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"Flirting" With Your Customers


All over the world, there are classes that teach people how to flirt. A German university even requires their IT engineers take a flirting class—not to attract a partner, but to learn how to interact more effectively in the workplace. While it may sound “light” at first glance, flirting means connecting with others, and connecting is the key to good communication. That is what the first principal of the Agile Manifesto: individuals and interactions over processes and tools is all about.

Talented Agile Project Leaders know how to connect to improve understanding—getting the requirements spot on, working through crises or unreasonable demands—and, ultimately delivering the right product faster. This article explores how flirting techniques translate to use in a business setting—inspiring us to create stronger connections and greater understanding of our customers.

What is flirting and what can we learn by it?

When we talk about “flirting,” we are not talking about acting amorously without serious intent, as Webster defines it. We are talking about incorporating authenticity into the process, and in that sense, flirting is better defined as connecting with people—or better yet, making people feel valued through every interaction.

Seen from the business perspective, there is surprisingly much to learn from flirting. You can apply the same methods you would use to “score on a Friday night” to create greater understanding in the workplace. I’m not talking about romance at the office—this is simply about making connections that help you go from the “being-aware-that-you-want-to-connect” stage to the “mutual-desire-to-work-together” stage faster. A critical learning point is how you develop those relationships that make working together easier, more productive and more fun. A talented flirt asks questions, really listens for the responses and then takes action together with the person they are connecting with. Agile projects are built around this kind of great communication.

My partner, Ole Jepsen, and I have discovered there are 8 Steps to building a connection with customers to enhance communication and build business value. Flirting with your customers can create the connections that make a significant difference in a project’s success.

8 Steps to Flirting With Your Customers


Acknowledge importance of engaging the customer. Be aware that you want to connect.

Some people have their radars “on” when they go out—and some don’t. If you want to connect in either a romantic or business situation, you need to be aware of who is out there and who you need to connect with. You do that by acknowledging that you want to connect, because connecting is the first step in building a relationship and trust, both of which are extremely important in any Agile project.

This step sounds easy. Believe me, it’s not. You need to open yourself up to the possibilities of connecting. That takes confidence and awareness. Confidence comes from inside: knowing who you are and knowing that you are good at what you do. If you don’t always feel that way, there are some things you can do to increase your confidence level: exercise everyday, wear a clean shirt, pop a breath mint in your mouth, practice an opening line, smile. Prepare like you would for a blind date. Don’t change who you are, just make yourself even better—that increases confidence.

As for awareness...I just returned from the Agile2009 conference, where I spent nearly half an hour talking with some folks who sell Agile tools. The next morning, the two sales guys walked right by, completely unaware of me or any of the people around them (most of whom were also conference attendees—and potential customers). They simply walked with their eyes glazed over oblivious to what was happening around them. It was not on purpose, but it definitely was a missed opportunity to connect!


Find the power in the organization. Determine who you want to connect with.

The next step is to figure out who it is you need to connect with. If you need more detail on user requirements, having a connection with the business customer makes getting that information much easier. Know what you want to achieve by creating the connection. Is it to get a clearer picture of the project? Is it to deliver in shorter iterations? Is it to vent your frustration with the work? The purpose of the connection determines who the target is.

Sometimes the appointed user-representatives are not the ones with the real knowledge or the real power to help the project succeed. As an Agile project leader, you need to find out who you really need to connect with and then do so. If you don’t, chances are they will pop up when all decisions have been made and the product is being developed. And if they are strong enough, the can destroy the value that you just created.


Show and prove your interest in their perspectives. Show openness and interest.

Here’s your chance to practice your opening line...perhaps it’s something like this: “I’m working hard on this particular requirement and I’ve heard you made a difference on a similar project. Could we get a cup of coffee and talk more about what you did?”

This works the same way a good opening line works in a romantic situation. You want to make the other person feel noticed and valued. Don’t overdo it or you come off like the sleazy guy hitting on all the women in the bar. Make sure that when you show your interest, you have done your research. (Google your target if you need to.) You must genuinely compliment the one you are “moving in on.”

Remember too, that there’s a big difference between stopping by someone’s workspace to pass along information and stopping by to pass along information AND to ask them how their daughter’s swim meet turned out. If you are friendly and interested in the other person, your interactions become richer. People are more likely to share vital information with people they feel they are friends with.


Stand back and see what happens. Let the other have a chance to show that they are interested.

Connecting is a two-way. You must listen to understand where the person you want to connect with is coming from. Since I’m an American living in Denmark, I think it is appropriate to quote both Søren Kierkegaard, a prolific Danish philosopher, and Abraham Lincoln, a great American president, both living around the same time in the 1800s.

Kierkegaard said, “If one is truly to succeed in leading a person to a specific place, one must first and foremost take care to find him where he is and begin there.”

Lincoln said nearly the same with, ”When I’m getting ready to reason with a man, I spend one-third of my time thinking about myself and what I am going to say, and two-thirds thinking about him and what he is going to say.”

The next step to connecting is to give the other person a chance to come to you, and for you to listen.

