leadingIn(tech)#18: The value of asking good questions

October 2022

Oct 24, 2022

Hi there! 👋🏽

Welcome to a new issue of leadingIn.tech newsletter. I’m Roberto, and this is where I share ideas, practices, and learnings toward becoming a better leader in technology.

This week’s issue is about the value of asking good questions. As an engineering leader, you will find that you spend much of your time talking to people, trying to understand what are the most important problems that need to be solved, how things work, or understand the root cause of issues, to clarify requirements, interviewing candidates, and much more.

All of these activities involve plenty of active listening and asking useful questions. For this reason, being good at asking questions is definitely one of the most valuable skills any engineering leader needs to develop. Let’s explore in this issue some situations where engineering leaders typically need to display this skill.

Photo by Dominik Van Opdenbosch on Unsplash

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1:1s

In the first two issues of this newsletter, I’ve talked about how I believe that one-on-one conversations are the holy grail of management, as the most important tool you have to connect with your team. These conversations give you the opportunity to listen to your team and understand their concerns.

If you have been doing 1-1s in the past you might have noticed that often it's hard to kick start a topic to discuss, “all is fine” responses become very common. It is here where as a manager you need to put your questioning skills to shine. How do you pick a question that helps the other person open up to you about topics they are hesitant to talk about?

The Coaching Habit book offers you fantastic tools to help you ask questions that trigger valuable discussions that can be used to understand the root cause of problems, help your team to reflect on issues, provide feedback or understand where you can help as a manager to help them succeed. From the book, these are the 7 core questions:

What worries you? What’s on your mind?
And what else? (A.W.E. Question)
What’s the real challenge here for you? (Focus Question)
What do you want? (Foundation Question)
How can I help? (Lazy Question)
If you’re saying yes to this, what are you saying no to? (Strategic Question)
What was most useful for you? (Learning Question)

Additionally, on the leadingIn.tech toolkit, I’m compiling a list of useful questions that can be used as variations of these.

Do you have a favorite question to ask in your 1-1s? Share it

Retrospectives

I’ve dedicated a full issue to my other favorite tool as a manager, retrospectives. I usually use these sessions to kick off discussions within the team to identify areas of opportunities to improve how we work together or with others.

As described in that newsletter issue I’ve compiled a set of activities that aim to question the team in multiple ways to gather inputs about areas that can be improved. Starting with classics like What Went Well?, What We’d Like To Improve? or What Went badly? questions.

Additionally, these conversations drive questions such as “What can we do today to mitigate this problem?”, “Is this process still adding value?”, “What can we learn from this?” and many more. The goal of questioning in these sessions is to collect the necessary information to make informed decisions about what is working and what is not, but also to create a space for open and blameless discussions that drive action to solve the issues at hand.

Blameless, in the paragraph above is an important word, as a manager you need to make sure that the questions are not asked in a way that leads to pointing fingers. You want the team to work together to identify the issues and collaboratively act on solutions to them.

Post Mortem's

Similar to retrospectives, Post Mortem is a must in any engineering organization that wants to make improve the resiliency of its systems. Blameless is also an important word here, as mentioned in the Google SRE book, the goal of the postmortem activity is to identify the contributing causes of an incident and have the team work together to identify ways to prevent them from happening again in the future.

The Five Whys technique is a fantastic tool to try to reach the root cause of most issues, repeating asking why’s to subsequent responses of the first why will eventually lead you to the source of a problem that you can act on.

Project or Design Reviews

I see design reviews as fascinating tools for engineering leaders to stay in touch with the internals of the systems their teams build. This is an opportunity to be genuinely curious about what your engineers are proposing to build, to ask challenging questions to make sure that they have looked around the corners. To make probing questions to figure out if what we are building is really aligned with the business goals and is solving the problems that need to be solved.

What is the main problem we are trying to solve here?
What other alternatives have we considered?
Why we chose option A vs B?
What are the trade-offs?
Does the solution scale? Does it need to?
What is the cost of not building it?

These and many more questions can drive to really interesting conversations that will challenge your thinking and your teams. Having your team be able to articulate these answers will also help them grow and improve their skills for future designs. The important thing here is to be genuinely curious and not judge. Your team is the one on the grounds closer to the information to make better decisions, your role is to use your experience to challenge their thinking and come up with better solutions by themselves.

Hiring

As an engineering leader, you are not only responsible for managing your teams but building them. This includes hiring as the principal activity you need to be continuously doing. As a Hiring Manager, your role in the interview process is usually about understanding if the candidate has the right experience needed for the role and if they have the right alignment with the company culture.

I really enjoy interviewing and in my experience, I've seen that the best interviewers are the ones that again, are genuinely curious about the stories that the candidate is telling you. As an interviewer, your role is to ask questions that drive the candidate to tell you about their past experiences based on a context that you set up in your question, then based on the responses the skill needed to get valuable responses is to ask the right follow-up questions.

Follow-up questions, help you dive deep beyond the surface of what the candidate is responding to you. Your job is to try to identify how they managed the situation, what they tried and what they didn’t, what they learned about it, and what actions did they take to meet their goals. You want to understand how they manage challenging situations and what resources they have to overcome them as an exercise to predict how they will use them in your team. You are not looking for specific knowledge but for attitudes and reactions to different situations.

And remember to be genuinely curious, your questions should not include any kind of judgment about their responses, you want the candidate to open up and express themselves openly.

Wrapping up

We covered, 1-1s, Retrospectives, Post Mortem, Design Reviews, and Hiring on this issue, but these are not the only situations where you can exercise your questioning skills as an engineering leader. You will find yourself needing to use these skills with customers, stakeholders, service providers, and shareholders. If you noticed, I’ve made emphasis on the two main aspects of how I like to ask questions being blameless and genuinely curious. What I like about being in an engineering leadership role is being able to engage in insightful conversations that drive valuable outcomes of any kind.

Thank you for reading this far, hope you enjoyed it. To continue the conversation, can you tell me what other situations you have found yourself using your ability to make great questions?