There is really no one “right” way to pitch a VC. Whatever approach gets the job done is “right”. Having said that, the pitches I would rate as most effective over the years are those that caused me to engage by asking the right questions at the right times. As an entrepreneur, this is exactly what you want; the VC playing straight-man. The alternatives (the wrong question or the right question at the wrong time) can totally disrupt the flow and logic of your pitch. It is a bad sign if the VC is asking questions that don’t make sense or seem out of place.

Getting the VC to ask the right question at the right time is all about the logical structure and layout of the pitch; what you say when. What follows is a generic logical flow that I think optimizes an entrepreneur’s chance of getting the VC to play straight-man.

• Tell ’em what you are going to tell ’em: Pretty simple, really. Tell the VC the three to five conclusions they will take away from the visit if they are paying attention. End this with an introduction to your team. Keep the team description short, just high-level backgrounds and skill sets.
• The market: Articulate the market that you have specifically assembled this team to attack. This is not the addressable market for your particular solution (we’ll get to that later), but rather the umbrella market under which you are operating. How big is it? How fast is it growing? Is it dominated by giants or fragmented? Is it profitable, efficient, etc. Provide whatever information is necessary get the VC thinking about what the problem might be with this market; the unserved or underserved need. You want the VC to start trying to figure out the problem you are solving in that market, before you tell them what you do.
• The problem: What is the problem, the pain point you have identified. Why does the problem exist? How big is the problem? What pain does it cause. Can you quantify the $ value associated with solving the problem? Is this a problem that has been around for a long time or is it a new/emerging problem. I’m not looking for a solution yet; we’ll get to that later. By this point, you want the VC asking: “What is the solution to this problem?”
• The solution: Don’t tell me about your solution yet. What I want to hear about are the requirements to solve the problem. What technology needs to be developed? What added layer of the value-chain needs to be inserted? I want to hear you say things like: “What is required to solve this problem is …” Is cracking this problem non-trivial? Why has it not been solved yet? What is new (technology, etc.) that finally enables this intractable problem to be solved. What are the rewards that accrue to the player that leads the market in solving this problem? By this point, you want the VC asking: “Tell me how your products align with the requirements of a world-beating solution.”
• Your solution: Introduce me to your specific “version” of the solution. Show me how it aligns with the generic requirements that you outlined. What is unique and proprietary about how you have approached the problem and architected the solution? Why will others have difficulty replicating what you have done?
• The economics: Tell me how you get paid and why customers are willing to pay that amount. Use the economics of your business to show the size of the addressable market for your solution. You can flash your financial projections, but don’t dwell on them.
• Team: Return to the team and show how the team you have assembled is perfectly suited to executing against the opportunity you have articulated.
• Tell ’em what you told ’em: Revisit the three to five key takeaways you want the VC to walk away from the visit with.

What I have found is that pitches that follow this logical flow make for engaging discussions with lots of participation from the VC. Remember, the goal is not to “prevent” the VC from asking questions; that is unavoidable. The goal is to get the VC to ask the right questions at the right time. Getting a VC to play straight-man to your pitch doesn’t guarantee they will invest; but it will make for more effective and productive meetings and will increase your chances of raising money.