chat, discussion, meeting

It’s a desperate feeling trying to keep a conversation going. You can start to sense the awkward pause incoming… So your mind starts scrabbling around, desperately trying to find something to say. Anything to avoid the silence.

We’ve all been there.

Especially as introverts. Thoughts in our brain actually travel via a longer route, called the Long Acetylcholine Pathway. It means that in social contexts, stimuli goes through different parts of our brain. An event or conversation is never really light-touch as we process what’s going on in so many ways. We do this in a lot more detail than extroverts, which is why situations with lots of information can be overwhelming. There’s simply too much to take in at once.

This also means that you might struggle coming up with something to say in the spur of the moment.

There are a couple of strategies you can use to help with this.

I’ve written before about using context cues, which is one such strategy. Context cues is when you take advantage of the environment around you to spark questions and conversation.

Look at what’s around you right now. Every object, item, thing is a potential talking point. It’s a never-ending list of things you can use to fuel conversation.

Another strategy that helps to keep a conversation going is having questions in your back pocket, ready to whip out and use when you need to.

The strategy behind using back pocket questions

This is a great way to feel more confident in a conversation. You’ve come prepared and ready.

However, what tends to happen is that we memorise too many questions. Instead of it being helpful, we fall into a pit of becoming overwhelmed.

The trick is to pick questions that are adaptable and versatile. It’s better to have 5 solid questions that you can apply to a large number of situations, rather than trying to memorise 30 questions.

Another thing to note is that us introverts are vulnerable to being trapped in our head. It’s when you start to overthink everything.

Thoughts like “I haven’t spoken in ages, I need to say something right now”, and “I can’t ask that question, they’ll think I’m weird”.

Overthinking is something that stops us when we try to keep a conversation going.
By the wonderful Introvert Doodles

It’s because the two parts of the brain associated with thinking (the frontal cortex and Broca’s area) are very active in introverts. The frontal cortex is associated with decisions, decision-making, planning, and organising while Broca’s area is associated with self-talk (what you say to yourself).

(This might be the reason why you spent last night thinking about the time years ago when you accidentally called your boss “mum”).

So, the best strategy to use back pocket questions to keep a conversation going is:

  1. Pick 5-8 questions that are relevant to your life. Make sure they are broad enough to be applied to multiple situations.
  2. Write them down and practise saying them out loud. This helps move them into your long term memory.
  3. Try to relax in a conversation and allow the questions to naturally guide you. If someone is talking about pets, you could use a pet related question.

And finally, if the worst happens and the conversation becomes awkward… it’s okay. It happens.

How to get over awkward pauses in a conversation

Awkward pauses are the worst. It’s like your skin is standing on edge and you just want to sink into the floor.

Perhaps the worst bit is the lingering feeling of cringing, shame, and blame that sticks with you afterwards. We start beating ourselves up: “Why did I have to make everything awkward?” or “Why can’t I just say something instead of staying quiet?”.

chat, discussion, meeting
“What do I say?!?”

Jeff from Become More Compelling (a fantastic resource on how to be charismatic) created a technique that helps us get over awkward pauses.

It’s called the “FFF” strategy.

1. Flush:
Take deep breaths to flush all the embarrassing emotion out of our system. Picture yourself in third person in the embarrassing situation, peering at yourself from the outside in. We tend to give other people the benefit of the doubt and kindness (that we don’t usually give ourselves), and this trick can prompt your brain to give you self-compassion. It will reduce the self-blame we tend to allocate to ourselves. 

2. Fix
If there’s anything you can fix about it for next time, do it. For example, find a better joke or practise sharing your stories. Give yourself a game plan for the future and know that each time this happens, you’re becoming better at handling it.

3. Forget
The situation has happened and ruminating about it won’t help you in the future. Try to forget about it as much as you can. It’s not serving you

The first time going through FFF can feel weird. 

However the more you practise this, the quicker you can go through the steps. Doing it in “real time” means you can get back to the moment quicker and be better socially. A good way to practise this is by thinking about past experiences or events that make you cringe with awkwardness and running them through FFF.

50 questions to keep a conversation going

And here they are! 50 questions for you to use as you wish. Remember—try not to go overboard. Take your time reading through and selecting questions that work best for you.


