This has been a week of pitches for one of the businesses I’m involved in, and I’ll be seeing five more in a Capital Factory practice session this afternoon.  Whether you’re seeking to recruit a key person, to motivate an employee, to make a sale, or to land an investment, as an entrepreneur you’re always pitching.  That has to become your most finely honed skill.   The great successes I’ve seen have been the ones where the out-front person could make the pitch under any circumstances and cause good things to happen.

There are plenty of venues in Atlanta and Austin for coaching on this art.  I always liked the informal format of Startup Gauntlet at the ATDC, where the winner gets a certificate that says something like “your pitch sucked less.”  It’s a good chance to practice in front of seasoned reviewers who aren’t bashful about giving advice.

Practice does make a difference.  I’ve already seen the Capital Factory companies twice, and there was huge progress between those two sessions.  I expect even more today.  Good entrepreneurs are coachable and can improve with guidance.  They may get 5 completely different ideas from 5 different advisors, but they can synthesize something from each to improve their next outing.

Practicing first with “friendlies” is a good step.  Trying out your pitch on those already on your team as advisors or investors is a great way to get honest feedback and to help you develop a good style – forceful and succinct in making your points but relaxed and genuine at the same time. 

You have to match your presentation tools and approach to each audience.  You need to be ready for an individual, five people around a conference table, or a full-blown audience in a stand-up “séance” with whatever dogs and ponies help you get your message across.

And, you need to get to know that audience.  Is the decision maker in the room, or are you being screened?  Does someone there have the right frame of reference to evaluate your proposition easily, or is more background required?  How much real time do you have – not what’s on the agenda but the elapsed time before your listener starts checking emails?  (Looking at the watch seems to be passé now.)  What is the hierarchy in the room, particularly if you are presenting to a sizeable group working for an established corporation?

It’s good to do a round of presentations to real players you seek to persuade.  Perhaps you warm up with ones you think are more long shots, so you have a chance to be tested under “live fire” before you attack the targets you absolutely must win.  Even cold calls, if abetted by warm introductions, can be a good testing ground like this.  You’re better talking to anyone who might act on your request than sitting around just waiting for something to happen.  Force yourself into action and into staying in that action.

Some things that can happen are these:

You learn that your idea or the way you pitch it isn’t yet ready for prime time.   It’s better to learn that early from friendlies and give yourself a chance to refine your concept before you’ve blown any “must-have” opportunities.

You will get an introduction that matters.  Even if you pitch into a clearly losing cause, you never know what personal connection might come to the listener’s mind that leads you to a very positive next step.

You get that next meeting.  Often the major goal of any initial presentation is just to get to the next meeting where you can tell a more fulsome story to the real decision maker.   You’ve accomplished your mission on that alone.

You realize you need better ponies.  Very few people are truly visual when presented a new idea.  You may have to ratchet up your presentation with a movie, a magic show (saw one of those at a conference in San Francisco), or something else dramatic to be sure your audience “get’s it.”   This is particularly true in this era when you are competing with so many other new technology deals, many of which may go as quickly as they came but are still enough to overwhelm and confuse your listeners.

You realize you are pitching all the time.  Every time you run into someone who asks about or cares about what you are doing, you are pitching.  In my sports CD-ROM days I landed a deal with Tom Kite just after he won the US Open because someone in my church in Atlanta asked me about the company I had at that time, also happened to know Tom, and gave me a good reference.  I went from “who is that guy?” to “we want to do that deal” on that one reference.  (It didn’t hurt that the referring friend was also the Secretary of the Augusta National Golf Club.)

I won't repeat in this post all the standard rules about PPT’s, plans, models, etc.  I’m focused here just on the interpersonal skills.  Whatever happens, you next pitch will not be your last; as long as you are a tech entrepreneur you will be pitching, sometimes from strength and sometimes through adversity.

<Image from Paper Hounds>