Today my grandmother turns 95. She's in amazing shape for someone who's nearly a century old. She drives herself around, does her own grocery shopping, and still goes to the beauty parlor every other week to get her hair set.
Growing up less than a mile from her and my granddad, we spent a lot of time with them over the years. Of all of the support, comfort, and wisdom they imparted to me over that time, one piece of advice from my grandmother has stood the test of time. No matter where I was in the world, or what I was doing, it has been relevant and helpful. That advice is:
You never know ‘til you ask.
Simple and powerful, it has guided me throughout my life. Here are some ways you can put this to work for you.
Ask for the Introduction
Whether you're fundraising, hiring, selling, or just looking for feedback, you need to expand your network to reach the right people. The best way to do this is through strategic introductions. In the Catalyst program, making connections is part of our offering to companies. Introductions are such a regular part of my work in the startup community. In my experience, people want to help other people, so as long as you're not taking advantage of it, ask for introductions. You're likely to get a nice warm introduction, which can lead to a meeting.
Ask for the Meeting
Now that you have that introduction, ask for a meeting with a purpose in mind. Even if you don't have an introduction, many people in the startup world are approachable with a cold email.
Guy Kawasaki, former chief evangelist for Apple, and author of 13 books including The Art of the Start 2.0, wrote a fantastic post, "The Effective Emailer," on how to craft that all-important message with your ask.
Another great take on the email ask is from venture capitalist Brad Feld, "If You Want a Response, Ask Specific Questions." This post offers advice on how not to approach someone. The title of the post says it all, if you want a response, ask a specific question.
Ask for the Sale
Many startup founders don't have sales experience and so often miss this incredibly simple, yet incredibly important part of sales: asking for the sale. Even in mass-market B2C businesses, you'll be surprised how easy and effective it is to ask people to sign up. Your first sales will be high-touch and likely require a big time investment from your team. But all of that work will go to waste if you don't say, "Will you sign up to be our customer?" And if the answer is a no, then ask, "What are the next steps for working with you?"
It's empowering to ask for something that you want. This is the heart of my grandmother's advice. She is and has always been an empowered woman. I believe a big part of that came from not being afraid to ask for what she wanted. As long as you're polite and respectful in your approach, step up and ask.
The opposite of this is to meekly watch the world go by. If you do not ask, it will sweep you away on other people's directions. This is the path to failure as an entrepreneur.
The way to empower yourself in this world starts with asking for what you want. Whether it's something as simple as asking for a special order at a restaurant or as big as asking for an investment, make that ask. After all, you'll never know unless you ask.