How To Start A Conversation With Anyone 

When giving a recent presentation at a women’s networking group one of the questions that I was asked was “how do you start a conversation when you’re an introvert and can’t think of anything worse to have to do?”

I’ve always been lucky that I find it easy to start a conversation with anyone so I suggested 10 questions that she could ask in different situations.

As I looked around the room I noticed that a lot of the women present were writing these suggestions down. So clearly this is something that many women struggle with.

Striking up a conversation can be intimidating for even the most extroverted person.  So, if you want some ideas on how to break an awkward silence, start a conversation with your CEO when you bump into them in the lift or are off to your first networking event then check out the tips below:

1. Small talk

An easy way to start a conversation with someone is to engage the person in small talk.

If there’s a holiday coming up try asking them a question about that – such as “What are you doing for Summer holidays?” or, if you’re meeting them at the beginning of the week, “How was your weekend?” or alternatively at the end of the week “What are you doing this weekend?”

2. Ask for their recommendations

Most people are flattered to be asked for their recommendations. So, if you’re attending an event try asking if they’ve been to the event before. Then, if you get an affirmative answer, you can ask what they recommend seeing or doing. Should you be at a restaurant try asking the person/people you are with what they’d recommend from the menu.

3. Make them feel comfortable 

You can do this by asking them a question that’s easy for them to answer. If you’re at an event you could ask “Have you been here before?”, “Which talks are you looking forward to?” or “How was your journey in?”

If you’ve just started a new job then “How long have you worked here?” and What do you enjoy most about working here?” are good conversation openers.

4. Ask open-ended questions 

If you ask closed questions such as ‘Do you like reading?” it’s possible you’ll get ‘no’ for an answer. And that’s that conversation killed. Instead try asking them what their favourite book is and why they enjoy it so much.

5. Ask about their kids, partner, holidays, and hobbies

People like to talk about themselves so ask them what they like doing outside work. And then, if they say it’s taking the children to swimming and football, you can follow it up by enquiring how many children they have.

6. Remark on your surroundings 

This is a great way to start a conversation if you’re at an event and you’re getting a drink as you can turn to the person next to you and comment “Isn’t it a lovely location/room/restaurant? Deleting as applicable.

7. Give a compliment

Most people are more than happy to be complimented so you could say “I like your handbag, where did you get it?”  Be genuine in your compliments though. So if you think it’s the most hideous bag you’ve ever seen maybe comment on their shoes instead because a fake compliment will be spotted immediately!

8. Refer to previous conversations 

If you’ve met the person before but still don’t know them that well you could ask them a question about something they were doing last time you met.  Something like: “The last time we met I recall you were off on holiday to Greece, what was the best bit?” People will be impressed if you remember details about them.

So now that you have some examples of how to start a conversation let’s remind ourselves of the basics when talking to people.

1. Be approachable

Smile if someone catches your eye  because this will make it easier for them to join you.

2. Arrive early 

If you’re off to a networking event arrive early and then people will come to you as they join and you can introduce them to others. This tactic will help put everyone at ease.

3. Relax 

Remember that others may be nervous too so just relax and practice starting conversations so that you get used to doing it without thinking about it.

4. Say the other persons name occasionally 

This will help you remember it for the future and will also help you build rapport with the person.

5. Acknowledge that you’re listening

Let them know that you’re listening and interested in what they have to say by nodding your head and making appropriate comments and responses.


Caroline Arnold 

Executive Coach

T: @carnoldcoaching

F: Caroline Arnold Coaching


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