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Skills to Being a Better Entrepreneur: Part 3


Skill #3: Be a Squeaky Wheel – Ask, Ask, and Ask Again!

This is a skill I learned from my kids. Keep asking for what you want and you’re bound to get it. In any endeavor asking for what you want is more than half the battle. The kids version of incessantly asking for things is whining. You’ll get nothing without asking but if you ask more than once you’ll get tens times more than the next person. Get into a habit of asking for what you want. Don’t let people try guess what you need from them

If you’ve got kids or if you’ve watched a family in the toy store you’ll know that whining tends to work a lot of the time. It’s generally easier to give into a whine than it it so fight it. The adult version of this is to be a squeaky wheel. This works in sales, in project management and in collections. We always ask our prospects what their budget is so we don’t have to play the guessing game. If it’s too low we simply pass them onto our strategic partners who handle smaller web projects.

If a client owes you money then ask for it every second day until you get it. You don’t have to be rude, you just have to be persistent. Keep bugging them and you’ll train them that you can’t be ignored. If you’re managing staff then start a routine of asking them each morning what they are working on. Ask where the roadblocks are and how you can help them. Ask your sales people where they need more support or coaching. Ask your designers if they can show you what they are working on and explain what their optimal working times are.

Recently we were able to save over $150,000 on a 5 year lease by asking for better terms. When our first requests were ignored we just kept asking in different ways until the landlords came back with a better agreement.

Ask, ask and ask, then really listen.

Author Richard Banfield

As CEO, Richard leads Fresh Tilled Soil’s strategic vision. He’s a mentor at TechStars and BluePrintHealth, an advisor and lecturer at the Boston Startup School, and serves on the executive committees of TEDxBoston, the AdClub’s Edge Conference, and Boston Regional Entrepreneurship Week.

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