Questions to help you become a better leader
Article Overview/TL;DR
As you prepare for the new year, a new job, or want to reconnect with what matters most to you, it’s worth reflecting on who you are as a leader. This means celebrating your strengths and being brave enough to identify where you can do better.
Key takeaways:
Leaders bring the weather. They set the tone for the entire organization.
Leaders have a responsibility to grow themselves and their skills as leaders.
Start by assessing where you’re at now
Don’t forget to carve your own path, independent of any company or role you’re in as a leader
Identify your leadership values. In doing so, don’t avoid the difficult questions, and recognize where there is room for growth.
Set up your teams for success by reflecting on your impact and applying your values to how you work with them.
Who am I as a leader? I’ve asked myself this question a lot in my leadership career, most often during difficult times or when I had to make tough decisions. It’s a question that gets to the core of who we are: As leaders, we lead with skills, tools, experience, and frameworks, but also with who we are as people. In our busy work lives, we don’t often have time to reflect on our leadership path, and a lot of us don’t have bosses who actively support us in our career growth.
Make space to be intentional about who you are, so you can actively shape who you become.
In this article, you’ll find 28 questions to ask yourself about how you show up as a leader, to help you become the best leader you can be. I’m also giving away a free worksheet format of this article, for those who want to work through the questions on paper or distribute it to their team. These questions are worth spending some time on. Try jotting down some notes, going on a walk, or contemplating over a cup of coffee or tea. Use them as a reflection exercise, for self-coaching, or discuss them with a colleague. Reflect on them as you prepare for the next year, a career move, or to reconnect with what matters to you after a big change.
What is leadership really about?
“Leaders bring the weather.” (Jim Geiger)
While management is about managing complexity, leadership is about coping with ambiguity and change. I love this description of great leadership from “Scaling Organizations” - when a great leader walks into the room, everyone takes notice. The tone, mood, presence, focus and behavior of its leader is the weather in any organization. Everyone who works there can feel it, see it, experience it, describe how it impacts them and those around them. They know if this weather supports what they’re trying to create or destroys it, and how they should behave around this leader. They can also describe if this weather brings out the best in individual employees and teams, or if it lowers their performance.
“They know if they should relax, contribute, and take risks, or remain cautious, reserved, and careful. Leaders bring the weather, and they define to a large degree what can and can't happen in their organization.” (Robert Anderson, William Adams)
When we talk about the leadership as weather, we’re really talking about the leader’s profile in action. This encompasses the way we show up for our people, how we tend to respond to certain situations or crises, what is and is not permissible to discuss, and more.
Leadership is based on humility and humanness. Great leadership at its core is about how we show up, and showing up in more transparent, authentic, vulnerable, empathetic, passionate, and compassionate ways. Whether that's in the meetings we run, the emails we send or our everyday interactions with colleagues. Leadership is a call to continuously grow and evolve.
Growing yourself and your skills
There’s a number of reasons why it’s vital that leaders invest in themselves. Firstly, it’s leading by example - if you want your teams to invest in becoming the best versions of themselves, then you’re going to have to do it too.
As leaders we hold power. That’s a huge responsibility, and we owe it to ourselves and people around us to handle that carefully. So, on that note, let’s get started.
Review how you’re doing
“The very pressure that success, scale, and complexity bring is a force for our own evolution and transformation.” (Anderson / Adams)
Start by assessing the status quo. What is your current status as a leader? There are plenty of tests available to help with this, such as SWOT analysis, strengthsfinder, or the Big 5 profile. All of us have gaps in our skill set and leadership. They don’t mean there’s something wrong with us, rather, they are a consequence of leading in the very complex systems we all find ourselves in. They’re also challenges - a call to rise to the challenge of our own shortcomings. Ask yourself the following:
What do I excel at?
How and where do I have influence?
What brings me the most satisfaction?
What and who frustrates or challenges me? Which of my core needs may feel threatened in my interactions with them?
What is the most common feedback I receive? What feedback do I get which I disagree with, and what’s causing this reaction for me?
If I no longer worked in my current company, what would my team miss about me and my work?
Carve your own path
I’ve found in my work with leaders that this part easily gets forgotten, as many of us are so invested in helping the people around us grow. How can you carve your own path, independent of any company or role you’re in as a leader? Ask yourself:
How can I better utilize my strengths?
How can I increase my impact? Think about areas such as working across teams, your partnership with your peers and stakeholders, managing up, and taking on bigger projects.
Where do I want to grow? What excites me?
What challenges do I want to actively work on?
How can I mitigate other weaknesses?
What do I need to get there?
Identify your leadership values
“The cave you fear to enter holds the treasure you seek.” (Joseph Campbell)
These questions might seem difficult, but this means we are digging into our capacity to change. We don’t resort to scolding or belittling ourselves, but do one of the most productive things we can: looking at our own actions honestly, reflecting, and identifying how we can do better. Ask yourself:
How did I act in a contentious situation? How do I wish I'd acted?
What difficult decisions did I have to make? Why did I decide the way I did?
Where did I fail as a leader?
What am I proud of?
When did my work make a difference for someone? Why?
Setting your team up for success
Zoom out and think about what you can do in your daily work with your team.
Reflect on your impact
Think about how you’re guiding your team, and how you can become a better leader for them, by making sure they have the context, tools, and skills to grow.
When and how do I empower other people? When has that investment been easy for me? Or hard?
Where am I getting in the way instead of letting others shine? What work am I doing that others could be doing, either better than me or as a growth opportunity?
How can I grow more leaders on my team?
Do I have a development gap in my leadership? How does it impact my effectiveness?
If I were to leave tomorrow, what gaps would I leave behind? How can I close those gaps now? We all consider ourselves irreplaceable (and in many ways we are!), so this can be an uncomfortable question, but it is crucial. You’ll likely not be with your team forever, and they may have to work without a manager, or with someone who’s less invested in them than you are. Consider areas like helping them own their career growth through brag docs, coaching them on managing up, or helping them make their work visible.
Apply your values to help your team thrive
Now that you have more clarity on your values, consider how you’ll apply them in your work with your team:
In which areas can I live my values more as I’m leading my team?
What does my team need overall in terms of skills and capabilities, structures, ways of working, and support?
How can I show up as a better leader for my team, e.g. in my interactions with my team, or how I talk about their work with wothers?
What skills are missing? How can I support my team in adding them?
Who's ready for bigger opportunities? Who may I be overlooking?
How can I best balance team and business needs?
Reflecting on your leadership capacity as it stands now, and figuring out where you want to get to in the future, is an important exercise. It asks us to face potentially uncomfortable questions head on, but the growth we experience as a result makes it entirely worthwhile. Leaning into our capacity to change as humans and leaders is a great sign of strength and resilience.
If you’d like this exercise as a worksheet, and/or you’d like to distribute it to your team, you can download it here. You can also watch my full presentation of this topic here.
