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


How to communicate your release plan

A release plan is simply the dates you expect to deliver on major milestones for your project.

The beauty of scrum and its sister methodologies is there isn’t too much ceremony around this information.

Really, once you get past trivial projects, you very quickly realize what is to be built is not very well understood. Any plan you come up with that ignores this fact is guaranteed to become a source of pain in the future.

I see planning as a search for value, if well done, it helps us answer the most important question for any software team. What should we build?

Its a consideration of the features, resources available and important dates. This then illuminates a possible path for development.

I find it ridiculous that some people write a detailed document complete with dates and then think they are done with it all and no further revisions are needed. A release plan should reflect the current context. This means the format you choose should be one that helps you best express your most current thoughts.

In this entry, I will be looking at some of the formats I have found useful for communicating release plans.

Outcome buckets

In a previous entry, I talked about Why I don’t assign deadlines by date

For context here is how tasks bucketed into weeks would look like.

Well, as it turns out, planning your tasks as such is also really good for presentation. You can very easily get a sense of when you expect things to be completed.

Even better, the system communicates a level of uncertainty, because you don’t have an exact date for any of the tasks, you know it can be delivered on any date within the bucket and the plan would still be true.

For highly uncertain outcomes, you can increase the size of an individual bucket, say to 1 month. This communicates to all stakeholders there is much more risk to the outcome but we will get it done early if we can.


Maybe it’s my finance background talking, but I must say I love spreadsheets!

I find it to be one of the most powerful tools to establish coherence of thought within whatever your team is working on.

As part of our communication kit, spreadsheets allow us to play around with the quantitative bits of our plan. For example, if we need to model what would happen if a story point takes 5 days to develop as opposed to 3 days, it would be trivial to do so with the tool.

There is a perception in the business world anything on Excel is more serious than on a goofy tool like Trello. The perception is wrong but since its there, why not make use of it?

Gantt charts

A Gantt chart is a staple of the project management industry. They are highly visual and easy to understand. As you can tell from the fact am using a stock image here, I am not the biggest fan of them.

TeamGantt sample
TeamGantt sample


The problem I have with Gantt charts is it doesn’t communicate the uncertainty inherent in any software project. Furthermore, when a date changes, you don’t immediately see how such a change escalates across all other tasks and further how the other outcomes are now more likely to take more time.

Not all of it is gloom and doom, because of its visual nature, its far easier for non-techies to grok it over say a spreadsheet.

Furthermore, for a high ceremony executive, a Gantt chat will likely fit better with the rest of the reports they have to go through for the rest of the day.

How do you communicate your own release plans? Talk to me in the comment section below or on my twitter @jchex


Why you should always have an explicit agenda

I started my journey into the world of programming using PHP. Then there were no regular meetups in the community or at the very least I did not know of any.

Being one of the most popular languages of the day, it did not make sense to me why this was not happening, so I made a call for the first event. This was the first time I was organizing a community event, was not sure how it was going to go but my purpose was clear, meet and discuss all things PHP.

The turn out was good, the session started and essentially I said, welcome and discuss!

Nothing happened, everyone just stared at me blankly.

After a few painful minutes, Kirui, my boss at the time, swooped in to save the session. He took over and on the board wrote:

What will do for the next year?

What kind of events are we interested in?

What speakers are we interested in?

As if by magic, this constraint on what is to be discussed infused the session with energy and I learned a valuable lesson, one in which I hope to pass on to new group leaders today.

The group has now over a thousand members who communicate regularly on telegram and

In this entry, we will be looking at why your meetings should have an explicitly stated agenda.

Provides clarity and support to the meeting purpose

A meeting without a purpose is a useless one. The purpose of the meeting answers the question, why are we having this meeting?

Even if you have one, you need to know when you have been successful in the meeting. This means you not only need the why you also need the how.

An agenda communicates your plan of action to meet the purpose.

In this way, you are able to iron out any inconsistencies within the group and have an objective way of knowing when you are done. No one likes 2-hour discussion sessions.

Help in self-governance

Life is what it is, at times you may need to step out of the meeting midway, perhaps leave someone else to deputize you. A clear and agreed on agenda means you have the confidence to do this and when you come back, find the meeting is still on track.

What I have come to realize about good teams is they give you leverage, allowing you to do 10X or 50X what you could do by yourself. But the only way to achieve this is if you are in alignment.

For directors, ie your direct reports are managers themselves, it is useful to thrash out what their agendas with their reports will look like. In this way, you get more clear and consistent results without having to attend each and every single meeting.

Agendas are not meant to be dictated from on high. By having a short discussion on what the agenda items should be, you reinforce within them the mindset they are in charge and you get viewpoints which would otherwise be inaccessible to you.

Understand when the agenda needs to change

There is a saying by Lewis Carol:

If you don't know where you are going, any road will get you there

Even as you run your meeting, you must remember, the agenda serves the purpose of the meeting and not the other way around.

An explicit agenda by definition specifies what is not to be covered. This provides a chance for the team to tell you what you may be missing and just as importantly what need not be there.

You then have the chance to remove what is not absolutely necessary to achieve your purpose.

Meetings should be time-boxed, if the allocated time is 30 minutes and you realize there is absolutely no way you can cover everything, then reduce the scope, remove some items from the agenda.

With an implicit agenda, such value budgeting is not possible, so what happens is you either blow past the end time or worse cover only the first items with no concern to their value in relation to the purpose.

Do you normally have a stated out agenda at the start of your meetings?

Talk to me in the comment section below or on my twitter @jchex