Managing Up to The CEO

Photo by Prince David on Unsplash

“What do you really want from your people?” I asked.

I was speaking with the CEO of a growth stage technology company. After several decades of successfully delivering value to their customers, the market had been gradually shifting beneath them. Recognizing this, she had tasked her leadership team with finding a clear path to their next exciting chapter.

We were meeting to discuss their apparent lack of progress, these VPs that report directly to her and who are responsible for both the daily operations of the company, but also helping to set the strategic direction. Something was holding them back.

In our conversations with the members of the leadership team, they had described her as a tough and demanding boss, someone they each deeply wanted to make happy. Universally, they had come to the conclusion that she calls all the shots, and so they generally waited for her to set the agenda of meetings, and to tell them their next strategic initiative.

After about thirty silent seconds of deep thought, she finally responded. Her voice was clear and steady, and she held eye contact with me as she answered my question.

“I just want them to take more initiative, to be more assertive with their opinions, to tell me their good ideas instead of always waiting for me to tell them what to do. I don’t want to have to hold their hands.” 

She sighed, glancing out the window for a few seconds. “I just want them to act like a team!”

I have lost track of how many times I have heard CEOs and other senior leaders say pretty much the exact same thing about their leadership team. There is a clear contradiction between how the leadership believes the CEO wants them to behave, and how the CEO really wants them to behave.

And the stakes in this game are really high. For companies that are trying to execute some sort of radical transformation, to meet new and emerging market demands, to change the way they build and deliver products and services, to capture new opportunities for growth, the leadership team needs to be just that–a team!

As a new senior leader, your job can be confusing and frustrating. It's a huge relief when you finally figure out how to work with your CEO and the rest of the leadership team. Managing up to the CEO requires seeing them as a real person with feelings and needs rather than a power broker before whom you must always grovel. People think CEOs want to control them, but it’s actually the opposite. They want you to take initiative. Controlling people sucks!

We have worked with hundreds of executives over the years, and found the techniques that are the most effective in working with CEOs. They are also backed by all of the major leadership literature out there. These are specific skills that you can practice every time you interact with any senior leader, starting today.

The five steps to better executive communication are straightforward:

Keep it concise. The nature of their job keeps them at a high-level view of the business. That means there is a lot of information coming at them all the time. Use as few words as possible. Stick to only one point at a time.

For example, say you are asking for their buy-in on a new system that you want the organization to purchase and adopt. It can be tempting to list all of the ways this system will save time or money, to illustrate all its amazing features and benefit.

Scrap all that. What really matters to your CEO is something more like how does what you’re asking for align with the strategic direction of the organization? How will it create better alignment? There is probably one or two simple sentences that make that point concisely. Spend time before your conversation boiling everything down to that key point.

The more you can keep it simple, the easier it will be to get a straight answer. And if the answer is no, at least you can move on to something else.

Ask questions. Like Stephen Covey taught us, seek first to understand, then to be understood. Nobody stops to ask how the CEO is feeling about things. Take a moment to check in and get their point of view on the issue you want to address before you ask for anything.

Smart questions can also provide insight into their reality that will help you make progress in the conversation.

Offer to help. They are busy and overloaded, so look to add value not just add more weight to their decision-making fatigue. Create a feeling of reciprocity by making an offer to be of service. Be specific about how you can help; don’t make them do any extra work.

If you are seen as someone who they can trust to take responsibility off of their plate, it is more likely that they will consider what you need in order to be effective.

Ask for forgiveness, not permission. Arrange to speak with them after you’ve already got something underway. Show the progress you’re already making, and frame it to make them feel good about it. Always position your efforts in terms of how it helps them achieve their goals.

It takes a lot of initiative to get something started in an organization. Most leaders will not want to be the first to push for a new initiative. If you can take small steps or run experiments and start making some traction first, you’ll already be able to show progress when you present your idea.

And if you are worried that you’ll get your wrist slapped by moving first and getting support for it next, you’re thinking like an individual contributor and not like a leader.

Follow up. Once you’ve had your conversation, make sure you follow up. If you’ve offered to help, definitely do not drop the ball. If they offer to help, make sure you keep on them. Make sure you get their permission to keep them updated. And then do it!

If you follow these basic guidelines, you will quickly find yourself able to accomplish more across the organization. You’ll also be seen as someone who can handle more responsibility. If you don’t, you will likely remain stuck in the messy middle of the organization, taking whatever is handed down from above.

—

It can be hard to figure out where you should focus to unlock your next level of growth. That’s why we’ve designed a diagnostic that pinpoints the areas of your organization with the most untapped growth potential. Our clients love it. It asks you a series of questions that we’ve perfected over the last four years of development, and gives you a simple report so you can get clear about where you should put your energy. Reach out to us if you want to give it a try.