Tonight I’m writing about a topic that is dear to my heart – how to have a quality conversation in an introductory call. Coincidentally, it’s a question I’ve received five times recently – which is usually my proxy for sitting down to write a longer piece on it.
We often discuss the technical skills that you need to get a job – but ignore the soft skills that often play a much more impactful role than we care to admit. Knowing how to relate to someone else is, in my opinion, more important in a broad sense than crafting the perfect spreadsheet or writing excellent code. I fear when we tie our professional selves so tightly to our self worth, we forget our underlying sense of rich humanity and a foundation of compassion.
Conversing is a skill that permeates every other aspect of our lives, and an intro conversation is your first introduction to someone else. A wise man told me recently that conversations have two parties. It’s worth repeating that 5 to 10 times over – conversations have two parties. A conversation is composed of two pair of ears, two mouths.
Everyone you talk to has people they care about outside of work, a certain way they brush their teeth, a favorite book, a song they can’t resist dancing to, and some hard experiences they’ve lived through.
You may chose to embrace this humanity, this meeting of minds, or you may chose to ignore the humanity of the person on the other side and thus make a conversation transactional.
Yes, we are investors, product managers, engineers, students – but remember to remove your degrees and professions at the door while greeting someone else. They’ll be there if you want to run back and grab them for another part of the conversation, but we’re human first. Treat your conversations accordingly.
So let’s get a bit realer in our conversations.
Before entering a conversation – do some research on the person you’re talking to. Do a bit of Googling, I find personal websites and social media are great. If you’re following my cold outreach guide, you’ve probably compiled a little list of things that you admire about the person. Make a note of these as talking points. I find really obscure references, things they did years ago are the most intriguing to ask & also show you did your research.
Right before the call, take a minute to ground yourself. A friend of mine suggested humming as a way to warm up your vocal cords, and I also find it’s calming. Reflect on what you’d like to achieve from your call, whether that’s learning more about someone who you admire’s career or seeking advice from someone with a similar career arc or resonating with their values and goals. Write down a sentence or a couple bullet points of what you’d like to cover in the conversation.
I have a trusty notebook where I keep notes on conversations I have – and I highly recommend you do the same. Writing down keywords, follow up notes, and fun facts help jog my memory & write more personal thank you emails.
When the call starts, thank the person on the other side for making time for you. Starting off with an acknowledgement sets the tone that you believe their time is valuable. After this, some small talk about where they’re calling from, the weather there, any anecdotes you have related to that place warms you both up. Don’t jump straight into any prepared questions.
After some small talk, start with a loose agenda and your intention for the call. Here’s an example of how I would start off a conversation:
Again, I really appreciate you taking the time to speak with me. I’ve done some research on your background, but would love to hear more about it and what you’re excited about from your perspective. After that, I can dive into a bit of my background and what I’m excited about. Finally, I’d love to ask you some specific questions around {area of interest}, how you make decisions on {area of interest}, and any advice you may have for me {getting into x/stories from their career}.
Giving this loose agenda at the beginning of the call helps the conversation flow & also gives you more insight into what they’re thinking about at the beginning of the call. In The Art of Gathering by Priya Parker, she talks about how establishing explicit “rules” for gatherings helps everything else be more freeform. Counterintuitive, I know. But it really works!
While your conversational partner is giving their background, write down key words they mention & any questions you might have. Feel free to ask clarifying questions at this point, but leave more dense questions until after your introduction. The context of your introduction will help them shape answers more specific to you.
Next, give them a bit of background on you. Try to bring up points you have in common with their background and weave them in. I often talk about a common theme thats permeated my transitions: curiosity. From figuring out physical things(engineering) to software(studying CS) to companies(entrepreneurship program) to portfolios of companies(software venture capital) to serving developers(my current position), curiosity has been at the core of my journey.
Picking a common thread or personality trait serves two purposes: it gives them a key word to focus on and shapes your narrative.
After your respective intros are made, now you get to ask those denser questions you had written down! If this is a professional call, you might drill down into what their day-to-day looks like, how it’s changed over the years in different positions, difficult decisions they’ve made over the years. Let the conversation flow naturally, and don’t be afraid to sit in silence for a bit. The absence of words is also part of conversation.
Practice active listening techniques when they answer a question: repeat a bit of what they said, and then use it to segue into a deeper question on what they said specifically or a horizontally related question. These transitions keep the conversation from sounding like you’re reading from a script. Believe me – before I got lots of practice, I got accused of reading from a script – my face was beet red!
Everyone has a different way of conversing, so find questions that resonate with you and that you have insights to share on if the conversation comes to a lull. Here are some of my selected favorites:
from my favorite frank ocean song – futura free:
- What’s your first memory?
- What’s the most amazing thing you’ve ever witnessed?
- What three superpowers do you wish you had?
- Do you have any secret talents?
from Lenny Ice’s open ended questions:
- How do you measure how you are successful?
- In which are of life do you feel you have the best taste?
from my friend Minn’s
- What are you really good at, but never want to do anymore?
- What’s one critical piece of feedback you’ve received that was really difficult to hear? Why was it difficult and what did you do with that information? What did you learn about yourself?
- A big sacrifice you have made in your life for something you love that’s been worth it?
- Among the people you’ve worked with, who do you admire and why?
my personal favorite questions:
i think we all change each others’ paths. who has changed your life path significantly and why?
did you ever take a “detour” in life? if so, how did it inform your choices afterwards?
if you could describe your favorite homeade meal, what would it be?
As the conversations wraps up, thank the person again for their time, repeat a couple of info nuggests you learned on the call, and state any followups you may have. ALWAYS!! ALWAYS!! Send a thank you email/DM after your call 🙂 I try to draft them in the ten minutes after a call. They’re great to respond to as email threads later if you have
Intro calls are a learned skill – you get more natural as you practice more. Just remember, even though the person you’re talking to on paper may be experienced beyond your wildest beliefs – they’re a person with two ears and a mouth. A conversation has two parties & your job is to try and build a personal connection with the other party. You got this!
P.S. To get better at this skill, I watched A LOT of different interviews. I also interviewed music artists in college(a story for another time). Pick out questions you enjoy & watch interviews from all sorts of different public figures!