Influencing By Asking Questions

I’ve recently attended an exciting webinar about mastering The Art Of Influence By Asking Questions. Check-out this best seller that also covers this subject.

Have you ever received feedback that you need to “expand your influence” to grow your career? Have you ever wondered how senior leaders from large organizations influence without burning out? Have you ever struggled to find a respectful and collaborative way to influence in meetings? If so, this guide is for you. I will cover how to use the art of asking questions in practical situations to expand your influence. I will provide you with useful tips you can use to influence in a scalable way, scale yourself.

I’ll also discuss how senior leaders use questions to influence organizations and make big decisions. You’ll read mistakes and missed opportunities from my experience.

This guide is all about questions, and it’s mostly going to be about asking questions. I promise it will also be about answering them towards the end as answers are as important as questions.

While most examples and situations in this guide happen in a workplace or business environment, the methods and tips are applicable outside work. At home, with your friends, and with your spouse or partner.

Short in time? Here is a summary.

Ask questions when you are new.
Don’t be afraid. Seniority is, after all, one dimension of diversity. Don’t assume the more experienced people in the room are automatically right.

Ask questions when proposing new ideas.
There’s no need to wait until you’re 100% sure about a new idea. Instead, you can write the approach and ask open questions ASAP.

When you feel strongly, ask, don’t tell.
Resists the urge to tell people what to do. Use the Socratic method to educate gently.

Ask last if you are more senior.
Make sure everyone is heard during a meeting, ask questions last if you are the most senior person. The line of inquiry follows from the first question. Let everyone be heard, and it makes your questions better.

Ask when you don’t know all the details.
Ask questions when you don’t know all the details. And if you still need to give useful advice, it helps to abstract your questions and try to focus on areas where components come together.

Don’t use questions to harm.
Don’t use questions as a device to be unhelpful or disrespectful. It is at the opp of the attributes of an influential person.

Answer the damn question first.
Answering questions is as important as asking them. You want to give a direct answer first and then give your background later. You want to answer: yes, no, given number, a date, a few words, or answer “I don’t know”. If you don’t know, provide an estimate by which you will have one of the other answer types. It takes a lot of practice, but it is very effective.

What is a question?

Let’s start at the very beginning. What is a question? Oxford Dictionaries define a question as “a sentence worded or expressed to elicit information”. Ok, so what does that have to do with influence? Questions help you influence because they make you think and help you examine assumptions.

Questions are problems to solve

You can think of questions as problems. I have been in the field of Software Engineering for over ten years. As Software Engineers, we all have technical problems to solve. Chances are, you also have problems to solve, no matter what your area of work is. Answering a question from the perspective of your brain is like diving into a problem.

The best questions keep you thinking a long time after they were asked. Just like how a spinning top keeps spinning a long time after you pull the strength. It’s then effortless.

Here are some sample questions that may hopefully make you think right now.

  • What did you want to be when you were a kid? How does it related to what you are doing now?
  • Are you happy?
  • Would you like your children to follow your path? Why?

You probably haven’t been thinking a lot about that lately.

If you are a Software Engineer:

  • What happens to your service when there’s network partition (communication failure)? What kind of trade-off do you make? Do you choose consistency or availability?
  • What happens to your service when it comes under heavy load? Do you shut down, or do you have a backpressure mechanism in place?
  • My favorite question: does your service even need to exist?

Hopefully, these questions have got you thinking. Stay with me.

Why influencing?

Why is influence important? It turns out influencing is critical for your career and to grow your business. It’s one of the biggest differentiators at the highest levels. And if you’re like me, you may have received feedback that to get the next level; you need to expand your influence. What does it mean?

Influence is abstract

Influence is abstract. It is hard to know where to start and how to get started. If you don’t manage anyone, if you are not a manager or business owner, it’s harder to influence because you have no reports.

Below is a diagram of my direct reports at the time of writing this post.

My skip-level manager -> My Manager -> Andrew (me) -> Nobody

As you can see, that is pretty damn sparse!

