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 face time 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!), 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.

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.

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 next. 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.

Investing in Expertise

I’ve mentioned barely graduating high school several times to this point. I also shared that neither Cindy or I had graduated college when we started our leadership journey (and still haven’t). While my less than stellar performance in high school was more a factor of me being bored, our lack of college degrees - at least early on - was tied to finances. Neither of us had the finances to be full time students; we didn’t have interest in taking on the amount of debt that would have piled up and had both been working since our early teens. When we built a home and paid for a wedding within a short period of time, we found ourselves stretched far too thin for even an occasional class. That said, we were still very intentional about investing into seeking and developing the expertise we’d need in order to be successful in each role we held as well as the future roles we were working toward.

Acknowledging your limits isn’t that difficult when they’re hitting you in the face, and mine definitely were as soon as I moved into that first position where I was expected to get people to change how they did their jobs but had no positional authority backing me. Identifying the key experts I would need to learn from and being willing to ask the right questions made an impact right away. But even those most willing to share their wisdom wouldn’t have continued had I not been willing to invest in the process. While our finances were tight back then, we were able to invest a tremendous amount of time into seeking out knowledge from those experts and we invested significant energy into applying everything they taught us - which we’ll circle back to soon.

Earlier, I shared how I audited Terry’s session on “The ABCs of Behavioral Analysis” weekly for close to two years. That only scratches the surface of the time investment I made into studying the folks I realized that I’d need to learn from, many of whom began mentoring me directly through the process. While doing all I could to be around these experts in person, Cindy and I were working through every book and audio lesson we could afford to buy or that we could convince someone to loan us. All that helped us build a foundation so the questions we did ask were more specific to our situations rather than being something general or something we could get from a few clicks on Google today.

Even then, had I only been a face in the crowd, rather than deliberately nurturing relationships with each expert I studied, I doubt I would have gotten much (if any) of their attention. And if I would have asked the same questions time and time again with no results to show for it, any attention I did receive would have been short lived. For more than a decade, we’ve challenged every group we’ve trained, spoken with, or coached to identify at least one specific action step they could apply from what we shared. More than anything else, the energy we’ve invested into applying what we’ve learned from the experts we’ve had access to has helped us leverage leadership growth and build great professional relationships. Before we work through the importance of application in more detail, I’ll challenge you to identify (and schedule) a time where you can invest in learning from someone who has knowledge that you don’t.

Applying Expert Insights

Over the last twenty-five years, Cindy and I have been extremely focused on building a knowledge network that would help us compensate for our leadership limits. Recognizing who knew what we didn’t know was the first step. Being willing to invest whatever we could, even if that was only our time, into pursuing their expertise and asking the right questions to have a shot at moving forward followed. But those things alone would never have produced results. And sooner or later, our opportunities to continue asking even the best thought out questions would have dried up. Without applying expert insights, few of the people we worked so hard to get time with would have allowed us to get more of their time. 

I once heard John Maxwell share a story about how the mentorship he received from the late, great college basketball coach John Wooden got started. Maxwell explained that a mutual friend set up their first meeting. He arrived prepared with a list of questions. What was initially supposed to be an hour or so turned into an afternoon, and they still only worked through a few of the questions. As they wrapped up the conversation, Wooden suggested that Maxwell visit again to build on that interaction. As their second session began, before asking a single question, Maxwell started off by sharing what he learned previously, what he had taken action on since, and the results he had achieved. This was very late in John Wooden’s life. Seeing how deliberate John Maxwell, already extremely successful at that point, was in applying what he learned through their first meeting was all Wooden needed to know that any time they had together would bear fruit.

I’ve never had one-on-one time with legends like Wooden or Maxwell, but I have had opportunities to learn from leaders I would have never believed possible just a decade ago. But even early on when the only mentorship I had access to was from the men I worked directly with, I worked as hard as I knew how to apply everything they taught me. I had seen so many folks get time with leaders, ask impressive questions, then show back up later having changed nothing and ask the same questions yet again; or even worse, ask completely different questions while acting like they had never asked those mentors anything before. In a few cases, I saw those mentors ask them how they had taken action since the previous conversations and receive blank stares.

The leaders who have provided me with the most insight and the most direct mentorship in my career have also been the ones with the most stringent demands on their time. Had I not done everything in my power to apply their expert insights, could I have really blamed any one of them if their availability waned over time? At this stage in my career, I’m not excited about working with paying clients who don’t take action on what we discuss. But I rarely pass up an opportunity to invest my time and energy into providing mentorship to someone I see making the rubber meet the road.

Whether we achieve immediate results or not, applying expert wisdom strengthens our leadership capacity. That’s crucial in overcoming any of the knowledge gaps we each have so we’ll dig into that next. Until then, I’ll challenge you to be intentional about applying one expert tip to a task you’re working on currently - and do it right away!