Questioning Axioms

I’ve written before about the types of things that I look for in senior tech leaders as I interview candidates. One amazing indicator of success I haven’t found a good way to interview for is the capability to push back tactfully. It makes sense that most people avoid appearing argumentative during interviews. However, too often, this same mindset remains in effect as we do our work, and that’s a real shame.

Leaders who know how to ask “why?” at the right points are priceless. They usually find more opportunities to leverage their roles and provide more value, they generate more innovation regularly, and they are less like to burn out quickly. Sounds good, right? You can do it, too. Let’s consider different areas of this capability. These are all based on common occurrences I see in my work. For each, consider whether you are utilizing your Socratic questioning chops enough.

Guiding Employees’ Careers

Managing talent is a considerable part of senior leadership nowadays. Even when the market is cooling off a bit, the best people are always in high demand and tend to try to propel themselves forward constantly. I’ve worked with executives who lamented the fact that they didn’t have the “magical skill” of being able to sit down with employees and tell them what the best next steps for them would be. I don’t think you should aim to be that omniscient. Regularly talk with employees to hear what they are thinking about their career paths.

However, when someone mentions a specific direction, don’t be afraid to ask, “why?”. This is where your experience can be invaluable for less senior employees. For example, there’s nothing wrong with considering why someone thinks management is the right next step. Many miss the fact that there are other options or imagine the role as different than it really is. By merely asking, you can help them crystalize the right choice. The worst-case scenario is that you just better understand that person’s needs. Sometimes you don’t need to say anything, just be an active rubber duck asking more questions. Easy, right?

Product Goals and Scope

This one applies at all levels of the product engineering work, as low as discussing the scope of specific tasks and as high as considering the company’s product vision and roadmap for the year. You should regularly ask “why?” and ensure you understand the reasoning behind decisions. Moreover, you should ensure that your teammates are doing the same at their levels. Suppose we don’t understand the context of a task, the business goal that a particular effort should achieve. In that case, we cannot reliably make the many micro-decisions that are part of software development.

When we ask “why?,” we get the ability to weigh different options in their proper context and, therefore, might find opportunities to limit the scope, achieve the results faster or in another manner, or show that something does not make sense. I keep hammering into engineering managers that no one is looking for soldiers that hear a request, pipe “yessir!” and get going. Healthy curiosity and prodding are the difference between an R&D department that’s an equal partner and an expensive software factory operating in-house.

Clearing Communication

Leaders that have their team’s trust are often told about things that are going on that need to be addressed, which is good. The problem is that it has become quite popular for many people to provide this feedback “in confidence”—they don’t want the manager to use what they said. And then, I end up trying to help these executives handle concrete issues where they attempt and operate from a glovebox. They cannot be direct, and many beat around the bush for months instead of taking the problem head-on when it is most crucial.

An axiom to question here is whether this request for confidence even makes sense. Assuming that you ensure that no one will get hurt because they brought something to your attention, what’s there to worry about? If the issue was so critical that they spoke up about it, why wouldn’t they want you to be able to do something about it? You might not be able to change everyone’s mind, but a good leader strives for directness.

Managing Up

One last area of healthy questioning is when you are dealing with your manager, often the CEO for the executives I work with, but sometimes also relevant for discussions with the CFO and similar. Were you told to make do with a budget that doesn’t make sense? You should, at the least, make your case about it and ensure that everyone understands the limitations or risks of doing so.

The same goes for various policies and decisions you don’t agree with or don’t understand well enough. For example, I’ve had to help many CTOs recently who were given limits on how and where their people could work. Can your people work remotely? Hybrid? Can you hire people from other countries? Just because the company currently has a particular policy doesn’t mean that’s the one right path for everyone and forever.

Don’t be afraid to ask and prod. As long as it is being done from the right place and not as an automatic practice of contrarianism, you are providing helpful, often much-needed, perspectives. The best CEOs I worked with always appreciate candor and thoughtful opinions, even if they disagree with them. The alternative is a C-suite of yes-people, which no one needs. Are you incorporating this thinking already? If not, “why?

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