Hello from Europe! I’m taking some time off and writing this on a 5-hour train ride. I FINALLY have some mental capacity to write after taking a couple of days off from the craziness of work. I know, I know, I haven’t been writing even though I said I was going to do more writing this year.
In January, I came across David Perrell’s Shiny Dime challenge where he sends subscribers one writing prompt per week. I signed up for the challenge, hoping that it would reignite some writing momentum for me… and then promptly ignored it. This week, I’m digging through my old emails to find those writing prompts, and doing my best to kickstart it 3 months late. So that I don’t spoil the surprise, I’ll only share the prompt at the end of each post. Here we go:
Talking Too Much
“If I’m being honest, this is my first time networking.” I could feel myself cringing. That’s NOT the kind of thing you say at a business event.
I was at a college senior at a business society networking event. I was only there because as a senior, maybe it was time to stop mucking around and do something “serious” like apply for a business society.
I had no idea what I was supposed to say at events like these, so I just overshared. I talked about my interests, my resume, my terrible understanding of finance (which I had just memorised from that day’s Wall Street Journal). Any topic that I thought would impress my speaking partner.
He wasn’t paying attention. He kept looking over my shoulder. After a few painful minutes of listening to me blabbering, he mumbled something about getting another drink, and left. I didn’t get selected for the society.
Ugh. Classic rookie mistake of talking too much. We’ve all been in those conversations where the the party just won’tshut up, and we know what a big turn-off it is.
The solution to that, of course, is asking more questions. Asking a question is like throwing a ball to the other party. It’s an invitation for them to speak, and demonstrates that you’re interested in what they have to say.
Learning from this mistake, I read the classic sales book SPIN Selling as I prepared for my first partnerships jobs. The premise of the book is that asking effective questions is the key to successful selling. Asking the right questions can get the other party to open up about their problems and share their concerns. And then you can frame your solutions in a way that matches their concerns.
I internalised those lessons for my first client-facing role more than 10 years ago, but I made another rookie mistake.
Asking Too Much
Fast forward 5 years, and I’m in a fancy meeting room of an international hotel chain. I work for a travel tech company, and my job was to convince hoteliers to work with us. I had a list of prepared SPIN Selling questions that I was confident would help me win over the hotel’s VP of Marketing.
The VP of Marketing arrives. She’s 45 minutes late for a 1 hour meeting.
Wasting no time, I dive in and ask: “What’s your biggest challenge today?” She mentions something about getting more customers.
“Got it. What are you doing today that isn’t working?” She says that everything is working fine, but they’d like to capture more market share. Undeterred, I fired over more questions: “Have you ever tried this approach?” “What’s your opportunity cost in doing it this way?” “What kind of customers do you want?”
Her answers got shorter and more generic. When my 15 minutes were up, she thanked me and left. She never replied to any of my emails.
What was my mistake here? Fearing that I would talk too much, I swung to the other extreme and asked too many questions. This wasn’t a conversation, it was an interrogation. And it made the VP super uncomfortable.
There’s another subtle point on why this approach doesn’t work. Think about it: Who got more value out of the conversation? Obviously I did, because I got some great info about the VP’s challenges. But from her perspective, answering my questions was a complete waste of time. She didn’t get any value from the conversation. No wonder that she ignored all of my emails after that.
My Conversation Rule
Both of these extremes – talking too much and asking too much – sucked. If I wanted to avoid awkward situations like these, I needed a better plan.
I know that it’s weird to think about getting better at something as mundane as conversations, but I was desperate. I started watching videos online and reading books about social skills. I practised.
Over time, I found the right balance between talking too much and asking too much. I call it the “Two Questions, One Idea” Rule. The concept is simple: For every two questions I ask, I’ll add one idea of my own to the conversation. Why does this work for me?
In general, people like talking about themselves. Even introverts do. Have you ever had that experience where you had a fantastic conversation, and then walked away realising that you know very little about the person you were talking to? In all likelihood, they were probably really skilled at asking questions naturally and encouraging you to share more about yourself. So I try to ask more questions, and I do my best to listen instead of thinking about how I’m going to respond (this is easier said than done).
On the other hand, I don’t want to ask so many questions that it becomes an interrogation. So for every 2-3 questions I ask, I’ll respond to the other person’s sharing with my own ideas or personal experiences.
One little trick I use here is that I’ll share an interesting nugget, but I won’t elaborate on it unless the other person asks more about it. That way, they can decide if they want to keep talking, or shift the spotlight away from themselves.
Here’s an example of a conversation that follows this rule:
Me: “So how long have you been in this role?” (QUESTION)
Person: “For about 5 years now.”
Me: “Oh wow, it’s usually hard to find someone who stays in the same role for 5 years, especially in our industry. What keeps you here?” (QUESTION)
Person: “I really enjoy the work life balance. It’s really important to me at this stage of my life.”
Me: “I know what you mean. Once I worked at a role where I went home at 9pm every day and I was miserable. Have you ever worked at a place like that before?” (IDEA, followed by QUESTION. Notice how I don’t elaborate on the idea, but left the invitation open for them to ask more about my experience, if they wanted to.)
If you’re a naturally good conversationalist, you probably don’t need to remember rules like this. But as a natural introvert, it’s a helpful mental shortcut for me to fall back on – especially when things get awkward.
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(Did you guess this week’s writing prompt? It was “What is one rule you live by?“
I’m curious to know what is one rule YOU live by – let me know!)
