Questions I always carry in my backpocket


At some point in your career as a developer, you will come to a fork, you will need to decide whether to continue majorly on the technical path or go into management.

If you do choose to go into management, you will come to notice you very quickly lose touch with the finer details of software development. It gets very hard to remember all the vim key bindings when you rarely fire it up.

An even more insidious problem is the fact information more easily flows down the organization than up. To illustrate this point, imagine a scenario where you as the manager come across a problem, would you have some second thoughts at reaching out to the developer responsible and having them fix it? Let’s flip it over, if you are the developer, would you report issues especially ones you know you may be the cause of?

With time, you find yourself operating somewhere in the cloud out of register with the realities happening within your own team.

I have come to find questions, are a useful tool to bring you back.

In this entry, we will be looking at some of the questions I always keep in my back pocket when walking into any kind of meeting.

Would you mind telling me more about why this is true?

In his book The Discoverers, Daniel J. Boorstin writes:

The greatest enemy of knowledge is not ignorance, but the illusion of knowledge

As a technical manager, you will tend to confuse the familiarity you have with the product with a true understanding of how it works. Thus when a discussion is going on, you don’t bother to truly dig into what they are talking about.

By asking the question stated above, you are able to get more clarity on the problem. It works better if you compliment it with the question “Who else has some insights into this”. Then you are able to see even more viewpoints.

Have you considered this option?

Given my technical background, at times, I do have some contributions to make to the discussion. The problem is you may end up having an opinion which you have offered up for discussion being interpreted as a decision.

This is especially true for senior-level managers such as CTO.

To counter the effect, offer the contribution as a question. This seems to soften the need to comply. It points out that your ignorance maybe in knowing the answer or is it not even knowing the problem being tackled in the first place.

In this way, you support thoughtful disagreements that explore and weighs people’s opinions in proportion to their merit with the end result of the best idea winning.

Is this discussion more interesting than it is useful?

No one likes two-hour meetings. Yet it’s very possible to get into this spiral especially when having a discussion on which technology tool or process to use.

Like moths, developers will get attracted to questions related to newest and shiniest technologies.

This is inherently good, after all, if you are not willing to abandon your tools and pick up new ones, your career in technology is likely to be short-lived.

Still, you don’t want to waste more than is needed touching on the nitty-gritty. At one point you have to decide to park the issue or just make a decision and proceed on to the next item.

What is the cause of that?

As I mentioned in an earlier entry Why you should never give off the cuff estimates making instant decisions is not likely to end up well.

When an issue comes up and you immediately start looking for a solution, you risk missing out on possibilities for a deeper understanding of the problem.

For example, The email service failed yesterday so key managers did not get their morning brief. Why? Because we exceeded our service limit on mandrill and there was no credit card to bill. Why? Because we did not expect to send emails to so many people. Why? Because we did not expect the organization to scale to this size.

From the series above, you can see not only do you need to solve the current problem. But all other problems which may arise from your assumption your organization will not scale or even other key providers who you may need to upgrade to a premium account.

What kind of questions do you normally carry in your own back pocket? Talk to me in the comment section below or on my twitter @jchex


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API Engineer