Three Reasons Why Asking Questions Helps Leaders

I started a new role in my company the week before lockdown. I now support one of our most senior leaders in her business strategy role. Her responsibilities include ensuring our business unit is implementing our market strategy effectively and is meeting the needs of our clients. She is also responsible for ensuring our consultants are receiving the training and support they need to be high performing and in demand by the market.

My role is to support her fully in her directive. I’m empowered to come up with ideas and solutions, and she specifically wants me to bring my own fresh perspective into the role.

Of course, what no one saw coming is that one week into my new role, the way we do business changed dramatically. I was still in the middle of my handover when we started working from home, and it was a strange experience to learn about event planning and recruitment strategies in a time when neither looked to be happening in the foreseeable future. The 15-page handover document I created over the two week handover remains saved in my folder for reference, but has not been touched since I clinked glasses (virtually) with my predecessor, thanked her for all her wisdom and wished her the best in her also-unknown new role that she has moved to.

Unfortunately, there was nothing in the handover about how to handle a pandemic. Or make sure people are staying socially engaged and connected when they are in lockdown. Or how to bring new solutions to a market that is in a state of shock.

I had to make it up as I went. The anxiety that comes with starting a new job and wanting to impress was heightened. How would I know the right thing to focus on? My first week on my own without the guidance of my predecessor, I felt like I was drinking out of a firehose. I could not keep on top of my inbox, every task was taking ten times longer than usual because not only did I need to understand what was required, I also needed to figure out how to solve the problem. No one knew how to solve these problems. No one had done it before. It was overwhelming.

But thankfully, I've had coaching for just this sort of moment.

I started keeping a list of questions that I needed guidance on from my leader. I knew that I only had snippets of her time here and there to ask, so I wanted to be prepared. I have access to her calendar, and I know what her day looks like. With back-to-back meetings for nearly 12 hours a day, I couldn’t bring myself to burden her further with my questions. So, I adopted a new mindset: assume I’m doing the right thing, until I’m told otherwise.

That mindset helped me scratch off a lot of questions from my list.

But some, I really needed to talk to her about. I found a 15-minute slot, over her lunch hour, and scheduled a check-in with her.

I prepared to tell her how sorry I was for taking up her time. I had my list of questions ready, so she could move on as quickly as possible from our meeting and get on with Important Things.

And here’s what happened.

She was so grateful for the break in her day to talk to me. She apologised to ME before I even had a chance. She was sorry that her emails to me seemed terse, and she didn’t have the time to connect with me like she would’ve normally. Our conversation gave her a break from saving the world and instead she could focus on helping me. It made her feel valued. I was so grateful I booked in that time.

Later in the coming weeks, someone asked me how my new role was. I mindlessly stated how challenging it was because I had So Many Questions but “felt bad” for bothering my leader. My colleague said, “I know exactly how you feel!”. And then I caught myself.

This was not the message I wanted to put out.

Having had time to reflect, here are three reasons why I think it’s important to ask your leader questions.

1. Questions give leaders the opportunity to think about things in a different way.

There have been many stressful and busy times in my own projects where I have delegated tasks mindlessly to move them off my plate. It’s only when I’m asked some good questions about different approaches to the task that I think through what I really want. Being asked questions makes you look at things from a new perspective that you wouldn’t have had otherwise. Often when I’m asked a question, I’ll reply with “that’s a great point. I hadn’t thought of that!”.

2. Questions give leaders an opportunity to connect and help others.

Rather than thinking that your question is a burden, think of it as helping someone else to shine. People feel good when they help others. Especially when the person asking shows they’ve thought through different ideas and are grateful for direction. A good leader will welcome the opportunity to connect with someone who shows they’ve considered a task and wants to do it the best they can. They will support you in that. It gives the leader the chance to connect and help. Don’t take that away from them!

3. Questions give leaders a break from their own problems to solve.

Assume the question you have for your leader is one that is easy for them to solve. In which case, it gives their brain some respite from the difficult challenges they are working on themselves. They may be in a state of “How am I ever going to solve this incredibly difficult thing?” and you ask an easy question. They’re thinking: “Oh, I know the answer to this one!”. Sometimes, the best way to solve a problem is to simply take a break from it and focus on something else.

Coaching has definitely helped me thrive in my new role. Asking questions will be something I do consistently now, knowing that I am not only helping myself but also giving others an opportunity to thrive as well.