How to Speak Up at Work Even When You Feel Awkward
Ever stayed quiet because you were afraid of sounding awkward—then replayed what you should have said all afternoon?
In this Quick Lift, Betsy shares the biggest takeaways from her conversation with Henna Pryor about building confidence, moving through uncomfortable moments, and making sure your good intentions actually come across. Because speaking up is one step. Getting your message to land is another.
You’ll learn:
- Why feeling awkward doesn’t mean you’re an awkward person.
- How small “social pushups” prepare you for bigger conversations.
- How to recover when you stumble, blank, or say something that doesn’t land.
- Why well-intended emails and quick replies can undermine trust.
- How acknowledging a difficult reality makes reassurance more believable.
Listen to the full conversation with Henna Pryor → Here
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0:00 Welcome to Loud and Lifted Quick Lift. I'm Betsy Hamm, and this is where we take the biggest ideas from my longer conversations and turn them into something practical you can use this week. What's something you've been putting off because you know it's going to feel awkward? Maybe it's asking for an opportunity you want, telling someone you disagree or walking into a room where you don't know a single person. You know there could be something good on the other side, but first you have to survive the part where you feel a little uncomfortable. And apparently, we will reorganize our entire inbox to avoid that part. We tell ourselves we'll do it when we feel more confident, when we find the right words, or when the timing is better. But how many opportunities are we passing up while we wait to feel ready?
0:45 That's why I love my conversation with Hannah Pryor, author of Good Awkward. She talks about learning to handle the uncomfortable feeling so it stops making our decisions for us. Because if we want to do something bigger, Different or new, some awkwardness is probably coming with us. Hannah is a workplace performance expert, executive coach, keynote speaker, and author of Good Awkward and The Signal Gap. We started with awkwardness and confidence, then got into communication, credibility, and trust. Because being brave enough to speak up is only part one. Making sure people understand what you're trying to say is another. These are the five takeaways I wanted to bring back to you, so let's get into them. Takeaway number one. Feeling awkward doesn't make you an awkward person. Hannah explained that awkwardness is an emotion. It's a feeling that comes up in social situations often because we don't know how someone will respond. But listen to the way we describe ourselves. I'm so awkward.
1:46 I'm terrible at networking. I'm just not good at talking about myself. We take something that happened or even something we're afraid might happen and turn it into a permanent description. of who we are. And then it starts limiting us. We skip the introduction. We don't ask the question. We let someone else take the lead because we've decided that's just how we are. I like Hannah's distinction because it gives you room to do something different. You can feel awkward asking for the opportunity and still ask. You can feel uncomfortable introducing yourself and still walk over. You don't have to wait until you're completely confident. And you also don't have to assume that an awkward response means you did something wrong. Sometimes you share an idea and people need a minute to think. Sometimes someone disagrees and sometimes the timing is just off. We can turn all of that into, well, that was embarrassing, I'm never doing that again. But one moment doesn't need to decide how you show up for the next one. Your action item, think about one thing you've been avoiding and finish the sentence. I'm worried that if I do this, they'll think I'm pushy. They'll say no. They'll think I should already know the answer. Be specific. Then ask yourself whether that possibility is a good enough reason to keep avoiding something that matters to you. You can prepare for an uncomfortable response. You just can't guarantee you won't get one. Takeaway number two, build your social muscle before you need
3:18 it. Hannah calls this doing social push -ups. And once she explained it, I thought, of course, we can get through so much of our day without having any unexpected conversations. Order lunch on an app. Send a message instead of calling. Put your headphones on. Choose the option that lets you get in, get out, and keep moving. I understand the appeal. We're busy. But if we're constantly avoiding the little moments where we might interrupt someone, forget a name, or not know what to say next, We are also missing the chance to practice. Then we want to ask for a raise or introduce ourselves to someone whose work we admire, and it feels like a huge undertaking.
3:58 It's a little like deciding you're going to lift the heaviest weight in the gym when you haven't picked up a dumbbell in six months. Hannah also made the point that this applies to extroverts. You can enjoy being around people and still feel awkward asking for something, talking about money, or putting yourself in a situation where you might hear no. So we need those small reps too. Your action item, find one small opportunity each day this week to engage instead of avoid. Ask the question in the meeting, introduce yourself to someone you've seen a few times, ask for help instead of spending an hour trying to figure it out alone. It doesn't need to be a big networking event or a perfectly planned conversation. You're practicing staying present when you don't know exactly how the interaction will go. Takeaway number three, confidence includes knowing how to recover. This was one of my favorite parts of the conversation. Hannah said confident people make mistakes all the time. What we notice is how quickly they can come back from this. And I could relate to this from even speaking events.
