As an entrepreneur who works in the association community, I’m always aware of the differences in these two worlds and the circumstances that influence their distinct perspectives. Associations are cautious diplomats. They try so hard to avoid a misstep that sometimes they don’t see the edge and fall off the cliff despite themselves. On the other hand, us entrepreneurs are bold upstarts. Our willingness to grasp at straws of opportunity can prove equally disastrous.

Neither group is immune to an extreme approach to risk; but, as the digital revolution continues destabilizing the business environment, it’s clear that to keep their balance, associations need to gain momentum. They must borrow a little entrepreneurial courage and run faster and closer to the edge.

After a year in sweatpants, you’d think it would be easy to get the diplomats to unbutton their collars. But for associations that cherish stability, risk is like a rude guest at the party. It invites debate and controversy into the discussion. And no one likes to see the board meeting stalemated or tainted by negative energy. How can leaders help volunteers and themselves to become accustomed to exploring  opportunities that may also pose significant challenges?

Invite Risk to the Party

This was one of many topics related to the impact of technology that inspired my business partner, Kevin Ordonez, and me to write our Association 4.0 books: Positioning for Success in an Era of Disruption and An Entrepreneurial Approach to Risk, Courage, and Transformation. The leaders we interviewed have ventured deep into the digital marketplace. So, we were not surprised to see risk emerge as a predominate theme.  I’m going to share some of their insights as well as a few ideas of my own to talk about how to invite risk to the party and keep this rambunctious guest under control.

Innovation and risk are opposite sides of a coin. All but the most unambitious plans can result in negative consequences. The first step in controlling problems or complications is to admit that they exist. Most corporations already have risk management programs in place as well as systems for vetting the benefits against the challenges of new ventures and products.

Association strategic plans typically acknowledge the risk inherent in untried initiatives, but risk is often given short shrift or viewed as grounds for tabling what could be an opportunity for growth. Although the pandemic triggered an interest in scenario planning, I have yet to encounter an association with an ongoing procedure for evaluating risk. If your organization is the exception, I would love to hear about it.

Assess Your Portfolio

While board members may not be accustomed to dealing with risk in the context of their association, many people are familiar with evaluating their finances. Anyone with an investment portfolio has probably weighed their tolerance for uncertainty against their desire for growth.

It can be helpful for associations to view strategy through a similar lens. Think of the mix of goals and objectives as including both high and low-risk opportunities. Boards can consider these initiatives as a portfolio of assets. Some projects may be “hedge funds” that offer the promise of big rewards but little safety. Others are more like “bonds” that preserve the status quo but limit growth. Find out how to balance your group’s portfolio so that the cowboys and the conservatives are all comfortable.

Take Control of the Future

The digital environment is more bull than bear.

The CEOs we interviewed agreed that the digital environment is more bull than bear, and even the most button-down boards will need to find the stomach for an increasingly aggressive future approach. As the former CEO at the American College of Chest Physicians (CHEST), Stephen J. Welch relished his spot in the crosshairs of disruption.  

Medicine is an area where technology is constantly reshaping the landscape. The speed with which the Pfizer vaccine was developed is a good example of how quickly advancements occur. To keep pace with science, CHEST continually updates its educational programs. Well before the pandemic, CHEST was studying how to make on-demand online education more readily available and exploring how to deliver high-quality clinical education experiences to a wider audience. Welch advises, “A risk-taking culture is a must. The associations that are successful going forward must be committed to creating their vision of the future. That means taking risks, taking control, and making decisions.”

Lay the Groundwork

Rob Miller, Chief Revenue Officer at Gravitate Solutions and former Senior Vice President at 340B Health, is another dyed-in-the-wool risk-taker. Miller, who leads from an entrepreneurial perspective, notes that most associations are not prepared for change. “Associations can talk all day long about being entrepreneurial, but generally they’re not,” Miller says. “Most everything works against creating momentum related to innovation – mission, governance, regulations, legal, and brand reputation.” 

To introduce risk and innovation to his team, Miller engages them in conversations early in the brainstorming process. “I throw ideas out there before we validate their merit or even decide if it is a good idea.  Normally, I would have done more homework before telling people, but I have learned that the team needs time to think about how the initiative might relate to the mission, our culture, or potential regulatory restrictions. It gives me an opportunity to develop a business case as they warm to the idea and own it, as opposed to spending too much time upfront and finding out there is a legitimate reason we cannot proceed. Giving my colleagues a chance to embrace the new idea may actually result in faster adoption in the end.”

Preparing a board to tolerate risk is a sales process.

Sig VanDamme, former Membership Software Evangelist, Community Brands, and co-founder GoJectory, emphasizes the importance of educating your team. “Preparing a board to tolerate risk is a sales process,” says VanDamme. “To convince you to buy from me, you must believe that I can increase revenue, decrease costs, reduce cycle time, enhance the member experience, and finally, mitigate risk.”

VanDamme notes that leaders must be able to communicate each of those points to both staff and volunteers and to present risk within a cognitive framework. “I have a friend who is a scientist in a large engineering company,” he recalls. “The organization has a multilayered process for innovation. The first step is intensive brainstorming. Hundreds of ideas are generated. Then each concept is tested against a series of predefined criteria until only the most viable remain on the table. I don’t see many associations doing that type of vetting.”

Promote Diversity

Like the proverbial glass, some people see opportunity where others see danger. Boards that are professionally, ideologically,  and demographically diverse are more likely to view risk in a broader perspective. Joanna Pineda, Founder, CEO, and Chief Troublemaker, Matrix Group International Inc., recommends looking outside your members’ professional expertise to provide a spectrum of opinion among leaders. 

“I had an interesting conversation with a client about association boards,” says Pineda. “He was considering the benefits of expanding representation to include expertise from outside the profession. Specifically, he suggested giving experienced association executives a seat at the table. If you don’t have leaders with a range of professional backgrounds, there will not be a lot of new thinking. The average pharmacist, librarian, or dentist has limited experience with the challenges that are involved in running an association. It’s a good idea to include people from outside your organization’s playing field who can introduce a different point of view and push the group forward.”

Find Balance

Loading your team with innovators and experimenters isn’t necessary or desirable. Ben Martin, Co-Founder, 100Reviews, puts it like this, “It’s important to recognize that being a risk-taker is not for everyone. The CEO doesn’t need to be an entrepreneur. But they must empower some people in the organization to do that work.”

If your board includes diplomats and upstarts, along with people who sit comfortably in the middle, chances are good that you will find the necessary momentum to safely move a little faster and closer to the edge.