It was only when Cindy Alvarez went to study at Harvard that she started using this incredible machine we are now all familiar with – the computer. It was a terrifying and amazing experience. Her first college job was doing tech support for some of the most brilliant people in the world, including Nobel prize winners, helping them to resurrect a file from a floppy drive, or find a file that they have lost.

When she saw the smartest people struggle to use computers and software she was inspired to learn more about what makes people decide when and when not to use something. Few years down the line, while trying to decipher people’s behaviours, she started doing product management for a couple of startups and had the opportunity to join Yammer which was acquired by Microsoft for over a billion dollars.

Now Cindy works at Microsoft, evangelizing customer development and lean methodologies, and as such is one of the intrapreneur case study speakers during Intrapreneurship Conference Silicon Valley. As a taster to her talk “Practice, Not Perfect”, we asked her a few questions.


Sounds like a fun job – what’s it all about?

Customer development is about figuring out who is going to buy your product as you’re building it and even before you’re building it. At the time, Microsoft started to realize they were getting their butts kicked by start-ups who were building products that customers really wanted, and were able to build these products a lot faster.

Consequently, there were suddenly a lot of teams and leaders who had to figure out what the customers really want.

The new mantra in Microsoft was: sales is a trailing indicator; if people are using our products revenue will follow.

Looking back- how is doing customer development at Microsoft different compared to Yammer?

If you look at how customer development is different in a start-up and a large company, you see that in a large company there is a good chance employees are saying, “We just can’t do that”, and if you dig deeper you realize that they don’t want to do something because it has never been done before.

The first step is understanding why something has never been done before.

For example, in Microsoft you have the issue of customer privacy. This is where having connections across the organization is essential because you need to cite prior law and have friends in the legal department to help you out.

The other difference is honesty. Startups can easily talk to people, tell them about the product they want to build, then abandon it and nothing happens.

But in a large company if you lead people to believe that something is going to happen and then don’t follow up, customers get disappointed and your reputation may be in jeopardy.

In the past some teams in Microsoft would promise customers, following a feedback session, to make a certain upgrade or add a feature that they asked for. Now most teams at Microsoft take a different approach, which is being really straightforward with their customers and telling them that based on their learning they may or may not add a certain feature.

In my experience, if you are open and manage expectations right, customers are quite amenable. It’s about shifting the relationships a little bit.

However, shifting relationships can be quite a challenge in big companies that already have established relationships. It can become really awkward to interview someone who has been your partner or customer for 10 years, and realize that you don’t actually know what their typical day looks like.

What can help with this problem is having a research team, because they can enter a relationship that has been going on since years and ask all the questions without having this awkward feeling attached to it of “I should have known”. The results are usually shocking, revealing a main problem their customers had that their partners had no clue about.

Another major difference is accepting uncertainties. In a startup it’s okay to tell your colleagues that you are going to talk to a bunch of people but you are not sure what you will learn.

Companies on the other hand, have created this fiction around predictability. We cannot predict what is going to happen next year yet they behave like they do. Going into an interview with an attitude of not being sure what will be the learning outcome is very jarring to people in large companies.

So, what’s key to getting customer development right?

Besides doing interviews guerilla style, and later detangling the learnings and see what is really important and where you need to dive into more deeply, it is also important to ensure that the feedback you get from customers is unbiased.

To get unbiased feedback you need to understand how customers are making decisions, what drives them, what their constraints are, and what their budget needs are. The focus of interviews should really be on how customers have been making decisions.

What often happens is people fall prey to a lot of cognitive biases when they talk with customers. People tend to ask leading questions (wouldn’t you say that, don’t you hate when..) and ask future predicting question (would you buy, would you use, if you had the opportunity…).

Humans are just very bad at answering these kind of questions – we tend to discount long term benefits, we like to think about short term benefits, and we have aspirational future selves.

People would say they want to go three times a week to the gym, but if you look at their calendar for the last week or month they may have not gone a single time. Past behaviour doesn’t lie. And there is a very good chance future behaviour is going to look a lot like that past behaviour.

Another mistake that people tend to do while interviewing is asking yes/no questions. In this way you give people a very limited choice, and you don’t actually learn much.

Give some space for open-ended question. Not everyone will take the time to answer open-ended questions, but you can get really valuable insights from the people who take a minute to think about the answer. Therefore another thing to do is try to phrase questions in a way that trigger this thinking process.

Besides bringing in a different department to conduct research, you need to identify the right customer to talk to. The right customers are the most amenable to changes, they are the ones who will quickly try and adapt to a new release. Furthermore, choose the customers who are dedicated to your product or service, a big name company that paid high fees but doesn’t have high usage is not the right audience.

One thing that I always does at the end of an interview is asking the interviewee who I should talk to next.

Even when you don’t have a specific target, and just want to reach a general audience, you still need to think about how to approach people wisely.

One bad habit, which is quite commonly used, is accosting people in coffee shops. Most people hate that. Someone on my team came up with a really great idea when it comes to getting the average person on the street to talk to you in such an environment.

What she did was approach the barista, give her credit card, and asked him to offer free drinks to people who didn’t seem cranky or in a hurry and who were willing to talk to her for about ten minutes. This saves the social awkwardness of when people have to turn you down because they really don’t want to get interviewed.

Last but definitely not least, don’t worry about talking to customers. A lot of time people wait until they have better interviewing skills, but the truth is that you will never do it perfectly. The best approach is just to start.

And finally: never ever treat customer-interviewing as something you will get to when you have the time!


Forget “practice makes perfect” – we just need practice!

On stage during #IntraCnf Silicon Valley, Cindy will talk tactics about how Microsoft’s Cloud & Enterprise division has encouraged the practice of listening to customers and being experimental.

Check out all 39+ sessions here