Listen Your Way to Funding – Master Listening (Part 2)

Fast track to funding #4 by Intelliversity

Listen Your Way to Funding - Master Listening (Part 2)

Fast Track to Funding #4

Last week I introduced you to the concept of mastering listening as a skill set that we all think we’re good at, but few of us truly are – and to the idea that listening is a skill that can be mastered, just like time-management or public speaking. We looked at four specific things that masterful listeners do in conversations:

  • Ask questions to the speaker that provoke insight and discovery
  • Build the self-esteem of the speaker and create a safe space for discussion
  • Build relatedness, rather than trying to “win” the conversation
  • Make meaningful suggestions to the speaker AFTER doing the other three things

We ended with what I hope was quite an insight:

Masterful listeners actually get their own ideas, concepts, dreams, and visions heard by others more effectively than poor or average listeners.

This week I want to apply these principles specifically to the funding of your enterprise.

Funding is generally going to involve several conversations with one or more potential investors and it’s natural to approach those conversations from the context of needing to “win” the conversation – that is, convince the investor that you’re talented, a good leader, a bold visionary leading a great team, have a good product or service that a defined customer base is going to want and a way to deliver it to customers profitably and sustainably. Oh, and at the same time come across as trustworthy, likable and of good character.

That’s a lot to achieve in one or two or even several conversations!

But that’s what it takes, right?

That’s what this blog has been teaching, more or less, and what business gurus and successful entrepreneurs tell you.

Yet it’s fairly daunting to master all of the things in the paragraph above if you have to tick them off one by one while engaging in high-level conversations.

Fortunately, there is a shortcut – a way to fast-track the process towards the outcomes that you want. It’s a way to accomplish most of those factors holistically because it influences each of them and surrounds them all.

Masterful listening.

Last week I provided you an overview of what excellent listeners do and say within a conversation. We discussed the fact that these things could be learned. But in order to learn them, you really do need to have an intention to reap value from what others have to offer.  If you come from a place of “already knowing” the right answer or approach, you can’t really be an excellent listener.  It takes a good healthy sense of humility to acknowledge that you, the vision master, might not always have the best answer to the issue at hand. A little humility makes you more open to what others have to say and that breeds the conditions for good listening.  Add the intention to boost the esteem of others and a willingness to “volley” back and forth in the conversation and you can be an excellent listener.

With investors, this is absolutely crucial.

Here’s why . . .

Most investors want to offer more than just their money to you. They want to offer their wisdom, experience, and specific skills.  That’s one reason many investors like to invest in industries where they have past experience – they know they have something valuable to offer beyond money.

However, if you’re only interested in the money, they’ll sense that in the way you listen – or actually don’t listen to their suggestions, ideas, and wisdom.  Listening is an aspect of something called situational awareness. Situational Awareness is the ability to identify the critical elements of what is going on around you.  It’s a skill taught to police officers, special forces and, yes, James Bond.  Entrepreneurs need to understand it as well.

With investors, situational awareness requires that you understand that you’re speaking with someone that has far more on the line than their money.  He or she has more interesting things to do than investing in someone who is closed off to all the other contributions they can make.  It requires you to understand their motivations for meeting with you in the first place. And it requires that you know a bit about their interests, fears, hopes, and goals.

How do you learn all that?

If you said “research” you’re only partly accurate.  I highly recommend doing research on every investor with whom you get a meeting.  Then listening to them is the most important thing. And remember one of the tenets of good listening is asking good questions that open a dialogue.  It’s in the dialogue that your investor will reveal all of these important things.  But not if you aren’t interested; not if you don’t ask him or her to expand on what they’re saying; not if you’re clearly uninterested in them.

Instead, be genuinely curious about the investor and his or her life, interests, goals, fears, dreams and ideas, in the same way that you are genuinely curious when working on product design or business modeling or research. Masterful listening happens within this space of humility, curiosity and genuine interest in another person.

Now, this may or may not be all be new for you and, if you’re honest with yourself, you may realize that, at best, you’re an average listener. Work on it, you can master it and it will pay dividends throughout your business career.

But Rob, I have a big meeting in two days! I won’t be a masterful listener in two days. What do I do?

You could write a CPR for this!

That would help immensely, and I highly suggest that you do use a CPR for every investor meeting. In fact, I’m going to write one for you right here, right now, to help you set the right intentions as a listener that can produce the best outcome.

A CPR for one meeting should be brief – a few points at most on each section.  Short and sweet.

Recall the image I gave you about a CPR – the Context is the wrapper holding the purpose and purpose is the box holding the gift – the results.

Using this metaphor it's obvious that we have to go and shop for a gift before we box and wrap it . . . so as always we begin with our intended results:


  • Our investor trusts us and we trust him or her
  • Our investor is someone with whom we want to build a long-term, successful relationship
  • Our investor feels appreciated
  • Our team feels excited, hopeful and motivated to succeed

Next, we look at purpose – why are we producing the results we’ve stated.  Using the metaphor, we’ve selected our gift and we need a box in which to put it.


To create real trust and connection with our potential investor so that:

  • He or she is likely to fund our company sufficiently so that;
  • We can fully develop our product and get it to market so that;
  • Every stakeholder is excited about our future.

Finally, we need a context for the whole thing – the perfect wrapper:


Listening Like Masters, Winning Like Moguls

How’s that?

Play with it.  Make it your own.  Create a CPR that empowers you and reminds you to cultivate masterful listening and you’ll find that your investor meetings are enjoyable, productive and fulfilling. Even if a potential investor doesn’t fund your company, if you listen masterfully they are likely to form a positive impression of you, your team and your ideas.  Most importantly, you never know to whom they’ll say good things about you. Even if they don't invest in your company, they may like you and introduce you to someone who will. Empires have been built on such things and businesses have been funded this way, too.

Key takeaway:  To get funded you’re going to have to engage in multiple conversations with potential investors. Don’t try to “win” those conversations. Instead, endeavor to build trust and relatedness, because without those things investors simply won’t fund you. To accomplish this, practice masterful listening.  To do this, focus on situational awareness with investors, by listening for what’s most important to them and engaging them to talk about those things.  To help you remember to focus on them, not on you, create a CPR like the one provided here so that your context empowers you to listen masterfully.