How to answer difficult questions

We are living in uncertain times. I spend some of my time trying to be in the present, and the rest with my mind whizzing forward to the future, wondering and speculating about what’s going to happen, and when, and how, and how it’s going to affect me. And I know I’m not alone on this. We are all full of questions. The big ones about what is going to happen to society; and the smaller, more personal ones, about what is going to happen to us, our jobs, and how we will cope.

Leaders often bear the brunt of this: if you are a leader, there’s a very good chance that you will have been on the receiving end of many such questions. Questions about jobs, about finances, about office space and all those other uncertain various other elements of the corporate future.

It’s not new, of course, for teams to be asking tricky questions. In a management position, you will routinely be staring at questions that, for some reason, you are unable to answer. But right now, our inability to answer seems more likely to create a sense of obligation, or of guilt. With so much uncertainty, how can we as leaders try to answer those unanswerable questions and provide a sense of stability in these difficult times?

So – what should you do if you find yourself facing questions that are unanswerable?

1. Figure out why you’re being asked that question

The first, useful step in being able to answer unanswerable questions is working out why people are asking them in the first place. There are a whole host of reasons why people ask questions. The most prominent reasons relate to thinking that you hold some information that they are not party to, and so they ask you because they want to learn or understand. This may be practical learning – ‘what is our new office going to look like?’ or it may be to help them deal with emotional turmoil and a sense of needing answers so they can shore up how they’re feeling: ‘how will this office move affect me?’

But there are plenty of reasons that people ask questions which have nothing to do with wanting a direct answer. It can also be a clever way to table something that they want to talk about, without stating an opinion on it: ‘What are the benefits of this office move?’ It can be a way to get attention, or to shine a light on an issue that is important to them. It’s how to ask ‘How do you think the office move will affect my job? Am I going to be made redundant? Am I still going to have the same amount of power?’ without actually asking any of those more pointed questions at all.

Understanding what lies behind the question will help to work out how to answer. In other words, you are looking for the questions behind the question. This will provide you with an initial idea of how to craft a response that is going to be useful to them. And if it’s not clear? Then you can ask them: ‘Talk to me about where this question is coming from’.

2. Figure out what it is that makes them unanswerable

A question can be unanswerable for a whole host of reasons. Most commonly:

  • You don’t know the answer.
  • You know the answer but can’t share it (one of the trickiest elements of leadership)

Knowing which category the question falls into will help you to set the parameters on what you’re going to be able to say.

For example, if there’s an answer you’re not able to share (regarding possible future furloughing, or selling office space), you will be limited in response in a different way to a question where there isn’t, to your knowledge, an answer at all (when will this all end? Will our company survive a recession? What’s going to happen to my job next year?)

3. Find the answer that best suits their needs and yours

Once you’ve established why they’re asking the question and you’ve set the parameters around how you can answer, then you should have more clarity on your choices. People generally appreciate an answer that is truthful, and it establishes a better long-term relationship built on trust. So if you know the answer and you can’t share it, then instead of fobbing them off, you can find a way to tell them that you just can’t share that information at the moment which makes you feel bad as you know they’re finding it distressing.

But the most difficult sort of question to answer will be one where your team member seems to require a direct answer, and you don’t have one. ‘What is going to happen next month?’; ‘How is this going to affect me?’; ‘Will I be made redundant?’ I would counsel against shallow reassurance. Offering reassurance with no grounds for doing so can be very counterproductive in the long-term. Employees typically value as much honesty as you feel you are personally and professionally able to give. Even if that honesty is ‘I don’t know what next month will bring, but at the moment, here is where we are at.’.

You can also revert to their reasons for asking. Talking to them can help to chip away at some of those reasons. For example, if they are feeling stressed, you may not be able to answer their questions about whether they will be made redundant, but you may be able to talk to them more generally about the things that are going well for the business at the moment and where you are finding glimmers of hope. Are they enjoying their work, what would they like to do more of? It’s important for this not to sound as though you’re downplaying their concerns, they may just need you to listen, so getting them to open up and discuss more around their concerns, can make them feel more at ease. You haven’t answered the question, but you’ve helped them feel like their needs and concerns are being heard and that they’re important.

Some other things to remember:

  • The value of difficult questions

In the work that I do, I find myself listening out for questions (and statements) that are repeated by many in the organisation. These are often the key to unlocking something important culturally or strategically. Why is this question hanging in the air? What tension or contradiction is at its heart? When these questions are played back to the organization, it can be key to unlocking something bigger at stake, and inform a wider dialogue that is relevant to many, kickstarting a necessary conversation. This is not to say that the organisation will always have the answer – but so often the answer isn’t what’s important.

  • Where and how you answer

If the question is being asked by more than one person, you may have identified an area that is of concern not just to an individual, but to a whole team, or the organisation more widely. If it’s a wider question, you’ll need to be even more careful if it’s on a politically sensitive matter. It can be easier to be candid with an employee you have a good rapport with, in your office, in a one-to-one conversation, than with a regional office in a town-hall type meeting. I’m not suggesting underhandedness, just the ability to be able to adjust the message, tone and approach.

  • Authenticity pays

We may, in the past, have glorified strong, assertive and certain leaders, but they are not fitting for our times. We no longer, as a collective, need a battle commander; we more often appear to need leaders who can deal with our vulnerabilities because they have empathy and vulnerabilities of their own. (In other words, there is such a thing as too much resilience). It’s fine to voice your own anxieties and uncertainty. As long as you are doing it in a way that is designed to show that you’re in this together, as opposed to heaping your worries onto your team, then it can work very well to improve rapport and to help your team to see that you’re not keeping lots of secrets.

Much has been made already of the idea of the authentic leader. Whilst i would argue that we can’t be our authentic selves at work all the time (though some would say you can), we can tap into our honesty where it’s appropriate to help employees see that you are struggling in this situation, too.

  • Keep ‘em comin’

Perhaps the most critical learning point, however, is to encourage your team and colleagues to keep asking questions. They provide a fantastic insight into what they are thinking and how they are feeling. Their worries, concerns and ideas can be the fuel for innovation and change. And their questioning can encourage you to question, too, and to develop and learn.

However, you may find that you have team members who are simply not good at asking questions. They bombard you with their insecurities or challenges at totally inappropriate times. Or they ask questions which feel personal and inappropriate, leaping straight in at the beginning of the meeting with, ‘do the leadership feel they have been fair with bonuses this year,, because I’m not happy with mine?.’ In this situation, you can probably guess that the person isn’t interested in how you feel, not really… they’re clearly unhappy with their bonus. They make you feel defensive, which as a leader can be a difficult space to occupy.

You know, as they should too, that there are better ways to air this. Different questions, not in a big meeting, and with a better approach and tone. As a leader, you can be clear on each of these points, and coach them into asking better, more appropriate questions which will make them more satisfied in the long-term. Why? Because you will be able to answer their question because you will better understand what is actually being asked.


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