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Why Leaders Should Love Difficult Questions 

There is something I’ve noticed self-proclaimed leaders doing - it saddens me and it's a mistake I've seen all too often before - and that’s shutting down any conversations where they are questioned.

Most recently I’ve noticed this happening a lot in the online business world from the leaders in how to run an online business in particular, but it’s nothing new - I’ve seen inexperienced leaders in the corporate world and new leaders in other situations make exactly the same mistake.

Now, you know I’m a big fan of questions and their power to help us think at our best and in this episode, we are going to get curious about how leaders react and why they should celebrate when people ask them challenging questions.

So are you ready? It’s time to get curious about the importance of being questioned and make some choices about how we can benefit from those questions.

What have minced beef and carrots got to do with this?

I want to take you back to one of the first jobs I had and an incident I'm not proud of! Like many students, I was working in the school holidays to get the money I needed for essentials like the latest albums and that new pair of shoes I wanted. I mostly worked through a temp agency and did a number of jobs working in kitchens and serving food.

After morning peeling potatoes I was not in a great mood when it came to serving lunches, and it seemed to me everyone who worked in this particular company was very dense and all asked the same question. What kind of pie is that?

The more I was asked the shorter and more curt my answer got until I started just nodding towards the sign. The lady next to me asked me what I doing, and when I told her I was fed up with answering the same question, she asked me something that has stuck with me ever since - not, as you might have expected, What do you think you are doing? or Why aren't you answering them it's your job?

Instead, she asked me you may have answered the question a lot but has anyone asked you the question more than once?

She helped me see that even when something is obvious to me, even if I've told lots of people when someone asks they are asking because they want information.

Oh, and the answer, by the way, was that it was a cottage pice with minced beef and carrots.

And that for me is the key - finding out what is behind the question, but before we get to that there are a couple of things we need to keep in mind.

Not all questions feel like challenging or difficult questions

Imagine the scene, you bump into someone and they ask you a question, how do you react?

It's not a trick question but it is one that has an infinite number of possible right answers and no wrong ones. It's going to depend on who you imagined bumping into, What you imagined them asking you about, how strong your relationship is with them, how you feel today, how confident you are in general, how you imagined they asked you the question and what you believe their intent was when they asked you the question. That's a lot of variables for you to manage all at the same time.

Not all questions feel the same when they are asked. Some are easy, like do you want coffee (the answer is always yes!) and some are much harder and those are the ones we are going to focus on since those are the ones it's tempting to avoid.

Some questions leave you feeling supported while others leave you feeling vulnerable and challenged.

Here's the thing though - you can control how you react to the question you are being asked both in terms of how you answer it and in terms of how it makes you feel.

It's easy to take on board any heightened emotions behind the questions you are being asked - if the person asking it is anxious, fearful or cross those feeling can be transferred with the question and subconsciously you may have chosen to take them on board.

But, you could get curious about the intent behind the question and choose to react differently.

The words someone chooses when the ask a question have a big impact on how the question lands when we hear it - when for example we are asked why we did something our automatic reaction is to justify what we did, we naturally become defensive. We can choose to put that defensiveness to one side and react more positively.

People ask difficult questions to help them understand

And that leads to the second thing we need to keep in mind, we need to remember that almost always the questions aren't about us.  They are about the person asking them trying to understand something, trying to get things to add up.

Our minds work by making connections and we ask questions to help us find connections between new information and the information that we already know. At a very basic level, that's how we build our understanding and how we learn. It enables us to process the vast amount of data that bombards us moment by moment.

Beyond that people are also looking to align what they have seen and heard you do as a leader with what you have said you will say and do. That integrity of action is vital to a trusting relationship. When someone asks you a question they are looking for the missing piece that either confirms that you are aligned with what they see as your values or proves that you aren't and so they shouldn't trust you.

If when they ask you a question you shut the conversation down they will naturally assume that either you are hiding something or that piece that makes the puzzle fall into place does not exist.

And what if you are being challenged about a decision - like the on line leaders who held a series of in-person events during lockdown or who were questioned over their reaction to the racial tensions and black lives matter movement.  

It can feel personal but the people questioning assume you know something they don’t and are giving you an opportunity to make things better and make things right in their minds. When you close the conversation down or blame yourself social media team you confirm their worst fears about you, you break any trust that there was and getting them to believe in you as a leader again is going to be extremely difficult if not impossible.