But what if he or she doesn’t indicate interest? There are obstacles to creating valuable relationships. The biggest obstacle is that you may be talking too much, using up all the interaction time with what you have to say. The other person doesn’t have a chance to get a word in. Stop talking. Start listening. If you need help with this, I highly recommend using the Agile Analysis/9 Boxes questioning technique. It’s a great way to get people to talk with you. You can read more about it on Portia Tung’s blog: (This technique was developed by Solution Selling® as a tool to help avoid customer rejection.)

In the event that the other person truly shows no interest, just as you would in the bar, move on. Repeat steps #2-4. Determine the next best person to connect with in order to create the understanding you desire.


Share more. Be open.

In order to really understand customer requirements, it is critical to have an open and honest, and probably deep conversation about what is happening between the business and the project. Conversation like that only happens between people who have a close relationship. Sharing more about yourself, about your concerns and successes with the project, about whatever else is relevant will help create these close relationships.

It’s important too, to acknowledge “The Grey Zone.” Ole, my partner in all of this flirting business, is a firm believer in this. It helps lay everything out on the table. The grey zone, as Ole puts it, is the difference between what the customer hopes to get out of the project – and what the supplier hopes to get away with. It’s like buying oil-lamps in a Jerusalem bazaar: The tourist wants to get as many lamps as possible for his money. The salesman wants to get as much money for his lamps as possible. They are both valid viewpoints.

This natural conflict of interest exists in all development projects, even when there are “precise and complete specifications” – because there is always room for interpretation and misunderstandings. Requirements are “rubber bands sold by the meter.”

Even though this grey zone is always there, it is usually not talked about openly.

If we talk with the customers about this early in the project, then we share some honest and open thoughts with the customer, and chances are that the customer will do the same – even admitting that he is usually asking for more than he actually wants because he knows that he will probably not get everything he is asking for.

If you’re open, you are more likely to create an atmosphere that is equal and honest. People respond to openness. Sharing more with another person is risky, however. Opening up means making yourself vulnerable to being hurt. But if you are willing to take the risk, offering yourself up to someone shows trust—and most times that trust is returned. These trust-based relationships create value in your organization by allowing you to get the right information sooner to deliver the right product faster.

Enhancing the richness of the connection, increases understanding and business value.


Go out with the customer. Have some fun.

Strong relationships are multi-dimensional. To see the more relaxed side of a person and get to know them better, you need to go out and have some fun! We playfully say “dance,” because you’ve had your drink at the bar and shared some experiences, now it’s time to go out on the dance floor. Fun does have a purpose.

Spend some time out of the office, it can be as simple as going out to a bar, mingling with your team and your customers. Don’t sit down. Maintain your ability to move around and connect with the folks you want to connect with. Your fun activities should enhance the opportunity to communicate. The opposite happens if you have a “Paintball War,” or go to the shooting range. Even bowling inhibits conversation, because just as you get started connecting, it’s your turn to bowl. You can’t connect in the 30 seconds between turns.

If you come up with activities like playing board games, or going to an art class, or any activity that allows on-to-one communication, you build your relationship. You see another side, and that makes your connection richer.


Work through a crisis together. Get real with the one you’re connecting with.

Nothing solidifies a relationship more than having survived a crisis together. The key to this is surviving the crisis. Many romantic relationships fall apart when the couple has an issue that one or both parties cannot deal with. On the other hand, if they get through their difficulties, the relationship becomes stronger. There is a feeling of “we survived this, we can survive anything.” The same happens in a business relationship.

A few years back I worked as a project manager for a large public relations agency. Our team was given two weeks to deliver a multi-faceted program for our client who specialized in international risk management. After one week, the client called and said he was going to Paris the next day and needed whatever we had. Panic struck. This would be impossible. Anthony, the graphic designer on our team was the one who had to produce the mock-up our client would show in Paris. He told me he could not get it done. I said, “We have exactly 20 hours before Allan, our customer, gets on that plane. What can I do to help you make this happen?” I got in my car, drove around getting all the supplies we needed, and then headed to Anthony’s home office where we worked through the night developing the product. We were dead-tired when we finished, but proud of what we had accomplished. Anthony called me as I drove to the airport to deliver the materials. He thought what we had just done “rocked” and he hoped I never asked him to do that again. However, if I did, he knew I’d be there right in the trenches with him to make it happen. Needless to say, our client was also delighted by the speedy results.

I was able to convince Anthony by laying the cards on the table: this was our next-to-impossible task. Then by staying positive through all the doubts and solving the “crisis” together, we developed an even closer working relationship. We created trust, and this in turn created great value for our company.


Enjoy the relationship with the customer. Take advantage of the mutual desire to be together.

Congratulations, now you are connected! It’s not all light and fun. It’s impossible to deliver the right product on time without help. You depend on others for your mutual success. It’s a mindset: you approach a situation differently if you believe you cannot succeed by yourself.

Creating these connections is truly a way to build value in your organization. You learn how to understand your customers and the subtleties of their needs. Keep connecting. Like all good relationships, maintaining it and finding new ways to keep things fresh strengthens your connection even more.

Flirting with your customers is important. It helps build relationships that create business value—and these relationships don’t just happen by themselves. It requires desire and commitment—in other words, it takes work.

