The Courage to Ask

Why Putting Yourself Out There Is Already a Win

Two weeks ago, I found myself on both sides of the workshop experience: both as a presenter and as a participant.

I was leading a workshop for Women in Bio on building authentic professional relationships. And that same week, I was participating in Kara Loewentheil's How to Ask for What You Want Challenge.

At first, I thought of them as two completely different topics.

One was about networking: how we meet people, build genuine connections, and develop professional relationships over time. The other was about something much broader: identifying what we want and being willing to actually ask for it.

But as I went through the week, I started to realize how closely connected the two really are. Networking requires us to put ourselves out there. We introduce ourselves to people we don't know. We follow up after meeting someone. We invite someone to coffee, ask for an informational interview, request an introduction, or simply say, I'd like to stay in touch. And every time we do that, we're making a small ask without knowing exactly how the other person will respond.

You made the connection. Now what?

Think about the last time you met someone interesting at a conference, professional event, or even through a friend. You had a great conversation. Maybe you discovered a shared interest, learned that they work in an area you're curious about, or simply thought, I'd really like to get to know this person better.

You exchanged contact information or connected on LinkedIn. And then what happened? Did you reach out? Or did you start thinking: I don't want to bother her. She's probably really busy. Maybe she was just being polite when she said we should stay in touch.

And suddenly three weeks have gone by.

We often think the hard part of networking is walking into the room and introducing ourselves. But sometimes the harder part comes afterward, during the follow-up. At that point, we have to be willing to put ourselves out there.

Why don't we ask for what we want?

One of the things I've been thinking about since Kara's workshop is how many different reasons we come up with for not asking. For me, it's things like: I don't want to be rejected or I don't want to impose. For others it might be not wanting someone to think they're too demanding or worrying that they'll look silly. And sometimes (especially for women) we're simply much more comfortable helping others than asking them to help us.

There's another pattern that I found particularly interesting: waiting for someone else, particularly someone in authority, to figure out what we want for us. We hope our boss will recognize that we're ready for more responsibility. We assume our colleagues should realize we're overwhelmed. We hope someone will think to introduce us to the person we've been wanting to meet.

But other people can't know what we want if we don't tell them (they aren’t mind readers!), and waiting for someone else to notice can leave us feeling frustrated, resentful, or stuck.

Of course, avoiding the ask protects us from hearing no. But it also dramatically reduces the chances that we'll get what we want. And sometimes we end up frustrated or resentful that someone hasn't offered us something we never actually told them we wanted.

Confidence comes after the ask

We often imagine confidence as something we need to acquire before we do something uncomfortable. But what if we have that backward?

One of my biggest takeaways from the challenge was that making asks can be one of the ways we build confidence. Every time we make an ask, we're practicing identifying what we want and articulating it clearly. Every time we do that, we get a little more comfortable getting clear on our own desires and then actually asking for it.

Asking is a skill

This is where I started seeing an even stronger connection to the networking I teach. I talk a lot about networking as a skill. Sure, some people may find it more natural than others, but all of us can get better at it. We can practice starting conversations. We can learn how to ask good questions. We can get more comfortable following up.

Asking for what we want works the same way. You don't have to suddenly become fearless. (You probably won't.) You just need to start, and that start can be very small. Maybe instead of asking someone for a big favor, you ask if they'd be willing to have a 20-minute conversation about their work. Or, maybe you tell your manager that you're interested in taking on a new project rather than waiting to be offered the opportunity.

The goal isn't to force yourself through something that feels terrible. Start with one ask, take care of yourself through the discomfort, and then try again. Over time, something that once felt really scary may simply become something you can comfortably handle.

Your ask doesn't have to be perfect

This is especially important for my fellow perfectionists. We can spend an enormous amount of time trying to figure out exactly what to say. What's the perfect LinkedIn message? What's the perfect way to bring this up with my boss? How do I phrase this so the other person won't possibly misunderstand me or feel uncomfortable or say no?

There is no such thing as a perfect ask, and there isn't a perfect response. Making an ask is simply the start of a conversation.

You might ask for one thing and learn that it isn't possible. The other person may need time to think. You may realize halfway through the conversation that what you originally asked for isn't quite what you need after all.

It can be messy, and that's okay. The goal isn't to control exactly how the conversation unfolds. It's to get the conversation moving.

What if they say no?

One of the biggest reasons that we don't ask for what we want or need is that we don't want the pain of rejection. But another one of the ideas from the workshop that has stayed with me is the possibility of thinking through ahead of time how we want to respond if the answer is no. Before making an ask, we can consider: What am I afraid they'll think about me? If they say no, how will I feel about myself?

Maybe a new professional contact doesn't respond to your LinkedIn message. That doesn't have to mean you shouldn't have sent it. Or maybe the person you ask for help says they can’t right now. That doesn't mean you were wrong to ask. A no can be disappointing. We don't have to pretend otherwise, but it doesn't erase the value of having asked.

There is a reward in putting yourself out there

This may be the idea I've been thinking about most since the workshop. We usually judge an ask by the outcome. Did I get the meeting? Did they make the introduction? Of course those outcomes matter. We ask because there is something we genuinely want. But they're not the only measure of success. There's also value in becoming someone who is brave enough to ask. Someone who can tolerate the possibility of a no without deciding that she should never have asked in the first place.

That's what I hadn't fully appreciated when I walked into two seemingly unrelated workshops in the same week. Building relationships requires us to put ourselves out there, and so does asking for what we want. Both of these things may feel scary at first, but they get easier with practice.

So I'll leave you with the question I've been thinking about myself:

What are you waiting for someone else to offer that you haven't actually asked for?

And maybe an even more important one:

What's one small ask you could make this week?