How to Start a Conversation Online

As a business owner I’m no stranger to the hard sell. Unfortunately, the two main messages I see whenever I meet someone new, or open a stranger’s email, fall into one of two categories:

  • Look how good this is
  • Shame on you for not knowing better

These messages, I’d estimate 95% of them, make me cloister up and not want to talk to you. They are given in haste and they are obvious. The person is trying to convert you without getting to know you first.

The Current State of Things

We are bombarded on a daily basis by calls to action, and most evoke a negative emotion. Either we feel inadequate that we can’t measure up to the unique selling points of the product offered, or we feel defensive that someone is trying to take us in a direction where we lack control. Oftentimes this is done from the moment we meet a new person. How many times have you read a generic, pre-fabricated pitch, only to groan as to the worsening state of human interaction and flagrant advertising?

If you’re looking to grow your network start, or pitch an article, or just get a conversation going you only get one shot at a first impression. Here’s how to do it positively and effectively.

(Pro tip: Save the hard sell for the end).

Pick a Convenient Time

Try to message the person when they’re online. It may be easier to get a conversation going in real-time than to count on someone to respond later on. Stack the advantages in your favor. Talk to someone when they’re online, and when you’re not distracted.

Ditch the Pitch

The pitch is comfortable. The pitch is tried and true. Except when it loses it’s magic after about the dozenth time you’ve used it. Just like stand up comedians that repeat the same routine, you can tell when a salesman is on autopilot. It feels forced, and the other person can just tell that you didn’t put enough time into it.


Offer before you ask. The best salespeople I’ve ever worked with put an average of fifteen hours into a relationship with someone before it is finally completed. Too often we approach a situation with bravado and a willingness to save the day, and we should if we believe in our product, but this feeling has to be suppressed in favor of giving the client value first. Don’t product dump on your future connections. You would not want it to be done to you.

Give 51%, Expecting 49% Back

Give more value than you expect. Personalize your message to your contacts. Find out what school they went to. Ask them about their travels. Starting a conversation online becomes easy when the person feels that you are there to genuinely help. You can’t go for the jugular from the first message. Focus instead on sharing your knowledge and expertise. The more generous you are with your time, the faster people will connect with you online and want to do business with you.

Approach First

We love notifications. I don’t know about you but I get a warm feeling in my heart when I see a +1 in my notifications or message inbox. It makes me feel wanted and loved. Why not share that feeling with someone else? Too often, we have this fear of rejection that often proves to be unjustified. By approaching first you show initiative and give the receiver a warm feeling. It will also set you apart from the individuals that are afraid to approach first.

Play the Statistics

At the end of the day, you will fail more than you win. Doesn’t matter. Keep playing.

Dale Carnegie once said: “You have to be interested to be interesting.” By approaching the relationship from a place of gratitude, you show that your intent is genuine. Ask questions, be interested in them and consider the key point in each message between the two of you. Actively listen “between the lines” – as an attentive psychologist or loving mother would do. This will help you decipher the motivations behind the response, putting you in a position to better help them in the future. Sincerity is the name of the game and it will carry you a long way.

Sources Consulted

Janis Krums is the co-founder/CEO of Opportunity, a business network driven by real-time interactions and opportunities around you. He’s a member of the Young Entrepreneur Council (YEC), and an investor in startups: memSQL, Plangrid, Lenda, FiscalNote, just to list a few. His expertise lies in growing businesses, fundraising, scaling and strategy. Find him on Twitter @jkrums