4 Questions That Get Your Boss to “Yes”

You have a great idea. You run it up the flagpole to leadership. They love it! Then, nothing happens. You wait. You push it up there again. They love it again. They gush over your creativity and forethought. Then, nothing happens.

Turnkey faces this same dilemma with our clients. “Great idea! It will raise us money! It will make our world better!” Then…. nothing. We needed the same kind of help that our clients need – how do we get decisions made? Heck, we’ll take “no,” just give us any decision so we know whether to keep trying, or move on.

We recently hired Dan Schultheis, the author of, Willing to Buy, a Questioning Framework for Effective Closing. What strikes you first when you meet Dan is how much he looks and sounds like the guy on those Farmer’s Insurance commercials:

Source: ispot.tv

Source: ispot.tv

That’s not really him, but Dan has his own level of coolness. Dan’s tried-and-true framework was designed to help account executives figure out which prospects are real and ready to do business, and which are not. His method helps us know where to invest precious time. 

It turns out that this same process can help fundraising executives understand if their initiatives are likely be adopted by their own leadership, or if their time is best spent elsewhere.

I’m translating the language a bit from sales and into nonprofit as we move forward, so if you read Dan’s book you will note the differences. Here are the four elements to understanding if your leadership is ready to move forward:

  1. Is the organization’s leadership willing to act,
  2. Is the justification for the project/product/service evident to leadership,
  3. Are the resources/money available, and
  4. Is the decision cycle clear?

If you just ask the elements above as questions, your leadership will say yes to each and then do nothing, like most always. The magic in Dan’s method is probing more deeply. For example, in regard to the first element – whether leadership is ready to act – if you just ask, “Hey, are you ready to act?” the answer is yes. She will say, “That’s really interesting. Let me think on it and see how it fits with other priorities.” Here’s the magic:  you say, “What if we don’t do it?” You gently continue, “What makes this a good time to do this? Why today? Why not wait? What does it really cost not to do it?”

What you are looking for is a really important reason why it has to be done now, like, “If I don’t turn revenue around I am out of a job by October.” Or maybe you might hear, “I have a directive from my leadership.” Or maybe you’ll hear, “It’s just a good idea.” If it’s just a good idea, that means it will probably not go forward, and you can go do something else.  Typically, the lack of a compelling imperative to act is not diagnosed, meaning everyone continues to invest energy and time as if it is a viable effort. I could have saved years of my life if I simply had asked for the compelling reason to go forward in each and every conversation with clients and moved on when it wasn’t there.

Element #2 is about justification. This is about more than return on investment. You are asking your leadership, “Can you pitch this successfully up your food chain? (Think – board of directors). How are you going to do that? What makes it an imperative to your leadership?” If they can’t tell you, they probably can’t move it forward.

Elements #3 and #4 are pretty straight forward. Basically, “Do you have the budget?” and “Who else is in this decision-making cycle?” When you ask, be nice, of course.

If you can’t get these answers, your likelihood of moving your project forward with your superior’s blessing is low.

It is so easy to take, “I love it” and run with it, pretending that you’ve come to agreement when all the thinking probably hasn’t been done. For Turnkey, we are looking for the reasons clients should not invest in our services. If we can help prospective clients determine that they really aren’t ready, we can leave the conversation more gracefully, freeing us to work on initiatives that will happen. Often, when we go through this question framework, we help the client understand their own situation better, gaining clarity on where they should spend their own time… what’s smoke and mirrors and what’s not.

When we hear, “We have to stand up a P2P campaign across all our affiliates next year,” our question will be some form of, “Or else, what?” Change is hard, and if there isn’t a compelling reason to invest the energy and resources needed to overcome inertia, your chance of success is going to be low. And it’s always better to find that out sooner than later.