“I didn’t ask enough questions”





Keith Rollag in his HBR article "Succeed in New Situations" wrote: "According to several studies, including those by Elizabeth Morrison at New York University, the more questions new employees ask and the more help they seek, the better they perform. Research shows that question askers are also more satisfied in new jobs and more committed to new organizations. But when interviewed about what in hindsight they got wrong in starting a new role, executives most commonly say, “I didn’t ask enough questions.”


This sentence punched me in the face. What they got wrong in starting a new role? They didn’t ask enough questions.


Why do we ask the questions we ask - and don't ask? Why people don’t ask more questions? What holds them back? In the research “It Doesn’t Hurt to Ask: Question-Asking Increases Liking” published by Alison Wood Brooks, Karen Huang, Michael Yeomans, Julia Minson, Francesca Gino and popularized by Rachel Layne we may find 3 possible answers.


“One reason might be ego. People may be so focused on sharing what they know that they aren’t considering what they might learn from others. Or, they may think to ask a question but are afraid of asking one that is perceived as rude, intrusive, or incompetent. But, there’s a third, darker reason. Potential questioners, such as a manager, may not ask because they don’t care about the answers - they may feel apathy or disinterest in what the other person has to say”.


Of course, we have to be careful. Asking too many questions can have the reverse effect. “Asking a barrage of questions without disclosing information about yourself may come across as guarded, or worse, invasive” – warns Brooks





The Danish philosopher Pia Lauritzen has devoted her life to understanding questions. In her TED talk “What you don’t know about questions” she said: “Questions have the power to change the world. But for us to solve the problems that matter the most we must remember that questioning and answering should be like a dance where we constantly shift position in order for us to connect with each other and the world we share”.


"You think you have the answers to all important questions?" – asks John Hagel III in his article “Good Leadership Is About Asking Good Questions”. “That suggests that you are either clueless — you have no idea how rapidly the world is changing — or that you are lying”.


“Leaders who ask powerful questions have the greatest success in both seizing new opportunities and addressing unexpected challenges — and they build cultures that will carry these benefits into the future” – summarized Hagel.


In the discussion that followed the article Pia Lauritzen commented: “I disagree. My 20 years of research on the nature and impact of questions shows that good leadership is NOT about asking good questions. It's about empowering other people to ask good questions”.


Christina Bradway, Integrated marketer and Program manager added: “I keyed in on the section related to how questions build collaboration. How many times have you heard comments that a team is too rouge or a business is too siloed? I know that the word silo appears regularly whenever there are data discussions. How many times have you seen a business invest in a PMO office to help combat scattered and segmented initiatives going on resulting in fractured and failed rollouts? What could be changed if there were regular round tables? Not round tables where leaders update each other to prove their performance. But instead, round tables where leaders ask each other to describe what they find exciting or innovative about the projects they and their teams are working on. Now imagine opening up those round tables to management staff and operational staff. I think you’d quickly discover where the investment lives, where the pushback will come from, and where the collaboration is possible on any given initiative. And you’d have far fewer people sleeping than through the standard departmental slide shows. In fact, all of that departmental staff could be a pre-read to prepare for an actual, productive question and answer event”.


How does it work with the projects you’re managing? Aren’t you afraid of asking questions? What kind of questions do you ask? Do you allow and encourage others to ask questions?


“I didn’t ask enough questions” - I couldn't agree more. As always – the truth lies in the middle, it's both - leader asking questions and empowering people to ask questions. And people willing and asking questions.


People on lower levels of the company hierarchy exactly know what is not working in their organizations. The problem is if you’re asking and actively willing to listen to their opinions.


Thanks, Tom Fishburne & Marketoonist for bringing humor to business with cartoons.


If you want to see the whole discussion – click here.

If you want to watch TED talk of Pia Lauritzen click here.


Additional reading:

Good Leadership Is About Asking Good Questions, John Hagel III, January 8, 2021


Succeed in New Situations, Keith Rollag, December 2015


Asking Questions Can Get You a Better Job or a Second Date, Rachel Layne, 2017


It Doesn’t Hurt to Ask: Question-Asking Increases Liking, Karen Huang, Michael Yeomans, Alison Wood Brooks, Julia Minson, and Francesca Gino Harvard University, 2017