If you are like me, without direct reports, no one has to listen to you. You have to earn it. That means you need to influence in a centralized way without authority. You’re not telling people what to do. You’re helping people think about problems and solve them with the utmost solution instead. Easier said than done.

Earn Trust

Influencing without authority is all about Earning trust. Influential people earn trust over time by showing a few specific attributes.

  • Thought-provoking: this means simulate careful consideration. They bring new ideas to the table.
  • They’re helpful, useful, ready to help when thought upon.
  • Finally, respectful. They help in a respectful way that shows the difference.

Asking questions is a natural way to build trust by influencing without authority. Questions have a natural way to challenge assumptions while being respectful.

Socratic method

Let’s talk about history for a minute. Questions are ancient. And they form the basis of one of the oldest forms of truth-seeking philosophy, which is the Socratic method. The Socratic method arose in ancient Athens about 2500 years ago.

Let’s jump right into an example of the Socratic method in action.

I want to feature my favorite fictional character, Claud. Claud is reviewing a teammate’s project, and they’re talking about failing. The teammate says, “Hey, I’m ready to scale to 10 million customers! No problem.”. Claud is battle-tested. A veteran of many philosophical debates. And years of meeting reviews as well. He’s a little skeptical, so he starts asking questions to probe.

Claud: Do you have any sort of user testing? I wonder if user acceptance testing should come first? What do you think?
Teammate: User testing should come first before you're ready to scale.
Claud: Hey, since you agree that user testing comes first, did you conduct those testings?
Teammate: Well, no, I didn't.

Both are concluding that the teammate is not ready to scale up after all! The teammate will get back to Claud with a date for when he’ll have completed user testing.

Influence happened!

This is interesting because Claude influenced the teammate without Claude telling him what to do. No authority was used in this exchange. Claud was thought-provoking, helpful, and respectful. And therefore, in this exchange, he was influential.

A cooperative dialog

The Socratic method can be thought of as a cooperative dialogue where people ask and answer questions. And the goal is to stimulate critical thinking. Draw underlying beliefs about some topics.

The Socratic Circle

The Socratic Circle is how you can use the Socratic method to understand and examine the information in a text. With the Socratic circle, you’re trying to ask questions, test the logic and beliefs in a specific text with a group. Most importantly, a Socratic Circle is not a debate. Instead, the goal is to cooperate. Think critically to find an answer. Not to win an argument or prove someone wrong.

The Socratic method is very powerful. It’s been long used in philosophy, law school, and law debates to answer timeless questions like “What is the best moral system?” or “What is justice?”. The following is just my personal favorite: “Is our universe merely a simulation?”.

You can still see the Socratic method appropriately used across companies such as Amazon (from which I attended this webinar from) because there’s plenty of questions everywhere.

If we keep the example of the tech giant, Amazon, as Engineers, we build systems using logically connected components. So our questions usually have factual answers. We can create a foundation of learning over time, so we don’t ask questions that we answered 20 years ago. In a design review in 2020, you don’t see many questions about legacy systems. Whereas 20 years ago you probably would have.

Document review meetings at Amazon are our Socratic circles. As Amazon SDEs, we come across documents that have plenty of built-in questions that could help us get started. So there’s the PR FAQ (Press Release FAQ), which demonstrates how Amazon is customer-obsessed and works backward. The Operational Readiness checklist is full of questions.

Designed documents could be full of questions, too.

In the next few sections, we will explore practical situations to influence by asking questions.

How to influence

How senior leaders do

So let’s start with an extreme example. You are an executive, and you’re in charge of an organization with thousands of employees. At that scale, you can’t possibly review every decision. You wouldn’t keep up.

It’s impossible to know what everyone is working on. You can’t even know everyone’s name. Dunbar’s number states that you can maintain stable relationships with about 150 people. Or if you’re like me, that’s more like 10.

