Guest Post by Kent Stroman

If I could give anyone anything to enrich their life, it would be better asking tools.  I’ve spent years in the world of fundraising trying to ask better questions and engage with donors at a level that goes beyond dollar amounts.

The mark of a great question is that it causes someone to pause before they answer. 

A few months ago, I was able to spend some time with a colleague who I’ve known for several years. During our conversation, she asked me 5 terrific questions that caused me to pause before I was able to answer.

Here are those questions:

“What’s a big shaping factor from your childhood or youth?”

“What would you like your legacy to be?”

“What is most financially rewarding in what you are doing right now?”

“What is most professionally rewarding in what you are doing right now?”

“What is most personally rewarding in what you are doing right now?”

Those questions led to some of the richest conversation and self-examination I did all of last year. I’ve started using these five questions as a template for important conversations I need to have with other colleagues or team members. I encourage you to think about how you’d answer them and look closely at what your answers might mean about your current path.

Like my friend Bob, I too believe that asking great questions is an important part of leadership. I specialize in conversational fundraising, and some of the best conversations I’ve had with organizational leaders or prospective donors has come from a time of asking strategic questions.

The first question causes me to look back on the early years of my life. My family has been such an influence on so many different parts of my life, and thinking about my heritage causes me to be humbled and extremely grateful. My four years at MidAmerica Nazarene University shaped my early adult life in ways that still manifest themselves today.

As for a legacy, from a professional standpoint, I want my legacy to be two generations of leaders that are equipped for true success in fundraising. I want them to be able to fund the solutions that their mission provides in ways that are impactful, efficient and build relationships.

For years, the most financially rewarding aspect of my job has been providing counsel on capital campaigns for organizations. This involves a larger engagement with an organization over a longer period of time, and I’m proud to have been a part of so many great campaigns over my now 15 years as a full-time consultant.

In 2013, I started The Institute for Conversational Fundraising. Along with that came The Asking Academy, and it quickly became the most professionally rewarding aspect of what I do. I get to really equip leaders with tools they can use for success. I’m not giving a man a fish or teaching a man to fish, but rather we’re teaching people to run fishing enterprises! I so enjoy watching the success that graduates of our program go onto achieve.

And from a personal standpoint, the most rewarding thing I do is public speaking. Those opportunities stretch me and force me to refine my material and hone my craft. They also allow me to meet people that I might otherwise have never met! The relationships that become possible because of public speaking make it the most personally rewarding part of my job.

What about you? Do those questions give you pause? I hope you’ll take the time to really think through each of them and formulate answers, and I hope those answers lead to reflection.

Try asking these questions the next time you have lunch with a good friend or longtime colleague. It may just bring about some of the richest conversations you’ve had in a long time!

Note from Bob:  If you are involved in Fund-raising or know those who are, you need to connect with my friend Kent Stroman!  I have been through his Institute for Conversational Fundraising!  Stellar!  You can connect with Kent @  And please tell Kent “Bob sent me!” 

Kent Stroman, CFRE, teaches passionately, consults wisely, writes creatively, speaks inspirationally and helps willingly. His counsel has been honed by decades of experience in nonprofit leadership, board governance, fundraising, strategic planning, capital campaigns, and financial management. Kent is the author of Asking about Asking: Mastering the Art of Conversational Fundraising and the soon to be released The Accidental Intentional Board.




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