The Art of The Uncomfortable Ask

The Art of The Uncomfortable Ask

April 23, 2020
PV Bóccasam

“Can you help me?” 

What seems like a simple question may prove to be the most difficult, especially given our current reality. In times of hardship and struggle, everyone seems to be in need of something, and it may not seem like the most appropriate time to ask for help. 

There are times when everyone, everywhere, will have to ask an uncomfortable question. 

With the novel coronavirus causing a worldwide pandemic, our reality is one of uncertainty. There is no set timeline as to when this will all end or how long it will take for businesses to recover. We don’t know whether it is going to be a “U”, “V”, or “W” recovery curve. All we know is that it won’t happen overnight, even though we all wish it would.

The “Art of the Ask”

So how can we adjust to this new normal? Businesses and individuals alike will need to master the “art of the ask.” 

From asking your teenager to socially distance herself from her friends; to enforcing a “no handshake” rule in the office; to proposing a moratorium on payments from the vendors you do business with; to requesting your top customer to pay their renewal so you can pay your employees; or even recognizing the unasked questions, like giving your college nephew or niece unsolicited money to pay their rent. 

Unprecedented times demand unprecedented questions, and although they may seem inappropriate or unnatural at first, it is important that these questions be asked, and heard. 

Why? Because we all must move forward. Although it seems as though the world has come to an abrupt stop, life and business must continue. We all have bills to pay, payrolls to meet, obligations to satisfy, and an indefinite future to plan for, whatever it may hold. This means asking for a shared sacrifice amongst people with shared values and a shared commitment to your teams’ success.

No company, nonprofit, or institution is able to escape the inevitable situation that will require a difficult conversation. Let’s start with the retrenchment discussions we recently had at WealthEngine. We believe our purpose is to provide unwavering support to our customers’ mission – both nonprofit and financial institutions- who are doing everything they can to survive, so they may continue to protect the health and wealth of their constituents during these turbulent times.

So we asked all our WE’rs, as they are affectionately called, for a shared sacrifice to protect their fellow associates and to prevent mass layoffs in a time of global uncertainty. Every single one of them obliged, with key c-suite executives going on a $1 paycheck indefinitely. This was truly a trust exercise, and we responded with an abundance of gratitude and humility. With a hopeful agenda, we view this pandemic not as a hindrance but rather an opportunity to grow as a collective company. WealthEngine is not unique in this, for we know many other organizations and institutions are hosting similar difficult conversations. The Chronicle of Philanthropy offers a blueprint for how organizations can work proactively in the face of recession. As a company, we are eager to learn how others are working to support one another in this new age of the “shared-economy,” or as some put it, “shared-pain!”

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Nonprofits and organizations, who have to keep their museums, theaters, kitchens, educational and healthcare institutions funded, are seeking creative ways to aid both their patrons and staff during this crisis. However, to support a staff of artists, researchers, teachers, janitors, nurses, security guards, technologists, and scientists is difficult when institutions are forced to close, causing financial downturn. It’s important to recognize that the “art of the ask” occurs both internally and externally. Even after asking staff to contribute to a shared sacrifice, sometimes that isn’t enough, and companies must turn to their communities for assistance. 

Be Your Own Lobbyist 

In Washington, it appears that lobbyists have mastered the “art of the ask.” They continue to be their client’s best advocates, seeking to maximize the government bail for the industries they respectively represent. They are unrelenting in their requests, and regardless of the crisis at hand, they appear comfortable asking, and demanding, what is best for their client. Yet, it seems as though no one is lobbying for the nonprofits across the country, or the local preschool chain, or the performing art houses. That is why these institutions must become comfortable with the “art of the ask” and lobby for themselves.  

What can nonprofits do to become comfortable with the ‘“art of the ask”? 

Be bold. Be fearless. Be shameless about the cause that you believe in. Now is the time to reach out to your donors and benefactors to solicit for help. With their doors shut, the Smithsonian and other institutions are putting their natural treasures online, fostering their patrons’ curiosity by creating online art galleries and historical exhibitions. And in return, these organizations ask that their patrons continue with their monthly subscriptions, and in some cases, ask their patrons and members to pay monthly dues in advance. José Andrés, world famous Spanish-American chef, responded to the “ask” by closing down his restaurants in order to support a make-shift kitchen to provide those in need of a hot meal. There have been innumerable cases of everyday heroes doing extraordinary acts of kindness. 

What can healthcare providers and managers do to become comfortable in the “art of the ask’”? 

Be the community organizer and ask with persistence for people to practice social distancing and good hygiene as well as encourage community members to volunteer their time and dollar to their local hospital. Ask benefactors and patients already identified through Grateful Patient Programs to consider donating a portion, if not all, of the stimulus check they will receive from the government. Highlight the fact that protective equipment is in short supply and that their donations will support the production of more masks, ventilators, hazmat suits, and the sanitary material that will help fight this virus. #EverydayGiving

What can educators do to become comfortable in the “art of the ask”? 

Be confident headmasters that demand their students (and parents) to be disciplined in their at-home studies. Encourage them to utilize the variety of free online resources to develop new skills and continue to pursue their education. This is new territory for both teachers and students, and educators must collaborate with their students. Maybe it looks like teachers having an open conversation with their students (virtually, of course), asking their students what would best support their learning. And in return, teachers may ask their students to uphold a daily learning routine while asking for parents and guardians to be more involved in their childrens’ at-home studies.

What can wealth managers do to become comfortable in the “art of the ask”? 

Be calm, cool, and a trusted advisor to them. Advise and assist your client to stay with the plan they have already devised and tweak things as you have new information. Remember that before this crisis began, your client chose you to provide long-term planning and thinking through turbulent and stagnant times. If there is anything to do right now, perhaps it is to take no action, thereby reducing the volatility of your clients’ own lives and their company’s status in the market.

Next Step: Ask with Gratitude, Humility, and Hope

On a personal note, as someone who is in constant search of personal and professional growth, I find myself in intentionally uncomfortable situations. From leaving my home country of India for an American graduate school only to drop out as a Ph.D candidate to join a small company in Redmond; to requesting to be in a big client meeting as a lowly developer, with a very thick-Indian accent, at Microsoft in the early 1990s; to proposing and being happily married to an Italian-American and boldly introducing her to my deeply-conservative, south-indian-brahmin family in Bangalore; to telling my Microsoft boss that I was quitting in order to start my first VC-backed business (@entevo) in 1997, even though my business partner and I had no clue how to run a business; to deciding that it was the right time to begin a brand-new software startup (@approva) and asking a band of loyal associates to join me the day after 9/11; to jumping at the opportunity to be in the complex world of venture-capital (@novakbiddle) and private equity, an industry that involves constantly investing in unknown risks with unpredictable outcomes, a month after the Great Recession of 2008! It seems as though uncertainty, chaos, and volatility have been my best friends for years. I embrace it when it happens, and try not to ignore it but rather face the realities head-on. It helps to focus on what’s now and what’s next.

However, the majority of people view uncertainty, chaos, and volatility as foes rather than friends, which is why we all need to become more comfortable with being uncomfortable. Whether it is an uncomfortable conversation with boards, colleagues, co-workers, extended family, or friends, these uncertain times will require all of us to ask difficult questions. And more importantly, be patient with the answers we may receive.

For now, all we can do is ask with gratitude, humility, and hope.