[On] Point to Ponder: If You Don’t Ask Questions, This Could Happen to You.

Last week Forbes.com sought to debunk the myth that asking questions makes people look “dumb.” I promised a follow up post. What follows is the story about the day I learned the value of asking questions at work…and what can happen to you and your team when you don’t:

BBDO Chicago, 1990s:
It was a pretty big moment for the creative team. We were about to gather in Tonise’s office (the CEO) to reveal the top 3 campaigns for our client. The creative team, sporting button downs and decent looking jeans (a major improvement) was ready to go. They’d been working for weeks to perfect their ideas. Now it was time to sell.  This is one of the moments creative teams live for.


Because if their idea wins the CEO’s approval – and then the client’s – it goes to production. It comes to life. Then it goes on their reel – their “resume” of work. They might win an award. The ad might help the client hit financial goals. It might help them make a great career move later. Pay raises and promotions are now on the table.

It’s important to note that before we present in the CEO’s office, the account service team (that’s me) and the creatives evaluate many rounds of work together before choosing what to present to the CEO. Throughout that process, we have chances to make edits, seek clarification – to ask questions. Once we get to Tonise’s office, we’re a united front.

Storyboards in hand, we march into her office. The creative team is confident and excited. The account service team is proud and supportive. Tonise may be not be tall, but her personality is big and bold. Plus she’s Italian. She runs a tight ship, has great instincts, and always wears a smile.

The creative team presents campaign #1 with great gusto. Tonise is nodding, even smiling. We’re all happy to see this.

Then we hit a rough spot.

After seeing campaign #2, Tonise had a furrowed brow. She stopped and waved her hand. “Wait a minute guys, I don’t get this. Does the light bulb represent our client’s product? Or is the light the competition –  and our product will turn their light out?” It got quiet. I sat there thinking, “Huh. I had the same question when they presented to us last week.” But being new, I thought the question was dumb, so I didn’t ask it. Now I’m in the meeting and the CEO has the same question. I proceeded to feel pretty good about the fact that Tonise and I thought on the same wavelength. I began to daydream, wondering if this meant I had CEO potential…

Then, something terrible happened. I piped in and said, “Yeah, I was wondering about that too.”

More awkward silence.

Opening my mouth at that moment proved to be a rather poor decision. I got glares from the creatives, my boss, and my boss’s boss. I think Tonise even glanced at me in surprise. After that creative idea was killed and the meeting was over, I got some “constructive feedback” from my boss. The long and short of it was, if I had questions or didn’t understand a concept, I should have raised it earlier. We were supposed to go into this meeting as a team. Everyone was supposed to be on board as one big happy BBDO family.

In short, I’d shut my mouth when I should have opened it; I opened my mouth when I should have kept it shut.

The aftermath:
That experience is all it took. From then on, I eschewed advice I’d once received to “just stay quiet for the first 6 months.” That’s sound advice for new hires in certain areas, but once you have the lay of the land – which I did by the time we had this meeting – it’s time to demonstrate your value by asking questions.

After this “teachable moment”, I became smarter about asking questions. I started by listening to other people’s questions. I listened critically, and after many years studying the field of Communications, I concluded that contrary to popular belief, it’s often the speaker’s fault that you don’t get what’s happening. They can be too close to the concept or idea. They’re not explaining it as well as they should. Unfortunately, this is common, especially among entrepreneurs. So what can people do to improve this skill?

Tips on Asking Questions:

  • Complement and/or thank the speaker, either directly or indirectly.
  • Speak loud enough for everyone to hear.
  • Form a question the speaker can answer in a short period of time, 1-2 minutes.
  • Be specific about what you want to know; think before you raise your hand to ask.
  • Don’t ask too many questions. If you have more, converse off-line.
  • Don’t ask questions if the reason you’re asking them is because you didn’t do due diligence on the subject before the meeting.

Examples of Follow Up Questions:

  • [At a new product pitch] I have the gist of your product and what it does, but can you talk more about it from the user’s perspective? Who is your primary audience and how do you solve their problem?
  • [In a Q&A session] Your chart says “Europe” is 72% of the market share and “Asia” is 18%. Can you explain that differential? (I asked this question last month. The presenter had switched the numbers by mistake.)
  • [At a cocktail party] I’m not very familiar with your field but it sounds interesting; can you give me an example of a client you’ve helped? Why do the seek out your services? By the end of the working relationship, what has been accomplished?

  • [New product reveal] How did you come up with this concept? It’s really interesting and I wonder if you had an experience that led to this discovery.

  • [General] You’ve clearly done your research – but there’s a lot of data on this slide. What’s the key takeaway for us?

  • [Seek clarity] You use the term “food economy” in your talk. When I think of that phrase I think of global food issues facing us today. Can you define that term based on your work? It might be different than mine.

  • [Negotiation] If we agreed to this proposal, what are the next two or three steps we’d take?

Ultimately, asking questions is nothing to get nervous about. If anything, they can really help a speaker’s case by providing them an opportunity to expand on an area that wasn’t fully covered in the talk. In hindsight, had I asked the question to the creative team about their ad, it would have sparked a conversation. It seemed silly to me to have that question, but clearly there was a gap in the work. If nothing else, the creative team would have had the chance to finesse the idea. When you’re so close to the work, it’s often hard to see beyond.

In the end, we’re all in the same business with the same objective. The business is to craft messages – whether visual, written or oral – and the objective is to do so as flawlessly as possible. Questions can be a great gift for speaker and audience. So next time, ask away.

Cindy Skalicky, is the owner of On Point Communications, LLC. She coaches speakers on storytelling techniques, speech writing, presentation presence, and overall content development. Master the Message. Contact Cindy at: info@onpoint-communications.com

Back To Blog


“The On Point ‘Investor Pitch as Story’ online course was a great fit because of my heavy travel schedule. It gave me flexibility as a student to learn and connect with Cindy as necessary. The videos and homework helped me to prepare strong, compelling presentations for potential customers (coaches, directors, school districts) and becoming investor ready.”

Justin Fleming | CEO at MyPerforma

Tim Ash, Agent at The Group Real Estate

You are a wonderful presenter Cindy! I have taken so much from your presentation at the conference. I noticed when you speak, you at times lowered your volume in a way where we still heard you, but it PULLED the audience in, as if you were confiding in us.

Your vocal variety was lovely, (as well as your content, of course!). The advice to gather your stories from your past and weave them into your presentations is spot on.

Julie Roberts, Linked In profile writer|Coach

“Cindy, I’m in your Career Thought Leaders Conference session right now and you’re absolutely delivering on what you promised when we first met! I’m so excited to keep making progress in developing my brand story.”

Mashaal Ahmed|DC Career Coach

“Last year, I reached out to Cindy to help me with a sales deck I use frequently. I learned how to personalize my presentation in an authentic and informative way, making it more interesting to deliver and for my audience to observe!  Cindy was professional, enthusiastic, and knowledgeable and her suggestions were spot on.  If you want to enhance your communication skills, gain confidence in speaking, and improve overall delivery, I definitely recommend working with On Point!”

Nicole Steed, Global Account Manager | Helms Briscoe