7 Telling Questions Leaders Ask to Propel Career Growth

If we want to grow as leaders and respected professionals, we must be champions of introspection. Great leaders, from CEOs and founders to managers and entrepreneurs, recognize that real, meaningful growth only comes with honest reflection: reflection on successes and failures, strengths and weaknesses, and ambitions and fears.

Carving out this time to reflect can be a challenge, especially if you don’t know how to examine yourself effectively. Here are seven questions I ask myself when I need to evaluate my growth and reach to the next level.

7 Questions Great Leaders ALWAYS Ask Themselves

Question #1 – If I were on the other side, would I be satisfied with my leadership?

Answering this question comes as both a thought exercise and an opportunity to solicit honest feedback from your team. If you were under your own leadership, what frustrations would you have? In what ways would you be satisfied or left wanting? This is especially pertinent when reflecting on your communication skills, ability to motivate, and method of correction. Would you feel like you could talk to you about a problem? Would you be eager to share ideas or discouraged from innovation? It can be tough to put yourself in the shoes of your team, but it’s a much-needed eye-opener!

Question #2 – What accomplishments am I most proud of?

Think backwards chronologically. List your most prized accomplishments and why you feel so proud of them. Maybe you overcame a big challenge and came out on top. Maybe you felt like what you did made a real difference! A red flag to watch out for is if you haven’t been proud in a while. It can be a sign of professional stagnation.

Question #3 – How am I going to challenge myself in the coming year?

We all have goals in mind and, at least, a bare-bones roadmap of how we want to get there. With that said, the daily grind can take its toll. It’s so common for enthusiastic young leaders to grow jaded and bogged down by it all that they’re just working for the weekend, doing what they need to for survival. But leadership is about thriving! Set goals and challenges for yourself related to your leadership know-how and plan to tackle them in the coming months.

Question #4 – Who is the best version of myself?

Leadership isn’t just about setting the example for your team. It’s about bettering you, too. When you think about your own professional success, what do you see? What defines success? How to you want to grow as a person? Who do you want to be in the next year? Five? Ten? Consider who the best you is and how you can make the moves to get there.

Question #5 – Is my motivation the same?

Time and circumstances can cause our goals to change – and that’s okay! Part of being a great leader is having a laser focus on what’s important. Are you doing what you do for the same reasons you started with? Do you still wake up with the same goals in mind? Revisiting what drives you is part of maintaining long-term motivation. If you lose sight of why you do what you do, then it’s a lot harder to achieve excellence.

Question #6 – Where am I falling short?

Ouch. This one hurts – but it’s absolutely necessary. You may want to recruit a trusted person (or two) to give you an honest evaluation. Give yourself a review: what do you wish you’d done differently or handled better? Where do you feel most insecure or vulnerable as a leader? What traits and habits are holding you back? When you know these things, you’ll be better equipped to do something about them!

Question #7 – What impact do I want to make in the world and how do I get there?

In leadership, the big picture matters. In this day and age, entrepreneurs, leaders, and their teams all want to be working for something meaningful. Meaning in work – the striving for a worthwhile goal – is key to long-term success and perseverance. Once you know what it is you want your legacy to be, you’ll find greater clarity as you develop short and long-term steps. Stay focused on this purpose. It will ground you when things don’t go as planned!