Be the one asking the hard questions

We’ve all been in these terrible meetings where one person presents a monologue backed by detailed filled Powerpoint slides, no one is engaged, and the speaker goes on and on. You’re bored.  The speaker feels disrespected. It’s a total waste of time.  For this article’s sake, let’s assume that the speaker’s topic is essential and relevant.   How can you move this meeting from terrible to useful?  Be the one asking the hard questions.

In many cases, the room is waiting for the most senior person to start peppering the presenter.  Too often, this never happens. Here’s where you come in.  YOU be the one to ask the questions.  Your seniority or role does not matter.  You could be the most junior person in the room.  What DOES matter is that your questions are relevant, you are prepared, and that you are respectful

Be Relevant

What are the right types of questions to ask?   They all revolve around why, what, when, and who.

Drill into the “reds”

If the presenter is sharing some bad news, then the team needs to know more about it.

  • Why do you think this area went south?
  • What are the consequences? Do we need to course-correct?
  • What can we do to help now, or help in the future?

These questions bring more light and insight into the issue and spur others in the room.  Plus, you’re demonstrating to the presenter that their unfortunate news is heard and needs attention.

Ask for context around the numbers

Frequently, the presenter includes many numbers and data that are unanchored by context.  “Our sales this month were $100,000.”  Um… okay.   Is that good or bad?  Were last month’s sales $25,000 or $250,000?  Press for context around the numbers so the entire room can better comprehend the data.

Challenge dates and deadlines

Deadlines should be the area that senior leaders drill into since deliverable dates are a key to accountability. Unfortunately, those questions are frequently un-asked, and a missed deadline skates by.

Letting deadlines pass unquestioned is destructive for many reasons. First, it breeds resentment among your peers who are working hard to meet dates and are being held accountable to those dates. Second, it’s terrible for team progress to ignore dates and pretend they don’t matter. Third, it sends the message to the presenter that their work is so irrelevant that a missed date is not important. If no one is asking about a missed deadline, then you should ask respectfully and curiously – “I notice that item #2 was due on May 15th, but today is the 20th?”

What are the follow-ups?

There are few things more wasteful than spending an hour in a meeting discussing what should be done but leaving the room with no call to action.  If a meeting is wrapping up, and there’s no clarity on who’s doing what and when, then ask.  “We discussed reaching out to our newest customers, but I’m not clear on who owns the follow-up.”   Keep asking until there is clarity on the action, one owner, and a date.

Follow-ups:  keep asking until there is clarity on action, owner, and dates.


Do NOT ask…

No one wants to hear a bunch of questions that are obvious, irrelevant, or high-handed.  For example, do not ask questions such as:

  • Why didn’t you think of this earlier?
  • How can we be so dumb?
  • What is “X”?  (When “X” is spelled out clearly on page 1, bullet 1… in bold.)

These types of questions come from people who talk just for the sake of talking.  It’s transparent, and your teammates don’t appreciate it.  If you don’t have suitable questions, then keep listening and don’t say anything.

Be prepared

The best way to ask relevant questions is to be prepared.  Preparation gives you a base of knowledge and, more importantly, provides you with the confidence to speak up.  When you know the topic and have considered the issues, you will demonstrate strength with your tone and body language.

When you know the topic and have considered the issues, you will demonstrate strength with your tone and body language.

Here are the ways I prepare:

  • Pre-read the documents or deck and write down my questions.
  • Ask the presenter questions beforehand and get their point of view.
  • Know the agenda and the goals/non-goals of the meeting.
  • Ask key stakeholders beforehand about their perspectives and concerns

If this level of preparation sounds like a lot of work, it is.  But if you want to achieve excellence, you must invest the time.  It’s this type of unseen work that is required to grow your career and reach your potential.

Be Respectful

When you decide to try on the “asking difficult questions” hat, tread lightly.  Remember, the people you’re talking to are your peers, or perhaps even superiors.  Some tips:

Respectful speaking tone and word choice

Your choice of words must be polite, and your tone of voice collegial.
Do say, “Can you share one of the reasons customers reported decreased satisfaction?”
Do NOT say, “Why are your customers so mad?”

Assume best intentions

Start from the position that the presenter is both telling the truth, and that they are working in the best interests of the organization.  Having this inclination will demonstrate respect to the presenter and the rest of the room, and you are more likely to get a positive response.

Do not monopolize

Ask your question, absorb the answer, and step back.  Hopefully, other people in the room will follow your lead and get engaged.  Keeping listening and find the right spot to ask your next question.

It’s not a trial

Your questions should not mimic an attorney interrogating someone on the stand.  These are your co-workers, and they deserve your respect.  If you act like a tyrant, you will get low-quality answers, everyone in the room will resent you, and they will work against you in ways that may be hard to discern.

Observe the impact your questions have on others

Once you’ve asked-the-hard-questions a few times, you’ll notice that the people around you will treat you a little differently.  It will be subtle at first, but once you notice it, you can’t un-notice it.  They will seek out your opinion and input a little more.  You’ll be included in the loop more often.  You will be asked to more meetings and more pre-reads.  People will pop-by your desk more frequently.  When you’re talking with them, they will listen with greater intensity.  They may even lobby you to ask their hard questions for them.

These are all signs of respect.  Respect that you have earned by preparing and then putting your neck out by asking the questions that everyone else wants asked.

Senior people will notice

Leaders of any organization must have a leadership bench.  They need to identify and train the next set of people who could step into their job, and their eyes are constantly open for talent.  In fact, it’s tough for a leader to move to their next role unless they have a replacement on deck.

When you ask smart and insightful questions, you bring value to the organization and demonstrate to leadership one of the critical skills required to move up the ladder.

The higher up in the organization you go, the more often you need to hold your peers accountable.  Doing this in a considerate and positive manner helps everyone around you, earns you respect, and creates opportunities for your future.


In 2018, I published my 11 most important lessons from Microsoft email, and over 25,000 people read it and forwarded it to their friends and colleagues. Many people asked me to write in more depth about the topics in the email, so that’s what I’m doing. I’ve spent the last year writing and will share more of that content at If you find this interesting, please forward the articles, subscribe to my email list, and follow me on LinkedIn.