The Art Of The Pointed Question


Issue: It is difficult to ask pointed or awkward questions. It is even more difficult to then push for honest, insightful and often supremely awkward answers. If CEO’s fail to ask these questions, private equity leaders will ask them. And if PE leaders have to ask them, they may question the ability of the CEO to lead – resulting in diminished trust. Trust is the whole enchilada when it comes to increasing your profile and rising through the leadership ranks. Asking the awkward questions and eliciting insightful answers is a really big deal.

It is easy to avoid doing the things we aren’t good at. Just place those “I’m Not Good At” tasks at the end of our “To Do List” and we will never get to them. Mission accomplished. The problem is that some of the things that we aren’t good at are really, really important and avoiding them can make matters worse.

One of these “I’m Not Good At” tasks is taking on the “Elephant in the Room” or asking a pointed question that may highlight inefficiencies and incompetence. These types of awkward questions will undoubtedly open a Pandora’s Box that can easily snowball and begin to escalate tensions in other areas, if not handled properly. So, how to finesse the awkward question?

Prepare A Written List Of Questions Ahead Of Time
One way to overcome this gap in aptitude is to prepare a list of questions ahead of time. Don’t blow this step off as a few minutes of prep time can result in amazing insights. Or said another way – why bother to participate in a meeting if the likelihood of forward momentum is elusive. Write the questions down sequentially in an easy to understand, conversational style – like a deposition but less inquisition and more team building. Then, refer to the list of questions during the discussion:

“Let’s begin by chatting about some overall topics and then I would like to focus on specific questions I have that I believe will help us move more quickly into insights and new frameworks, if necessary.”

A list of questions is a more neutral approach – it’s really the piece of paper that is asking the question and you, as the questioner, are merely the conduit. Not really, but you get the idea. A list approach can also help with reluctance to press forward once things being to get awkward.

Ask A Question
Ask the first question in a matter of fact, conversational style. Once you ask a question, LISTEN to the answer. Did the respondent answer the question? Did the correct respondent(s) answer the question – the one with responsibility for oversight as well as the one who contributed to the issue? Look and avoid, if possible, the dynamic in which managers cover for their employees and vice versa. It’s about insight, not about the buck stops here at this point – that’s for another meeting, if necessary.

Nine times out of ten, you will need to ask a follow up question or set of questions because the respondent will generally err on the side of less is more, particularly when the question is awkward.

An enormously helpful technique, which is often overlooked, is to parrot the response, rephrasing if necessary, so that everyone is one the same page. Expect that the responses will get more sophisticated and/or more specific over time when this technique is used. Soon, the respondent will begin to understand the depth to which you would like him to respond to the question so that you won’t need to ask as many follow up questions. For example, “Thanks Jerry for your help. Let me see if I understand this . . . I may need a little more information . . .”

Stick To The List
After a few questions, you may feel like an insightful discussion has begun. Don’t let the discussion distract you. Continue to refer to the list, make notes, and check items off the list as they are discussed. Keep track of which questions need more information – who will gather the information, when and how they will respond, and to whom they will respond.

Be Aware Of Running Out The Clock
If you wrote the question down prior to the meeting, then you should have planned ample time for the appropriate level of discussion. Don’t anticipate a return to the list at a future date – it won’t happen, as new “priorities” will take center stage.

You will find that the respondent will try to run out the clock on questions he likes to avoid questions he doesn’t like. President Obama is a master at running out the clock.

Always Maintain Control
While you can allow someone else to take the reins in responding to a question, everyone should understand the reins are yours to control. You control the tempo and tenor of the meeting – this avoids the ramping up and spinning into sensitive areas. People will be more forthcoming with information if they can trust that the leader has the reins and will not allow the conversation to degenerate and veer off course.

Keep reining in the respondent and keep working down the list. You can say – “I appreciate your insights on the safety concerns. If you’d like to continue to share those insights you are welcome to do so by group email. We have a few more questions to discuss before our meeting ends.” Then, don’t look up – and ask the next question.

The Big Finish – Review Next Steps (aka To Do List)
Wrap up the discussion by looping around on the questions that need more information – who will gather the information, when and how they will respond, and to whom they will respond. You may find that responsibilities may shift as you run through the list. Most likely the questions that still need to be addressed will provide the most insightful answers.

Hiring Someone Skill In “The Ask”
Finally, if you still find “the ask” too awkward, then hire someone with a proven track record of asking the awkward questions and eliciting insightful answers. Don’t assume that their job title encompassed “the ask,” as they may have had a sidekick that assumed that role. Also, don’t assume that they were good at “the ask” or that they want that role now.

Ask them to share examples of times when they asked the awkward questions as well as examples of times when they worked hard to extract the insightful answer. Give candidates examples of real challenges faced by the company that should involve asking awkward questions. Ask them how they would handle the situation. Listen for the questions they would ask and how they would handle getting insightful answers. This skill set is very hard to find so don’t be surprised if most candidates fall flat in this area. In fact, it’s better to have that awkward conversation with the candidate now then to have to default to the role of “the asker” yourself once the new hire isn’t able to deliver.

Specific Take Away: Practice makes perfect. No better time than today to begin.