The Art of the Ask: How to Ask For and Get What You Want in Business

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A recent business connection on Linkedin resulted in a fun and insightful conversation. My pen flew across the page to capture how she leveraged the information to get “unstuck” and in motion as we chatted. Enjoy and read the course of action she implemented to break through her resistance to ask.

A small business entrepreneur’s day is filled with opportunities to ask for – and get – what we want—asking leaves some small business owners fearful and hesitant — especially when unaccustomed to their requests being realized. As a result, some small business owners grab hold of the “ask” in a manner that triggers an inability to achieve their quest. 

On the other hand, victorious entrepreneurs seize the opportunity to “ask” and forward their objectives. Why do some entrepreneurs succeed while others fail at asking for and getting what they want? The triumphant entrepreneurs employ “the art of the ask.”

business ask

The Art of the Ask in Your Business

Most small business entrepreneurs are masters of their craft. They are highly skilled in their area of expertise. Their competence may be legal, financial, design, communication, project management, process improvement, technology – the list is endless. Seldom is “the art of the ask” taught at the advanced learning institutions attended.

Consequently, this means using trial and error (i.e., mostly error) to hone their “asking” skills. In contrast, people who ask for and get the “yes” regularly have become skilled at “the art of the ask.”

Does This Make My “Ask” Look Big? 

Asking for and getting what we have in mind isn’t the same. We ask for permission, a referral, the sale, to be paid, for help, approval, an introduction, special treatment. Getting to “yes” depends on the skill and the size of your “ask.” Here are a few pointers to get you closer:

1. Be reasonable. Consider the desired outcome of your ask. Is it directly proportional to your relationship with the supplier of the “yes”?

2. Keep it simple. Research indicates that one (1) reason gets the best results. So, avoid the need to pile on the reasons for someone to do what you want.

3. Draft your request before making it.

4. Be kind/honest/professional. No BS allowed.

5. Be specific and brief. Don’t him-haw around.

6. Provide an easy out. Make it easy for someone to say “no” without damaging your relationship.

7. Show your gratitude.

8. Be willing to give in return.

9. Make it WIIFM compliant. WIIFM stands for “what’s in it for me.” It’s the question that subconsciously goes through the mind of each provider of a “yes.” If your request is WIIFM compliant, your “yes” broker will quickly see that your “ask” imparts something for them as well.

The ability to ask for what you want to increase the likelihood you will obtain it is a crucial business skill. With a bit of practice, you’ll master “the art of the ask.”

Now, go ahead. Ask me anything!

A Brilliant Step by Step Ask

Here are the steps my new Linkedin connection took to overcome her resistance to asking for help:

1. Make a list of people she wanted to contact.

2. Noted her relationship with each. 

3. Identified one “ask” for each. 

4. She considered how to provide an “easy out” if she heard hesitancy.

5. Made the WIIFM (What’s in it for me) crystal clear.

Your turn. What’s your ask?

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Brooke Billingsley

Vice President
Perception Strategies

Synnovatia is a strategic coaching firm that is detailed and knowledgeable about business. i have a small business that grew from $150K to $750K because of the goal setting and resources that Synnovatia provided. It saves me years of learning on my own.

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