The 4 essential questions to ask yourself as a leader

Instead of seeking answers, becoming a better leader starts with asking ourselves the right questions.

You want the answer. The silver bullet, the trick, the hack, the leadership best practice, the new manager checklist. There’s got to be some secret point of leverage that you don’t yet know about to becoming a better leader… It has to be out there, right?

We’re obsessed with wanting to know the answer. The 1-2-3 steps to follow so we can right our wrongs and make progress faster.

Yet when it comes to becoming a better leader, I’m not convinced there’s is one. Scholars can hardly agree on the definition of leadership, alone. As Ralph Stogdill famously wrote in 1974, “there are almost as many different definitions of leadership as there are persons who have attempted to define the concept.”

Perhaps the sheer number of articles I’ve written on this blog is further proof of the variance and nuance involved in figuring out how to become a better manager. Sure, I’ve shared stories, data, and insights. But I’ll be the first to admit that none of what I’ve written contains some singular, sweeping answer to the question, “How do I become a better manager?”

Rather, I think any attempt at an “answer” to becoming a better leader lies in the questions we can ask ourselves along the way. We’re each vastly different, operating in distinct environments, interacting with unique people and dynamics and obstacles. The “answer” is more complex than any new manager checklist could hope to capture.

So, I’ve got a different kind of new manager checklist for you. Rather than providing answers, I’ve got questions – four in particular. Questions to ask yourself that reveal what action you need to take, what shift in mindset you need to make. From the thousands of leaders who use Know Your Team, the 1,000+ managers in The Watercooler, and the many leaders I’ve chatted with on my podcast and beyond, it’s an accumulation of the best questions they’ve asked themselves. I hope you’ll find your own answers in them.

Question #1: How can I create an environment for people to do their best work?

A leader doesn’t shape people – a leader shapes an environment. This distinction is critical. When you’re focused on influencing an environment instead of people, you concentrate your efforts on the inputs within your control: How you communicate priorities, the decisions you make, the gestures of care and support you show. You no longer try to manipulate inputs outside of your control, and that frankly don’t matter: How a team member chooses to accomplish a task, or if a team member likes you. You’re not as susceptible to letting fear or your ego to get in the way of serving your team.

Question #2: How can I create as much clarity and coherence about what needs to get done and why?

The vision, the mission, the goals are crystal clear to you. But are they only for you?  🙂 Remember that no one can read your mind, and you’re the one person on the team whose job it is to say where you’re trying to go, and why getting there is important. Reflect on how you’re communicating the long-term vision of the team, and how it’s relevant and connected to your team. Yes, the work is meaningful to you – but how is it meaningful to each individual team member?

Question #3: How can I personally model the behavior I want to be true across my team?

You can’t expect your team to behave in a certain way if you don’t exemplify those actions yourself. Want your team to be on time to meetings? Consider how on-time you typically are yourself. Want your team to give you more honest feedback? Consider how honest you are in the feedback you give, and how you react when they share tough feedback with you. When you walk the walk, instead of paying lip service to platitudes, you earn the trust and respect of my team. Trust and respect is only earned, after all.

Question #4: How can I see things for what they are, instead of what I want them to be?

Our biggest problems as leaders arise when didn’t realize that the problem was going to become a problem. We were blindsided. Our model of reality didn’t match reality, itself. Rigorously examining what is actually true – rather than grasping for what we’d like to be true – is how we avoid being surprised by a key team member leaving, or when team member’s performance starts to suffer. As management theorist Peter Senge wrote in The Fifth Discipline: “The most effective people are those who can ‘hold’ their vision while remaining committed to seeing current reality clearly.”

Try asking yourself these questions every now and then. Perhaps before you head into your new job as a manager. Or, reflect on these questions at the end of the month, or every week… maybe even building up to asking them at the end of every day.

They can serve as different kind of new manager checklist: A personal reference point for new things to discover about yourself and new commitments to make to yourself to become the leader you’ve always wanted to be.

Deeper learning comes from this inquiry – posing questions, instead of imposing answers.

Finding your own answer is where the real answer is.


Claire is the CEO of Know Your Team – software that helps you avoid becoming a bad boss. Her company was spun-out of Basecamp back in 2014. If you were interested, you can read more of Claire’s writing on leadership on the Know Your Team blog.

2 thoughts on “The 4 essential questions to ask yourself as a leader

  1. #4 is tough. Leaders are human too and although it’s not the same as lowering your expectations, understanding where your team is now and what it’s going to take them to get to the next level is key.

  2. Thank you for your relevant, meaningful questions that will make a difference in an organization and department. Well stated.

    And… while not a question: Treat employees as if they are your customers. The impact in culture and business results can be transformational.

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