Asking the Right Questions

Equipped with only a high school diploma, and having slept through far too many of my classes leading up to receiving that, I had no shortage of gaps to acknowledge - even if my ego was standing in the way early on (and maybe a little still today). Identifying the key experts I could learn from as I worked to bridge those gaps became easier over time. That rock-solid work ethic I’ve mentioned repeatedly played a crucial role in how I earned facetime with many of those leaders that I would have otherwise only been able to access through books, audio lessons, or from a distance at large events. Even then, though, just having access didn’t mean their knowledge automatically entered my mind through osmosis.

Early in my career, I was very cautious about the amount of time I requested from even Rod and Terry - and I worked directly with both of them at the time. (I reported directly to Kevin and worked with him daily, so I had routine opportunities to ask him nearly anything I could come up with.) Outside of them, I was a bit timid about asking anyone else for support. Some of that was based on a level of arrogance (read: stupidity) that kept me from admitting that I needed input from others and some rooted in a misplaced belief that the folks who had the expertise I needed wouldn’t make time for someone like me anyway. I’m thrilled to say that I’ve overcome both! Although I’m still capable of displaying stupidity on occasion (we all are, and anyone who isn’t willing to admit will lie about other things, too!), but that’s rarely tied to thinking I know more than I do. And I’m VERY willing to ask questions - of anyone who holds still and some who just slow down enough for me to catch up.

Shortly after announcing Mark Cole as the closing keynote speaker for our inaugural LeadershipLegacy Experience in June 2025, a friend from Canada sent me a message asking how I was able to convince Mark to do that. I immediately responded, “I asked,” which was the same way I was able to get him to write the foreword for What’s KILLING Your Profitability?, the introduction to The Values Advantage, and provide the closing keynote for our 2026 LeadershipLegacy Experience. Following that same approach has led to so many of the great professional relationships I benefit from today, several of which I’ve referenced leading up to this point and lots more.

James 4:3 says “You do not have because you do not ask.” A similar variation I’ve heard frequently in recent years is “if you don’t ask, the answer is always NO.” In nearly every conversation I’ve had with Mark or his executive assistant, Kimberly, over the last several years, I’ve stressed that I’m okay with being told no but it won’t be because I didn’t ask. Interestingly enough, the strongest professional relationships I have today - with mentors and clients - started with me using that same approach. That said, bridging our individual knowledge gaps requires asking the right questions.

In 2022, Cindy and I had the opportunity to deliver our Emerging Leader Development course for a group of supervisors and managers at the largest North American facility owned by one of the largest printing companies in the world. The course produced more than the company’s leadership expected and that resulted in us delivering the material at several of their other locations, creating a tailored course we now call “Developing Effective Trainers”, and providing Strategic Leadership Coaching for several team members. Through all that, we had the opportunity to get to know their (then) Chief Operating Officer, Jorge Velasco. Since then, Jorge has contributed to each book I’ve written (the introduction to What’s KILLING Your Profitability?, the foreword to Leading With A Clear Purpose, and a segment in the closing chapter of The Values Advantage) and he’s served on executive panels at multiple LeadershipLegacy events. But more importantly than all that, Jorge has been instrumental in helping me navigate the printing and publishing process. However, none of that would have happened had I not asked for a few minutes of his time - on multiple occasions - and been incredibly intentional in asking the right questions.

Over the last two and a half decades, I’ve invested heavily in getting access to the expertise I’ve needed to compensate for each of my limits. We’ll dig into that more soon. For now, I’ll stress that strategic questions bridge knowledge gaps and allow us to compensate where we’re just not that good. And the most effective leaders I’ve ever known have been the most willing to answer those questions when asked. My challenge for you right now is to identify one expert you can ask a specific question that will help you bridge one of your gaps - and do it within the next week.