5:01 If I mess something up in front of an audience, I'll usually acknowledge it. Maybe I make a joke and I just keep going. I've actually gotten positive feedback about those moments. I think it helps people relax. They can see that you're OK. So they don't have to sit there wondering whether the whole thing is about to fall apart. I also told Hannah that I spill coffee a lot, which is a lovely habit when you're trying to look professional in a meeting. But once it's spilled, what are you going to do? Clean it up and continue? Spending the next 20 minutes being embarrassed doesn't get the coffee back in the cup. We talked about forgetting words, too. I've had so many conversations with women over the last year where someone loses the word they're looking for, and now we just call it out. Sometimes it's, okay, I'm having a perimenopause moment. Someone helps, and we move on. Do I love forgetting words? No, but being able to acknowledge it takes some of the pressure out of the moment. Hannah was clear that the responses needed to fit what happened.
5:56 Now, if you hurt someone, you need to address that and make a repair. But for small stumbles, you probably don't need a lengthy apology. Your action item, choose a recovery phrase you can have ready. Let me try that again. I just lost my train of thought. Give me a second. That didn't come out the way I intended. And when you use it, give yourself permission to just continue. You don't need to keep apologizing for being human. Takeaway number four, your good intentions might be getting lost. This is where we got into the signal gap, the difference between what you intend to communicate and what someone actually receives. Hannah shared an example of sending someone a project she worked hard on and getting a looks great thanks back within two minutes.
6:42 The person was trying to respond quickly, but from her perspective, there was no way they actually reviewed what she had sent them. So a response intended to be helpful felt dismissive. I shared something that I've seen in my consulting work. A leader who normally wrote short emails started sending long, elaborate AI written responses. He thought he was making better use of his time, but I could see his team getting really upset. The message felt cold. Sometimes the messages didn't even make sense. What the team was taken away was he can't give five minutes to come and talk to us or even read this email. That's a big difference between what the leader thought he was accomplishing and what people were experiencing.
7:25 And those little moments, they add up. They affect whether people believe you're paying attention, whether they feel comfortable bringing you something, and whether they trust your response. Henna's advice was to name your intent. Explain enough that people don't have to guess. I saw this come through, but I haven't reviewed it yet. I'll get back to you tomorrow. I'm asking these questions because I want us to catch the issues before we launch. The extra context can just make a real difference. Your action item before one important message or conversation this week, ask yourself two questions. What do I want this person to understand? And what could they reasonably take away for how I'm saying it? Then make your purpose clear. If you're unsure how it landed, ask. And if the answer surprises you, try to understand it before explaining what you meant.
8:18 Takeaway number five, reassurance has to acknowledge what's actually happening. This one is especially useful if you lead people. When things are difficult, we often want to calm everyone down. We want to be steady. We don't want to add to the stress. But sometimes that comes out as, it'll be fine. Don't worry about it. And the person listening is thinking, well, I am worried and I have some pretty good reasons to be. Henna used a surgeon as an example. You wouldn't want your surgeon saying, yeah, I'm nervous too, this is really scary. But you would want them to acknowledge that you're nervous, explain that they've done this before and help you understand how they're prepared. That reassuring because it recognizes your experience and gives you something to trust.
9:01 The same applies at work. If your team is stretched thin, a cheerful, we got this, might not be enough. They may need to hear, I know this is a lot, Here is what we're prioritizing and here is what we're going to put on hold. Or I don't have the answer yet, but I'll update you Friday, even if we're still working through it. You can be steady while acknowledging that something is hard. You don't have to paint a sunshine in Rosa's picture when people can see the thorns. Your action item, notice one situation where you're tempted to offer a quick reassurance. Before you do, acknowledge the concern and add something concrete. What do you know? What happens next? What support can you offer? You don't need every answer, but people need to know you understand what they're dealing with. So here's your quick lift for the week. Notice where there is fear of feeling awkward and is keeping you quiet.
9:53 Get a few small social reps in. Have a way to recover when your words don't cooperate. Pay attention to how your messages land. And when someone is worried, give them something more useful, then it'll be fine. What I appreciate about this conversation is that these are everyday moments, and we can get better at handling them. And to get better at handling it means speaking up a little sooner, recovering a little faster, or taking an extra minute to explain something clearly. If you haven't listened to my full conversation with Hannah, go back and listen to that. We get deeper into good, awkward, and the signal gap, and how these small choices affect confidence, communication, and trust. Also, you can read the first chapter of the signal gap for free by using the link in the show notes. Until next time, stay loud and keep lifting!
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