Ten Questions All New (And Old) Leaders Should Ask Themselves

You finally got it. You worked long hours, put forward some of your best thinking, and really put yourself out there to get it. And you’ve arrived. You are the boss.

Oh, wow. You’re the boss.

Sure, you’ve been dreaming of this promotion - the raise, the credibility, managing people, getting more responsibility. But now that you finally have it, you’re terrified. You’ve never done this before. Where’s the manual?

The bad news: There is no manual. Leadership has no rules. We all make it up as we go.

The good news: There is no manual. Leadership has no rules. We all make it up as we go.

It can be incredibly overwhelming and frightening to have so much responsibility all at once. It can also be invigorating and an opportunity to shine. I like that second perspective better.

As someone who has gone through both sides of this emotional rollercoaster myself, and as someone who now spends her days coaching leaders, this is one of my favorite topics. One of my clients just recently accepted a promotion and will be managing people for the first time. I am thrilled for her, and I also hold some of her nervous jitters. She immediately wanted to know what she should do to prepare, and I found myself tongue tied. There is so much advice to give a new leader - just google “tips for new managers” - that I didn’t know where to start.

And then I remembered, I’m a coach! I don’t give advice. Ah, a breath of fresh air.

Instead, I got to ask questions, questions so that she could build her own leadership roadmap. This session sparked some important insights - for both of us! - and showed once again, the power of questions over answers.

So, to my new leaders: here are 10 questions that we used to begin opening up some insights and ideas. Disclaimer: you might not be able to answer these all right now. That’s ok, and you probably shouldn’t answer all at once. These are questions you can come back to over time and use to put yourself back on track.

And to my more experienced leaders: these are great questions for you to reflect on as well. Use them to question what you’re doing today, how you’ve changed over time, and what more you can do to up your leadership game.

Old and new leaders alike, share your wisdom in the comments!

  1. What’s your leadership style? Often I hear people ask, “What’s your leadership philosophy?” That terrifies me. It just sounds so big and honestly, quite pretentious. You could spend years reading leadership literature, trolling the web, and listening to inspirational to TED Talks as you try to uncover and design your philosophy. All worthwhile activities, but chances are, you don’t have tons of time to do this right now. So, instead dig within yourself and reflect on who you are and how you want to be as a leader. What’s most important to you? What’s do you value at work, in your relationships, and in the world? How will those answers shape your leadership style?
  2. How will you build trust? Whether you’ve moved up the ranks in your current organization or have taken on a leadership role in a completely new organization, you’ll need to earn the trust of those who work for you. How will you build and sustain those relationships?

  3. What’s your vision? As a leader, you will be doing less task-oriented work and focusing on more bigger picture thinking. Your team is looking to you to set "the why" and to explain what success will look like. So, how will you establish you vision, get buy-in, and communicate it to your team and the rest of the organization?

  4. What are your priorities? Once you know your vision, how will you get there? Obviously, there’s so much you can do, so you'll need to determine the "big rocks" - the highest priorities - for your team. How will you determine your big rocks? And when you have to switch priorities - because you will - how will you explain this to your team?

  5. How will you manage your time? You are no longer just moving through a to-do list. You are setting a vision, inspiring others to get onboard, and probably, still doing a good portion of the work. How will you get your hands dirty and be in the trenches with your team without getting sucked into the weeds and leaving space to invest in more strategic thinking?

  6. How will you show the people on your team that you care about them? Think about the best bosses you’ve ever had. They cared about you as a person - both how you were at work, what was going on in your life, and your future career. How will you build and establish meaningful and productive relationships with the people who work for you?

  7. What can you do to create a culture of feedback? We all say that we want honest and critical feedback, but actually receiving or giving it is pretty hard. How can you solicit feedback from your team and ensure that you are providing regular criticism and praise for everyone who works for you?

  8. How will you manage not being liked? Because you won’t be. At least not by everyone. And if you are liked by everyone, chances are that you're not doing your job. Leadership is hard and requires making controversial decisions. The truth can't always be in the middle. People won’t like you, and for some, that can be the hardest and most debilitating part of being boss. How will you handle not being everyone's best friend?

  9. What happens when you fail? Just as you won’t be liked, you won’t always be right. You’ll make small mistakes and have epic failures. You just will. How will you navigate and thrive in the face of failure?

  10. How will you be you? I end on a question related to the first in our series. You’re constantly designing your leadership style and shaping your legacy. How will you not get lost in it? How will you ensure that the best of you shines through during the toughest of times? How will you continue to rely on your intuition and what you know is right?

Phew! That was a lot, huh? Before you feel overwhelmed, remember that there are no right or wrong answers. These questions will help you learn, refine, and grow into the leader you strive to be.

Go get ‘em boss!