No matter how experienced you are in the technical aspects of the role, being a tech executive requires knowing how to communicate with other executives in the company, and especially having a great relationship with the CEO. For some people, this is a scary and problematic aspect of the job, yet I’ve found that boiling common issues down and naming them can make a huge difference. Here are some of the most common six issues and how to tackle them.

Yes-ing Too Much

You might have a CEO who is more authoritarian or one who prefers collaboration. Nevertheless, you shouldn’t default to agreeing to whatever is being asked automatically. Don’t take this to mean you should be contrary to whatever is asked. That’s a CT-NO and no one needs those. You should not rush to follow orders, but ask ‘why’ and ensure that you understand the needs and intention of what you’re asked to do.

By having that extra context, you’ll be a real enabler as opposed to an order-taker. Perhaps you’ll find a better way of doing this or uncover an issue that needs to be addressed before the company commits to a direction. By all means, eventually say “yes,” but only after ensuring you understand how best to provide the company with what is needed.

Not Being A Team Player

It doesn’t matter how good your relationship with the CEO is if you’re essentially absent from your team—the executive team. I keep telling my clients that they’re not mentoring and coaching their executives enough, and still, I’ll be the first to admit that executives ought to learn to operate by themselves more freely. You shouldn’t rely on things being funneled to you by the CEO. Learn to work closely with your peers.

By establishing solid communication and collaboration with the other executives in the company, you’ll be more effective in your role and will be able to talk to the CEO about things other than just the day-to-day. Otherwise, your one-on-one time will be consumed by relaying messages back and forth.

Plate Filling

Everyone has too much on their plate nowadays. One of the worst habits you can have is to be a ‘plate filler’—that person who starts piling issues on the CEO whenever you talk. While it’s important to speak up about issues, an executive should solve things. How do you address the problems that you notice in your work?

You’ve probably heard the quote about bringing people solutions, not problems. That’s right, but I’d go further and say you should be bringing initiatives. CEOs often tell me they’d love for their executives to come to them with what they think should be done and the agency to say they’re willing to be in charge of getting it done. That’s taking things off someone’s plate.

Permission Over Forgiveness

Connecting to the concept of plate filling, sometimes even when you’re being active you might be operating too much with the mindset of a non-executive. The Manspider rule: With great responsibility—as a senior leader—should come great power. That means you have more agency and autonomy than you often realize. Rather than ask for permission for everything and run any idea by the CEO, you can and should be doing things on your own.

Use your common sense and start getting things done. Allow yourself enough operation room to iterate fast and not lose momentum. Yes, you might get things wrong from time to time. That’s the role of common sense: if the decisions you make are sensible, even when you do inevitably end up making a mistake, you can ask for forgiveness and move on.

Sitting by the Phone

Are you waiting to be looped into the right discussions? Constantly surprised when you find out about things too late? Yes, communication is often too haphazard in startups. Nevertheless, if you’re just waiting to be synced in and told what to do, you will likely find out about issues too late.

Instead, elbow yourself into the right discussions and meetings. If you realize that a certain meeting often results in changes that you weren’t part of (and causing issues due to that), get in that meeting. You’re not being rude, you’re being effective.

Misunderstanding the CEO Filter

(less data, thus something that happens twice might be observed as a pattern, always debug)

Lastly, there’s the issue of not being able to put yourself in the CEO’s shoes. The “CEO filter” is something I notice in many companies past the pizza team size. Due to the fact that CEOs do not routinely speak to people at all levels of the company (it’s just not possible), their “input sensitivity” sometimes changes. I routinely see CEOs announcing something is a grave issue because they’ve heard about it twice and assume that’s a pattern (sometimes they’re right).

You see this also happening when one fragment of a sentence from an IC as feedback turns into a pressing matter or when a request or two from prospects immediately turns into work plans. Instead of getting frustrated (or, in addition to it), keeping this in mind will help you think about what extra information can be used to ensure the right decisions are being made. Remember, you might know that a certain issue happened twice but is already being treated by someone, or that Joe always complains about things no matter what.

Any other common pitfalls of communication with CEOs that I’m missing? Let me know!