Answering difficult questions

Answering these difficult questions can be hard, it takes courage and you can feel very vulnerable when doing so. You are going to have to manage any Imposter Complex feelings that come up for you and put them to one side.

Remember, it's very rare that someone is looking to catch you out, and even if they are, how you approach answering their question will show them how capable you are as a leader and how good you are at getting to the heart of an issue.

And if you have to admit along the way that you were wrong about something that's OK too - you are human and good leaders acknowledge their mistakes and learn from them.

Interestingly when you show vulnerability in this way, people see it as a strength, as openness and as trustworthiness. Its when you hide behind not answering questions people assume there is something wrong and there is a vulnerability or problem with what you are telling them. It's a paradox that when you show vulnerability what people see is strength!

So how should you approach answering challenging questions from the team? You need to work out where things stopped making sense for that person. To do that you need to listen carefully and ask the person asking you to explain what's behind their question, and you stay in a place of genuine curiosity and remember what your looking to do is to provide the information that helps them make sense of everything. When you do this, you will be building a great relationship and almost certainly be learning a lot about yourself and the other person and the topic.

The benefits of answering difficult and challenging questions

And that's not the only benefit of facing these challenging questions.

When we face them and encourage conversations around them we encourage people to think and to really bring their whole self to work. If we want a high performing team, to surround ourselves with people who make things happen and get things done we need them to understand what needs to be done, why it needs doing and to think about how best to do it. We don't want a bunch of automitrons who blindly say yes to everything we ask - well not unless you are leading a cult or think the stereotypical head cheerleader, you know the one who is the cool kid who only likes people who do what they say, from teen fiction is a great leadership role model. Its time to make sure the geek squad with their great questions are part of your team too!

What kind of leader do you want to be?

And that is at the heart of this for me - knowing what kind of leader you want to be, and then allowing others to help you hold yourself to account for being that kind of leader by asking you questions.

And yes, sometimes those questions will hurt as you realise you maybe haven't lived up to your standards, but that realisation allows you to grow and be the best leader you can be.

Do you want to be a leader who brings out the best in people and leaves them feeling good about the world?

Then you need to face those challenging questions - they are going to help you and the person asking them grow and learn. It builds trust and increases how engaged and motivated we feel about our work. Engaging your team’s mind is at the heart of empowering them, it's not really empowered when you tell them they are empowered and then tell them what to say and do.

If you want to be a thought leader or an industry expert you need people to understand your perspective and unless you make it easy to build understanding of what you are saying people won’t engage and fully take on board your points. The questions they ask will help you improve your explanations and them to understand your expertise and the value it can bring. Being questioned and asked to clarify things will also develop your own thinking, the questions may well help you learn and think better too. In the same way, people ask questions to make connections, they can make new connections for us as we answer them. Again growing our leadership.

A final thought about challenging and difficult questions

And a final thought. As a leader you don’t have to know all the answers - let’s face it no one does, so it’s time to let go of that belief and stop making that new leader mistake.

What if instead you replaced it with curiosity and had an open discussion about the subject - your role is to collate the ideas, knowledge and thinking so you can make great choices. And yes your thinking matters too - and as I said, when people ask you questions it can really develop your thinking and help you explain things better. It can help you and your team innovate and come up with great new solutions. And it builds a working world where the people around you want to bring their best thinking and do their best work.

Summary & Taking Action

So in this episode, we have talked about why leaders should welcome questions from those around them. How it improves the quality and the quantity of thinking, how it engages people, boosts productivity and better ways of working and deepens your relationships.

When you shut questions down, no matter how good your intentions you send a torpedo through all of these and it can be hard to ever repair the damage.

How you react to difficult and challenging questions is a clear demonstration of what you stand for as a leader. It's your choice, are you going to close the conversation and your relationships down, or are you going to get curious, explore the intent behind the question and grow a mutual understanding of the subject so you all benefit?

The things I share in this podcast are based on my own experience and some of them are going to be more relevant to you than others. Some are going to take a bit more thinking about than others. What I hope is that by sharing them, it encourages you to get curious and make some choices about what you do with what you have heard. That's what being a curious choice leader is all about. So the question I would like to leave you with is, 

How can you improve how you answer challenging and difficult questions?

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