Sometimes the questions are complicated and the answers are simple. Dr. Seuss quote

No one comes to work to do a bad job; and I would argue that most people want to be exceptional in their roles.

For most of us we spend years in school, and then countless hours pursuing additional knowledge and honing our craft (and I know this holds true for anyone who choices a career in software).  To that end, we all like to think that when it comes to our jobs, we are the authority in our domain.  While confidence in your trade is good, being too confident can stand in the way of much greater success.

This goes for everyone from a new employee straight out of college to the CEO. No matter what the role, we all have more to learn, and reading books, going to conferences and keeping up on news will help keep you on top of things, your real understanding at work can come from asking good questions.

Each of these situations presents opportunities to leverage questions:


Dealing With Challenges

Most everyone is comfortable asking questions when they’re new to a job, but over time many grow uncomfortable with the idea of asking for help when they’re stuck on a problem. Whether it’s pride or something else, reluctance to ask questions can actually make you less effective at your job.

Problem-solving and being self-sufficient can’t be discounted; but when you are blocked and you’ve hit an issue you don’t know how to get past on your own, asking questions is how you move the process along and get back on track. Rather than cobbling together a subpar solution at the last minute that may lead to future problems, asking questions gets you to a better solution faster and prepares you to handle similar situations on your own in the future.

Think about your questions before you ask them, and make sure you’re as concise as possible while still getting the information you need.  Focus on actionable information and specific questions.  Some of my favorite ways to ask for help are:

  • Can you tell me where you would go to figure out ____________?
  • Do you know where there is an example that solves this same problem I could look at? (this particularly works well if you aren’t sure where a certain method or implementation lives in a large code base)
  • I have been struggling to figure out ______, could you point me in the direction of how you could solve it?

People are generally way more receptive to specific questions asking for resources than answers, and it gives you a chance to learn from their experience.


Working With A Team

Asking questions is a great way to make meetings and discussions productive, as well as avoid situations where everyone walks away without much accomplished.

Imagine sitting across a conference table from one of your peers who has just suggested a crazy new system to start tracking customer data. At first blush, their idea sounds expensive and overly complicated, but instead of saying “That won’t work”, asking them to clarify how this product will improve the current implementation and what the pros, cons and risks of this change.

Asking questions helps you keep an open mind and in turn, helps people around you keep an open mind too. If people feel their ideas were listened to and given credibility through questions, they’re more likely to do the same for their peers, which means more and better solutions to company objectives.  Learning to do pause, take a deep breath, listen to the other person and pose my retort as a question was one of the most useful skills I have learned in the last few years.


Making the Most of a Mentor

If you’re successful in your organization but you have aspirations beyond your current role, seeking out a mentor relationship (either with your boss, a colleague within your organization, or an outside contact) is an essential part of taking the next big steps in your career.

I’ve written before about making the most of your time with a mentor, and picking good questions is key to make meetings with them worth your time and theirs. The questions you bring to your mentor are up to you, but some will lead you to more fruitful conversation than others. For example, asking “what makes you successful?” is a kind of tough question to answer. A lot of successful people will say “luck” or “determination”, which doesn’t give you a very clear path of how to achieve that yourself.

Instead, a better question is “how did you handle transitioning into a management role?” or “what is the best way to give feedback to a team member?” These questions ask for specific answers. Imagine looking back at your notes a week later – would you rather have written “Be Lucky” or have a ten-point checklist for how to improve at giving feedback?

Sometimes the questions are complicated and the answers are simple. Dr. Seuss quote

Teaching Your Team

As a manager, you’ve usually got a million things on your plate all the time. So when an employee comes in with a problem, a busy boss’ first instinct is often is to give the employee the answer they need and move on. Which makes sense – you can’t sit down with everyone for every problem, or you’d never get any of your own work done.

However, studies have shown that the best bosses are so effective because they’re great teachers. And a great way to become a good teacher is to ask questions that lead your employees to come up with solutions themselves instead of just giving them the answer. (Which, in turn, means they’ll bring fewer issues to your desk for you to handle in the long run.)

The point of your questions shouldn’t be intimidating your teammate or make you feel smart. Your questions should lead them naturally to working out a solution to their own problem, and your ego should take a back seat during this exercise.

