The Art of the CEO Deep Dive

As CEO, do you really know what’s happening in your company? 

That may sound like a strange question. You would think CEOs would have a bird’s-eye view and be deeply informed. But no. In reality, most CEOs inhabit a bubble where the stakeholders around them exquisitely manage the information they can see. 

CEOs have to work hard to stay out of that bubble. This Harvard Business Review article offers great tips for ongoing CEO hygiene to that end.

But what do you do when reality breaks through the bubble and you find out that some part of your company is broken? How do you dive deep into understanding what’s wrong, and what needs to change, without alarming everyone? 

You might be inclined just to dive in. But let’s be clear: a CEO’s unexpected presence in any meeting or conversation dramatically increases the stress and the stakes. Imagine if your board chair decided to jump in and “figure out what’s wrong with engineering.” 

If you find yourself in this situation, here are some guiding principles to follow. Much of this advice also applies to executives at any level who are faced with the need to fully understand a struggling part of their organization.

Partner with the leader. Ideally you will lock arms with the person leading the function or division you’re learning about. Let them help you learn. This can be tricky if you are contemplating firing that leader. But short of that, the deep dive will be more productive if you have the full involvement and cooperation of the person in charge. In some instances, it may be possible—even preferable—for that leader to do the deep dive themselves. In either case, if you sense they are blocking you, you may need to have some challenging, direct conversations with them.

Frame key messages. How you and others talk about the deep dive can make a big difference, both in setting it up for success, and minimizing the added stress and workload in the organization. Keep the tone transparent and positive if you can. For example, instead of “Our Supply Chain organization is a disaster,” say, “As you know from the All-Hands meeting, Supply Chain missed their key objectives. Noor [VP of Supply Chain] and I are trying to understand the best way forward.”

Be curious, and listen well. If framing your words sends a message, so does your attitude as you proceed. Dial up your curiosity. Ask “open” questions with the intent of understanding, not interrogating. Open questions usually begin with “What…?” “How…?” and “Tell me about…?” For example, “What’s standing in the way?” and “What would make things easier?” Listen attentively to the answers, noting both the information being shared, and the emotions, which can be even more important. For more on listening, see our post.

Reduce the burden on the organization—both the work burden, and the psychological burden. Be explicit that you are not looking for polished slide decks. In fact, make it clear that’s not what you want. Instead, encourage people to prepare for meetings by having ready access to facts, and being willing to share openly. Also, reassure people along the way if you can do so without making commitments you might later regret.

Praise transparency. “I really want to thank Amanda for sharing so openly and candidly about some of the challenges with the Sales organization. Unfiltered comments are what’s most helpful as I get more up to speed and figure out how we can work together on taking positive steps.”

Communicate, communicate, communicate. When you’re satisfied both with what you’ve learned and what needs to happen next, communicate as openly and as frequently as you can with the people in that organization. As far as possible, be positive. Use inclusive language, and take ownership where you can.

Use consulting firms judiciously. An outside firm can help analyze what’s going on inside a part of your company and can help with benchmarking and best practices. But if you use them to justify your direction, people will see right through that. Use consultants to help assess the situation, but own your decisions 100%.

Of course, if you want to avoid surprises that burst the CEO bubble, the best thing is to build a culture of psychological safety before problems arise. To do this, frequently ask open questions, listen deftly, and reward people for speaking truth to power. The safer it is for people to share information openly, the more you’ll know what’s going on. 

As CEO, perhaps you can’t prevent the bubble from forming around you, but you can limit how much it distorts your view of reality.