Don't just think about it, ask for it.

I love sharing strategies on how to ask for what you really want! It took me years to find my voice, self-worth, and ability to ask for what I want. I know I am not alone with the discomfort around asking for what you really want and standing in the nerve wrecking moment right before the answer comes back to you, praying it's a YES!, and trying to keep your composure for the possible No. What I found over the years, that asking for what I truly want to help me propel forward, was a muscle I needed to condition, if I was going to build the relationships, business, connection to self, and lifestyle I truly desired. 

The easiest way for me to navigate this muscle flexing activity was in my work life. It's less intimate and more practical of an ask where the answer would help me decide my next move with ease. I definitely fumbled at a young age by overextending myself for a job in the hopes that I would be recognized and taken care of without having to ask for it; which lead to an amazing level of dysfunction and health crisis as a result. I had to find the words, speak them, face the answer, and decide what was next for me. Otherwise, I would always be living in someone else's limitation of what was possible for my life. 

Lately, I have been coaching different start up CEO's on implementing their growth strategies. One in particular is in the Pre-Seed round of their funding. When we went through her pitch process, the number of conversations she had with potential investors and the ability to close the deal with her "ask", we discovered something huge she was missing. She was not clear on what she was asking for, or how best to help her potential investors decide if they wanted to invest. We had to clear up this close to her conversations so she could make sure that when she did close out conversations, she had a clear answer on whether they were willing to invest, and even better, if it was a "Not Right Now" answer, to get some concrete feedback on what it would take to invest in her and her business.

Before I share this strategy with you, I want  you to think about something that you have been hesitant to ask for. It could be in a relationship, it could be monetary regarding your work, it could be a strategic partnership you are hoping to gain, it could also be around something you want to ask to let go of. What is it? Do you have it in mind? 

Great! Now let's make that ask crystal clear so you can stop hesitating and jump into action. 

Getting Clarity on the ASK:

  • I have been hesitant to ask for: ____________________________.

  • The story I tell myself about why I am not asking for this is ________________________.

  • If I do not get what I ask for, I will feel ______________________.

  • If I do get what I ask for, I will feel ______________________.

  • What's the worst thing that could happen if I don't get what I ask for? (Make a list, keep asking yourself this until you are exhausted.)

  • List 5 things you are grateful for right now in your life, that if everything stayed exactly the same, it fills you up.

You can apply the above to any arena you are hesitant to ask for. Doing this exercise gets you clear on why you are hesitant and why you really want the outcome of the ask to be YES! You have now empowered your ask with your truths which will help you jump into action. When you know and have sat with the question, "what is the worst that can happen?" you realize that the ask is not so scary and that even if you stayed exactly where you are right now, and received the No to your ask, you still have so much going on for yourself that you can be grateful for, see the No, and decide what your next move will be.

Unless the worst that could happen is that it would lead to death or harm, you really have nothing to lose to find out if there is a YES on the other side of your question.  (If any of you do have death or harm as a worst that can happen result, please seek out the appropriate help you need, that is way beyond my skill set.) 

I share this first exercise with you because when you continue to only talk to yourself about what is possible, unless you truly are the answer to your own question to move forward, and don't require assistance from another, which is rare, you need to dialogue your ask out loud. When I was learning how to flex this muscle, I would practice with people that I trusted had my back first to prepare for the person I really wanted to propose this question to.  The clearer and more confident you are about your ask, the easier it will be to hear the response for what it is, and decide on your next move.

To share the strategy I worked on with the CEO I was coaching for the close of her pitch, especially in 1:1 conversations with her potential investors was to breakdown the ASK into levels. When you have a large ask of let's say $1.5M at the end of your pitch, it may be an unreachable number for the person you are speaking with, so have the levels ready to discuss options of how to invest at different amounts. 


  • For $500K investment, we are will to offer X

  • For $250K investment, we are willing to offer Y

  • For $100K investment, we are willing to offer Z

*X,Y,Z - are the terms you come up with for the valuation of your company and SAFE methods you have outlined with your legal team. The way you present the information to your potential investor at this point is high level to gain interest. Make sure whatever you do say, you can follow through on. 

Be clear on what they receive for their level of investment. You can break it down however you need. Think about why Kickstarter is so successful, they clearly define what the investor gets for the amount they offer, same goes for the early stages of friends, family, and angel investing. Be clear, so they know where they can meet you and quickly assess if what they are able to offer could work. 

Then the value of this next question is everything. I learned this from a mentor of mine and it has helped me identify how to be of value to my clients, and close a deal that would be of value to both of us. You can also use this when having investment discussions. 

If the answer is No, this is not for me to invest in. The follow up question to ask is:

"I appreciate your review of the proposal and consideration for investment at this time, I am curious, however, what three things would you need to see happen, in order to invest in my plans to build this company?"

If they don't have three things, then they truly are not interested in investing in your, take the no and move on to the next potential investor. If they do have three things, you have now listened to what it will take for you to follow up with them at a later point when it is achieved, so  you can approach them with a future investment later. OR it helps you see if you are already doing what they ask, and just didn't present it, an area to outline to them and improve upon in your next pitch. 

Do you see how powerful the clarity on your ask can be? And if the answer is a No, or Not Right Now, how to walk away with something of value to enhance the next time you ask?

I still work on my ask, especially now that I am entering larger arenas and trying to extend my reach, I had to get comfortable with my ask, and detach myself from the outcome, a topic for another time. For now, sit with practicing getting clarity on your Ask. Give yourself permission to fumble, and keep putting yourself out there.

You can always be where you are today, so why not try?!


50% Complete

Join the UP-LEVEL list

Receive Tools, Tips, Event and Program Information from Kareen Walsh