the ask

Obstacles to Asking and How to Overcome Them

Heads you lose.  Tails you lose.  If that’s the bet, do you take it?  No.

For many people, that’s how they look at Asking.  Making an Ask can be a scary prospect.  If you don’t ask, you don’t get.  That’s a losing proposition.  Yet if you do ask, the result could also go poorly.  Another loss. 

How do you manage this?  The answer for many is – avoid asking.  But if you’re trying to bring an innovation into the world, that’s not an option

Instead, try these three steps:

1.      Recognize what’s keeping you from asking.

2.      Learn the tactics to overcome that issue.

3.      Ask, ask, and ask some more.

Over the past five years, Sara Whiffen of Insights Ignited has worked with Dr. Saras Sarasvathy of the University of Virginia’s Darden School of Business to uncover what it is that prevents people from asking.  They have interviewed and surveyed successful askers, unsuccessful askers, and those who avoid asking altogether.  While there is still a lot of analysis to be done, a few key obstacles to asking are already emerging.  

1.      Cultural Bias of the Self Made Myth

American culture is deeply rooted in the idea of being self made – lifting yourself up by your own bootstraps.  The idea that one person can do it all and grow a successful venture without assistance is completely unrealistic.  All innovative ideas require someone to take a chance on them, to opt in to participate.  Asks are necessary to grow ideas.

Tactics for Overcoming

Stories of legends are often written to inspire.  But they can gloss over many of the gritty details.  Take another glance at entrepreneurs you admire.  Look deeper into their stories for how Asks have fueled their success.  As a tool, Asking is amazingly versatile and can be applied in myriad ways.  

2.      Excess Empathy

No one likes to be put on the spot.  To be cold called, feel unprepared, or blindsided.  Everyone has had that experience at some point; feeling time stand still while you search for an appropriate answer to a tough questions. Some people hesitate to make Asks because they identify strongly with that uncomfortable feeling and don’t want to put others in that situation. 

Tactics for Overcoming

If you tend to exhibit a high degree of empathy, go ahead and put yourself in the shoes of the person you’ll be asking, but do so from a positive perspective. Imagine them wanting to help, wanting to build a relationship with you, wanting to connect with your idea and move it forward.  Phrase your Ask in a way that invites them to collaborate with you.  Don’t make demands or leave them feeling as if it is easier to disengage than to form a partnership with you.  

3.      Fear of Rejection

This is the most common explicit fear.  “What if the person I ask says No to my request?”  In that case, you won’t get what you want.  Which would happen anyway if you didn’t ask.  Either way, the outcome is identical.  But by putting your Ask out there, you risk a loss of pride.  Fear of personal rejection can be even stronger than the fear of not getting your request.

Tactics for Overcoming

Separate yourself from the Ask.  A rejection of the request is not a rejection of you personally.  It might not even be a rejection of your idea. 

Why, then, is the person saying No?  For whatever reason they don’t feel that they can commit resources towards your request. 

Studies have shown that most people want to respond to requests in a positive way.  Take comfort in knowing that as awkward as you felt hearing a No, it’s likely the other party felt just as awkward saying No. Successful salespeople and entrepreneurs alike know you will often hear many No’s before you hear a Yes. 

 4.      Fear of Acceptance

You’ve asked.  They’ve said, “Yes”.  Now what?  You have to deliver.  This is when things become real.  Now you’re on the hook to make things happen.  This can also keep people from Asking.

Tactics for Overcoming

Start with asking yourself “Do I really want to do this?”  and “Why?”. Understanding your motivations for entering into this new venture can help you overcome the Fear of Yes.  Keep it front of mind when the panic of delivery creeps in or you feel a crisis of confidence and go back to why this new venture matters to you. 

Also, now is a good time to lean on your co-founder.  Leverage this relationship to ease doubts and improve your ability to follow through on new commitments. 

5.      Fear of Maybe

Sometimes, hearing a “maybe” can be even worse than a “yes” or “no”.  It leaves things in an ambiguous state.  It elicits more questions than when you began and throws the Asker back into wondering what the resolution will be.  Avoiding this uncertainty is enough to keep some from making an Ask in the first place.

