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A Leader’s Bookending: The 6 Simple Questions that Allow You to Build Leaders Under You, Regardless of Title

Mar 05, 2026


“Busy” is the word I hear most from people, friends, strangers, employees, and executives! No matter where you go, or who you’re speaking with, EVERYONE is their own definition of “Busy”, and you know like I know… “Busy” doesn’t plan on stopping. I remember being on a virtual call with an Executive, and he mentioned leading 8 projects at once. He was burning out, and as soon as one project would end, another would take its place.

 

These projects involved many people, spanned the globe, and obviously made the company a lot of money. I felt sad for this gentleman. He knew how important he was to the company, wanted to do a great job, but had zero time to digest the experience after completing a project, and little time to build those under him who helped him complete the project, and the company failed to develop him professionally… all they knew was the project was complete and successful; and as long as the boxes were checked and deadlines were met, then the next project could begin! Sound familiar?

Perhaps you’re on a smaller scale. As a Professional Speaker, Author, Leadership Trainer, and Founder of You Evolving Now most people see me on stages, at companies, and on social media and think it’s ALL ME… and that couldn’t be further from the truth. When I first started, yes, I did everything. However, nowadays. I get to Lead the best Team on the planet! We’re a small, but mighty Team of 9 and what we’ve been able to accomplish has been nothing short of amazing. Most recently, Ask Andre, our AI Pocket Leadership Coach; taking all of my content and answering your professional questions with my common sense and easy-to-apply concepts right away!

The point is, projects are always occurring and underway, but if your people aren’t digesting the experience, don’t know what they know, how it impacts other departments internally or clients/customers externally, developing or evolving SOPs (Standard Operating Procedures) from the experience, and how to teach it to someone else… then “Busy” is all your people will be, and that’s not Leadership! So, what are the 5 Questions to ask your Direct Reports or Employees to best impact, coach, and mentor them into Leaders regardless of title!

As a Leader, you’ve either been given the vision or have a vision for a new project, you’re ready to share it with your Team, delegate tasks, and make it successful. You share it with your Team, Project Managers, Direct Report, or whoever is leading or significantly involved in the project.

Before starting any project, ask:

1.     What are you most excited about regarding the project?
2.     What are you most anxious about… and be honest?
3.     How can I help you or what help do you think you may need from me?

Each question is massively important and will shed light on how you can be a great Leader; marrying what you want to do and give… with what the person receiving your effort needs most from you RIGHT NOW! These questions can be asked in your scheduled 1-on-1 Meeting, via email, Slack, or whatever communication style you prefer… be mindful when asking in a Team Meeting, where others' answers can sway or dilute honest feedback.; however, the Team approach has benefits related to brainstorming and problem-solving.

Question 1 allows your People to share what truly excites them about a project. Perhaps they’re getting an opportunity to match their professional superpower to a project for the first time. Perhaps they’re getting to do something out of their wheelhouse… and now you’re aware of the patience level you’ll have to muster. Perhaps they’ll say something they’re excited about that you would have never guessed!

Question 2 allows your People permission to be honest and vulnerable. This is why we ask it in private; as many Executives don’t want to feel small in front of their peers. When answered honestly, it helps you know how much mentoring, coaching, support, training, check-ins, or patience to set aside and place in your calendar so “Busy” doesn’t beat you and the projects flop or ruin your company's reputation with clients/customers.

Question 3 allows your People to identify their weak spots, ask for help, and evolve professionally. Not everyone will answer this question honestly, but it’s necessary for your Leadership and reputation to ask. It’s even more important to follow-through with the assistance they request… Be Mindful!

As with any project, be sure to document your 1-on-1 Meetings, Team Meetings, and set deadlines to ensure follow-through and a culture of seamlessness and efficiency.

What to ask after the completion of a project? These 3 questions are beyond valuable in creating Leaders under you, regardless of their Title… and building a culture that can begin Leading and policing itself without you ALWAYS having to be there.

1.     What did you enjoy most about the project and why?
2.     What was your BIGGEST Takeaway?
3.     If you had it to do over again, what would you do differently, and what would you teach someone coming up behind you?

Question 1 allows us to ALWAYS start with “The Positive” and them to reflect on what was good about the project, what they enjoyed, and possibly who they enjoyed working with! I love this question because you can’t guess what people are going to say, and it’s always a great experience to hear the joy your People experience while bringing something to life.

Question 2 allows your People to start DIGESTING the project! The first question is “Feel Good” and important, this question starts their journey into Leadership. By answering this question, they will begin to KNOW that they KNOW something that they didn’t KNOW before. You will also learn something new, and this is where the evolution of your SOPs begin.

This question is also the beginning of understanding how your People work and engage across departments. Most projects will require cross-departmental cooperation to pull off the impossible.

Question 3 allows refinement and turns your People not only into Leaders but also into Coaches who impact their peers and your New & Unknown Employees. Asking if they had to do the project/task over again, what would they do differently and what would they share with “A Newbie”, allows solid proof to your Direct Report that they KNOW what to do, have figured out an even better, faster, smarter way, sets an indirect expectation they are responsible to share and teach their knowledge to others, and provide you, them, and the company with a more competent and confident Team Member… regardless of their Title or where they are in the company; because anyone can be a Leader when and if they choose to be… and you just helped them to do that with 6 Simple Questions!

You just read A Leader’s Bookending; what was your BIGGEST Takeaway? What homework are you going to give yourself to implement as a Leader and with your Team NOW?

 
“Projects are always occurring and underway, but if your people aren’t digesting the experience, don’t know what they know, how it impacts other departments internally or clients/customers externally, developing or evolving SOPs (Standard Operating Procedures) from the experience, and how to teach it to someone else… then “Busy” is all your people will be, and that’s not Leadership!”

– Andre Young


Written by: Andre Young