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  • Mark Calleja

Awkwardness: Because Sometimes Social Interaction Just Doesn’t Work – Part 2/2

We’re back! You may remember in part one of this blog series that we spoke about the prominent quote from Mark Twain, remember it? Here it is again to remind you:

“All you need in this life is ignorance and confidence, and then success is sure.”

We discussed some tips to cultivate confidence and ignorance in order to set ourselves up for success. In this blog, we will be diving into the details of conversations, how to get them started and how to keep them flowing in a way that enables you make the most out of them. Let’s get started.

The Technology

This section is all about things you can say and do in your conversations to make them flow a little more smoothly. We’ll run through Openers and things to get a conversation going, to continuation tools and tricks, all the way to ending a conversation politely in two ways; Escapes - for those times you just need to get out of a conversation, and Closers - for setting up another conversation later to capitalise on all the charm you laid on today.


What do you do? Why are you here?

We’ve all had it asked of us; ‘So, what do you do?’ It’s lazy, it’s a placeholder for a real question, nobody likes to answer it - it needs to go. Much better to ask someone why they are at an event, and what they hope to gain by being here. It opens up a lot of possibilities in the conversation immediately and is a lot more personal. Even in the worst possible outcome; ‘My boss made me come’, you now have some common ground to bond over while getting more information - lame bosses.

Ask for personal opinions on impersonal topics:

Everyone has an opinion, they’re just waiting to be asked what it is. It could be on anything; the building decor, the start time, the glassware, the third speaker of the day, your shoes - it really doesn’t matter as long as it’s something you can have in common and isn’t likely to offend. Often, things about the event itself are best, as you have both definitely been there today.

Give a compliment that ends in a question:

Everyone is a sucker for flattery, but you need it to turn into a conversation. Avoid simply being thanked by asking a question about the compliment - ‘Nice shoes, where did you get them?’ is an obvious one, but you can do it with nearly anything. ‘I saw your talk today, it was really interesting. What was your research sample?’ ‘I’ve always wanted to work at [insert company here], it seems incredible. Is it true the CTO is a vampire?’

Ask for advice:

While very similar to the complinquiry (coining it) above as it relies on compliments, this one is a bit more targeted. You’re usually approaching someone you have identified already as being helpful/valuable as a contact, and they are usually more senior people in their field. While you’re still complimenting them by appealing to their sense of authority, you’re just asking them for their expertise, so you need to be a bit clever. Often, I think of an edge case in their field and ask them to solve a problem related to it: ‘I saw your talk earlier today, and was wondering - how would you…’ That isn’t to say it doesn’t work on less senior people, as while sometimes they may feel unqualified to answer your question, they’ll be flattered you feel they are.


Ask genuine questions:

A sure fire way to keep a conversation upbeat and moving along is to ask questions about the topic as they come up. People like to explain things they are passionate about, especially to someone who also seems interested and passionate. Asking a well-timed question can keep a conversation going, divert it toward a subject more valuable to you and endear you to the speaker all at once! So, cultivate your ignorance and ask things you really want to know.

Find common ground:

Once you have someone talking, start noticing the things they talk about and find things you also know about or have interests in. Sometimes having something common to the two of you up your sleeve, like the football or podcasts, can turn a dying conversation around by injecting a fresh and comfortable topic.

Be honest, but impersonal:

Some people feel that you need to be agreeable and obsequious to succeed at networking. I disagree. I think the most interesting conversations are had when there is disagreement between people that is kept impersonal. Make sure you aren’t attacking something about the person’s identity, but make sure you posit your actual opinions in conversation, even if that means respectfully disagreeing. (Avoid talking politics or religion where you can, people get very personal about those.)


Again, asking someone a complinquiry can refresh a conversation quickly. It boosts their self-image while inviting them to engage with you again.

Call for Backup:

his one is if you’re finding it particularly hard to keep a conversation going. Having two people on your side can make it much easier to steer conversations toward more useful topics, as well as provide another voice and perspective in the chat. You can also use it to swap someone else in to a conversation you want to leave - more on that now.


Call for Backup:

As above, sometimes bringing someone is to be a distraction while you bail can be a valid tactic to leaving a dead/awkward/difficult conversation easily. Find a reason to introduce the person from your conversational topics: ‘You were talking about sailing earlier...Joe is an avid yachtsman. Joe, come meet Rita!’ Let them talk about yachts for a bit, then need to see someone else.

Social Superhero:

If you need to get away from someone, you can always see ‘someone you need to catch before they leave’ and bail. You can also use the line ‘I’m going to go mingle some more, thanks for your time.’ Another more urgent one might be ‘I’ve just seen one of my colleagues who’s had a few too many, I must go and save them before they do something embarrassing. Excuse me.’

Get another drink/plate:

It’s an oldie but a goody - ‘Excuse me, I’m just going to get another drink.’ Then don’t come back.

Take a card:

If you really don’t want to communicate with someone again for whatever reason, make sure you get their card and not the other way around. Leaving yourself in control of the next contact means there doesn’t have to be one, or you can intro another team member later.


Plan a follow up:

This can be a meeting or just a call, it doesn’t matter. Once you have their details, make sure you set a time to talk again. ‘I have to see some other people before they go, but I’ll call you on Monday’ works just as well as pencilling in a face to face meeting - you just want to let them know that you will be in touch again, and that what you talked about is happening.

Ask for a card:

Just as before, being in control of the next communication is important as you don’t want to be fobbed off or forgotten. Make sure you get their card, or if they don’t have one, their email/phone in your contacts.

Offer to make an Introduction:

Sometimes, you’re not the person they need to talk to. Offer to introduce them to the person who is. You’ll look like a ‘fixer’ to both parties, and you will be able to say you turned a conversation where you couldn’t help, into a possible win for the team. If the person isn’t at the event, even better. This way, you can get their card, make contact after the event and reinforce the idea that you’re a connected person who gets it done.

Leave an Impression of collaboration:

Make sure you end the conversation with something like ‘I’m really excited to work with you on this.’ Leave them with the impression the thing you spoke about is a done deal, and already in the works. It will make you more memorable and convey a sense that something concrete is happening.

That’s about it, really. Keep in mind that I’m not a psychologist or a business guru; just a teacher who’s a bit of an introvert and had to teach themselves a bit about confidence by watching. These are the things that worked for me, so feel free to take or leave bits as you please. If you can practice these things at your upcoming social events.

Speaking of events, why not sign up for the next Cambridge Women in Tech event, you can put your new learnings into practice.

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