Photo: Samuel Zeller

How Dating Improved My Business Development Game

Like most people, I tend to make new year’s resolutions, but find reasons not to stick to them before the first quarter is out.

Last year was different.

In 2015, I resolved to get better at dating. Being a designer, I approached it with a prototyping mindset. I tried different techniques throughout the year. What became more obvious as I went along was that I wasn’t just getting better at dating, I was getting better at business.


A lot of what I learned with respect to dating came down to being more thoughtful about the quality of my interactions — my intentions and attitude. While we often think of interacting with people as something we’re born knowing how to do, it’s a fairly nuanced pursuit, and, as I soon learned, it can help us immensely to think about it a bit more strategically.

And ultimately, much of what we achieve in life boils down to the relationships we hold, and how we build new ones. To that end, I’d like to share with you five things I learned from dating about business development..

1. Make meeting new people a part of your daily routine.

Dating advice expert Matthew Hussey has a mantra: “In order to meet more people, you need to meet more people.” He rightly claims that we often fail to expand our social circles and then complain that there are “no good men out there.” If we never meet anyone new, we never know.

But I believe many of us get stuck on the sheer effort we think is involved in meeting new people. In fact, according to Hussey, it’s easier than you think. He recommends setting yourself a goal of meeting new people every time you go out. The key: focus on daytimes. It’s so much easier to speak to someone in the line at a coffee shop than it is to approach someone at an evening event, be it a party or a professional networking function. Often during the day, people are alone and in waiting mode, while at events they’re already in groups.

When I tried this and started to chat with people, in the bus or in the queue at the grocery store, I found that lines began to blur. I learned to explore all the ways a new acquaintance could be part of my life: as a passer through; as someone to draw into my social circle; as a potential date; or, more often than not, as someone with whom I might do business.

By being open to any of these scenarios, I significantly increased the range of people in my life. At a party, I met someone who had heard of my work in Australia, and we subsequently collaborated together on something else. At a work function, I met someone who became one of my good friends.

2. Get to know true connectors.

Another intimidating thing about networking, whether professionally or personally, is the feeling that we need to be extroverted and to be chatting with new people all the time. Of course, that is a big part of expanding your network — you must talk to new people. But I’ve found an effective way to jumpstart this is by getting to know the people who are real naturals at it.

Dating coach Elizabeth Sullivan recommends ensuring natural connectors are amongst your friends. These are people who thrive on meeting others and are constantly making connections; it’s part of their DNA. I was relieved to realise I didn’t need to be that person; I just needed to know that person.

In business, it’s the same. For IDEO in Singapore, one of our best sources of new connections is a former employee. He’s also a natural connector, and we’ve had several interesting client introductions from him, long after he left our employment. Because he knows us so well, the conversations we have based on his introductions are always rich and fruitful, whether or not they directly lead to new business.

3. Create a regular drumbeat of casual events.

The trick to turning someone from a stranger you’ve met briefly into someone you know better is having a low-commitment opportunity at hand to invite them to. In the realm of dating, Hussey recommends creating regular social events, once every two weeks, so that you can causally invite new acquaintances to something. It creates a natural excuse to see people again and reduces the pressure of “is this a date or not?”

At IDEO, where I work, we created the same thing on a bigger scale. Once a quarter, we hosted “Inspiration Nights.” At these casual evenings, we would gather a range of people, from friends to former clients to potential future clients. Two people would speak about what had inspired them in their lives or careers, and the rest of the time was a chance to mingle and meet new people. The best part is, no one feels pressure to do anything that night but enjoy themselves.

Paradoxically, one of my favourite outcomes of these events was when we invited potential clients we were courting. Not only did they walk away inspired and energised, they felt compelled to run their own inspiration night! And we ended up collaborating together on an ambitious challenge.

4. Give the unexpected a chance.

Anyone who has been single for any length of time has heard this one: “You’re being too picky.” Interestingly, most dating gurus don’t chide daters too much for pickiness — they encourage having high standards for people you date. However, they do suggest not being closed off from the beginning, but rather getting to know people before making a call. First dates can be awkward, and people aren’t necessarily at their most relaxed.

Likewise, in business, it can be easy to dismiss someone as not being the right kind of client. Perhaps they’re a small business and you fear they can’t afford you, or maybe the way they state their need doesn’t sound interesting or in your wheelhouse.

But the same truth applies here: people — and opportunities — may not always be what they appear to be at first glance. At IDEO, a lot of potential clients will come to us asking for us to make their products prettier or more usable. While these are valid aims, they aren’t our strength. We focus a lot more on identifying and designing products and services which are solving a fundamental need for people. But, often, when we have a first conversation, we find a lot of alignment between their needs and our offering.

5. Expand your definition of what good looks like.

Most of us have grown up with an image of what our ideal partner looks like. For me, I imagined a partnership much like my parents have because it worked well for them and they created a warm home for me and my brother. When I first dated, I looked to replicate that as much as possible.

However, I soon realised that my parents’ life, while great for them, isn’t the ideal life for me. For instance, while they’ve enjoyed living in one town for the past forty years, I’ve moved continents three times in the past ten years, and while they vacation in one spot every summer, I enjoy visiting new parts of the world.

So now I’m looking for a partner who wants the same version of being settled as I do — being in a committed relationship, having roots in one or two countries, but being open to moving when the spirit takes us.

The same applies in business. What worked in the past might not work today. At IDEO, traditionally we have worked on three-month projects, where we spend 100% of our time with one client at at time. We have mostly worked with large corporations who want help with new innovations. But in recent years, we have been experimenting with different ways to help companies. We’ve launched a recent experiment to help startups, by providing guidance at key moments over a period of three months. We’ve explored doing smaller or more nimble pieces of work just to give a jumpstart to companies of all sizes, and to help them unlock excitement for innovation within their organisations. It has worked: with one company we approached nimbly, we designed a new service that launched across India and had a 99% uptake rate across the company.

As I reflect on the start of a new year, I’m excited about continuing to leverage what I’ve learned. Being more intentional about meeting people in the past year had a spiral of positive impact on my life: I spent less time flicking through my phone in down moments and more looking around for people with whom I might have a chat. I built a broader network of people in a city I was quite new to (in fact, now more often than not, I can be the one to say, “I know just the person you should meet; let me introduce you”). And I helped land business and create a rich body of work for my company.

Like all good habits, these are not resolutions but smart things to consistently weave into my life. Over the past year, I felt they brought me joy as my circle of friends, acquaintances and colleagues grew and evolved. Perhaps that’s why they stuck.

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