When advancement leaders claim a desire for a stronger “culture of philanthropy,” what is typically meant is that they want a stronger “culture of giving.”  They want more people to be more generous.  From the Board, to advisory groups, to primary constituency groups, the idea is that more donors and more dollars are the best evidence for an increasingly strong “culture of philanthropy.”  The thinking goes, if the amount of giving and the number of donors are increasing, our culture of philanthropy is growing stronger.

But, giving totals can increase because one or a few donors decides to make unusually large gifts.  Or because someone passed away who decided during their life to include your institution in their will.  And the number of donors can increase because of a matching challenge effort.  Or because someone close and important to your institution’s community passed away and memorial gifts came flooding in.  In these scenarios, it is not likely that a “cultural” change around giving or philanthropy has occurred.

To better gauge the strength of your institution’s culture of philanthropy, I would suggest using a different lens through which to view the issue.  Specifically, ask yourself how regularly good and meaningful questions get asked at your institution.  The honest answer to this question is a fantastic predictor of the strength of your philanthropic culture.

For example, how regularly do you ask good, meaningful questions of your Board members?  Questions about institutional values and strategic direction, for instance.  Or how regularly do you ask good, meaningful questions of your team mates?  Questions about your institution’s strengths and how proposed strategies might affirm those strengths, for instance.  Or how regularly do you ask good, meaningful questions of your donors?  Questions about their interests and how or when they might most appreciate being solicited, for instance.

Institutions experience extraordinary advancement when a growing number of people more deeply share a sense of ownership.  Asking people to think with you, to share their opinions, ideas, perspectives, observations, feedback, and inclinations is the single best way to invite feelings of ownership.  If you want to strengthen your institution’s “culture of philanthropy,” focus your efforts on strengthening your “culture of questioning.”

In the U.S. space industry the term “go fever,” refers to project teams making rushed decisions while “overlooking potential problems or mistakes.”  The reasons that “go fever” can grip a team can range from budget pressures to individuals not wanting to be viewed as the person who slowed progress or questioned authority.  This concept has been cited as part of the cause behind such disasters as the Space Shuttle Challenger break-up in 1986.

Similar to “go fever,” I would suggest that leaders at some institutions experience “ask fever” — or the rush to solicit donors or prospective donors for a major gift while “overlooking potential problems or mistakes” of moving too quickly.  “Ask fever,” may be driven by budgetary pressures or a general misunderstanding on the part of an institutional leader that major gift solicitations are not transactional tasks that can simply be checked-off one’s to-do list.

The full problematic impact of “ask fever,” is not so much that the institution almost never receives the best possible gift when the fever strikes its leaders.  Instead, when leaders give in to “ask fever,” the biggest loss is the loss of donor engagement – and in many instances, that loss is long-term or permanent.

The reason that forgoing donor engagement is such a costly error is because giving follows involvement, volunteers give more than non-volunteers, and donors with more than one meaningful connection to your institution give more than less-connected donors.  Donor engagement, the research suggests to us, is the archway through which the best possible gifts flow.

If you find yourself or others in your institution coming down with a bad case of “ask fever,” go ahead and ask the donor prospect – but instead of asking for the gift, ask them for their advice and perspective.  Ask them to get involved more deeply and more meaningfully in your mission.  You may find that the gift that follows that ask is much larger than you could have imagined.

One way to describe the organization of advancement shops is the point at which they sit along the “centralized – decentralized” continuum.  “Centralized” shops are ones that provide advancement services to the institution they serve through one or several offices that report to one positional leader.  These shops are typically recognized as a “division of advancement” or some such name and they serve as the site for the planning, coordination, and implementation of all advancement-related efforts for that institution.

On the other side of the continuum, fully “decentralized” shops are those that have advancement services assigned and reporting to different functional areas of the institution.  For instance, each college of a university may have its own advancement function.

There is no “right” way to approach advancement centralization.  The complexity, history, culture, and needs of each institution as well as how donors relate to that institution should suggest how best to organize the advancement function.  However, one drawback of the decentralized model – however it is implemented – is the notion of compartmentalization.  Too often a decentralized shop becomes a compartmentalized one.

Just because an institution employs a decentralized advancement model does not mean that advancement efforts should be compartmentalized.  Even though reporting structures may vary for each advancement office in a decentralized model, the offices should still seek integration of their work.  For instance, integrated Prospect Management Team meetings should be held monthly so that leadership-level donors are encouraged to give their best possible gifts in support of the whole enterprise.  And marketing should be integrated across the enterprise so that brand elements are affirmed and communicated clearly to all constituencies.

To be both decentralized and integrated takes leaders with a long-view.  It means that staff evaluations need to affirm coordination and working across silos.  It means recognizing that our donors respond best when we approach them with a single comprehensive proposal, instead of multiple disjointed and uncoordinated solicitations.  It means that leaders need to have an ego for the entire enterprise that is at least as big than the ego they have for their individual areas.

