The Overture

Approaching and starting a conversation with a stranger is never entirely comfortable.  When it is at an event specifically billed as a mixer for different constituencies to access each other, it can be especially awkward (e.g. entrepreneurs to meet investors).  Even people with the best of intentions can have their guard up, make unfair assumptions, or slip into stereotyped roles. When you think about the fears and motivations in play, this is no surprise.  In the entrepreneur/investor context, the investor is afraid of being trapped for an excessive period of time in an awkward conversation where they have no interest in the subject, and to escape, will be forced to say something that might come across as hurtful, disrespectful or rude.  The entrepreneur is worried about getting and keeping the investor’s attention, laying their story out in a cogent way, and looking down the barrel of almost certain rejection.  Eyes dart, brows furrow, sweat beads, minds race.  Nobody sets out to be an oaf, but it seems to happen anyway. 

I was struck, at just such an event tonight, by the huge difference basic people skills and manners can make in terms of an entrepreneur’s overall effectiveness in this setting.

It is such a simple set of lessons, but we were all taught them so long ago that I guess we’ve forgotten.  No matter how important your message, it pays to use good manners.

Approach cautiously, wearing a smile.  Don’t invade people’s personal space.  Have respect for the person your target is already talking to.  Listen and gain some context while you wait for an appropriate time to break in.  Introduce yourself by name, not by company.  Even though you are in a hurry, toss in a pleasant, neutral ice-breaker about the event, the weather, current events, the other person’s well-being, whatever.  Give them a moment to change mental channels and engage with you on a human level before you dive in.  They know why you are there; they know you’ll get there soon enough – why not distinguish yourself with a more relaxed overture?  Nothing is more uncomfortable and hostility-inducing than someone who elbows in on a conversation and begins paving over whatever was going on.  It comes across as rude, disrespectful and self-absorbed.  Believe it or not, if you wait patiently at the edge for a graceful moment to enter, you will make a much stronger impression.  They know you are a hard-charger or you wouldn’t be an entrepreneur in the first place.  What they are wondering is whether you are a hard-charger with manners, people skills, self-awareness, poise, persuasiveness and grace under pressure.

Once you start in on your discussion of your business, remember the old adage: if you ask for money, you get advice; if you ask for advice you get money.  Approach the conversation with some humility and a genuine curiosity for what your listener thinks.  You can always chose to ignore their advice if you don’t agree it is brilliant; better to demonstrate a smidgeon of coachability and respect for their viewpoint.

As you segue into a discussion of the business particulars, start by setting the table.  A quick one line pitch explaining very succinctly what you do is very helpful.  You know: who your customer is and what problem you solve for them?  That’s always a good starting point.  This allows you to create some context and help the listener get oriented and begin pulling up relevant mental data and connections.

At this point, although the temptation to plow ahead is irresistible, you should not.  Instead, you should learn to pause to gauge comprehension and interest level.  Why?  Two reasons: (1) if you lose someone at the beginning, it is really hard to get them back – they just glaze over and check out; (2) if they are not interested, they probably have a pretty good reason and little you can say will change that fundamental fact – pushing them into the discussion anyway will trigger their flight instincts and confirm their worst fears (you know, about how they are going to be forced to say something rude or hurtful).  Don Dodge did a great post on this topic entitled “If they aren’t ready to listen, it doesn’t matter what you say.”

But even more damaging than confirming someone’s worst fears is the fact that you just missed your Plan B.  You took a fantastic opportunity to network with a high value target and turned it into a socially awkward cringe-fest.  So train yourself to yield at that crucial juncture.  Nine times out of ten they will ask a question which will draw out the rest of your story.  Then work through your story in a relaxed way, with room for questions and give-and-take.  Don’t be preachy or pedantic.  Don’t try to impress with jargon.  Don’t go into minutiae.  Your goal at this point is to connect as a person, generate a little interest and get a followup meeting or next step.  So let it unfold.

Once it has unfolded a bit, don’t lose track of time.  Brevity matters.  Remember the context – you are at a mixer.  This is not the place to conduct a due diligence review or secure an investment.  Leave them wanting more.  Acknowledge that they probably have other people they need to speak to (such as the ones politely hovering as you did), and suggest an appropriate next step.  Better yet, let them suggest one.  If things have gone well, they may ask to meet again or request that you to follow-up with a copy of your executive summary – make sure to follow up promptly and remind them who you are and where you met.

If it was just so-so, you’ll probably get a business card swap.  Ask if you can email a couple quick follow up questions.  If they seem open to it, follow up with a quick “great to meet you, thanks for your time” and be sure to ask a small number of very open-ended questions like what was your biggest concern with my idea; what was its strongest point; what was its weakest point; if you were me, how might you proceed on that issue; can you think of anyone it would be good for me to talk to, etc.  A well-bounded opportunity to give a couple bullet-points of quick feedback will generally produce the desired result.  An overly broad and vague request like, will you help me, will you meet with me, or can you fix my plan, will send them running for the hills.

If there is no suggestion of a follow-up, no card offered, and the body language is looking like an escape is being planned, don’t force it.  They have probably concluded that it is not a fit for them, and there really is no point in trying to force more engagement.  A dry well is a dry well.  Shrug it off and move on.  It happens.  My point is just that if you have good manners, it might happen a little less often.

Comments, questions or reactions to this post? Leave a note below and I will respond to your questions.

If you enjoyed this, you might enjoy: What I Look For In An EntrepreneurWhy Angels Chase ElectronsAre Entrepreneurs Wild Risk-Takers?Pick Your Founder/Co-Investors Carefully & Reflections on the Nature of EntrepreneursTop 20 Dos & Don’ts with Angel Groups & Early Stage FinancingDelusional EconomicsThat Vision ThingThe Power of An Advisory BoardLoch Ness, Unicorns & The First-Mover AdvantageShould I Wait For A Technical Co-Founder.

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