With thousands of employees, all you can do is just smile and wave, but you still need to know what’s going on. You need to know the deliverable statuses and what decisions are being made. And you still need to be able to convince people to do what you want.

So what can you do? Ask questions! It turns out that senior leaders use questions all the time. They’re used to make important decisions and influence dialogue. At scale, questions are one of the few tools available that work.

A concrete example of this would be Jeff Bezos, CEO at Amazon. I sourced this example from a colleague at Amazon.

My team and I met with Jeff to review a project. Jeff knew what our product was. But he wasn’t an expert on it and hadn’t reviewed it in a while. Jeff was coming into somewhat fresh eyes. And he only had 90 minutes to make an important decision: should we keep founding this project or not?

To make that decision, he asked a few questions and then gave some feedback. Jeff spent a long time thinking before he asked his questions. His questions were at the right level of abstraction. He was able to narrow in on a higher level. He was able to ask about how larger pieces fit together.

Here are examples of questions from Jeff:

Can you parallelize?
Can you do multiple phases of your project in parallel?
Can you optimize the current performance of your system at a hard limit?
Or can you do more work and optimize it further?
Can you go faster?
What if you hire more people?

Maybe a little bit less fun question:

I don’t understand your rollout plan. Can you explain why we’re doing it?

Influence happened!

In this meeting, influencing happened. Jeff influenced the team to adjust its rollout plan. A plan to get to market faster. He had multiple other meetings where he had to make similar decisions. As an executive, at every meeting, he can potentially impact a large group of people.

It turns out we can all use questions to do a lot of the same thing senior leaders do.

Asking questions when new

In this example, you’re new to a company, team or unfamiliar with the problem at hand. You are in a review meeting with other team members. To your eyes, what people say seems complex! You’re worried that it’s just because you’re new. And that you just don’t understand it and that everyone else has been there for a while. They must know what they’re doing… You stay quiet, not asking questions. Just assuming the more experienced people must be right and that you just don’t get it.

Sounds familiar? You should quietly ask questions when things are complicated or off, regardless of your tenure. Experienced folks are sometimes wrong too. No one is always right. And the amount of insight you can bring with a question does not correlate with your seniority! Seniority is just one dimension of diversity, and diverse perspectives are precious. You don’t want to rule yourself out just because you’re new.

Ask questions to knowledgeable people. Learn from them. Sometimes you’ll find that there’s an opening that people have missed.

Beginner’s mind

“Only when you’re a true beginner can you learn anything”. Being new can be a superpower. It means you can question things from different angles.

Ask questions to propose new ideas

In this case, your team is having a holy conversation about how to streamline a process or optimize a product. Assuming it is a service or website. Your team is trying to figure out how to fetch data in parallel. And you have an idea about how to make it work in practice. You want to jump in with your idea. But you’re not sure if it is correct.

When you have a new idea, you can express it as a question. For instance, “What if we were trying x instead? Would that work?” or “Maybe we could change A into B, what do you think?”.

If you’re writing your proposal, write out a list of open questions at the end.

New ideas can be scary

It is important to remember that new ideas are scary for everyone, no matter how senior you are. New ideas are unproven. And therefore, they can often be wrong. Open questions are expected for new ideas by definition. Best case, when you propose a new approach as a question, your question is answered, and you have a valid hypothesis, which is excellent news! In the worst case, the question is answered in the negative, and you have an invalid hypothesis. But even if the team doesn’t go with the proposed approach, you can still influence the direction a lot.

Limited downside, unlimited upside

Asking questions when you’re proposing the idea is an example of asymmetric risk. This is the math that underlies options trading and venture capital investing. With asymmetric risk, you have limited downside and unlimited upside. This is an excellent example of a situation where you can have a massive return if that works. If your idea is wrong, you just lose the idea that you proposed.

Don’t wait on the sidelines!

How asking questions when you feel strongly about something?

In this case, you are reviewing somebody’s work. And there is a mistake you have also made in the past. What people do wrong in these situations is that they just directly tell others they are wrong. This is bad.