At your institution, it may make exceptionally good sense for advancement functions to be decentralized.  But it never makes good sense for advancement functions to be compartmentalized.

As someone who is part of the advancement process for your institution, you are in the relationship-building business.  To be successful you must work effectively and efficiently with and through others.  At its core, the work is about people.

And you probably employ a task-filled “to-do” list in an effort to organize yourself and your work.

Notice anything odd about the nature of advancement work and how you organize yourself?  The work is all about people, and yet, many of us organize our work around tasks.

Instead of a “to-do” list, advancement professionals should create “to-who” lists to organize ourselves and our work.  Who are the donors you need to bring into a closer relationship with your institution?  Who are the key staff members with whom you need to coordinate to get that email blast sent?  Who are the prospects with whom you need to conduct discovery visits?  Who are the Board members you need to profile?

When we replace our “to-do” lists with “to-who” lists, we not only align our efforts with the nature of advancement work, we also remind ourselves daily that we are at our best when we seek to engage the important people around us.

“I’m not at all comfortable – and I absolutely think we should do it!”

This was a Board member’s immediate response to the Chair’s question: “Are we comfortable with Dr. McNeal’s campaign plan recommendations?”

I was giving a presentation with recommendations to this Board and leadership team to assist them with their campaign planning.  Without question, the proposed campaign represented the largest and most comprehensive fundraising effort the organization had ever undertaken.  Even before the presentation, I knew there may be resistance to the ambitious undertaking.

And, while there was some resistance, other Board members saw my planning recommendations as opportunities.  Opportunities to learn and grow as Board members and opportunities to do more to advance the organization than had been done over the last 30 years.

At the end of the presentation there was vigorous discussion.  Some liked the direction an ambitious campaign would take the organization.  Other Board members struggled with the idea of stretching themselves and stretching the organization.  What specific expectations would a campaign bring for me as a Board member?  How might my giving have to change?  What if the campaign were to be unsuccessful?  These and other questions, I’m sure, were at the heart of some of the anxiety.

Finally, the Board Chair asked everyone if they were “comfortable” with my recommendations.

The quoted answer above was the only response.  Within a minute or two the Board unanimously approved moving forward with the campaign plans.

“I’m not at all comfortable – and I absolutely think we should do it!”

How many times in work – or even in life – have we failed to try something different, decided not to attempt a new strategy, or talked ourselves out of a fresh approach simply because we weren’t comfortable?  Perhaps you are an annual giving director who could be more creative with your direct mail and direct response campaigns.  Or maybe you are a major gifts officer who has argued for setting a timid annual visit goal.  Or possibly, you are a vice president who has been indecisive about a personnel change that you know needs to be made.

If you want the kind of results that are deserved by your institution and those you serve, you can’t always do what is comfortable.  Stretching can make you uncomfortable – and you absolutely should do it.

It used to be that answers were power.  If you had the answers, you had the advantage.  You would get the best scholarships to the best universities.  You would get the best jobs.  And you would get promoted faster.  All because answers weren’t easily and readily available.  You had to work for them.

Today is very different.  Today, answers are a commodity.  They are easily accessible and most everyone can retrieve the same answers very quickly.  If we want an answer to just about any fact-based question, we ask Google.  And with mobile technology, we have access to cloud-based answers from just about any location through multiple platforms.  Answers, truly, are everywhere we want them to be.

In addition, these computer-constructed answers are getting more sophisticated and wide-ranging every day.  In 2011 the IBM computer, Watson, accurately answered questions faster than Jeopardy! champions on TV and won $1 million.  Today, Watson is helping healthcare providers make decisions about the best possible cancer treatment.

So, if answers are becoming ubiquitous and the playing field to access those answers is almost completely flat, what will separate the successful from all others in the future?  I would argue that the ability to ask insightful questions will be more important for tomorrow’s success than knowing the answers.  Especially, in our field, the more capable we are at asking thoughtful and meaningful questions of donors, the more money we will raise.

But the importance of learning how to ask good questions isn’t getting its due.  Our schools still largely teach students to memorize answers in preparation for standardized tests.  And in our workplaces, we are still conditioned to believe that the person with the “right” answers should be the boss.

Let me suggest, though, that the future will be won by those we are able and willing to ask important (and sometimes uncomfortable) questions.  If you are interested in starting a new program or assessing how to make a current program better, ask questions that begin with “why.”  Such as, “why this and not that?”  or “why are doing this at all?”  If you are looking to assess alternatives, ask questions that begin with “what if.”  Such as, “what if we decided to host this event in conjunction with Homecoming?”  or, “what if we were to increase our solicitation goal?”  And, finally, if you are looking to implement one of the “what if” alternatives, ask questions that begin with “how.”  Such as, “how can we increase our total solicitations with the same number of gift officers?”

It may seem that the person who asks questions is ignorant or even obstinate (or both!).  But, if you want to grow your influence with donors and with those on your team, mastering the art of asking insightful questions will be a key component of your success.