Improve Your Leadership, Team and Workplace Communication: How to Ask Questions Successfully

The tips we’re sharing today are equally applicable to all levels – executives, managers and staff alike. Primarily aimed at improving teamwork and relationships across the workplace, they are also equally effective in your personal life with family and friends.

Whether you’re a manager, leader, non-management staff, sales person, customer/client service officer, support staff, interviewer, or other, we all ask lots of questions every day – it’s a part of every job and a part of daily life. So, as we do it all the time, it should be easy…right?

Unfortunately not. In our experience (professional and personal!), it doesn’t matter what level in the organisation people are at, most people are not good at questioning. And especially when people are busy and under pressure trying to meet deadlines, as we get more used to telling than asking.

I’m sure you’ve heard of the saying “if you don’t ask, you don’t get”. What most people forget is that if you don’t ask in the right way… you still don’t get!

In fact, you often get something unpleasant that you really didn’t bargain for: miscommunication, misunderstanding, frustration, confusion, conflict, resentment etc. Not what you need for your professional success and personal well-being, or for the team around you. And you can damage your future chances of getting anything else too!

Asking the right question in the right way at the right time is actually a skill that takes a lot of thought and practice. But it isn’t rocket science, and with even a few small changes, you can make a very big difference.

What normally happens, is people ask a [good] question, then follow it up with another, a leading question and they intentionally or unintentionally  ’guide’ the person being questioned into a particular answer. The person being asked the question can then find it difficult to answer openly and objectively.

Whether intended or not, the person questioned can feel manipulated or railroaded into a response, usually because they HAVE been led into making the response the questioner wants. And of course the person questioning doesn’t really find out the full picture or all the information, just the bit they wanted to hear.

An interviewer did it on TV the other night. She asked “What’s it like being at the front-line of a bush fire? Do you get scared when you get close to the flames?” The fireman ended up being a bit confused about what to say and stumbled through an answer. He was effectively a puppet dancing to the interviewer’s agenda and was led to talk about whether or not he was scared of the flames (which he clearly wasn’t really comfortable talking about or prepared for) and didn’t get the chance to talk about anything else.

As a result, the ‘interview’ was a bit of a waste of time. The interviewer didn’t get any insight into what it’s really like on the front line of a bush fire, and I could imagine the poor fireman coming away from the interview feeling that he didn’t really have a chance to say what he wanted to say, and probably a bit railroaded & not listened to or appreciated. That’s usually NOT a good outcome for a conversation in the workplace, or in any professional or personal relationship!

As in the example with the fireman, the second question is routinely the one that gets answered. Consciously or unconsciously, the questioner is asking a leading question, that to the person being questioned invariably appears to be linked to the questioner’s personal agenda, not genuinely finding out what’s going on for, and appreciating the other person and their opinion.

There’s a time and a place for it, of course. When people do this openly and consciously to make sure they get the specific answer they need to meet their specific requirements, then of course it can be a useful tool i.e. if the reporter genuinely needed to know if the fireman got scared on the front-line, then fine. Even so, the person on the receiving end can still feel led by the nose, manipulated even, and not really listened to. 

More often than not, questioners either do it with a hidden agenda they want answered or do it unconsciously and without a particular purpose. That’s far more dangerous. They risk not getting the information they really need, which in itself leads to misunderstanding. Or worse, the situation can leave the person feeling dis-empowered, controlled, unheard and not listened to, and it can put ideas and emotions into people’s heads that weren’t even there.

The potential consequences then are deeper dis-empowerment and misunderstanding, conflict, erosion of trust, increasing anxiousness at the next conversation, etc. If communication habitually continues like that, more conflict can develop. Depending on the personality the receiving person can come obstructive, belligerent or challenging or outwardly compliant but inwardly obstinate or fearful. People feel dis-empowered, confidence can be undermined, gossip often develops. The relationship can gradually break down – ‘you’re not hearing me/interested in me – you’re controlling me – I’ll talk to someone else’, etc., and individual and even team performance can quickly decline.

Take a workplace example: a manager asks a team member: “how did you go with the project I gave you last week?  Did you manage to get hold of Davina and discuss the time-frame with her?”

