Pleasing Your CEO Demystified
What does it take to please the most demanding leaders?
What does it take to please the most demanding leaders? With so many startups led by highly opinionated yet unpredictable founders, that question can hang stressfully in the air over every key decision. Get it wrong, and all those long hours might have been for nothing. What a waste! Everything hinges on winning these leaders’ approval, but how remains a mystery. Good news: it’s a mystery you can solve with the right tools.
I used to work for a senior exec at Adobe who was always impeccably groomed: freshly pressed blue shirt, white goatee with no hair out of place, sparkling blue eyes with a tan and a big smile. A few sentences from him in a meeting could make or break you. But you never quite knew what he’d say in advance. His highly polished exterior just made his unknowable interior more mysterious.
I’ve worked with quite a few iconic tech CEOs, execs, and investors over the years, and there’s often an air of mystery about them. They’re seldom shy about expressing themselves, but what exactly will they say? That’s the question sweating their teams before a big presentation, performance review, or pitch meeting.
In pursuit of answers, those teams become armchair (or office chair?) psychologists. They strive to map out all the complexities of their fearless leader, piecing together their motivations from any clues they can uncover:
What does this leader care about?
What are their plans?
How can the team fit into them?
What is the leader expecting?
What will impress them?
What will turn them off or tune them out?
Yet these efforts are often fruitless. How is your CEO supposed to know how they’ll react to the presentation until they see the presentation? These are hard questions to answer even when you’re asking them directly, let alone when you’re trying to glean insights from between the lines of their Slack messages. Either way, seeking to plumb the psychological depths of your CEO probably isn’t a great way to prepare for your presentation.
Face Your Fears
So what should you do instead? Let’s say that high stakes conversation is approaching, and pleasing your leader feels more urgent than ever. Turn your attention to yourself first. What’s so important to you about winning their approval? What feels so dangerous about failing? Behind our sheen of professionalism there’s almost always a part of us that’s terrified to screw it all up. Often our questions directed at others are really pointing at fears we’re not so comfortable naming in ourselves:
Fear of not getting our way
Fear of being judged lacking or unworthy
Fear of upsetting others
Fear of losing our job and the security it represents
These poorly-hidden fears explain much of our mysterious behavior! And of course the same applies to leadership: my cheat code for understanding your CEO is imagining how you’d behave if you were terrified to fail—and let your whole company down.
I often name these fears with my coaching clients, and I can’t help but laugh at the pushback! “No, no, no, I wouldn’t say I’m scared! Worried maybe, stressed definitely, potentially on my way to burnout if this doesn’t change.” But everyone gets scared at work, whether we admit it or not. Worry, stress and burnout are just safe-for-work terms for fear—and the consequences when we avoid it instead of facing it.
So what are you scared might happen if you can’t please your CEO? What’s the worst case scenario you’re trying so hard to avoid? Let go of your polished professionalism for a moment and embrace your inner drama king or queen. What would it mean to fail here? Often there’s a dark corner of our soul that fears we’d not only lose our job but our reputation—that we’d never work in this town again. That’s certainly what was going through my mind when I was fired from Slack ten years ago!
I didn’t know then, but the best years of my career were still ahead of me. Our most dramatic fears are easily debunked when we look at them with clear eyes. But then there are others where the risk is very much real. Is there a risk you might fail to please your leader? Always! Is there a risk they will judge you harshly? Of course! Is there a risk you’ll encounter some uncomfortable feelings along the way? Well that one’s not a risk—it’s a certainty.
We’ve all navigated countless uncomfortable moments in our lives. Not just awkward meetings, but breakups, health scares, family drama, you name it. I’ve often found comfort in that considerable track record! I’ve been able to handle everything life’s thrown at me so far, why not trust that I can handle what’s coming next?
Being fired might not even make my top 10. I’ve watched products I poured my heart into become obsolete and irrelevant. I’ve made terrible mistakes I couldn’t take back. I’ve sat by helpless as people I love suffered and died. That’s life. So when I have a spicy piece of feedback for a CEO they may not like, I’m not too worried. I know I can handle anything they dish out—and so can you.
Reveal Your Goals
If poorly-hidden fears explain half of our own mysterious behavior at work, well-hidden goals might well explain the other half. But why on earth would we hide our goals? Aren’t we all just trying to change the world for the better? Well, we’re afraid of how others will react: revealing what we want is vulnerable. Usually the whole reason we’re trying to please our leaders is to avoid rejection or conflict.
But we seldom find the easy stamp of approval we’re hoping for the first time around. Having worked through our own fears to share our goals, our reward is hearing about our leader’s fears—all the things that concern them about our plans. Whomp whomp! No wonder we hesitate to freely share our goals.
Yet the alternative is far worse. When we don’t reveal our goals, we’re not just being unclear. We’re shifting from good-faith negotiation to coercion—trying to trick people into doing what we want without revealing why. As you can imagine, leaders do not like feeling coerced! Having sniffed out some ulterior motive, they make their own conclusions about what our mysterious motivations might be. Our leadership might decide we don’t care about, don’t understand, or even aren’t capable of pleasing them.
There’s a simpler way forward. Instead of guessing how you might please your leadership, you can just reveal your goals and ask them directly:
Here’s our plan. What do you think of it?
What are your concerns?
What would it take to earn your approval?
Will you offer us the support we need to get there?
Turns out clearly stating your goal and asking nicely for help achieving it is pretty foolproof. It just takes a willingness to be vulnerable by revealing your desires, to accept any concerns you hear with grace, and to try again using what you learned. Trust yourself to make your own case, and trust them to make their own decision. It’s simple tactically, but complicated emotionally.
It’s heartbreaking sharing your dream, only to have someone in power poke holes in it! But that’s the price of glory. Everyone disagrees with their leadership at times, and that’s OK. You’ve endured far worse heartbreak and come out unscathed. Great partnerships are built by working through those disagreements, not avoiding them. Prove you care about your leaders’ concerns by not settling for anything short of a win-win result.
Ask for Help
We all yearn to pursue our dreams! And our leaders often hold the power to make them real. So how do we find the courage to ask for their help? That’s the real mystery we’re trying to solve when we’re strategizing about what to say in our next meeting. We hope that by figuring our leaders out in advance we’ll feel confident enough to make our case.
But how can you feel confident when you’re avoiding your fears or hiding your goals? The best you can muster under those circumstances is a poor impression of confidence—and your leadership will notice. You find real confidence by facing your fears, revealing your goals, and asking for help. You’ve already proven you can handle the hard part! However your leadership responds, you can handle that too.
Sure, it’s nice when our leaders see the genius in our plans. But the real payoff is feeling fine even when they don’t. When it’s not the right time, or resources are scarce, or they want to see more data before they commit. It’s their right to say no! But it’s also your right to ask what would get them to yes next time around.
The irony is most leaders would be mortified by how hard their teams try to please them. They want allies in their mission, not people-pleasing sycophants! Many haven’t cultivated the right environment to achieve that, but at least that’s their intention. They want what we all want: genuine relationships with the people around them.
By finding the courage to face your fears, reveal your goals, and ask for help, you can do your part to build those genuine relationships with your leadership. You can learn what they think and feel by asking them directly! No longer burdened with guessing at their mysteries, you can join forces on a more interesting problem: how to change the world for the better.