After spending almost a decade in a startup, I've come to the conclusion that one of the most important traits an entrepreneur can possess is the ability to thrive within a state of perpetual need. There is never enough time, help, or money to meet the grand goals of most startups, so learning how to ask for what is needed is a vital skill.

While all of us have experienced the crushing disappointment of hearing no when we were hoping for a yes, it isn't always obvious exactly what went wrong or what we might have done differently to get a different outcome.

Finding the courage to ask for what we want is only the first step in getting to that coveted yes. It is also just as important to know how to ask - and how to respond to the answer we receive.

Make Yes Easy

Sometimes the best way to get what we actually need is to ask for more. While it seems counterintuitive, making a bigger ask extends the boundaries of the negotiation - whether it is asking for a much lower lease rate because we know the agent is having difficulty filling the space or by setting a tighter deadline for a contractor's deliverable than our client may expect. But this tactic can also backfire if our ask is so extreme that the other side sees us as unreasonable and permanently closes the door on further conversation.

See Their Perspective

After negotiating over 150 international kidnappings for the FBI, the founder and CEO of The Black Swan Group, Chris Voss, knows a thing or two about seeing things from the others' perspective.

In his book, Never Split the Difference: Negotiating As If Your Life Depended On It, Voss explains that the real desires and needs are rarely what we see on the surface.

"All negotiations are defined by a network of subterranean desires and needs. Don't let yourself be fooled by the surface. Once you know that the Haitian kidnappers just want party money, you will be miles better prepared."

And while most of us will never have to negotiate with kidnappers, his insight can certainly help us get to yes with even the most difficult requests. When we can understand the why behind an investor's interest (or lack thereof), a colleague's resistance to our proposed idea, or our customer's underlying drivers, we can effectively adapt our approach.

Timing is Everything

While we'd all like to think our decisions aren't affected by the time of day, a new study revealed that we may have a greater propensity to cheat and lie as the day wears on. Scientists believe that the barrage of ordinary decisions and experiences throughout the course of the day can wear on us and eventually impact our ability to resist moral temptations. So if you have a difficult request, you might want to find a way to make that request earlier rather than later in the day.

Make the Right Ask

In Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist, Investor Brad Feld offers up the age-old advice, "It doesn't have to be all business - engage at a personal level, offer suggestions, interact and follow the best rule of developing relationships, which is to give more than you get. And never forget the simple notion that if you want money, ask for advice."

Before you make any ask, make sure you know what is the most important thing for you to gain and be sure your request isn't short-sighted.

Make It Interesting

When I used to work as a writer, I quickly learned that one of the fastest ways to a yes with an editor was to pique interest by starting out my pitch with a teaser of the article I wished I write. Not only did it provide an immediate flavor of my writing style, but it left them wanting more. Whether or not you're pitching a magazine editor or not, when your ask stands out from the crowd it can go long way to generating a positive response.

Be Direct

Sometimes coming right out with what you need is the best way to get past the discomfort of asking.

Alex Iskold, Managing Director of NYC Techstars, recommends in their first meeting that founders directly ask whether an investor is interested in potentially investing and, if so, what next steps might be merited.

"Be direct. Do not be shy ... By asking this simple and direct question, you will know exactly where you stand."

Oh, and being direct is not a license to be obnoxious, rude, or inappropriate. That will not result in a meaningful yes. Being direct in our communication simply allows us to cut out any confusion by making sure our communication is clear and straightforward.

Understand the Many Meanings of No

We've all witnessed someone who believes that no is code for "escalate the drama" as well as the person who gives up at the slightest sign of rejection. While no definitely means no, understanding the reason behind the no can help us determine our next step.

An local startup team prepping for their first pitch contest recently asked for advice on dealing with their pre-pitch jitters. My advice?

"Assume you won't win. Take it mentally off the table and don't escalate your nervousness by talking yourself into this being all or nothing. Remember your longer-term goals and all of the wins that can happen whether you win first place or not. And then, when you walk out on stage, pitch like you're the star of the show, the only one there."

We can see finality and give up too soon when we fail to appropriately frame the goal. Sure, it's awesome to win. But it's also awesome to be invited on stage to pitch your startup. The next yes may actually be someone in the audience.

When the answer is no, allow yourself to be disappointed but not derailed. Understand that each no is just information that helps reframe the path forward. Find the next option for a yes and make the ask.

Published on: Oct 10, 2016