CEOs Wish They’d Known These Things on Day One

What would experienced CEOs tell their younger selves? I asked them.

After publishing my article, “3 Things I Wish I’d Known as a New CEO,” I became even more interested in what other CEOs wish that they had known on day 1. As a CEO advisor, I was fortunate enough to be able to ask this question of a number of CEOs.  Most of these are under 40, with their first day in the top job still fairly fresh in their minds. Their views, though wide-ranging, had clear common themes.

“This Job Is Fundamentally Different”

Several CEOs were surprised by the sea-change they experienced between their new CEO role and every previous job they’d had. This aligned with my own experience when I was a new CEO, which I’ve previously written about as, “the job transition for which there is no transition.” All spoke to the sense of increased performance pressure and the weight of responsibility. All had serious responsibility in prior roles. But across the board, they said that pressures of the CEO role were not just more of the same.

“The job is fundamentally different from all prior roles,” said the CEO of a major building materials supplier. “It’s impossible to make every decision. Plus the skills that got you here – for example, execution or good ideas – are not nearly as valuable as before. I’m more of a caretaker of an ecosystem. I need to give my leadership team what they need.”

The examples he gave of these needs included:

• Reconciling intra-team conflict (IT is under-supporting sales, which is in turn ignoring HR directives). 

• Giving the leadership team clear direction, a culture of empowerment, and a defined appetite for risk.

• Giving your team both the guidance and the freedom they need to make good decisions.

“I Should Have Prepared More In……”

There was nearly universal agreement that new CEOs wished they were more prepared when they took the role. Some part of this desire seems inevitable. After all, we are always learning and growing, whatever our current level may be. But these CEO’s spoke compellingly about specific preparation they wish they had done. It’s this feedback that’s actionable for others following in their footsteps.

“I wish I’d worked in advance on communicating the ‘why’ behind my decisions,” said the CEO of a major retailer. “I realize now that I made decisions based on my values. But I hadn’t prepared myself with the words to articulate those values to myself and to others.” Consequently, others had more difficulty understanding her: how she prioritized her time, what she chose for investment, etc. “Things could have been easier, smoother if I had been better prepared to articulate my values.”

Most of the executives I talked with would advise their younger selves to gain greater exposure to critical business issues before stepping into the CEO job. Expertise in compensation, transactions, negotiations, marketing, authority, performance management and accountability were high on the preparation list.

 “I should have diagnosed my weaknesses,” said the CEO of a large distribution business, “and immediately shored up those areas.” 

“There were management performance issues I didn’t recognize and inadequate business results that I didn’t see. Family employees and relationships initially fogged up my thinking and my recognition of problems.”

Several other CEOs echoed these sentiments and pointed to the value of an outside thought partner to help them identify and address their weakest areas.

“Relationships Will Change”

“I was surprised that my position altered relationships,” noted the President of a business in the housing industry. “People could no longer just be nice,” operating with the intent to go around and above her. “Now they had to deal with me. Even though I perceived a consistent relationship, they now had more at stake. That increased the tension and the previous standard for satisfying them.” Dynamics were more charged than she expected. In fact, she also noticed more gender-loaded language coming her way – designed to help them get their way. She thought, “I don’t think you would ever say that if I was a man.”

Many CEOs have been surprised and even hurt by how much their relationships with colleagues are changed by the new leadership role. Even if we’d wish it otherwise, leading people is different from simply working alongside them. Since you are the final decision-maker, every conversation has a variety of potentially loaded implications. Feedback you give may be taken differently, and communications directed to you may come with an “agenda.” One has to find one’s independent perspectives elsewhere.

“Seek Outside Help Sooner”

The shift in relationships with in-house colleagues is a key reason the CEOs I talked to emphasize the value of relationships and perspectives beyond company walls.  

As the CEO of a financial services business put it, “There is huge value in a network outside of the business.”

“I wish I had developed more independent relationships outside of the business before the stakes increased,” said the housing industry President. 

“With broader perspective, I would have raised expectations faster, made changes to personnel faster, and articulated benchmarks earlier,” said the CEO of the distributor.

While many CEOs wish they’d sought outside support sooner, they ultimately did find it or, when required, create it. “Establishing a board with independent outsiders was invaluable in helping me cut through the fog and make the changes that have made a huge difference,” said the distribution CEO.

Multiple CEOs recommended possible sources for these outside relationships including: peer organizations like YPO or Vistage, board members, retired executives, and executive coaches with operating experience.

The Right Answer Is . . .?

Several CEOs talked about dealing with more ambiguity than in previous roles – entering a world where there may be no obvious “right answer” to apparently intractable problems. Just because everyone is now looking to you for the answers doesn’t mean you always have them. Despite the value of outside advice, the CEOs I spoke with ultimately had to rely on their own judgment amidst this uncertainty.

“If I had hired consultants to tell me what was possible, we would have failed,” said the financial services CEO. 

The upside of not being perfect was that mistakes were turned into a discovery sequence: “We just got surprised. Clearly we didn’t know something important. Dig in and learn. Then, change the angle of our approach.” This organic process built problem solving skills that became a critical part of company culture.

A common theme was that there is “no grand playbook” from which to execute. “We’re all trying to figure it out,” was the consensus. And “the future is made one decision at a time.”

Cut Yourself Some Slack

“The older I get, the more I realize there is more I don’t know,” said the CEO of the distributor – a  theme that was repeated by other CEOs. This goes back to the need to grant yourself some grace to realize that you don’t know, or have to know everything in order to do the job. 

Whatever these CEOs might wish they’d known on day 1, every one of them learned as they went and has produced success for their companies and people they lead.  One CEO unknowingly echoed the exact words of my father in law, Duke Workman, who I admired as my second father. Her words, like Duke’s were: “Do the best you can.”

Do you have thoughts to add, or questions to ask of someone who’s been there? Feel free to reach out.