Tactics for Overcoming

Try asking in a more open way.  Instead of using “closed” Asks, drive towards a commitment by asking “What would it take to...” or “How could we…”.  These lead to more conversational opportunities and give the person being asked more room to discuss options and possibilities.  As the asker, you get more insights into how they make decisions, their priorities, and considerations.  Even if the discussion results in a “maybe”, you will have more information at your disposal for future interactions. 

Moving Forward with Asking

You can’t be a successful entrepreneur without the Ask.  It’s a necessary component of bringing innovations out of your head and into the world.  If you identify with any of these obstacles to asking, try the tips suggested.  And then Ask away.  Whatever the answer – you can’t lose. 

--Written by Sara Whiffen, Founder & Managing Partner, Insights Ignited LLC

Asking is the Answer

“I have so many great business ideas, but I don’t know how to get started.”  This is a common refrain.  Where to begin?  The most effective way to move your ideas forward is by Asking.

Effectuation offers a process for innovating during times of uncertainty.  As you look at each principle, its foundation is an Ask.  Dr. Sarasvathy at the University of Virginia’s Darden School of Business, originator of Effectuation, has identified the “Ask” as the single most important granular unit required for entrepreneurial success.  Mastering the concepts around Asking increases the likelihood of favorable entrepreneurial outcomes. 

Four Categories of Asks   

There are four phases in delivering innovative ideas.  The first is identifying what you want to move forward with.  The second is getting stakeholders to buy into helping you bring forth the idea.  The third phase is getting participation from those outside your stakeholder network.  And the fourth phase is scaling the idea.

Each of these phases requires a particular type of Ask proficiency.  

1.      Ask Yourself

At the beginning you’ll want to become adept at Asking yourself some key questions.  These include: 

  • Who am I?
  • What do I know?
  • Who do I know?

The answer to these questions will clarify your interests, values, and priorities.  Truly ask yourself these questions.  Be honest with your responses.  The results will surprise you.  You will see that you already have a significant amount of resources at hand with which to begin your innovation process. 

For example, when asking yourself “Who am I?”, consider your likes, dislikes, experiences, passions, etc.  Dive deeper into this by asking yourself:

  • What is my reason for doing this?
  • What outcomes would I like to see happen?
  • What am I most afraid of?

This also becomes the building block for your story.  The more you understand yourself and your motivations for pursuing this innovation path, the more authentic you can be when making Asks of others.   

2.      Ask Others

It’s not always easy to ask someone for something.  But for entrepreneurs, it’s essential.  After asking yourself, one of the first Asks required to advance an innovative idea is asking someone to partner with you to make it happen.  Getting a co-founder on board, a champion, or an advocate of some sort who complements your skill set and can bring additional resources to the table is a fundamental requirement for entrepreneurial success. 

Many venture capital groups won’t even talk to an entrepreneur unless they have a co-founder vested in their concept.  Why?  Having two founders significantly increases your odds of succeeding.  In order to get this person to commit, you’ll have to Ask.  Once you’ve achieved this, and begin to see the value that this one Ask can bring to your venture, you’ll be more likely to continue increasing the number and complexity of your Asks to others.  

3.      Get Others to Ask You

As word gets out about your innovation, you’ll find yourself in situations you hadn’t anticipated – meeting with new people and organizations.  In this phase, you again broaden your experience with Asking by getting others to ask you.   As you have co-creative conversations, you’ll want to present your ideas in a way that invites others to join. 

Forget focusing on pitching where you throw out a series of facts, features, and fantasy about what your innovation could grow to be and ask someone if they’re in or out – take it or leave it.  Instead, paint a picture of opportunity where you give others the chance to identify ways in which they see a role for themselves in advancing your venture.  Give them the time and space to create a role for themselves and Ask you for the opportunity to participate. 

4.      Get Others to Ask for You

In the final phase, your idea is out there and growing.  At this point, the focus is scale.  How can you broaden your impact?  Get others to Ask for you.  Create a culture of Asking in your organization.  Don’t just promote it, but put it into practice.

This increases the amount of influence an entrepreneur is able to have and expands their reach.  In order for someone to Ask on your behalf, they must feel vested in the outcomes.  Continue to be open to stakeholder participation.  This further magnifies the effect. 

Figuring out the first step in an innovation process can appear daunting at first.  It’s not.  Start with Asking.

--Written by Sara Whiffen, Founder & Managing Partner, Insights Ignited LLC