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Tech Career Insights: Why Continuously Asking Questions Is a Superpower for Tech Leadership
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Why Continuously Asking Questions Is a Superpower for Tech Leadership

15 July 2022, by Jomiro Eming

As a Co-founder of a tech company, not having a background in software made it challenging for Aidan Quin from ServiceMyCar.co.za to work effectively with his dev team. He quickly realised, however, that by continuously asking questions – no matter how ‘dumb they seemed – was the best way to connect with his developers. Here, he shares some insights on why prioritising curiosity is valuable for both the team and the product, as well as how he approaches asking questions.


Being a non-tech founder at a tech startup can make it really hard to properly understand and engage with a development team. This means it can be more challenging to build trust with developers when you don’t understand everything they do and care about on a daily basis.

As a Co-founder, Aidan, believes that building strong relationships with his teams is a critical part of his role, and something that he needs to be involved in daily:

“It’s quite hard. A lot of the time you feel like you are a dead weight in the process, but every second of it is valuable. This whole hands-off type approach would never work because the product that you start off with is never gonna be what it ends up as. There are so many dynamics that change the way the product turns out, and the only way you solve those issues is by being there, with the dev team, daily.”

The most effective way for him to be actively involved in an ever-changing product — without micromanaging his developers — has been to ask questions, and ask them often. In this discussion, he unpacks why asking questions helps him engage more usefully with his development team, and his advice for anyone – tech or non-tech – on how to ask better questions.

Asking questions helps him understand problems and processes

Understanding how his developers approach problem-solving has been important for Aidan as his business has scaled. He explains: “I can’t do the actual coding, sure, but I’ve started to understand why something’s a problem by asking as many dumb questions as I can.”

For example, Aidan says that there’s often a difference in how a business person and a technical person think about impacts of certain changes. In his case, he knew how to bridge that gap because he had spent the time asking ‘dumb’ questions:

“In the business world”, he explains, “we might say, ‘We’re not going to invoice like this – this is how we’re going to deal with it’ – and it happens immediately. In software development, I’ve learned that that ‘little’ change in one direction can take three weeks to develop.” Without asking questions about delivery time, for example, Aidan would never have known that and would always irritate his development with tight deadlines.

Asking questions ensures he doesn’t lead from a distance

In Aidan’s opinion, the worst thing he can do as a leader is give instructions without being actively involved. He says that this demotivates a team, and ends up in longer — and therefore more expensive — development cycles.

Aidan makes sure he shows up for his developers, and is fully engaged in the work they do.

Especially as someone sitting on the outside of development, building trust requires him to be there even more than a technical lead.

He explains that it’s not enough to just ‘pop in’ every so often; he wants to be there with them as often as he can, so that they know that he’s their to support them:

“When they hit an obstacle, I’m there immediately. They don’t have to phone me, they don’t have to wait for me to arrive at the office… there’s none of that lag time. It’s about having a routine of making sure you’re there every day, and you have constant engagement with your developers.”

This puts him right in the middle of not only the delivery, but all the pains, all the challenges, and all the bottlenecks, which helps him be a more effective leader across his teams. When it comes to his dev team, taking this approach gives him a fuller picture, and lets him understand the software problem with a bigger picture view — which helps him make decisions that take his devs into account.

Asking his devs questions positions them as the experts

As a leader, Aidan has no problem admitting when he doesn’t know something. As he’s working on improving his technical knowledge, he doesn’t pretend to know better than his developers:

“It’s about understanding what you’re good at. I’m good at business strategy and solutions, and I understand that I am no good at software development. My software developers are the experts there — and I ask questions because I trust them fully to know where to look for the answers.”

His developers understand the product, Aidan understands the industry and the vision. By asking questions, Aidan consistently makes his developers feel like they are as important to the product as the founders and executives of the company. This drives motivation, improves trust, and improves Aidan’s relationship with his team.

Advice for asking the right question, at the right time as a leader

Part of Aidan’s approach to building trust and asking questions, is to make sure he asks his developers questions in the most useful way, and at the most useful times. Here’s how he approaches this.

When to ask questions

In general, Aidan tries to ask questions as soon as he thinks of them. That way, he doesn’t risk derailing something or someone with a last minute question or issue at an already busy or stressful time.

To do that well, Aidan makes it a rule to never miss a meeting with his dev team: “It really is about being present always, so that you share the problems that they face, and how they solve those problems. One of the things we have in place is a daily meeting, with the developers and myself, at 10h30 in the morning.”

Using these cadences to ask questions means that he doesn’t need to pull his developers out of the time they’ve blocked off to work on features.

Where to ask questions

That said, Aidan is very deliberate about where he asks certain questions. For example, with minor things — quick clarifications about tech jargon, or easy-to-answer problems — Aidan asks his developers in person during their daily meetings. These would otherwise be noisy if he pinged his developers online constantly.

For the bigger, more serious issues, Aidan prefers to use something like Slack. Meetings need to stay on track in order to be useful, and the harder-to-answer questions could cause tangents during a meeting. Slack also gives his developers more time to answer questions with examples or links. Plus, it’s easier for Aidan to have a paper trail of what is actually discussed, which helps him have something to reference and come back to in case he needs the reminder.

How to ask questions

Finally, Aidan has found that letting go of his ego and being completely vulnerable is the best way to ask useful questions:

“The way I do that”, Aidan explains, “is to set the bar very low, and ask the dumbest questions I can. I ask those questions, and learn from them, so that the bar of ‘stupid’ question gets raised constantly.”

This curiosity that Aidan brings to his approach to asking questions is the ‘edge’ that he says is the ‘edge’ that helps him feel more confident as a leader. It not only speeds up his own understanding about the software industry, but it helps build a stronger, more trust-driven relationship between himself and his devs — because they know that he’s engaged, he’s willing to learn, and he won’t pretend he knows something if he doesn’t. This means that his team can develop faster, and output a higher quality of work.

To get in touch with Aidan, you can reach out to him via LinkedIn!

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