7 Questions CEOs Ask Engineering Leaders

Posted on July 21st, 2021
Written by Andrew Lau | Strategy & Planning

We’ve all worked for “that CEO” before. “That CEO”, in the most generous way, challenges you as you’ve never been before, asks you a million questions, and never ceases to surprise you. Okay, so here I go caricaturing the business leader again, but most of us have had some version of “that CEO” at some point in our career (or you will at some point). 

I often feel for engineering leaders and an inkling of self-awareness because I’ve been on both sides of the table. I spent a decade running engineering teams fielding a barrage of questions from execs and now I’m a CEO talking to leading engineers.

For this reason, I’m uniquely qualified to offer my CEO-Translation-Services™, free of charge! I’ve compiled a cheat sheet of some of the questions “that CEO is going to eventually ask you and I’ve broken down what they really mean.

1. CEO: Get me a list of what every engineer is doing!

Translation: Let’s start with my favorite odd request. What’s often going on here is that features aren’t coming out fast enough and he or she happens to think that one of the reasons it’s not going fast is that the wrong people are working on the wrong things.  

What to do: Your CEO needs to be bought into the way your teams are constructed. Talk them through why you organize the team the way you do. Show them the work that arrived at your structure. It’s critical that your CEO believes in your choices and philosophies, and it starts with showing them how thorough you are in your approach.

2. CEO: What’s Sandy working on? She’s a 10xer – she can’t be wasted! Can’t she do this thing over the weekend?

Translation: Yes, their favorite engineer was Sandy, 2 years ago…The bottom line is that they think the team was doing so much more stuff before because she was shipping market-moving features weekly. They can only focus on how fast they used to go when the team was smaller and they ran things. She did everything important; that’s why they used to be so fast. Naturally, she must not be working on the most important things. You clearly are managing her wrong!

Obviously, they don’t understand why things are slower now. They attribute the current slow progress to you or more likely they don’t understand what progress means anymore. The CEO doesn’t realize both the cost of maintaining old stuff and (while Sandy is amazing!) we need to have a whole team of Sandys if the engineering team is going to be efficient as we grow. 

What To Do: Your job in this scenario is to get the CEO to understand the reality of WHY you go the speed you do, what we are doing, how important growing and diversifying the team is, and why the dev process works the way it does. 

3. CEO: How’s hiring going? When’s that fifth team coming online (when you only currently have two)?

Translation: There are two things that your CEO is signaling on this one. First, your CEO is getting impatient about why we can’t build more stuff. They have also made up their mind that the only way we build more stuff is to hire more people. In their eyes, they did the hard work to get the plan and budget approved to hire more engineers, and now they’re wondering why aren’t we getting those hires done so that we can make more stuff done. 

What To Do: When you’re cleared to hire, do so as fast as you can. Everyone, including the CEO, thinks it’s done as soon as it’s approved. As we’ve learned, the world can change very quickly and you might not always get the chance later to grow the team. Lastly, make sure you’re projecting a realistic ramp time for your new hires, and clearly articulating when you’ll see the productivity gains from the increased headcount.  

4. CEO: Did you know how Facebook does stuff?  Have we tried that process?

Translation: Dear CEO – does this mean “break things”?… 😉 

This is probably the most direct one, but it’s a special variation on asking: why can’t we do more? They’re romancing about the good ol’ days and they don’t fully understand what is hard or expensive to maintain. 

What To Do: Like the first question, they lack understanding of why we organize & operate the way we do. Explain the different ways we could operate, get them on board with how you arrived at the way you organize today, amongst all the different options possible.  

5. CEO: Why aren’t people here after 5 PM? 

Translation: They’re not so subtly assuming your team isn’t working hard enough especially when there’s a big deadline looming. This may or not be the case, but it’s more likely they don’t understand what’s happening in the first place. 

What To Do: This is an important variation on the, “why things aren’t going faster?” question.  Be sure to see that answer above, as it’s important they understand delays are attributed to different problems/complexities now.

6. CEO: Have you ever thought of using these offshore guys? 

Translation: This could mean one of two things depending on their intentions. Where do these ideas come from? It’s possible that the board gave the CEO the idea or your CEO met another company that expressed some value from having leveraged services from overseas.  

Either way, it’s worth unpacking WHY. Does the CEO think this is faster or cheaper?  If they think it’s faster, see all the above about what is actually keeping you from being faster. If they think it’s cheaper, it’s worth understanding why they care. Often as companies mature they are forced to make their costs look like peer companies’ “comps,” but the company still wants to build X, Y, and Z new products and features.

What to do: You should ideally get ahead of this.  Ask your CEO or CFO what are our “comps” as we grow – what do we have to look like when we grow up? 

7. CEO: Have you seen this Jellyfish thing?

Translation: They don’t have enough visibility into what engineering is doing. They don’t understand the work of engineering because it’s not framed in the context of the business objectives. They heard about this Jellyfish thing and they think it can help. Crazy thing is, we think it could too, but not because your CEO is harassing you about it. 😉