Fifty coffees

Each time I make a significant change in my life I have coffee with fifty people to get their views on what I’m up to. If you’re raising investment for a startup, changing careers or moving to a new city then you owe it to yourself to have coffee with fifty people before you make the jump.

Setting the goal of having coffee with fifty people forces you to be clear about what it is that you’re up to. Making the goal public (one person at a time) also makes it much stronger. Having fifty coffees is good because then you have to commit to the specific move that you want to make and tell other people about. You’ll also get input from smart and interesting people to help you make a better decision.

Meeting with 50 people about one topic could change your life

I first came across the idea in the book What Colour is Your Parachute? (back then it was called informational interviewing). More recently, Mark Suster reminded me of the idea and put a number on it in his article Why you need to take 50 coffee meetings. Until Mark’s article, I’d just aimed for as many coffees as I needed until I had gathered enough input to act on. Now I aim for 50 because it simplifies the process, makes the goal concrete and is large enough to be a stretch target.

Megan Gebhart became a bit of an internet celeb and travelled the world meeting new people for the 52 Cup Project. She was inspired by a quote from Charlie Jones:

“You will be the same person in five years as you are today, except for the people you meet and the books you read.”

The hidden insight in the fifty coffees idea is that the biggest changes in your life will only happen through the people that you meet and the conversations that you have. Human beings create and convey meaning through stories and conversations. If you change the conversations that you’re a part of, then your life changes automatically.

Who to have coffee with

This isn’t fifty coffees with complete strangers. The coffees will be mostly with friends and existing acquaintances. You know that favourite former colleague who you keep meaning to catch up with. Now is the time.

Mutual introductions are good. Think one degree of separation. Ask your friends, investors, clients and colleagues if they know anyone interesting who you should meet. I usually focus on friends-of-friends.

Having coffee (with a purpose, but without an ulterior motive) has made me more confident about meeting new people. I still get nervous about asking someone new for coffee (hi Haiyan and Tom) but I’ve met great people and made some real friends (hi Anas and Richard).

Having fifty coffees is worth it if you’re making a big life change

I had fifty coffees when I left being a lawyer to move into design (people I met included Tim Brown, Brian Richards, Peter Roband and Stuart Macdonald). I did it again when I moved to London and most recently when I published a book. The fifty coffees idea has worked so well for me in the past because:

• My best ideas always come up during a heated conversation. My brain seems to be wired up to my mouth (not always a good thing). But it means that I literally ‘think’ better when I’ve got an intelligent conversation partner to debate an idea with. (Hi Josh and John.) Caffeine is a great fuel for conspiracy.
• Other people know more than I do. For any big life change, there are people out there who have already done what I’m thinking of doing. I can get more from their personal anecdotes than any book, blog or article.
• People that I know ‘less well’ know lots of people who I don’t know. People who I already know really well generally know the same people that I do. To get better variety of input I try to meet people who have very different backgrounds to me.

We’re not talking about generic catch-up coffees and awkward first-time meetings with sales prospects. Instead, we’re looking for a focused debate with an intelligent peer. The best coffee discussions are about an idea that you’re both interested in or where the other person can give you input on something that they feel good talking about.

How to make the most of the coffee

The focus on a real project or issue is what makes this coffee different to a catch up. Instead you’ll be conspiring, debating and swapping stories. Being specific about what you want to talk about makes the coffee feel much more valuable. There are a few things I’ve learned about how to get the most out of it for both people:

1. Be intentional and focused. Keep the coffee meeting under twenty minutes. I usually meet people at their office and use the walk to and from the cafe to get the conversation warmed up and warmed down. We think better when we walk.
2. Be honest about what you want from the meeting. Tell the other person up front that you want their input and advice on a big move.
3. Don’t ask for anything from the other person. Let the conversation be the value. No selling, no pitching, no interviewing. The other person’s time, advice and story is all that you can ask for in a short coffee meeting like this. There is a time to make bold invitations. This isn’t it.
4. Think ahead. Formulate 5-10 questions in your head that would be interesting for the other person to answer and that would help you to triangulate your problem.
5. Take notes. A general chit-chat will be lost in the sands of time. For your fifty coffees you should be taking notes because it shows you’re there for a reason and it’ll help you find common themes. Bring a small moleskine notebook.

You can use a small tickle to warm up someone before asking them for coffee. Stef and Paul from startup foundry Makeshift add people to a Twitter list like “We should meet” or “Would like to chat“. You can do simple things like follow the other person on Twitter or favourite one of their Tweets. Don’t overdo it and add the other person on LinkedIn before even meeting them. – It’s a bit too forward. But it’s nice to make some sort of connection in advance.

Tip: Don’t waste people’s time

Having coffee is contrary to a lot of the popular startup buzz. Many investors and consultants are sick of ‘catch up’ coffees with strangers who waste their time. I even found a popular article entitled ‘10 ways to say no when someone asks you to grab coffee.’ Rob and Sal from FounderCentric and LeanCamp invented Startup Burger Nights to avoid coffee meetings and I know several London investors who use the “just grab me at Silicon Drinkabout” line as a fob off to avoid coffee. It’s hip these days to make yourself harder to get to. Which is fair enough, but your fifty coffees shouldn’t be the type of banal time-wasting catch ups that people want to avoid. You should be making the experience fun, easy and productive.

My trick is to watch the other person’s drink. When they finish their coffee, the meeting is over. The theory is that if they’re enjoying the discussion they’ll be too engaged to drink their coffee. We all reach for our glass in a moment of awkward silence or when we’re bored. Their coffee cup is your hourglass.

Tip: Don’t steal their time

If the other person gives people advice for a living (think consultants, coaches and creatives) then don’t ask them for ‘advice’ on your specific problem. Instead, just absorb their way of approaching problems. Ask them for war stories of interesting projects that they’ve worked on. Ask them about how they got started in their field. Let them talk about what they’re interested in.

How to get a coffee with anyone

There are lots of ways to ask someone for a coffee but I like to keep it simple:

1. Make it easy for them with a good place. Think from their perspective and offer to meet at a high-quality independent cafe close to their office. I’m lucky because my blogging for The Coffee Hunter takes me to cafes all over London. You can use FourSquare or the London Coffee Map to find a good place that’s close to their offices.
2. Make it easy for them with a good time. Some people like to do quick meetings in the morning to get them fired up. Others prefer a regular morning coffee or a quick lunch. The Brits have a culture of ‘stopping for just one’ on the way home from work and that can be a good time to meet people. The most important thing is that it suits them.
3. Be interesting. Figure out what they are working on or would be interested in talking about. Put that in the initial email.
4. Be direct. Put the invitation in the first line of the email. The other preamble stuff is nice but don’t ‘bury the lead’.

Secret tip: Travel for coffee

People are craving novelty so ask for coffee with a local when you travel. I’m now in London and would love to have coffee with someone who has just arrived from New Zealand. Likewise, when I was in New Zealand I would have been happy to hear from someone who had just arrived from London. Even if it’s a purely vacation trip, you can always put on your special jeans and a nice t-shirt to ask a local for coffee.

My next fifty coffees

When I was working on Tickle: Digital marketing for tech companies I met with just over 50 people to discuss the project. My current big move is to get back into consulting with big companies on innovation and social media. I’ve been loving working with startups in London and will continue to contribute to the startup scene through Converge and the Innovation Warehouse. But it’s time for the next phase of my career. I’ll be reporting back on the coffees that I have along the way.