How to date your customers

I’ll admit that it’s been a long time since I’ve been on a date. Having been married for 13 years, I will forgive you for being a little skeptical when I dish out dating advice.

Although my memory on this topic is a little hazy, I do remember this much:  The kinds of conversations you have with people depends on what stage of the relationship you are at.  You will ask different types of questions when you are just starting to get to know them, then if you are already in a relationship.

There are distinct phases in relationships, each coming with different sets of questions.

Initial checking out phase:  You are trying to figure out whether or not there is some basic compatibility there.  Do you like this person?  Do they like you?

Typical questions:  “Tell me about yourself.”  “What are your interests?”

Getting to know you phase:  You want to learn more details about this person because you are genuinely interested.

Typical questions: “What are your parents like?”

Negotiating the specifics of dating:  At this stage, you are routinely checking in about specific plans, and maybe increasing the commitment level.

Typical questions:  “Do you feel like Thai food tonight?”  “Can I leave my toothbrush at your place?”

Getting feedback:  Periodically, you want to check in with your partner about how things are going.

Typical questions: “Did you like that birthday party I threw you?” “Was that good for you?”

Just like romantic relationships, customer relationships have distinct phases that each come with their own set of queries.

I often get asked, “what are the specific questions we should be asking customers?”

And I always counter with a question of my own (I’m annoying that way).  “What stage of the relationship are you in?”

The fact is, there are times when you should be doing a quick check-in, “Was that good for you?”, and there are times where you should be just getting to know them, “Tell me about yourself.”

A common mistake is to ask too many different kinds of questions at once, at the wrong time, and in the wrong way.  It would be like asking “What are your interests?” quickly followed  by “Can I leave my toothbrush at your house?”  Awkward.

No wonder nobody filled out your survey.  No one wants to date that guy.

For instance, when you are exploring innovation ideas in a particular market, you need to be asking questions like “Tell me about yourself.” “What are your challenges?” “What keeps you up at night?”.  This should never be done as a survey.  A survey is simply not a good tool for this type of question.  You need to have an actual conversation.

On the opposite end of the spectrum, when a customer has completed a transaction, that’s a great time to ask them “Was that good for you?”.  Skype does this very effectively with their call quality survey after a call.  It takes a few seconds to answer and you can continue with your day.  This would be a terrible time for Skype to ask you about your deep challenges with communication in general.


If you already have a relationship with a customer, then it is a good idea to periodically check in with them to see what other needs they might have.  You should ask things like “How satisfied are you with us?  Would you recommend us?” “Is there anything we can improve?”  “What kinds of things would you like to see from us in future?”  These kinds of questions can be done effectively through a survey.

The next time you are thinking about what to ask your customers, pause for a moment and ask yourself these questions.

  • What is the status of your relationship with them?
  • What are you trying to find out from them?
  • How can you deepen that relationship?

Once you know the answers to those key inward-looking questions, you will know what questions to ask your customers.