I remember not so long ago. I was new to a team and proposed an idea to improve their test environments. The engineer in charge of this area instantly replied: “Oh no. Never going to work. We tried that.” And he directly moved on to the next topic. This is way too harsh feedback.

This kind of feedback style is career limiting. Changing people’s minds is hard. And it’s even harder to turn people around when they think you’re an asshole. You being harsh and ruthless is what people will remember about you.

Trust is hard-earned, easily lost.
Jeff Bezos, CEO at Amazon.

People realize they are wrong

In my previous example, my teammate could have used the Socratic method to educate and ask questions gently. When you ask questions to test the logic of an approach, people often realize that the approach itself needs more thought or that they’re wrong on their own. You don’t need to tell them directly that they’re wrong, pretty great.

The Rule of Three

Many leaders use what’s called “The Rule of Three”. This is where you ask a question politely three times and then gently prescribe the solution. After that, it’s a good rule of thumb to follow to ensure that your feedback is not received too harshly. The goal of the Socratic circle is cooperation and not proving someone wrong.

Asking questions to ensure everyone is heard

Ask questions to ensure that everyone is heard in a meeting. So in this example, you’re in a review meeting. You’re the most senior person in the room. Everyone is done reading the document, and it’s time for questions.

Quite commonly, you’d just ask your questions first, as the most senior person. It’s not ideal. It makes the meeting all about you. And the line of inquiry follows from the first question. This could make it harder for other team members to ask questions and make it harder to voice their concerns.

I just happened to have attended a meeting recently where three senior leaders stole the show by asking questions one after the other. Out of 20 other engineers, only one other dared to ask a question.

Jeff Bezos, CEO at Amazon, follows this rule.

So when everybody was finished reading the document, we went from the most junior person in the room to the most senior. Jeff knew that if he went first, the meeting would be all about his questions. Jeff is more inclusive just by waiting and asking his questions last.

Your questions may even be better as you can incorporate information from other people into your questions. That makes them more inclusive!

Senior leaders do this intentionally. It’s something that we can all put into practice. Just changing when you answer questions could have a big impact on the inclusiveness of a meeting.

Asking questions to give useful advice

In this example, you’re in a meeting review. You are a senior leader in your group. You don’t know much about the matter at hand, though. You have a rough idea, but you’re not the expert. You still need to advise the team to help them look around corners.

So most people do wrong in these situations is just pounding, matching the problem against what a similar problem solved before—assuming that the differences with previous experience are oversight.

You won’t be the expert. Abstraction is your friend. Instead, it’s better to ask questions even though you have seen a similar problem before. You may learn something new. You don’t want to assume any differences or opinions are oversight.

Finally, don’t opine too early. You won’t be the expert. You won’t have all the details, and you will know less than most people on the team. Yet, you still need to help them solve a real problem and provide useful advice.

One thing you can do is to have your questions be a high enough level abstraction to be useful. Take a step back and identify how pieces fit together at a higher level.

If you are in the software engineering field, one thing I’ve learned in my career is that technical risks often occur at the boundaries of systems. These boundaries, at a higher-level of abstraction, are good places to look for questions. If you look there first, you can scope your questions.

Asking questions to scale

In this example, you need to provide expertise to multiple teams at once. You are probably wondering how you could do your existing work and help with all these other projects. This will be asked from you as you become more senior in your company. And it will be daunting at first.

So you may try to keep up with everything: all decisions, all document reviews. If you keep that pace, you will reach a scaling breaking point. Where you can go no further. You may likely burn yourself out before learning your lesson.

Instead, you have to learn to let go. Learn to review only the important decisions. Focus on what matters the most. And since this is much easier said than done, I’m going to share some practical tips for how you can use questions to scale yourself.

Tip 1: Ask fewer or better questions

First, scaling is easier when you ask fewer or better questions. One way to do this is by asking questions in your head first. This will help you come up with better questions. You’re are going to be asking yourself more general questions. Then focus your thinking on more specific things. You can first ask yourself, “Hey, what’s missing that should be here?” or “Hey, can we make this reusable to the rest of the company?”.

