Dive 16: What your interactions with your boss say about your company

Sometimes, team members are attacked with unfair criticisms. Good leaders defend them.

Hey, it’s Alvin!

As FinTech recruiter Jennifer Widerberg pointed out recently, company cultures change constantly. And we don’t always have all the details on how well the company’s doing. Luckily, our daily interactions can offer us clues that give us a heads-up on whether the company’s on its way up, or whether it’s heading more towards a fiery end.

We can glean information from all kinds of interactions. Today, we’ll look at one example from software development: software estimations.

For those who don’t know, software projects are generally broken down into tasks. In an ideal world, the company funding the project would want to know exactly how long it will take to finish each task. Unfortunately, software projects are full of unknowns, so it’s almost never possible to have exact numbers. That’s why project managers ask software developers for “estimates.”

Here are examples of interactions I had over the years, and what they told me about the managers and the companies:

1.    The Authoritarian

Boss: How much time do you need?

Me: 2 weeks.

Boss: That’s too long. Get it done in 2 days.

The Authoritarian plans projects without consulting the dev team. They’re not interested in hearing you out. The leading question is just a formality. Or, it’s only to gauge your response. If your estimate is within expectations, then they can nod in agreement to give you the impression you had control over that decision all along.

This is either someone with a lot of power in the organization, or the budget for the project is insanely tight. Either way, it’s a terrible omen.

If it’s the former, they’ll face little to no consequence if the job’s not done on time. But you will face consequences for failing to meet their deadline.

If it’s the latter, it can be taken to an extreme. I’ve seen a few executives over the years threaten to cancel projects if they can’t be done by a specific date. In hindsight, that has consistently been a sign of severe financial issues. Because it means the benefits of continuing the project no longer outweigh the costs already sunk into it.

Either way, you don’t want to work for someone who doesn’t listen to you or work with you. And if there are signs the company isn’t doing well financially, it may be time to seek other opportunities.

2.    The Diplomat

Boss: How much time do you need?

Me: 2 weeks.

Boss: Can you get it done sooner?

On the surface, “can you get it done sooner (or faster)” is a dumb question. The only reasonable answer is “no,” unless you want your initial estimate to look like a lie.

No, the question is an indirect, diplomatic way to nudge nice people to lower their estimates because the Diplomat doesn’t have the courage to give you a number instead. They want you to give an estimate within their expectations as an indirect way to impose a deadline. Except you carry the burden if you miss the deadline because, technically, the estimate came from you, not them.

If you insist, you can’t get it done sooner, then the Diplomat might turn Authoritarian or one of the other two personas below.

With the Diplomat, you have to wonder if they have any ability to fight for resources. If they can’t bear the consequences of setting a deadline, what other responsibilities are they deflecting?

Will they have the courage to stand up for your team when others accuse your team of taking too much of the budget?

Or is the company having financial problems that are limiting the budget so much that they can’t push for more money?

You might not want to work for someone who can’t stand up for the team. Your team will need resources, and if your boss can’t fight for them, then get ready to work a lot more for a lot less. Get ready to say goodbye to your evenings and weekends.

3.    The Deferrer

Boss: How much time do you need?

Me: 2 weeks.

Boss: Well, we don’t have that much time. Let’s see how much you can finish, and we’ll re-evaluate from there.

The Deferrer takes a “wait and see” approach. At least, they acknowledge your estimate. This approach is more common for tasks with unclear requirements. Clarifications are typically provided as you work through the task.

The better Deferrers monitor task progress, at least, daily. They constantly assess how progress is trending. So, if it looks like the task won’t be done by the deadline, they can start taking remedial action beforehand. That could mean reducing scope, extending the deadline further, getting help from teammates, etc.

The best deferrers will also check-in with you periodically, and work with you to set you on the best path forward. Very much like…

4.    The Partner

Boss: How much time do you need?

Me: 2 weeks.

Boss: Well, we don’t have that much time. Let’s work together to figure out what we can accomplish.

This is the best kind of boss I ever worked with. They work with you to figure things out, which means they listen to you.

They want to work with you so you both clearly understand what can be done in the time you have. That might mean cutting scope (e.g., features), or asking for more time. But they strive to know exactly what needs to be cut or how much more time is needed so they can raise the issue with their boss(es).

The Partner is the boss that fights for their team.

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These are just a few examples of interactions I had with various managers over the years. But as you can see, there’s a lot more we can learn about our bosses and our companies from everyday interactions than we might think.

The caveat is that we don’t want to read too much into any one interaction. The idea is to observe patterns; especially changes in the way you’re being managed. Because changes in those interactions show changes in the company. And if the company is changing for the worse, you’ll want to get ahead of that.

I hope you enjoyed this dive Below the Surface of everyday interactions related to software estimations. Reply to belowthesurface@substack.com if you have questions or comments. What kind of bosses have you had? What did you learn about them? Let me know what you think. I’d love to hear from you.

Thank you for reading. Have a wonderful day. And I’ll see you in the next one.