Five questions you should ask yourself








One of the first steps I take with new coaching clients is having them complete a personal development plan. The objective is to have them finish the first section − which includes a series of questions − before we meet next. While the task seems simple enough, most clients have at least some level of difficulty finishing by the initial deadline. Some struggle with it. Others agonize over it. I’ve had one or two not finish it.

The questions are not intended to be simple, but they are not intentionally difficult either. The purpose is to make people think about where they want to goQuestionsprofessionally and personally by looking inwardly and gaining a greater understanding of who they are. They are the first steps on a journey of self-discovery and self-knowledge.

It is not easy for us to be objective about ourselves. However, if we ask the right questions, take the time to reflect, and search internally for candid, truthful answers, we can better understand our potential and reach our goals while quieting the voices in our heads and those around us.

While these are not the exact questions included in the personal development plan, they are questions that can help you know yourself better.

  1. What things are most important in my life? – One of the basics of time management is having the discipline to not let the things that are urgent get in the way of what is truly important. A first step in achieving that is understanding what really is important to you and remaining focused on it.
  2. What is one thing I’m really good at? Have you ever seen someone with half your talent seem to get twice the notice you do? Ever wonder why? There are many things that could be at play, but a lack of self assurance can be a major hindrance. If you make the world’s best chocolate cake, you’re able to bake a great one every time in part because you know you can. That same kind of confidence can make a difference in much more ambitious endeavors.
  3. What is one thing I really wish I were better at? Why? As a workplace coach I would saw talented managers and executives who would sometimes obsess over minor shortcomings. This kind of insecurity is natural, but it can undermine self confidence. All of us want − and often need − to do some things better. In addition to working with clients on skills that need remediating, I encourage them to identify something they’re “pretty good” at, but with some work could be “really good.” In my experience, this approach can help build the kind of confidence to face more difficult challenges.
  4. What’s one thing I’m really proud of? Many of us are taught to believe that humility is a virtue. However, learning to talk comfortably about achievements without appearing immodest is essential to demonstrating the ability to handle new assignments and challenges. You’ve probably heard that saying “give credit where credit is due.” If you’re the one who is due the credit for accomplishing something, take it.
  5. What unrealized dream would I still like to fulfill? Who doesn’t have that “what if” question looming in the back of their mind? You can’t go back and recreate missed opportunities. But adding a bit of adventure to your life can reignite creativity at work and make your personal life more satisfying. That doesn’t mean you have to do something that upends your existence and strains your relationships. It can be something as simple as shaking up your routine, getting outside your comfort zone, leaning something new, or taking some time for yourself.


Robert Naylor is a journalist, consultant, coach, facilitator, and speaker who helps people become better leaders, improve workplace performance, and find focus in their careers and life. He is available for on-site training, private coaching, keynote presentations, and commentary. For more information visit naylorcoaching online or

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