Some might experience physical reactions like sweaty palms, your brain going into overdrive with self-deprecating thoughts before a presentation, or freezing up when a team member says good morning. In whatever ways it appears, shyness can stand between us and our best work life.

If shyness was a spectrum, I’d say I am somewhere in the middle between those who avoid interaction at all costs and those who summon the courage to speak when necessary.  

A spectrum showing the range of shyness from extremely shy to moderately shy to slightly shy.
The spectrum of shyness

I am comfortable speaking in 1:1s, but if I have to speak before a group of people or send a message to a Slack channel (most of which are public and open to a team of 40+ people), I immediately freeze up.

For someone who is shy, building the confidence to send async messages was, admittedly, a learning process.

33 slack drafts that may never get sent.
I'm probably never going to press send 😅

In my first year at Float, I avoided setting up meetings or making requests of anyone unless I absolutely had to.  

And when I finally did start a conversation, I became tongue-tied when people responded to my messages. I decided that I would get back to them (eventually). But the more time passed, the more awkward it becomes to send a reply.

How Float's async remote culture helps me communicate confidently

One day it hit me, our async work culture was a good thing! I could use it to my advantage as a shy person.

At Float, one of our values is to respect each other's time by defaulting to productive communication. In the 'How We Work' section of our handbook, you'll see our CEO Glenn explain that "we place an unusually high value and expectation on concise, proactive, and productive async communication."

Productive communication means that we only have to communicate when it is necessary and when there's a message to pass across. Hurray to less awkward conversations about the weather 😅.

Also, asynchronous communication enables me to share my responses only after I have thought about it. As our Senior Content Marketer, Nikoletta Bika says, "an asynchronous message is almost always a thoughtful message. You can think it through and self-edit." I do not feel the pressure to provide a quick-fire response. Instead I can fully evaluate what I am going to say and how I am going to say it.

And when I do respond, I can communicate in a context that is comfortable for me.

As mentioned earlier, I feel more at ease speaking to people when the conversation involves fewer participants.

I usually try to participate discussions in open channels, but there are times when I don’t feel comfortable doing that. During those moments, I tend to default to private messages. A best example is using a private message to refine a topic with another colleague, and then posting it in a public channel when I'm confident of the best way to share it.

Another strategy I use is recording Loom videos instead of engaging in live calls. Asynchronous communication like using Loom, allows me to share my ideas async instead of feeling the pressure of presenting during a meeting. Additionally, I can choose whether to have my video on or off while I speak through my points.

This allows me to opt for my preferred communication style while still interacting with my team members.

I often use Loom to communicate async with my team

However, it is important not to forget that you have to remain visible and be the loudest champion of your work. Async communication can become a trap when you use it to hide, instead of shining.

To avoid falling off the radar at work, I use reviews to my advantage and cultivate relationships with my team mates.

Reviews at work are an opportunity to turn the spotlight on myself and create a dedicated space for feedback. While sharing achievements might not come naturally if you're shy, I've found that reviews are helpful for me to reflect and share what work I'm most proud of. It's also great for seeking career feedback, which at Float, communication and leadership is a key skill for career and role planning.

Asides from reviews, my weekly check-ins via 15Five provide an opportunity to highlight my work with my manager. I try to share a win, even if it is a small one, and let her know any challenges I might be facing too.

I share weekly updates on my ongoing projects in 15Five

Our monthly marketing reports give me an excellent opportunity to discuss the outcomes of my work. I outline the articles I've written, the effectiveness of my strategies, and my plans for the next month. Since these updates are asynchronous, I can demonstrate my contributions to Float without the anxiety that comes with presenting to a room full of people.

Being intentional about relationships is also important. Familiar faces at work can form a support system.

To avoid staying in my shell, I regularly reach out to people who are open and great conversationalists. For example, I love chatting with Romina about Nigerian culture, having insightful discussions with Christian and Colin about our engineers and their work, and learning from Michael about the product and problem-solving.

Speaking to friendly team members like Colin makes it easier to initiate conversations

Thanks to these relationships, approaching my colleagues with questions or concerns, feels natural and comfortable.

Many of these connections blossomed through light-touch Slack rituals, e.g., our weekly weekend updates or chance conversations about shared interests, e.g., in our #general channel.

So even if you're shy, try to seize the small moments to connect more personally with your colleagues and build trust. Fortunately at Float, our operations team have put a lot of thought into weaving these opportunities into our async culture.

Four simple tips to help you thrive at work (even when you are shy)

Here are some simple tips that can make communicating in a remote team easier for shy people.

Always ask why

When negative thoughts creep into my mind while I'm working on something, I don't just accept them. Instead, I question them: Why am I thinking this? Is it really true?

For example, if I have to ask a colleague for their input on a topic and I worry that they won't respond, I examine this thought closely. I might discover that I fear rejection, which holds me back from reaching out. However, when I think about it, I realize there's no evidence that this person would say no. So, I decide to give it a shot.

Pausing, reflecting, dismissing unfounded thoughts, and seeking the truth help me fight negative feelings that disturb my work.

Get support

Let your team know when you are struggling so that they can support you.

Sharing your struggles with your team might seem impractical or uncomfortable. You might be thinking, "I'm already struggling to talk to people, and now I should bare my soul to them?!"

Yes, that's precisely what I'm suggesting.

Soul-baring might come easily to me because I am an open person. But I have found it very helpful to be candid about how interacting with others makes me feel. My team members step in to help in the ways that they can.

For instance, my team helped me review and improve the outreach templates I created for contacting subject matter experts. This act of support made a significant difference and boosted my confidence.

Keep your motivations on the wall

In 2020, I had to send over 200 emails to total strangers – CMOs, marketing directors, and content leads – asking them if they needed a freelance writer. It was nerve-wracking, and I found myself procrastinating for several days before sending the first email.

What eventually helped me take action was reminding myself why I needed to do it. At that point, securing steady work was essential. When I focused on my motivation, a lot of my self-doubt faded away.

Recently, I started applying the same approach to my work. Whenever a task needs to get done, I remind myself of the reasons behind it, making it easier to stay focused and accomplish things.

With great communication being an embedded part of our async culture, I can remind myself that this is part of the job! In fact, it's even said that, "there’s a 100% overlap with high performers and great communication at Float".

(I'd better hit send then!) 😉

Just do it

Push aside your discomfort and stop overthinking. Just take action without worrying about perfection.

This might sound like motivational advice 😅 but it actually does work.

Personally, I've started hitting 'send' on messages and then refining them later. I also proactively ask for interviews, accepting whatever answers come my way.

The worst happened–someone said no to me. And I am fine.

By acting without giving in to negative self-talk, I've noticed my work speed improving, and I'm becoming more resilient against such thoughts (which might always be there).

Remember, the worst-case scenario rarely happens. And if they do happen, you'll be fine. It's better to try and risk embarrassment or rejection than to never try at all.

You don’t need to change who you are to thrive at work

Much of the advice on overcoming shyness aims to transform introverts into extroverts, which can be stressful and unsustainable.

What works best for me is finding small compromises to push myself to speak up, express my opinions, or raise objections. I create comfortable spaces for myself and seek support from my team members.

I firmly believe that success at work doesn't require completely changing who you are. Instead, you can leverage your shyness to your advantage and actively address any negative aspects it may bring.

For async remote teams, overcoming shyness is an important factor to building trust and rapport with your team early on. Fortunately, async communication means that you can take the time you need to refine your message and choose the best medium to communicate via. The more you practice, the easier it gets to speak up—sometimes (yes, sometimes), you might even look forward to it!

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