  1. Tell me about your family?
  2. Where did you grow up?
  3. What do you like best about being a father/mother/son/aunt, etc.?
  4. What was it like growing up as [only child] [surrounded by siblings]?
swan, cygnets, family


  1. What got you into your current job?
  2. How did you come up with that idea?
  3. What was it like working on that project?
  4. What do you love about your job?
  5. What’s the career highlight you’re most proud of?
  6. What originally got you interested in your current career?
  7. What are some of the toughest challenges in your job?
  8. What type of job do you want to move to after this one?
  9. If you could change one thing about your job, what would it be?
  10. Are you more of a “work to live” or a “live to work” kind of person?
school work, write, still life


  1. Do you have a favourite type of exercise?
  2. Are you into any podcasts right now?
  3. How would you spend an unexpectedly free afternoon?
  4. What’s been your favorite vacation?
  5. What place do you never want to go back to?
  6. Was the last thing you read? 
  7. What skill would you love to master?
  8. What is your favorite city?
painting, pencils, paint


  1. Would you say you’re more of an introvert or an extrovert?
  2. If you could have any superpower what would it be?
  3. What’s the most exciting thing in your life right now?
  4. If you never had to sleep, what would you do with all the extra time?
  5. What are you most likely to be famous for?
  6. If you could live in any decade, what would it be?
  7. When was the last time you changed your mind about a big topic?
  8. What is your least favorite food?
  9. What would be your ideal way to spend the weekend?
  10. What would your perfect birthday be like?
  11. What is your most used emoji?
  12. What is the luckiest thing that has ever happened to you?
  13. What are you likely to be wrong about? 
  14. What is the best compliment you’ve ever received?
  15. What is one thing no one realizes about you?
face, faces, dialogue

The past

  1. Did you have a favorite pet growing up?
  2. What job did you want to do as an adult when you were young?
  3. If you could give advance to your younger self, what would you say?
  4. How different was your life 5 years ago?
  5. What was your favorite subject in high school?
  6. What was your college/university experience like?
  7. What was your first job like?
movement, church, stettlen

The future

  1. Do you have any fun plans this weekend?
  2. What is one experience you really want but can’t afford yet?
  3. How far in advance do you plan your vacations?
  4. What’s something that you’ve always wanted to do, but haven’t?
  5. What do you hope to be doing when you’re 80 years old?
  6. What big or small lifestyle change have you been meaning to make?
door, open, doorway

Advanced: Dig Questions

Dig questions go deeper into a topic. It shows we’re keen to really dive into someone’s thoughts and opinions around a subject. We actively want to learn more.

If your conversational partner starts speaking about something you’re interested in, use one of the below scripts to dig into it further:

  • “That sounds great! Tell me more about …”
  • “Oh interesting — how did you … ?”
  • “I’m curious, what did you … ?”
  • “What was that like for you?”

If you’re anxious about keeping a conversation going, keep a few “dig questions” as backup and helps you never run out of things to say.

This is especially good if you blank out. This happens to introverts more than we like to admit. It’s because we tend to favour long-term memory, over short-term.

(Extroverts go the opposite way).

Pulling information quickly out of our long-term memory can be… tricky. Especially when we need to answer under pressure. Job interviews, first dates, important conversations — these are times when it feels worse. 

Being unable to say what you know is in your head is a horrible feeling.  

Here’s how to handle it:

  • Try to relax and allow your mind to wander.
  • Buy yourself time by saying “I need a few moments to think”.
  • Be lighthearted about the information not coming and tell the other person you’ll get back to them later (by text/email!)

Knowing this in advance helps you feel more confident. And leveraging your introvert strengths helps you flourish!


Introverts can sometimes struggle keeping a conversation going. It might feel like wading through mud: you’re desperately trying to move forward, but to little effect.

Taking advantage of context cues and back pocket questions can really help.

When using back pocket questions:

  1. Pick 5-8 questions that are relevant to your life. Make sure they are broad enough to be applied to multiple situations.
  2. Write them down and practise saying them out loud. This helps move them into your long term memory.
  3. Try to relax in a conversation and allow the questions to naturally guide you. If someone is talking about pets, you could use a pet related question.

What’s next?

People skills, conversational skills, and social skills can help you have opportunities in life that previously would have passed you by. I know this because they changed my life (you can read more about that here).

Being able to communicate clearly is so important. Want more tips on how to connect with other people?

Click on the blue button below. 

I’ll send you the Introvert’s Ultimate Guide to Connection. 

In it, you’ll learn:

  • Strategies to melt away awkwardness when starting conversations
  • A  framework to ensure you’ll never run out of things to say 
  • How to navigate fears of saying the wrong thing  or social blunders



No responses yet

Leave a Reply

Your email address will not be published. Required fields are marked *