On a Sunday in Pasadena, California, two humans sat facing each other on tufted leather couches: a 50-something male, Founder and CEO of a 16-year-old, multi-million-dollar financial technology company, in his pajamas, and me, a then 20-something female Founder and CEO of a personal and organizational development start-up, The Glow Effect. Quieting my pounding chest, I drop my vocal tone to sound confident: “What do you think?”
He looks up from my overly-wordy description and says, “You seem to be bright. Perhaps you should meet with some female executives and figure out how they got where they are.”
Instead of asking more questions or hearing possibility, I heard rejection. My listening turned off. Smiling and nodding, he continued speaking about breaking glass ceilings and hitting financial goals.
I left the Pasadena estate with resolve: figure out how to make these asking experiences less excruciating. Since that dismal “Ask”, I have researched, conversed, and practiced how to ask for myself and others struggling, in business and otherwise.
Recently, I sat down with Elisha Avne, FLDWRK’s Startup Program Manager and my business coach, and discussed the components of a strong ask. While there is no one-size-fits all approach, here are five key principles to make big, bold asks with grace:
Define the core components of your ask.
Regardless of the subject matter, every ask has four main parts:
- You: Who are you?
- The Invitation: What are you asking? What are you offering?
- The Who: Who are you in conversation with?
- The Response: What is the outcome?
Clearly distinguishing the basic pieces of your ask will create more clarity around your strengths and areas of opportunity.
Once you establish the basics, dig deeper with these questions:
- What is currently holding you back in asking?
- What are your values and how are you expressing them in your questions?
- What are you giving to the world by asking?
- What is missing from the world when you withhold your ask?
Continually investigating these elements will only increase your asking competence.
Differentiate your value from your question.
In my conversations with Elisha, she said something that really stood out to me: “Often times the fear of asking comes from the insecurity of what you’re asking about. If you’re asking for someone to support you, some of that insecurity might be coming from an insecurity you have about yourself and some sense of ‘If I ask someone to give to me, am I worth giving to?’”
On that Pasadena Sunday, any answer he gave would be a direct commentary on my personal value, rather than hearing feedback about my offering. My ask was all wrapped up with my inner monologue, sounding like, “Am I good enough to get this done? Will he think I’m smart enough? Too young? Too poor? Too naive? Too female? Too spiritually woo-woo?”
When our value is blended with what we’re asking for, we avoid anything that doesn’t feel like approval. I made his response mean “rejection,” equaling “I’m not enough”, and my ask fell flat. If I didn’t interpret his answer as a reflection of my value, I could have listened for the information I needed. I could have asked more questions. I could have been available to discover more solutions. His unexpected response could have been an opening for learning.
Consider what else the perceived rejection can mean by asking yourself the following questions:
- Could this be a critical feedback opportunity to pivot what you are offering?
- Is this feedback in line with my values and the mission & vision of my offering?
- Is this an opportunity to seek guidance and counsel (from this person or another with aligned values)?
- Is it confirmation, protection or redirection for where you’re meant to be?
- Do you need to ask more questions and seek more information from this person to get helpful feedback and/or clarity?
- Was it wasn’t actually a “no”, or was it a “not yet”?
This is where differentiating your value from your ask is so vital: your ask is impacted by the variable of your confidence first.
Reframe the question.
Inside the brain is something called the Reticular Activating System (RAS), a set of neural connections filtering and directing the information that flows into your awareness. When asked a question, the RAS will focus on seeking the most appropriate corresponding answer.
If you ask yourself, “What’s wrong with me?” your RAS will find your wrong elements, which could correspond to creating a dark reality. In contrast, asking what’s great about yourself will guide your RAS towards a positive perception.
Successful askers like Steve Jobs, for example, didn’t ask, “How do I build the best computer in the world?” He asked, “How can I create beautiful, easy-to-use tool that encourages others to think differently?” A higher-level question gave him a higher-level answer —one reason why Apple is not just a successful computer company, but also a dominant force in technology and culture.
Notably, starting with the type of answer you’re seeking is the way to decipher this. If you want a yes or no, you will craft a different question than Jobs’ rhetorical approach.
Know the person you’re speaking with.
Elisha says, “The more that you know the other person, the more you can cater your message and ask to the specific pieces of value that you know they’re going to want.”
The values of the person you’re speaking with are just as important (if not more important) than your own. When your offering matches what the other person’s values, a big, bold ask feels natural.
Before your ask, take a minute to try to understand the person you’re speaking with (if you don’t know them already) and put yourself in their shoes. Elisha suggests that if you’re thinking about a people group, start by exploring demographics and psychographics, like age, what kind of clothes they wear, where they eat, how they think, behave, and feel. Understanding those things helps you craft and communicate value that resonates.
Invite, when possible.
Elisha explains, “People are looking for solutions. If you have something to offer them, it doesn’t have to be this snake-oil sales pitch – it’s inviting them into a resource you know they need - that’s going to help them at the end of the day.”
An invitation goes beyond a one-sided “Yes”. Instead, it invites someone into a bigger vision beyond the both of you.
The term “ask” can feel direct and point blank as if that one person or thing is the answer. Rather, framing your ask as an invitation allows others to choose whether to join the opportunity based on their values.
Like Oprah said, “You get in life what you have the courage to ask for.” So let’s break through our barriers and ask the questions that the world needs you to ask!
To hear the full convo with Elisha Avne, check it out on The Glow Effect’s podcast, Your Glow Is Showing.
Want in-person support for your growth? Check out our LA event on June 15: EmpowHER: How to Ask for What You Want.
Join me and other startups at Pitch Night on June 29th at FLDWRK Fullerton, where I will give my pitch about The Glow Effect. You’ll see my ask into action to a group of over 100 people including potential investors. Invite a friend and RSVP.