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

theartofaskA 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. Some small business owners grab hold of the “ask” in a manner that triggers an inability to achieve their quest. Victorious entrepreneurs, on the other hand, 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”.

The Art of the Ask

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 the use of trial and error (i.e., mostly error) to hone their “asking” skills. In contrast, people who ask for and get the “yes” on a regular basis 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 aren’t one and the same. We ask for permission, a referral, the sale, to be paid, for help, permission, 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 in direct proportion to your relationship with the supplier of the “yes”?
  2. Keep it simple. Research indicates one (1) reason gets the best results. 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 in a way that increases the likelihood you will obtain it, is a crucial business skill. With a little practice, you’ll master “the art of the ask.”

Now, go ahead. Ask me anything!

Other blog posts to say “yes” to:


  1. […] Share business ideas, small business news and social media tips with Project Eve's community of women in business and entrepreneurs.  […]