How Do You Manage Up with the CEO?

I’ve heard this question from managers and HR folks and directors for years. Typically it’s at a company 40-100 people. I get it from remote teams now, and I used to hear it quite a bit in the Before Times also. It’s not just a we’re-disconnected-because-Zoom thing.

What it looks like to the team member is this: they have something they feel is important, some critical issue. It’s not typically something urgent, but more like something that’s been festering. Casual mentions haven’t brought about meaningful improvement. They feel like they need to bring it up directly with the CEO. So they do. And…it just doesn’t seem to land. Maybe at the time they get a “thanks for the feedback”, but there’s nothing substantive.

Often, this has to do with behaviors of the CEO themselves. For instance, they keep inserting their own commentary into creative decisions. Or they circumvent an existing process for hiring or promoting someone. It has downstream impact that the CEO doesn’t stick around to see. It makes other team members feel undervalued, or that they’re wasting their time.

It’s worth noting that the CEO gets to make the decisions. Especially in a small or mid-sized business that they started. Your company, your prerogative. I get it. I’m not fomenting rebellion or fanning the flames of entitlement.

But rational CEOs who want their company to stay healthy shouldn’t be in favor of making their direct reports feel undervalued.

My advice to the direct reports is to approach communication with empathy, and to share what they’ve got from the standpoint of “these are the consequences of what you’re doing” rather than plating it as an ultimatum. CEOs rarely respond well to threats.

If You’re the CEO

Please appreciate that your people are closer to the metal than you are. Just because Topic X doesn’t seem like a big deal from your vantage point doesn’t preclude the generation of a ton of stress for them. A little empathy from you goes a long way. That doesn’t mean you’re beholden to create solutions for every issue brought your way. But validating someone’s experience can be meaningful even if they don’t get the result they want. Sometimes they’ll even be happier if they just hear you say, “Thanks for mentioning this. I’ve thought it over, and we’re not addressing X right now.” Ask them if your response lands with them, even if it’s not the response they hoped for.

At a company of this size, you’re counting on your lieutenants to shoulder a lot of the workload you need off your plate. If these folks don’t feel heard amidst stress – especially if they view it as stress you created – it’s unlikely they’ll stick around.

It’s really hard to delegate to an empty seat.