Deb: Why is the Sky Blue? 

Adult: Why do you ask so many questions?


Deb: How will I use the Pythagorean Theorem in everyday life?

Teacher: Can you see me after class, we have to get through this lesson!


Deb: Shouldn’t this be our decision on who to hire for this position

Boss: You shouldn’t have asked that question!


Deb: Before we get to the tactical details of running this meeting, shouldn’t we land on the outcome we want to achieve?

Colleague: Ahh, Ahh, you’re right, we should!

Asking so many questions has and always been my way of seeking to understand the world around me and navigating situations in front of me.

Why then does this superpower often collide with the world and people see it as an annoyance?  Challenging the status quo is not taught in our society as much as it should be and stifles creativity and higher levels of understanding. Compliance is mainstream because if you fall in line you won’t realize the backlash or conflict. Without this skill, people fall victim to the status quo and never learn how to ask better questions of themselves, others and society. 

I was recently at a networking event for which colleagues were sharing stories of not getting ahead due to lack of equal opportunity in the workplace. While I believe there are challenges in front of us, I was saddened to see the acceptance of the perceived obstacle. They were not asking deeper questions of why they thought the problem existed and even more upsetting was lacking the confidence to find ways out of the current situation.

When we allow ourselves and others around us to fall into acceptance, we stagnate our progress and our teams.  If you don’t, the people who look up to you will perpetuate the cycle of accepting the status quo and will also fall victim to narratives they believe. If you are an aspiring C-Suite leader, let me share with you my best tips to break out of the status quo and be the leader who asks better questions.

Have courage to ask questions that others won’t ask

If you don’t understand something, more than likely others will not understand as well. I recently asked the board of one of my professional societies a question. In the flurry of year end planning, people were deliberating details. I asked the question, “what do we want to be known for as a chapter?” to which people said I was right, we should answer that first. I said when we can define who we want to be as a chapter, we can make better decisions about the details. 

When you take the courageous position of asking “why”, you gain clarity and your silent colleagues will thank you as well. When you take a risk, others will be attracted to you and also learn important skills by modeling your behavior. I once had a personal trainer say something to me about risk-taking. He said, “what do you have to lose? You might actually be successful.”

With that suggestion, I err on the side of causing conflict because in the end I have engaged in conversation. Ultimately, we want people to interact in healthy dialog to achieve an outcome or decision. We want harmony and unified levels of performance in our workplace. When people don’t understand something or can’t relate it to their situation, over time compliance wanes or teams are misaligned. When we ask better questions and gain consensus or a unified outcome, team performance is higher. So what do you have to lose? Ask a better question, you gain clarity. Ask an even better question, you gain followers. 

Ask questions to get to the truth faster

Back in 2010 when I was getting impatient for a promotion I asked my boss to help me define my career path. They were honest with me that for my role, there was not a clear path to promotion. They offered me the advice that I was free to look elsewhere in the organization for opportunities. That truth short circuited a cycle of potential frustration; wondering if I would be recognized for my accomplishments and would be offered a promotion or new position. In that moment, I realized the truth and had information that enabled me to navigate to different roles. I saved months and possibly years of waiting and frustration. What I did was take control and have the courage to ask the question. A year later, I was working for a different company. 

The point I want to make here is so many aspiring C-suite leaders wait and hope. That simply doesn’t work and you’re losing the best years of your life. When you take the chance and ask a simple question, you gain back years of your life. If you’re nervous, the best advice I have is to write it down on a post it note or an index card (if they still use these!). 

Challenge the status quo to regain control

I’m often asked if I am a fractional CEO, COO or fractional (fill in the blanks) to which I say no; I’m the Drop In CEO. I catch people off guard, because they can’t put me in a box for which I fall in line with the sea of people doing the same thing. When we allow others to put us in a box, we are not seen, heard or respected.

When I respond that I’m the Drop In CEO, I become the leader that organization or team needs at that time and place in their journey. It challenges the status quo, but it makes me interested in which people want to learn more. It’s a lonely journey to position yourself differently, but over time, alternative thinking becomes interesting and in the long term, people will follow you to new lands vs. crowded spaces.

If having followers is not important to you, then the greater outcome of thinking differently is taking back the balance of power to control your situation. When people put you in a box, you have to fight to get out of it and prove your value. When you build the box and stand on it, people will come over and see how you constructed the box you’re standing on. You become interesting and you become the person people will ask more questions. As an aspiring C-Suite leader, challenging the status quo gives you the power you need to get ahead and stand out. 

Challenging the status quo is a lonely journey, but it’s liberating. Think about when you remained quiet and festered over a situation. You lost minutes, days or months of your precious life on earth. When you challenge the status quo and stand out as different, you speed up your ability to navigate your career. Ultimately you become the leader others will follow. You become the person you want to be and do the things you want to do with complete confidence. Does this sound better than falling in line? 

So what are you waiting for?  Five seconds have passed and you’ll never gain it back. What questions do you have that need to be asked? What ideas do you want to present that may change the course of your situation? Are you going to take control and change the balance of power in your favor? Let me know how it works out, I can’t wait to see where you take your career.

If this makes sense, but you’d like to learn more about applying these principles to your situation, you can email medirect message me on linkedin or simply grab a few minutes on my calendar.  

I find through casual conversation leveraging The CEOs Compass often has all the answers for you to get back on track. 

The CEO’s Compass: Your Guide to Get Back on Track – If you’re that leader who feels in their gut something is off track, this could be the resource for you.

No alt text provided for this image


Good Reads

Stand out by Dorie Clark I’ve shared this resource before with you, but it’s in this season that you should think about who you are and who you are meant to be in the coming year. You are talented and courageous, but still unsure about the future. Take control and think about how will you stand out and be different than the pack. What questions will you ask that challenge the status quo. What stake in the ground will you make towards building your stand out statement in 2022. Be inspired and be great!

Good Music

When Leaves Dance by Shoshan Michel – this peace is calming as it sounds like the transition from fall to winter. It’s light and airy but also deep in emotion. As we reflect on 2021, I ask you to think about what went well and what will you bring forward into 2022. It’s a time of closure and new beginnings. Slow down and reflect as you listen to this song. Be inspired to be the leader you want to be for yourself, your team, your family and community. 

Good Advice

“It’s not about how many contacts you make anymore. It’s about how deep you go on each conversation.” – Ari Galper  

 Listen and subscribe now: