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Difficult Conversations – Asking Questions

By Mario Pistilli

I reached out to some colleagues asking if they had any ideas for a topic for this article, and the overwhelming response was “difficult conversations.” Managing people is a very large part of what we do, and many times those conversations may be tough. It is what I term, “the Pistilli Law of P’s” which states that, “people problems permanently persist.”

These problems generally occur because of the differences in perception, emotions or breakdowns in communication. A recent article in Inc. (Schneider, 2018) noted that 70% of employees were avoiding difficult conversations and that is a whole lot of avoidance going on. One technique that I have found really effective is what author Parker Palmer calls, “turning to wonder.” In my last ICE talk, I largely covered eight very high-value questions adapted from the book, “The Coaching Habit: Say Less, Ask more & Change the Way You Lead Forever,” by Michael Bungay Stanier.

The Kickstart Question

“What’s on your mind?” This is an effective opening question as it leaves room for a person to take the conversation in any direction they want. One of the reasons we avoid difficult conversations is that we don’t know where to start. This question is open and inviting and allows people to get to what is most important to them. You might have to tease it out by asking more probing questions such as; “What’s exciting?”; “What’s provoking anxiety?” or “What’s keeping you up at night?”

The AWE Question

“And what else?” This question is powerful because it invites more insights or more wisdom. Three big reasons this question is so powerful are that it opens more possibilities, allows you to reign yourself in and buy yourself time. You can use this as a follow-up to the kickstart question to elicit even more information.

The Focus Question

“What’s the real challenge here for you?” This is where you avoid the urge to jump in to fix it and spend time honing in on the problem. This question helps you slow down so you can later spend time solving the real problem not the first problem. This question allows you to cut through the fog created around the problem. One source of fog is that there may be many interrelated problems all popping up one after another – you might ask “If you had to pick one of these to focus on, which one here would be the real challenge for you?” Another source of fog is when the conversation turns to complaining about a person not in the room – if only he would do that or if only he wasn’t so lazy. Using this question to bring it back around by asking “So, what’s the real challenge here for you?” You cannot do anything about a person not in the room only coach the person in front of you. Don’t forget the AWE question as an add on to this – when the person talks about the real challenge for them and you sense that there is more ask the “and what else” question.

The Foundation Question

“What do you want from this conversation?” We typically make a lot of assumptions about what the other person may want. The best way to find out is to simply ask. At times, the person may not even know what they want and may say “I don’t know.” You then need to decide to continue the conversation or just end it right there and say “Would it be OK to give you some time to think about what you want and get back to me?”

The Lazy Question

“How can I help?” The power of this question is twofold; it forces your colleague to make a direct and clear request and also stops you from thinking that you know best how to help and leaping to the rescue.

If you are afraid of asking this question because you are afraid of the answer then you need some self-reflection around why you don’t have the self-confidence to ask this. Sometimes the person may come back with some version of “I want you to handle this or solve this for me” essentially attempting to make their problem all your problem – don’t accept that. Instead you may try something like, “I do have some thoughts around this, but first I would love to know more about yours what you think a solution might be?” Use the questions we already covered such as the AWE question to drag out solutions from them. When you feel that they have exhausted their ideas and you can’t drag anything else out, then and only then, do you move to sharing your thoughts.

The Strategic Question

“If you are saying yes to this what are you saying no to?” This question is more complex than it sounds. You are asking people to be clear and committed to their yes. One way to clarify this commitment is to ask “ so let’s clarify what you are saying yes to.” Then, follow up with “What would being fully committed to this idea look like?” The what you will say no to part is meant to uncover two types of no – the no of omission and the no of commission. The no of omission is simply what exactly is the thing you will omit if you say yes to this – If I say yes to this meeting I will not be available for some other meeting at the same time. The no of commission will likely take the conversation deeper and is about the things you will need to do in order to make the yes happen – it puts the spotlight on how to create the space, focus, energy and resources to make that yes happen. What projects do you need to abandon or postpone? What relationships might suffer (the people component)? Or, what habits would need to be broken (the pattern component)? Unleashing this question when engaged around a difficult conversation relating to taking on a project can be very powerful? It can show the employee that you don’t just care about shifting work but you care that they have what they need for a good outcome.

The Learning Question

“What was the most useful for you?” This is where you learn to wrap up conversations in ways that make you look great! People don’t necessarily learn best when they hear something or do something. Real learning comes when they reflect back on what they heard or did. This is the question that allows the person to pull back and gain insight. This also helps make the conversation more personal because you added the words “for you.” It allows you to ensure that the conversation didn’t leave any loose ends – if the person says nothing then the conversation is not over and you probe further by asking, “What do you think was missing?” If you want to go next level, share what was most useful for you personally – this exchange of learning only strengthens the bonds.

We are often too quick to jump to conclusions. We are by nature fixers which is what got you were you are – we need to resist that urge by opening it for the other person to get their ideas out. Don’t be so quick to leap in and offer advice, ideas, suggestions or a recommended way forward.

Even though we don’t fully know the issue or what may be going on for the other person, sometimes we are sure we have the answer they need. Try using these questions to open a true dialogue and do more listening than talking. The best leaders are world-class listeners. •

Mario Pistilli, CRA, MBA, FACHE, FAHRA, is administrative director for imaging and imaging research at Children’s Hospital Los Angeles. He is an active member and volunteers time for ACHE and HFMA organizations. He is currently serving on the AHRA national Board of Directors. He can be contacted at



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