Avoid What Actually Hurts You, Not What You Fear

We all roll our eyes at the weird people who are so afraid of flying that they choose driving, despite the massively increased risk of injury and death. Data show that driving is approximately 190 times more fatal than commercial aviation per mile traveled.

But, in teamwork and delivery, many people let fear be the driver, and ignore actual risk. Here’s how it works:

You are an engineer on a software project. Your part is on track for delivery, but a colleague’s work is behind schedule, or completely opaque. This colleague has demonstrated defensiveness any time someone has poked them about their work in the past. They seem angry all the time and you’re worried they might quit and then the project would never ship.

Do you speak up?

The underlying question: Which are you more afraid of blowing up, your relationship or your project?

The underlying dynamic: You’re probably trying to avoid the outcome you fear, rather than what actually hurts you.

So, which do you preserve, relationships or project schedules?

If you say “relationships”, then, when the chips are down, you’re going to be resistant to pushing people when the project schedule is in danger, which means that your projects are going to ship late or they’re going to be low quality. If you say “project schedule”, then you’re going to be preserving that and pushing people, and maybe pushing them away. One project might ship on time, but good luck getting people to work with you on the next one.

So, we optimize to avoid the outcome we fear. Relationship-driven people spend endless time on soft skills and communication, when they should be spending time on project management and assertive, candid communication. Project-driven people spend endless time on scope and schedule, when they should be building better relationships—relationships that can survive a little stress-testing—with the humans around them.

If you follow your fear, you become well-developed in the exact wrong place, and remain weak in the place with the most upside.

So, what do you do about it? Well, the temptation is to look around for world-class role models and try to emulate them. That’s admirable, but misguided. People are good and bad at things for lots of different reasons. You are not trying to get good. You’re trying to get less bad, and that’s a very different goal.

Don’t go buy a book to read. You don’t need a book. You need a shift in values. Here’s my recipe.

• If you want to stop ignoring people-risk, memorize this question: “How are you?”
• If you want to stop ignoring project risk, memorize this question: “Where do we stand?”

I personally am a “stop ignoring project risk” person. I would usually say “Where do we stand with Project Nutter-Butter?” I have some greatest hits follow-up questions like:

• Where would I have looked to see that without bothering you?
• Do you know clearly what we are delivering?
• Do you think we are on track?
• What worries you about this project?

Being relationship-preserving, if a project is at risk and I want to signal that I’m not afraid to push the relationship a bit, I might ask something pointed like:

• Is this up to your standards?

Here’s a few basics for building rapport:

• How are you?
• What do you like to do for fun?
• What does [upcoming holiday] look like for you?

If I was a project-focused person and I wanted to signal that their long-term satisfaction is important, I suppose I might ask:

• Knowing what we now know, what would you change about this project?

But the best advice in this matter is from Andy Grove, founder of Intel. Grove’s Rule of Didactic Management says “Always ask one more question.” When I tried to get good at this, I was shocked at how hard it was to formulate an honest question that didn’t have an opinion lurking inside it like a Trojan horse. It’s still hard, but I’m less bad at it.

Again, for heavens sake, don’t go buy a book. Management books are written by people who are good enough at project or people management to say to themselves “I should write a book about this.” You don’t need their advice. You need the basics.

If you want to go beyond what I have above, just go to your favorite AI and say “I want to be better at project management and I don’t want to buy a book. How do I start with the basics?” or “I want to be better at connecting with people I work with and I don’t want to buy a book. How do I start with the basics?”

When several years ago I was confronted with the fact that I’d over-optimized on relationships and left project management on the table, I suggested to my team that we just do the most basic Agile/Scrum workflow. Maybe not the workflow that’d make everyone the happiest, but one that would be relatively easy to run for me. Good enough. They agreed and things went well.

As I’ve said elsewhere, getting a group of smart people to work together to achieve a common goal is pretty much the hardest and most rewarding thing about work. Getting them to do so repeatedly is even harder and even more valuable. Bringing a project in on time is great. Even better if your team is hungry to build the next success together. If you can pull it off, you’ll always be in demand.