Tip 2: Look for new information

Scaling is all about saving time. New information could help you save time. You want to skim over the parts you’re already familiar with. Look for bits of information that have changed. This is a good place to focus your questions on.

Tyler Cowen, who’s a famous American economist and professor, a very well-read guy, uses this technique to read multiple books about the same topic quickly. He reads cover to cover the first book about a topic. He then read subsequent books on the same subject by skimming over the parts that he already knows. And look for new information instead.

Now, I’ve got to be honest. I’ve tried that back in the days at university. It never worked for me. I’d be interrogated on the pages I skipped every single time. Leisure reading is different in the sense that there is no knowledge test down the line. Yet, you want to make sure you absorb as much information as possible. My technic for this is to take notes, structured notes. Lots of them.

This method feels like cheating at first. But it can work. You do need to be careful that you don’t miss things.

Tip 3: Bring the questions to you

Even more scalable yet is bringing the questions to you. In this case, you want to encourage people to come to you before the next big decision. This is much better than people coming to you too late with an official proposal (like a design document) you don’t agree with.

When you do this, you’re delegating judgment to other people—letting them decide what’s important. This ensures that you spend time on only impactful questions.

Throughout my career as a Software Engineer in big corporations, I have witnessed many styles of leadership. The most successful were the ones where leaders delegated, offloaded some of their responsibilities by empowering their direct reports to make decisions and drive their projects.

So if you do this right, you can expect questions come to you like: do you have any concerns with this approach, or are you aligned with significant architectural change we want to make?

Tip 4: You don’t have to be there

So even better than bringing the questions to you… is not being there at all. In the field of Software Engineering, this could take the following form:

Have a design document template with a series of questions predefined. Where you just have to answer the questions. If you answer all the questions well, that means that your design will likely workout. And I love it because there’s no excuse for the writer’s block. You don’t have to worry about how to format the doc; you just answer the questions.

Pitfalls of asking questions

Questions can be used for harm as well. Let’s review common pitfalls of asking questions and some anti-patterns to avoid.

Pitfall 1: Disrespectful questions

Disrespectful questions are designed to make others look bad, harsh, or rude.

“How did you think this was a good idea?”
“Don’t you see what is wrong with your approach?”

Pitfall 2: Don’t dominate

You don’t want to use questions to dominate the conversation, so you don’t want to keep asking questions and talking over and over. And think that it’s ok because you’re using questions.

Pitfall 3: Obscure questions

You don’t want to ask obscure questions to make you seem smart.

“Are your four loops SIMD vectorized?” There might be a few obscure cases where that’s a valid question.

Pitfall 4: Derail the conversation

You don’t want to ask questions that intentionally derail the conversation.

For example, if you’re in an operation review meeting talking about a legacy service: “Hey, should we just rewriting this service altogether?” That’s probably not the right time and place to ask. The time and place that you ask your questions matters, too.

Pitfall 5: Too many questions

Finally, you don’t want to ask too many questions. This can manifest himself when you always answer questions with other questions. It is taking the Socratic method too far and only answering with questions.

How to answer questions

It turns out that asking questions well is not enough. You also need to answer questions. You want to answer questions directly first, give the background after. Direct answers to questions usually take the following forms:

  • Yes.
  • No.
  • Number.
  • Date.
  • A few words.
  • “I don’t know”. You want to give a date of when you will have one of the other answer types.

It takes practice. As engineers, we want to tell stories about how we solve interesting technical problems. But you don’t always know why someone is asking you a question. Your interlocutor could have a meeting in 2 minutes. Or he just wants to schedule his vacation and want to make sure he is not on vacation when your project is gonna be ready. So, in that case, he doesn’t need the whole back story.


We learned a lot about the power of questions to influence in various situations. Senior leaders use questions all the time to influence downward, at scale. Questions are one of the only tools that work on a huge scale.

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