Introverts Guide To Asking Your Professional Contacts For Help—Without Feeling Awkward

As introverts, we’re amazing in our roles, especially when left to our own devices. We possess superpowers that make us geniuses in our craft, because we process information internally. If anything, our introspective nature is what makes us excellent in understanding and supporting others to a different level.

But when it comes to advocating for ourselves, well, that’s where things get challenging. It somehow feels embarrassing to seek help for ourselves, although we are fully aware that it shouldn’t be the case. We have many who adore us and would love to help us, as we have helped them, but it still feels strange to ask. The more we think about it, the more doubt kicks in.?

So let’s talk about realistic ways we can step out of our comfort zone, to leverage our networks effectively without making things awkward for us, and without imposing anything on our contacts in the off-chance they can’t help.

First and foremost, you need to understand that your core network would be flattered that you thought of them for advice, career guidance, intros, opportunities, etc. The same applies to old professional relationships that need to be rekindled—it’s nice to feel respected and remembered for all the right reasons.?

Now let’s dive right into how to approach this with tact.

How to ask your core network for help

We can all agree that core networks are amazing, because you can skip a lot of formalities, and just cut to the chase with them.

Get straight to the point, and keep it concise. It’s okay to be a little vulnerable. It might even be a bit of an ego-boost for them.?

“Hi Denise, I need to ask you something. I’m a little hesitant, but you’re the best person for this. I see you’re close with Mr. Big Investor. I’m looking to raise for my startup, and it’s totally up his alley. Would you mind making an intro? I’ll share my deck with you first if you prefer.”

If you’re not comfortable with doing this in-person or over the phone, email is fine too—just avoid sending anything that can’t be read in a glance.

If you decide to reach out to people you’re cool with on LinkedIn, I recommend spending some time engaging with their posts beforehand. That would help serve as a smooth preamble to your request.

How to reconnect with lost contacts

If you’re looking to reconnect with professional contacts you used to be close with, but ended up falling out of touch—it will be a piece of cake to pick up from where you left off.

I recommend this formula in your approach: Personal touch >> Update >> Interest in Them >> Soft ask.

Here’s an example:

• Personal touch: Hi Ben! I thought of you last week while at ABC Expo, and how we used to hate setting up the booths by ourselves while at XYZ Company.
• Update: I’ve worked with 123 Corp since then, kind of as a stepping stone, but you know me, I thrive in fast-paced environments.
• Interest in Them: I noticed you’ve been doing great in cybersecurity, and I saw the content you shared about how lucrative cybersecurity is.
• Soft ask: I’m actually exploring opportunities in this space. What do you think??

Send it all in one shot if you’re planning to shoot over an email, and try to keep it concise.

If you’re sending a text/direct message over to them, maybe send your messages in segments instead, to see if they respond before you get to the “soft ask.”

How to casually ask your contacts to keep you in mind

This is the approach I tend to take, mainly because it doesn’t place pressure on anyone. I feel like this approach is the one that offers a chance for anyone who genuinely cares to step up. As far as people who don’t step up, well, at least those relationships won’t turn weird from your simple request not being fulfilled.

There are two ways to go about this casually. My preferred way is to naturally slip it into a conversation when the opportunity arises. The other option is to offer reciprocal assistance.

Here’s how you can naturally slip it in. Let’s say you’re already talking about the hottest topics in the industry anyway, that would be a good time to slip in a little something like:

“Speaking of aerospace, let me know if you hear of open managerial roles in SpaceX. With all the connections you have there—I’d appreciate a heads up!”

And if you would like to offer reciprocal assistance, you can instead approach it like:

“Yea, there’s so much going on in aerospace, and I saw your buddy Elon posted about the new CTO opening. Mind putting in a good word for me? I’ll gladly help you with the strategy for Q4.”

How to follow up without looking pushy

If you’re anything like me, you might get tempted to check up on your contacts every few hours to see if they’re ‘on it.’ However, as difficult as it may be, I suggest waiting about two weeks before you circle back.?

The key here is to be polite, and express gratitude.

“Hi Maria, you were excellent in that webinar! I took a lot of notes that I plan on sharing with the team in the next meeting. By the way, did you get a chance to show Blake my RFP? I’d love to know her thoughts. Regardless, you know I love your insights, and I’m looking forward to the next webinar!”

As you can see, reaching out to your professional contacts for assistance doesn’t have to be daunting. It’s just as much about what you can offer, as what you can receive. Don’t sweat it! Just make sure you approach it with a blend of tact, sincerity, and respect for their time and expertise.