What I Wish I Had Known Then … As a New CEO

By: Deborah P. Rubin

Many successful CEOs admit that they experienced a steeper learning curve than they had initially anticipated. To help accelerate new chief executives through this arc, we asked experienced CEOs what they wish they had known when they first stepped into the role. Their responses converged on six main themes.

1) Align Strategy and Tactics

Depending on the CEO’s background, the dance between strategy and tactics can be challenging. The pull into tactical issues can lead some to neglect the 50,000-foot view, while the more strategic-oriented can underestimate the need to ensure that conversations go deep enough to link to actual movement on the part of others. As one CEO noted, “What I wish I had known when I took my first CEO role was how challenging it is to navigate the horizon of difference between strategic thinking and tactical thinking—where strategic thinking merges into tactical and where tactical actually helps define your strategic initiatives. In the initial period in my role, I found that I got more bogged down in tactical and day-to-day issues than was necessary.”

Lesson: Engage your leadership team both in defining the strategy and thinking through how it will be executed; make sure everyone involved in implementation is clear on their role.


2) Elevate and Delegate

The ability to remain at a strategic level requires a realistic appreciation for what the CEO can no longer control or lead. While most senior executives have led large parts of the organization, the step into the CEO role represents a surprisingly exponential change in complexity, requiring rigorous prioritization and delegation. As one CEO notes, “I would have liked to have had a better grip on the breadth and scope of the responsibilities. I understood the position description intellectually, but I admittedly (now) had not digested the physical and emotional tug-of-war that ensued. I was initially frustrated by the competition for my time and energies and the difficulties in assigning priorities and combatting the urgent.

Lesson: Invite input from the outgoing CEO, board members, and key members of the senior leadership team on translating the job description into time allocation. This will allow you to deploy yourself according to the priorities set by you and your board.


3) Track Progress

With the increase in delegation comes the need to track progress and ensure that the impact matches the intended goals. One executive wished for earlier awareness regarding “the importance of having a trusted system for tracking desired outcomes, next actions, and agendas/talking points/questions simultaneously for various meetings/departments/people for a busy schedule.” Another noted,It is not always clear that the day-to-day tactical work is being done in a way that is consistent with the overall goals of the organization because so much of it takes places at a level that it is hard to see as a CEO when you are dealing with so many different constituencies.”

Lesson: Set up the metrics and dashboard you’ll use to gauge how your objectives are being accomplished, and use them to adjust your actions and those of others as needed.


4) Communicate

CEOs must manage a diverse group of internal and external stakeholders, rapidly filling their calendar with an unremitting cycle of calls, meetings, and travel. All together, this can quickly generate wear and tear on the executive. Many CEOs underestimate the personal investment needed to build relationships with board members and ensure alignment on key issues. As one CEO reflects, “I do not think anyone realizes how much time is required of a public company CEO to keep shareholders and people informed, not to mention the board.” However, as time-consuming as communication can be, it is also a key lever for the CEO in creating a shared view of the roadmap, building commitment and energy, and highlighting the challenges. One CEO wished for earlier insight on two areas relating to this communication theme: the realization that “conversation is the most powerful alignment tool” and ”the importance and power of asking good and appreciative questions.”

Lesson: Identify the stakeholders who are critical to the agenda you are leading and with whom you need to communicate directly. Delegate in other areas to make room.


5) Cascade Change

For new CEOs stepping into the role with a compelling change agenda, realistically calibrating the pace can be challenging. When the roadmap is clear, it can be easy to underestimate the time needed to cascade the change throughout the organization—the critical point where logic and human dynamics intersect. “I wish I had understood the amount of time it would take to reorient the whole company to a new structure and leadership model. Although the leadership team quickly coalesced around a new model, the digestion time further down the organization was longer than I expected—or maybe better said, longer than I hoped it would be.” 

Lesson: Set and convey realistic expectations for what can be accomplished with interim benchmark goals. Be prepared to recalibrate.


6) Find and Keep the Right Talent

The human side of the equation was cited frequently as a critical driver that CEOs wished they had appreciated earlier in their tenure, including “the importance of establishing a culture of values and recruiting and retaining the best talent possible.Ensuring the right leaders are in the right roles is a familiar responsibility for most executives. However, a clear-eyed view of what is required is even more critical for the CEO role, given the conflicting pulls on his or her time.  While an executive may have been able to shore up a direct report’s gaps in the past, a new CEO is unlikely to have the bandwidth for this type of triage. As one experienced CEO observes, “I wish I had understood the importance of hiring like-minded and talented people. I thought I could help anyone improve.” In addition, senior executives with deep experience running the organization’s business units can tend to underestimate the importance of having top-notch players leading the functional positions such as the CFO, CHRO, or GC, and how strategic, savvy people in these roles can generate real momentum for the organization.  

Lesson: Conduct rigorous assessments of everyone who is in a mission-critical role and act quickly to ensure you have the right team to drive the culture and results you are being paid to deliver.


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Successful CEOs typically bring a mix of confidence, curiosity, and a realistic view of both their limitations and the levers they can pull in the organization to realize their agenda. We hope these hard-earned insights will help move areas to the foreground that may have been less clearly in focus. Our goal is to accelerate the learning curve without diminishing the fresh perspective, energy, and sense of purpose on the part of a new generation of CEOs.


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