5 Reasons Why 'Asking' Is an Essential Skill for Every Entrepreneur

5 Reasons Why 'Asking' Is an Essential Skill for Every Entrepreneur
Image credit: Kai Schreiber | Flickr

How do you feel about asking for what you want or need? If words like shy, nervous, anxious or even apathetic describe you in this context, you could be missing out on a good many opportunities.

Related: This Dapper Young Entrepreneur Just Schooled Mike Rowe on How to Negotiate

Whether it’s favors, negotiations, or routine interpersonal communications you're seeking, taking the initiative to ask and knowing how to do it well can make all the difference for both new entrepreneurs and established businesses.

From my experience, there are five key reasons that make asking important and necessary for success in business.

1. If you don’t ask for it, you probably won’t get it.

It seems kind of obvious, but it’s worth keeping in mind that things rarely fall into your lap and people usually won’t give you things just "because." Even when someone does want to help you or make a deal, you can’t count on that person being a mind-reader.

Knowing how to ask is important, though many people feel intimidated and shy to do it. Remember, the worst thing that can happen with a well-framed question is usually a simple “no.” On the other hand, your request just might open doors and provide information that otherwise wouldn't have come your way.

2. Asking can save you money and time.

For business owners, the benefits of asking can be enormous. Obtaining better pricing from vendors, better terms from banks and discounts on purchase orders even in small amounts can save a company good money over time that would otherwise be lost if not for the better deal that's been obtained. In other cases, delegating tasks and asking for help frees up time and makes you more efficient.

Entrepreneurs-in-the-making can score better salaries or more beneficial employment packages when they negotiate raises and offers. Hiring managers, in fact, expect valued employees to negotiate; and, even if as that employee you know higher pay isn’t in the cards, more vacation days or other concessions can have monetary value.

3. It pays to get comfortable with negotiating.

Negotiating is a key part of business, and at its most basic, negotiating is just knowing how to ask for what you want or need. Getting comfortable with asking during routine situations will make you a more effective negotiator during important ones.

4. Asking others what they want helps you communicate better.

The benefits of being a skilled asker extend beyond the transactional realm. It's a real skill to learn how to ask others what they want occasionally, because the more you ask, the more you know. Asking the right questions of employees, vendors, partners and customers helps you better understand other people and facilitates communication.

Asking your employees how you can help them work better and seeking their input on other aspects of the company can provide crucial insights. Asking your customers how you can be of more value to them and seeking their input too can help you solidify relationships and grow.

Related: 10 Questions Every Entrepreneur Needs to Ask Suppliers

5. Asking gives you an advantage over non-askers.

You have probably heard the phrase “the world belongs to the takers,” but really it belongs to those who aren’t afraid to ask -- for what they want in life, what they need to succeed or what they want to know.

There are many people out there who feel too shy, intimidated or proud to ask, and others who do not even realize that asking is an option. Asking gives you a distinct advantage, when all things are considered. It puts you in a better financial position, gives you access to more information and helps you make employees and customers feel valued.

So, flex your asking muscle.

Asking is crucial, but so is knowing when and how to do it. Being strategic can make all the difference between being savvy and smart or prying and greedy. Here are some ways to do that:

  • Prepare your talking points in advance. Narrow the focus for your meeting or conversation by determining what is most important for your goals and success. Then, get more specific about the kind of changes or concessions you want to see and why. Also, think about what you have to offer. In an interview, salary negotiation or vendor contract, have a few points in mind about what you bring to the table and how you or your business benefits the other party.
  • Have (realistically) high expectations. Expecting the best helps boost confidence and attitude in most situations, but it is also important to make sure your expectations are realistic and plausible. Research in advance when possible to see where you stand. If you want to negotiate better payment processing rates, research online or ask peers to see what other places are offering and what other people are getting. 
  • Identify the best time and place. A big part of being an effective communicator is the ability to identify the appropriate time or place to broach a subject. For larger concessions, picking opportune conditions can make a significant difference. Would it be best to bring the subject up in a group setting or in private? Who is the right person to speak with? Would it be best to meet in your office, theirs or a neutral location? 
  • Ask good questions. There may be "no such thing as a bad question," but there are impolite, extraneous, unfocused and poorly-worded ones. When thinking about what you want to ask of someone else, being polite, level-headed and respectful can go a long way. Be mindful of wording and what information you’re actually seeking, and include "please" and "thank you." Avoid coming off as accusatory or demanding.

One area that may require more finesse is the use of leverage. Oftentimes, you do not want to just flatly state that you can do better in a congenial situation, since that might sound offensive. Say you are negotiating an account with your bank. Do not be shy to seek or present other banks’ offers, but approach it in a smart way. Explain that you value the relationship but need to a make a wise decision "for the company." Then, ask if the second bank can match or beat the earlier, competing offer.

Sometimes, framing requests in a social rather than personal way can make people more receptive. This might involve describing how something could be mutually beneficial or allow you to help others.

Another way to get better results is to be creative with your approach. If a vendor is unwilling to offer a flat discount, he or she may offer a rebate for a portion of sales based on monthly, quarterly or annual totals. Banks may also be willing to waive fees for a period of time for new customers or new accounts as an added incentive.

Don’t let “no” get you down.

It's important to be prepared for a no, despite your well-researched and worded ask. But don't let a no make you feel upset or defeated. No one always gets 100 percent, and that's okay. There is always next time, and you never would have known had you not asked.

When you sense a conversation is not going your way, ask the other side what he or she wants. Getting a clearer idea of that person's perspective can give you a point to work from and open up a negotiation.

If you do get flat-out rejected, ask how you can still make it happen, or how you can work together to get to where you want to be. Sometimes the response might be something fairly small and conquerable, and at the least you have some potentially helpful feedback.

As with any other skill, some people will naturally be better at asking and negotiating; but actively practicing and making an effort can make anyone more comfortable and confident. Asking is worth the effort, and is an entrepreneurial skill as necessary as leadership, strategy and focus in the modern business environment.

Do you find asking easy or is it something you have to work for? Is there a situation where taking the initiative to ask made a big difference for you? Share in the comments.

Related: Why Banning Salary Negotiations Won't Close the Gender Pay Gap