When Defensiveness is Masked in Explanation, Investors Notice (and so does everyone else)

We run QuickPitch sessions every month to scale the process of hearing short pitches from companies asking us to invest. We also run QuickPitch Bullpen sessions for earlier stage ventures that are still in the formation phase.

A recent QuickPitch helped solidify a reaction I have to pitches that I’ve never fully explained. I shared it with the pitching CEOs, and they found it helpful, so I decided to share it more broadly.

Here’s the scenario that sparked the discussion. It happens often.

Pitching CEO pitched her startup.

I gave some feedback.

Some of my feedback was in the form of a question or an expression of concern (as it often is). This time it was: “When I saw your competitor slide, I really appreciated that you included the most formidable competitors. However, I think you undermined your credibility when you summarily dismissed those market leaders: ‘their sites and models are totally outdated.’” I said I wanted a better, more specific argument for why her upstart company could beat these giants.  

The pitching CEO provided a three-minute, rapid-fire answer summarizing all of the great research and insights they have secured to prove that people no longer like the market leaders and want this exact solution.

I interrupted the pitching CEO (these pitch and response sessions are fast at QuickPitch), thanked her for the response and realized that I actually processed very little of it.

This time, I paused to share how I felt about the interaction. It had happened with two of the CEOs in that day’s QuickPitch.

I shared my gratitude and admiration for the backgrounds of these two leaders. They are the right people to build the businesses they are building. However, I let them know that what I as an investor am really hoping to do in a session like this is to start a relationship with a CEO.

Relationships are built with interaction, back and forth in conversation. I already know from most CEOs’ backgrounds that they know more about the sector than I do. What I’m looking for is a discussion that helps me learn something new, resolve a doubt, get curious about what I might be missing.

In short, it’s impossible to build a relationship with someone who quickly imparts everything they know about a topic in response to a question about a doubt I’m having. I likely won’t be convinced. And worse, I often read this kind of rat-tat-tat response as an explanation that feels pretty close to defensiveness.

Rapid-fire explanations without curiosity or engagement often feel like (and, I would suggest, are) dressed-up defensiveness. As an investor, I’m not terribly game to build a relationship (friendship, investor relationship, or anything) with someone who feels defensive from the start.

If you’re pitching your company, watch out for this. Notice if you’re giving a lengthy explanation without a lot of room for breath.

Intentionally pause to (a) breathe and (b) check in with the investor hearing your pitch. Great questions include: “How is this landing with you?” “Could you be a little more specific about your concern so I’m sure I am addressing it directly?” This not only helps to further a conversation but also shows you’re listening consciously. Your question or reaction must be authentic, but curiosity is something you can intentionally build as a muscle.

Give it a shot.

I’ll do the same with any feedback you have for this post.