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5 Ways Leaders Can Answer The Tough Questions Authentically

Kara Dennison

No matter how great a manager or leader you are, there will always come a time when someone asks you a question you might not necessarily know how to answer. A great leader strives to keep people motivated, but people often think that managers should have all the answers… an unrealistic expectation to have on your managers and on yourself. 

This is especially true as companies, organizations, and businesses are preparing to return in-person after remote working for 18 months. The changes we’ve seen are innumerable; people have different desires and expectations, and they’re justifiably ready to hold their place of business accountable. While this can be scary for many leaders, you should feel encouraged to think of these questions as opportunities for growth and collaboration. This is also a good time for you to reconnect with the kind of leader you’ve always wanted to be and think about how you can foster good faith moving forward in a world that looks very different today than it did a year ago. 

The common go-to is to admit, “I don’t know.” After all, being honest in this regard might make you look more authentic and human to your employees, right? But as a worker, this is actually frustrating to hear. It means you don’t want to go out of your way to find out, it’s a dead-end to a conversation they’re trying to start, and most importantly: it’s lazy. 

Here are some better ways to approach giving valuable answers to tough or impossible questions:

Try to Understand Why

A great leader is a compassionate one. You should always be ready to try to see any situation from the other’s viewpoint. If you’re asked an unanswerable question, you should first take some time to ask yourself what makes this question so tough. It is entirely okay to tell the person asking: “I’m going to need to think on this. Give me [however long you need] to follow-up.” At the very least, this will show them that you take this seriously enough to give their question the time it deserves. So, what makes the question so tough? Is it because it’s so complex? Is it the timing of the question? Is it because, deep down, you know that the answer is going to be something they don’t want to hear? Another thing to reflect on is what’s really at the heart of the issue. Think about what’s really going on if it’s not entirely transparent. Why are they asking this question? It may be because of something they’ve heard, or maybe they are fearful. It’s possible they have their own motivations, which is fine, as long as you can use your judgment wisely. 

Essentially, in almost any tough situation, there is a need that should be addressed. Take the time to find the need and work toward fulfilling it. Most importantly, if you promise to follow back up with an answer, make sure to keep your word.

Be a Facilitator

If there’s a situation in which you don’t know the answer, or don’t know the answer completely, this might be a good time to collaborate with others. Don’t make up a fake answer on the spot to look knowledgeable; your team can see right through that. Instead, use this as something of a brainstorming session. Invite the team into your thought process, come up with some realistic solutions, and ask your people what they think.

Leadership isn’t just about directing others and delegating responsibilities. Oftentimes, when someone asks the unanswerable question, what they really want is a dialogue with their leaders in which they feel heard. If you can be the facilitator they want you to be, you might find yourself generating some exciting ideas about how to better problem-solve. As a plus, you’re going to show your team that you are genuinely invested in listening and collaborating with them.

Don’t Get Defensive

You are just as human as the people who work for you, and it can be easy to feel like you’re sometimes being attacked. This can be especially true when the people asking you impossible questions are emotional. You might even be faced with certain accusations, like, “Shouldn’t you already know that this is going on?” 

First and foremost, you should understand that this isn’t about you, even when it seems like it is. You were not put in this position to take things personally. Whether or not you feel unfairly criticized, people are usually anxious and are looking for some comfort. As the authority figure in this dynamic, it’s truly on you to provide the reassurance they seek, without taking it personally.

Choose the Right Kind of Honesty

As mentioned earlier, the too honest approach aka the dreaded “I don’t know” approach can be tempting but it’s not enough. You can, and in fact should absolutely, admit that you need more information before giving them an answer. It’s also a good thing to follow-up their questions with more questions to understand and gather as much information as possible before responding. 

Another common mistake leaders will make is being too honest when they actually do know the answer. Try to remember that transparency is good in some instances and can be hazardous in others. For instance, you might be quick to respond with something like, “I’ve heard that we should be preparing to return as early as October.” While this might be the case, you might find that this can set off a chain reaction of more questions you’re not prepared to answer. Be careful not to be reactionary with your honesty and think strategically about how to respond in ways that will instead keep the peace. Also, when in doubt, refer to what’s been officially posted internally, or ask for more time to get an answer that is reliable.

Be as Specific as Possible

People don’t just want to hear that you will find an answer or solution. They often also want to hear about how you will find an answer or solution. Just as you expect deliverables and processes from your team, people should also expect the same of you. Invite your workers into the thought process when providing answers. What relevant information, and what resources, do you have to offer? Also, be specific about the people who might be involved in answering their question. It’s not great to let your team think of leadership as this elusive group of people with some power they don’t have who are controlling their workplaces. 

One of the biggest ways to assuage anxiety is to share the process of how you intend to find their answer and be specific. You should be clear about who you are going to talk to, what you will ask them, and when. Give a specific time frame, as well, and be realistic about what you’re capable of accomplishing. Don’t tell them they’ll have an answer by end-of-business unless you can absolutely guarantee that you can follow through. Even if you need a few days, more often than not, your employees will be grateful that you’re going to follow-up with them and take the time to authentically grapple with the situation at hand.

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I'm an Executive Career Coach, the CEO of Optimized Career Solutions, and host of the Attagirl Podcast. I’m a certified Senior Professional in Human Resources (SPHR) who

I'm an Executive Career Coach, the CEO of Optimized Career Solutions, and host of the Attagirl Podcast. I’m a certified Senior Professional in Human Resources (SPHR) who spent my career as a corporate recruiting leader, working hand-in-hand with decision-makers. I’ve personally reviewed over 200,000 resumes throughout my career. I've helped thousands of career professionals to land their dream job through my executive coaching program the 6 Figure Career Boost, and have worked with companies on creating a culture that's inclusive and fosters growth.