The Questions You Don’t Know to Ask

Ever had an experience trying to do something new and having all the little things go wrong? It ends up taking way too long and is so frustrating. That was my weekend. Trying the simple task of changing cell phone providers. Oh, if only I would have known what questions I should have been asking in advance! The right questions could have made this situation go much more smoothly.

I thought it would be simple. We did some research and found the right provider. Made the call to get started only to find out there were some steps that needed to happen before we could even begin. Your phones need to be unlocked. You need the IEMI number at your fingertips. Your phone must be backed up. Don’t forget to listen carefully because there is some “fine print”, too. Four hours later and we still weren’t done. But the process has started!! Maybe next weekend it will only take another four hours to finish. 

What a frustrating experience! There is so much I wish I would have known up front. First and foremost, what questions could I have asked to be better prepared for this? It’s a mess and turned into a lot more than a simple phone call.

I needed a guide to see me through, not someone pressuring me to buy something!

And yet another example, one of my coaching calls this week started with a barrage of concerns fueled by an urgency to figure it all out and make a move. Then, the nugget of the conversation came out. “I have all this information, but I don’t know what questions I’m supposed to be asking.”

I thought of my phone fiasco and I could relate. I had all this information about cell phone plans, but it was the process that was tripping me up. This happens often as leaders. Information or ideas in abundance but we have to find our way. We just wish we had a guide to see us through, instead we feel the pressure to act now!

So, if you are stuck with all the circling possibilities, options, ideas, information that comes with being a leader, then here are some questions you can ask to find your way through:

  1. What is my goal here — the target I am aiming for? With my cell phone problem, it was to save money. With my client, it was to restructure the department to grow. 
  2. What will help me achieve that goal? With my cell phone problem, I had narrowed it down to a new provider even though I eventually wondered if it was worth it. With my client, it was getting outside of her head and putting it down on paper to make it actionable.
  3. What do I know about what has worked in the past? With my cell phone, experience has informed what services are over-kill as well as what is not enough. With my client, there were specific past examples that gave guidance for next steps.
  4. What am I missing that someone else might contribute? With my cell phone, I could have asked a few friends about the process in advance. With my client, there are others on the team who have some insight and strengths to leverage.
  5. What are the steps that need to be in place for this to happen? Those of us who are idea people often catch an idea and just go for it! Yet, mapping out the steps can minimize frustration because it sets realistic expectations of what can happen. This is true in my phone project and with my client as they reshape their department.

I am an activator. The phone story is a great example of how I decide and do. I know many leaders out there are like that, too. There is wisdom in stepping back and asking a few process questions before you launch. 

“You can tell whether a man is clever by his answers. You can tell whether a man is wise by his questions.”

~ Naguib Mahfouz

Next Steps

Sometimes we lose too much energy spinning our wheels (like 4 hours on a Sunday afternoon). We need some good questions and a guide to help us through. 

  1. Think of an upcoming activity or project that has been circling in your head.
  2. Step back, slow down and ask the five questions above, write down your thoughts.
  3. Grab some research for information that might be missing.
  4. Find a friend, rely on a colleague or reach to other trusted counsel in your life who can help you navigate the questions (not give you all the answers).

Need a sounding board? Grab a complimentary strategic session with me to navigate the questions. 


Annie Perdue Olson

Annie is founder of Leading Better Together, guiding leaders through the relationship and people challenges that sidetrack ministry. With 20+ years of experience in nonprofit management and pastoral ministry she equips people and teams to work better together. She holds a Master of Arts in Human Resources and Change Leadership from St. Thomas University and received her coaching certification from the Center for Coaching Excellence.

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