It could easily come across that the manager really isn’t interested about how the person’s going, but that his underlying agenda might be to see if the person actually did get in touch with Davina or hear what Davina said about the timeline. Even if he is genuinely interested in how the person’s going, the person is quite likely to feel led into answering the second question, perhaps controlled or feel like there might be a hidden agenda. And nearly everyone hates a hidden agenda! Even if there was no agenda, just a poorly asked question, the manager’s probably going to miss out on the real information and likely to just get an answer to the second question. The first question will probably be lost. And as time is usually short because we’re all so busy, more than likely it becomes a fleeting communication only about what Davina said about the timeline, and everything else is missed.

The manager may be happy with this, but the team member may not. It may very much be a lost opportunity for the manager to find out the bigger picture and more information about how the person really is going. And it might be a lost opportunity for the person to discuss any concerns or achievements, get clarification on an uncertainty or ask for some help about a particular problem.

Asking leading questions is particularly problematic if a person questioning is trying to investigate a problem or need (i.e. a manager questioning a staff member, a sales person or customer service representative trying to find out what a problem is).

It is also problematic if the person questioned is a less forceful character who may be unlikely to say openly what they need and want, and is likely to comply with the question asked. Many people aren’t good at being assertive!

For example, a manager may ask a staff member “how are you going with that? Are you having any problems prioritising what you need to do?”

The likely instinctive response, answering the second question and not the first, is “no, I’m ok thanks, I can sort it out”. And probably answering it defensively at that, as the person may sense there’s an underlying perception that they aren’t good at prioritising and don’t want to admit it!

The manager has led the staff member to answer they are ok with prioritising (the staff member could easily feel that is almost the expected answer), and hasn’t allowed the person to talk about any other problems they might need assistance with to get the job done properly, or truly been understanding and helpful.

If the manager had asked just the “how are you going with that” question and stopped there and listened, they may have got an entirely different response & found out what the real problem was.

Same principle with someone asking their boss: “what did you think of the work I sent through? Was it detailed enough?”…

So, next time you ask a question, stop and think about the question you are asking. Make sure you ask just one question, and then listen to the response. You may find you might have to bite your tongue after the first question to stop yourself carrying on!

You might just be amazed what you find out and pleasantly surprised how much your teamwork, relationships and work improve…


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We’ve delivered the course widely across NSW Government, and have developed several customised versions that make it extremely effective at all levels in an organisation, from top level executives though middle and new managers to non-management staff.  As the principles in this program are practiced and mastered, participants build and enhance the key fundamental skills of an extremely effective leader. This applies to leaders at all levels, from CEO/DG downwards, and can be tailored accordingly. The course is most effective when the principles are modelled first at the senior level.

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“Since doing this training and the one-on-one coaching sessions, I have been able to manage staff in a very different and much more productive way. This has allowed the process of managing staff performance and follow up sessions to be more two-sided. What I mean by this is that the responsibility is shared by staff and manager, rather than just me as a manager – the ownership of the work is by the staff members. This has made my life as a manager so much easier, and the staff have been a huge amount more productive. In addition, previously under-performing staff members who I had been having difficulty with for some time are now performing to a satisfactory level, which has meant I now get better work from the team, I spend less time performance managing, and the team spends more time getting the important, core jobs done. I am excited with the progress and positive changes in our team.”
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Developing a culture of mutual respect and understanding through continuous constructive feedback and communication.

  • Through continuous positive, constructive feedback and communication, given in a safe and respectful manner, develop a culture where staff are given every possible opportunity to develop and maximise their potential
  • Good feedback and communication will ensure staff have every opportunity to perform to their best potential, and will be happier in the workplace – which means better results for the organisation
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  • That feedback should be frequent and continuous, both positive and developmental
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“As a result of this program I have managers happily doing things like their HR plans, which I have been trying to get them to do for the past 3 years. We now have some previously chronic under-performers now performing satisfactorily, managers are happier, and we are meeting KPIs above and beyond what we were, and especially in areas like uptake of our performance management appraisal targets.”
Executive Director

 Your Team at Southern Cross Coaching & Development