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Community comments

  • Great article

    by Josh Gough,

    Your message is awaiting moderation. Thank you for participating in the discussion.

    This was a great article, and I also think it is important to note that some of these techniques are not necessarily sequential.

    For example, in an environment where the culture is very silo-like and there is little connection between different departments, you can try the "DANCE" technique first to bring people together outside of the office, perhaps to volunteer together in a community service project to create a sense of team that may actually not yet exist or is strained within the office.

    People generally want to be involved in the products you are building, especially when they will sell, configure, and support that product once you and your team finishes them.

    It is up to you as an agile leader to "meet the company" wherever it is and use different strategies and techniques to build the relationships and interactions that create trust and teamwork.

  • Flirting? Really?

    by Dallas Vaughan,

    Your message is awaiting moderation. Thank you for participating in the discussion.

    Redefining the word "flirt" seems unnecessarily creepy. Especially since the metaphor doesn't fit well, since actual flirting is a very singular (mostly one-way, superficial) activity, whereas what you're describing has more aspects of a real relationship between you and the customer - more like a true "friendship".

  • Flirting?

    by Sakkraya !,

    Your message is awaiting moderation. Thank you for participating in the discussion.

    Probably not the most suitable term.

  • Your message is awaiting moderation. Thank you for participating in the discussion.

    +1 for stop misleading headlines

  • Why did you leave the post content and focused on the title

    by Mohamed Faramawi,

    Your message is awaiting moderation. Thank you for participating in the discussion.

    where you really thinking of romantic flirting with customers , and this is why you viewed it.. well sorry you are disappointed, but overall its a great post on explaining how you should deal with your client especially if you are working in an agile environment.

  • Re: .

    by Jenni Jepsen,

    Your message is awaiting moderation. Thank you for participating in the discussion.

    Thanks for the feedback. As I mentioned, this is about CONNECTING with people. The title is meant for fun--which is what flirting is. I don't see it as superficial, but I understand that some people do. I appreciate all the comments. It helps make my work better.

  • Re: .

    by Gergely Nagy,

    Your message is awaiting moderation. Thank you for participating in the discussion.

    I also found this strange at first, but now think there is something to it: more than that 'true friendship' blabla.
    Take the "BACK OFF A LITTLE" phase, for example. Of course it's not just flirting, but it's a more fundamental mechanism that may be easier to understand with such a shocking(?), silly(?) metaphor.
    It's actually cool to realise analogies between such disparate things.
    So, thanks, for the enlightenment:)

  • Re: .flirting

    by miko matsumura,

    Your message is awaiting moderation. Thank you for participating in the discussion.

    I like it... have to be sure this is operating at a metaphorical level though =)

  • Your message is awaiting moderation. Thank you for participating in the discussion.

    As sexist as this may sound, only a woman would write an article like this. Men, especially in engineering and science, interact in a completely different way with each other. The flirting game that is being promoted in this article is calculated and unauthentic; it is a job for marketing reps, not engineers. If I wanted to be a sales guy or a manager, I wouldn't have joined a trade that let me avoid all of that phony baloney kiss-ass behavior. Many people can sense it, and they don't like it. I would advise against it, and suggest something more traditional and authentic. I find that just being frank and honest with people gains their respect and is the best thing for a professional relationship.

  • Re: Pap

    by Tobias Mayer,

    Your message is awaiting moderation. Thank you for participating in the discussion.

    I disagree. Flirting is not inauthentic at all. A person doing it may be, but the article clearly warns against that. Flirting is a skill, it is the skill of connecting and valuing another person. Some people are very natural at this, others may have to learn it, but it can be learned. Not everyone will be good at it, and if not should perhaps be cautious.

    I like the connection between romantic flirting and creating good (customer) relationships. Flirting can lead to friendship, as much as it may lead to romantic involvement. It is simply about connecting on a level below the superficial.

    And by the way, I am a man, and a software developer.

  • Re: Pap

    by Justin Greenwood,

    Your message is awaiting moderation. Thank you for participating in the discussion.

    Flirting in itself is only as inauthentic as the intentions of the person doing it. When you go out of your way to target people you can use to your advantage, as the article suggests, then "flirt" with those people to get in their good graces - that is by definition calculating and unauthentic. As you said so succinctly, this is a skill (and to many, a game). It is not something that comes to most of us naturally, especially in people that spend most of their time in seclusion behind the computer screen. If you want to be a player, that's fine. As for me, I'm gonna be a player hater.

  • Re: Pap

    by Justin Greenwood,

    Your message is awaiting moderation. Thank you for participating in the discussion.

    By the way, I don't consider an "agile coach, trainer, and educator" a typical software developer. I'm not discounting your technical skillset, which is fantasic I'm sure. It's just that you're selling something - something that doesn't directly bring revenue to a company. I have no doubt that you must spend much of your time "flirting".

  • mutual benefit

    by LIN Jacky,

    Your message is awaiting moderation. Thank you for participating in the discussion.

    it is interesting and making sense to me. it is talking about how you get touch with and then earn the trust from the to-be-partner in terms of bilateral mutual benefit.

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