Glad you asked! This question is especially relevant to me right now, as I’m currently learning a new prototyping tool here at Slack. 🙃
Whether you’re trying to learn a technical skill, a new industry tool, sharpening your visual design chops, or leveling up a soft skill like public speaking, the only way to get over the hump is to roll up your sleeves and try it out. Allow me to break it down tactically.
1. Go to the source.
Chances are, if you’re thinking about learning a new skill, you got that idea from the work of other designers. Find someone you admire who is doing what you want to do. That might be an individual, but it could also be a collective (say, a product design team at a specific company), or even a community of people who are excelling in the particular skill you’re interested in. Take note of how that designer or team works—how they use the tool, how they arrive at solutions. Literally, take notes, document it all.
For example, when I joined Slack, I was particularly keen on improving my presentation skills, so in my first six months, I paid close attention to how my peers presented to execs and other designers at the company. I wrote down how they set up the context, how they kept the discussion flowing and on topic, even how their body language adjusted when receiving constructive feedback.
Go back to your own work and identify the exact gaps between you and that skill. If you can’t identify the gaps, chances are, you haven’t looked hard enough. Be honest with yourself. Being detail oriented is important when learning something new.
My biggest weakness when I evaluated my presentation skills was my body language. So, through watching my colleagues, and with the help of a book called You Say More Than You Think by Janine Driver, I realized that I had been communicating so much more than the words I was speaking or the content of my slideshows. My eyes, my posture, and my hands were all delivering critical information to them without me knowing.
3. Ask for (specific) help.
You may not always be able to get advice directly from that one designer you love — I was lucky that my peers were my coworkers and wanted me to succeed — but you can pay attention to what anyone is doing, to what makes them good at the skill you’re honing.
If you’ve done your homework on a designer, though, you can of course try reaching out—you never know when someone will be game to help out a fellow designer! If and when you do, make sure you have specific questions prepared for them—the questions you might not be able to answer for yourself by studying their work from afar.
4. Be relentless…
This has always been the hard part: attack the gaps in your own skill set with what you’ve learned. Practice, perfect your craft—the only way to really level up a skill is to just do it—a lot, over and over again, until you conquer it. For me, it took writing down the new habits I wanted to practice with my body language, reviewing and practicing them before going into every meeting/room to present a project. One time, I even booked a phone conference room to meditate, saying out loud the body language I wanted to keep during the meeting and specifically calling out what I was going to perfect during the upcoming meeting.
Don’t forget to be kind to yourself, though. Growth is about the process. Take your focus off the end result, and learn to celebrate every step of the process, because each one is a choice you’re making to improve yourself.
5. … But don’t be afraid to be vulnerable.
Lastly, in my eyes, part of “learning” is also sharing. It’s not enough for you to learn that new skill in the shadows. To test if you really improved your presentation skills, visual design chops or product thinking, you’re going to have to get uncomfortable. Present to a larger group, bring high fidelity work to a group of designers to critique it, etc. That moment of discomfort? Those butterflies in your stomach? They’re a sign that you are stretching that muscle. Keep stretching!
Best of luck!