This technique also works well when trying to persuade someone, or help reach consensus.  In order for a person to embrace an idea, it needs to be meaningful for them, and each type of person has a different way of assigning meaning.  By asking them questions you can lead them to your conclusion, or potentially uncover rationale that could convince you to change your position.  Both outcomes are clearly positive for the organization and your relationship.

Keep your tone patient and make sure your questions lead them to answering their own questions through problem solving on their own. Make it a conversation, but resist the urge to tell them your opinion. The more you practice this skill, the easier it will become to ask the right questions to help your employee evaluate their situation and take effective action themselves.



Asking Good Questions

As with everything, the way you approach asking questions will affect your rate of success.

If you think in advance about what kind of information you really need before you start asking questions, you’ll be more effective and get better responses. If you are like me (or a lot of other engineers), you may suffer from an excess of bluntness – which means short, to the point, questions, and these don’t always elicit the helpful answers we were hoping for.

Instead of just asking the first question that comes to mind next time, remember: phrasing, timing, and consideration can have a huge impact on the response you receive. And it just takes an extra second of thought before you head into your next meeting. One technique that has helped me is to deliberately try to talk slower, and relax in conversations and in meetings (and it is easier said than done).

Asking questions is a way of letting people know that their opinion is important to you – and everyone wants to know that their input is valued. Good questions communicate an authentic interest in the other person’s expertise, which makes that person much more inclined to share that expertise with you, rather than shooting back a terse, equally to-the-point answer.  If you can predict how your question is going to hit the listener (what is it telling them about you and what need from them?), you’ll meet with faster and more effective results.

You can categorize your questions for best results by breaking them down into four distinct types (types taken from the book Just Ask Leadership: Why Great Managers Always Ask the Right Questions):


#1 Questions that give you perspective

These questions help you clarify, and can keep brainstorming sessions and meetings moving forward. A perspective question helps you to get inside the other person’s head and explore possibilities. This kind of question can be used in a teaching situation to encourage an employee to consider the big picture, or can help a team come to a unified mindset.

“If we implement this change, how will it impact the daily work of engineering staff?”
“How would this new product fit among the products introduced by our competitors?”
“What were the sales numbers from our last release of similar scale?”

These questions open up a discussion, and relate to the possibility. Ask a perspective question whenever you want to learn more.


#2 Questions that help you evaluate

Evaluation questions get you concrete answers and narrow your focus to one goal. Whereas perspective questions help you see all the possibilities, evaluative questions help you test theories against data and make decisions. If you are guiding a team to make a big move or if you need more data to help you complete a project, think about asking an evaluation question to get the precise information required.

“Which of these features will be the fastest to produce?”
“Why were your traffic numbers down last month?”
“What members of your team have the most experience with UX design?”

Evaluative questions ask for specifics, numbers, data. They help you pinpoint solutions, so use evaluative questions to bring everyone into alignment and make decisions.


#3 Questions that lead to action

This kind of question is your lead-in to making changes, motivating teams, and setting future directions. Questions that ask for action create accountability by asking the answerer to set goals and create a path for achieving them, and they also help turn data into actionable plans.

“How can we ship this product in [X] weeks without bringing on new staff?”
“When will the team complete this new feature?”
“What strategies will you implement to ensure your team is aligned?”

Action questions are an effective tool for leaders to empower employees, by giving a form of decision-making power to them. They are also effective for turning ideas into plans, and creating ownership of plans.


#4 Questions that lead to knowledge

Knowledge questions are perhaps the most simple, but not the least important of the four question types. Gathering information about current projects, past projects, goals, and technical processes are all important for performing at the highest-possible level. In addition, managers can ask employees to explain a recent project to them to both learn more about it and to gauge the employee’s understanding.

“Can you explain to me how [xyz] process works?”
“What results did we achieve with the last email campaign?”
“What is our customer profile?”

Knowledge questions solidify understanding and alignment, and keep teams operating as efficiently as possible.


When you ask the right questions, you not only get the information you were seeking, but you also develop more effective relationships with your coworkers. Formulating the right question for the right time gives your question clarity and gives your coworkers the most information they need to help you, which makes the whole process easier for everyone. And, over time you’ll develop your skill for determining the best kind of question for a given situation and begin to see the process move even more smoothly.



How do you incorporate good questions into good business strategy? 

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