How My Boss Taught Me to Think Like a Leader

The best leaders ask more questions and give fewer answers.

Great leaders inspire teams, influence colleagues, and develop strengths in others. But before leading others in practice, the best leaders master the art of thinking like a leader long before formally leading a team or having a ‘manager’ title bestowed upon them.

Before starting my own talent consulting firm, I began my corporate career as a Recruiter. I was fresh out of school and quite comfortable navigating the black-and-white environment of a classroom where there was a right and wrong answer for every question. I had a knack for mentally organizing new information and subsequently plucking said information from my memory to correctly answer any question asked on an exam. I assumed that the same skills that had garnered a strong GPA would also guarantee success in corporate America.

I was wrong.

Unlike the classroom environment, there’s rarely a single ‘right’ answer to any one dilemma in the working world. Just a few months into my professional career, I was struggling to succeed in the world of metaphorical shades of grey. Every day, questions popped-up that I didn’t yet have the answers to.

With the weight of wanting to make the ‘right’ decision on my shoulders, I marched my way down the hallway to my boss’ office and swiftly dropped the problem squarely into her lap to solve.

Or so I thought.

Met With Questions, Not Answers

Rather than being met with an answer to my question, I got the opposite. I was met with more questions. And lots of them. Even worse, they were questions that I did not have the answers to. In fact, I hadn’t even considered them.

That promotion I had asked about was met with questions like, “What was his last performance appraisal score?” “How was he performing compared to his peers?” “Did the work warrant a full-blown promotion, or was it just a small increase in scope?

The questions went on and, as they did, I felt smaller and smaller. “I’m not sure,” I said, “I didn’t think to ask that.” At this point, I was still hopeful that she might take pity on me and tell me how to proceed with solving the problem at hand.

Instead, she sent me packing with a long list of questions that I needed to answer before she would share her opinion. I called the manager with my tail between my legs and diligently walked through each of my boss’ questions, carefully taking notes on the manager’s responses.

Back down the hall I went where I quickly rattled off the additional information I had gleaned. We were getting closer, but we weren’t entirely there. The answers to my first set of questions had prompted yet another round of new questions which I had also failed to consider. I had been so focused on answering each specific question she had asked that I hadn’t slowed down to take in the full picture of the situation at hand.

Tap Into Your Natural Curiosity

Tap into your natural curiosity,” she told me. “If you were running this HR department, what would you want or need to know to make a sound decision on this?” Back to my office I went, this time with a shorter, more fluid list of things to look into. My ego was bruised, and I’m sure the poor manager didn’t understand why this simple request necessitated yet another conversation. But this time I focused less on securing answers to specific questions and more on gathering the information I would need to come to a decision on my own.

They say the third time’s the charm, right? I certainly hoped so. I made my way back to my boss’ office and shared the additional information I had gathered. This time, she asked only one question, “What do you think we should do?

Not exactly an answer.

But, to even my surprise, I myself had an answer. I had a point of view, and it was an informed one that weighed the pros and cons of several different decisions we could make.

It turns out that by not giving me the answers, she instead gave me the most powerful gift of my career. By coaching me to worry less about getting to the ‘right’ answer and focus more on asking the ‘right’ questions, she empowered me to seek out answers on my own and taught me how to think like a leader. She challenged me to think critically and strategically, even when giving me the answers would have been easier for her in the moment.

Rethink Your Role as a Leader

If you’re a leader, stop giving your team all of the answers and start asking them more questions. Yes, it will take more of your time upfront and it will likely be uncomfortable (maybe even painful) for both of you. But, it will also cultivate high-performing, empowered leaders in spades.

As leaders, we know that there’s never one ‘right’ answer. Leaders are in leadership roles because they have demonstrated the ability to take in lots of information, critically evaluate its relevance and impact, and make the best decision they can with the information they have at that moment in time.

Pay it forward, and help your team learn to do the same.

Are you interested in becoming a stronger leader?

My mini-course will teach you how to be a better, more effective leader for your team. Sign up for free.

The Startup

Get smarter at building your thing. Join The Startup’s +724K followers.

Jessica Donahue, PHR

Written by

I help startups and small businesses design and implement HR solutions at AdjunctLeadership.com → Join my free mini leadership course: bit.ly/307AheB

The Startup

Get smarter at building your thing. Follow to join The Startup’s +8 million monthly readers & +724K followers.

Jessica Donahue, PHR

Written by

I help startups and small businesses design and implement HR solutions at AdjunctLeadership.com → Join my free mini leadership course: bit.ly/307AheB

The Startup

Get smarter at building your thing. Follow to join The Startup’s +8 million monthly readers & +724K followers.

Medium is an open platform where 170 million readers come to find insightful and dynamic thinking. Here, expert and undiscovered voices alike dive into the heart of any topic and bring new ideas to the surface. Learn more

Follow the writers, publications, and topics that matter to you, and you’ll see them on your homepage and in your inbox. Explore

If you have a story to tell, knowledge to share, or a perspective to offer — welcome home. It’s easy and free to post your thinking on any topic. Write on Medium

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store