CEO Whispering

The job of a startup CEO is multi-faceted and endlessly challenging. Yet, there is no degree or comprehensive playbook out there to provide the training for how to succeed. Enter the “CEO Whisperer.”

Stepping into the role of startup CEO for the first time is a bold and courageous act. While each of the following experiences is helpful, none are enough on their own to cover the entire gamut of skills required to tackle the job:

• An MBA provides business vocabulary, tools, and frameworks, but typically lacks practical application in the multi-disciplinary management demands of a startup CEO’s role.
  
  
• Big company functional experience is a great way to get foundational expertise in one of the core operating disciplines (sales/marketing, operations, technology, etc.). Big companies are often well-equipped to provide that initial practical education a new professional needs. However, it is easy to become dependent on the resources of a big company, so the experience ultimately becomes just a good building block, but don’t stay there too long.
   
• Business consulting can provide diverse experience that helps produce the breadth of problem-solving a startup CEO needs. However, consulting work is often project-based and does not build the core operational skills a startup needs, so again, it is a useful but incomplete set of experiences.
  

• A non-CEO job in a high-potential startup provides profoundly helpful experience in the challenges of a startup. Yet, no other job has quite the mix of responsibilities that a startup CEO must cover. Common gaps include fundraising, investor relations, product-market fit oversight, team recruiting/management, and financial, legal, and regulatory strategies.
  
  
• Incubators, books, online resources, and talking to experienced CEOs can help identify and fill in knowledge and skill gaps. Developing the skill set of a startup CEO will demand some self-education to fill in the gaps, so be sure to talk to experienced CEOs and start learning as much as possible. The key is that you have to be willing to learn about all kinds of different topics because you likely will not have a team of people you can delegate to, so you have to prepare to do or actively supervise many business-building elements yourself.

While these experiences can provide useful building blocks, figuring out how to weave them together and tackle the never-ending stream of challenges a startup CEO must face is demanding. When I stepped into the startup CEO role for the first time, I had touched on each of the above to a greater or lesser degree, yet I was still confronted by doubters and had to figure stuff out on the fly. I sought out and cultivated relationships with other successful startup CEOs to fill in the gaps as I clamored up the learning curve as quickly as possible.

Now, decades of experience later spanning many startups, I find myself leveraging those experiences to help other startup CEOs, especially first-timers, in their learning journey. In the last couple of years, I have settled into the space of being a “CEO Whisperer,” as a consultant-coach, as a Board member, and as a blogger and contributor to the startup ecosystem. With this new perspective, I thought it might be worthwhile to describe what I have learned from both sides about the role of a CEO Whisperer.

The descriptor “CEO Whisperer” was a term I was introduced to as I pursued some Board service education. It refers to one of several common roles for Board of Directors members to fill, and looking back, I can spot influential mentors in my journey who clearly filled that role for me early on. Certainly, there are other Board roles, however, the role of a “CEO Whisperer” usually is filled by someone who has done that job before in a similarly sized organization and industry. The CEO Whisperer Director can leverage their experiences to help the CEO of the startup succeed, which is why this is often a valuable and sought-after skill set in independent director searches.

Besides an independent director, there are other ways to introduce a CEO Whisperer with enough commitment and capacity to make a difference. A consultant/coach with the right experience can fill that role, and sometimes, I have been hired by early-stage investors to help some of their possible portfolio company first-time CEOs. One of the possible value-adds of incubators and accelerators is access to CEO Whisperers, however, make sure there is enough time built-in to provide significant coaching. I have found that sometimes finding someone who can spend a few hours a month over many months is the most helpful, but that can be ramped up to someone who can connect every week. Regardless of the source, make sure you find someone who has done the job themselves and figure out a relationship that can work for both sides.

Critically, being a CEO Whisperer is not the same as being the CEO. In fact, it is crucial for both the CEO and the CEO Whisperer to be clear on the differences for the relationship to be successful. Now that I have been doing this role for a number of years (starting while I was an experienced active CEO myself), I have gleaned a few lessons to guide both sides to help find the necessary balance for a productive relationship:

• Often, the CEO is looking for a sounding board to help provide context-relevant information for sound decision-making. Relatively new CEOs frequently face new situations they have not confronted before, and they need an experienced and confidential perspective to help identify risks that might be present, steps that might be required, and actions that are likely to be wise and successful. In these circumstances, a CEO Whisperer with multiple experiences in similar size, stage, and industry situations can draw on those experiences to help.
  
  
• Recognize that the final decisions on what the corporation will do are the CEO’s to make. The CEO Whisperer can share past experiences, highlight essential decision factors, and make recommendations, but the decision must ultimately lie in the CEO’s own hands. Tempting as it may be, if the CEO Whisperer starts making the decisions themselves, they are usurping the role of the CEO. Similarly, if investors bring in a CEO Whisperer, they need to be clear that the Whisperer is not there to take over for the actual CEO.
  
  
• The CEO Whisperer’s most potent tools are thoughtful questions and real examples tailored to this startup’s circumstances. The value of a CEO Whisperer’s experience is in the application to the startup’s current circumstances, so carefully consider how their circumstances are similar or different from the example being used as inspiration. Help unpack the variables and reasons why so the CEO is equipped to make a wise call as they grow their own reference scenario base.
  
  
• The CEO Whisperer should use phrases like “I recommend” or “I suggest” instead of “you must” so that the CEO is constantly encouraged to make and own the final decisions. Then, if the CEO decides differently than the recommendation, the CEO Whisperer needs to remember their role and let the CEO’s decision stand. This is how the CEO continues to grow into their role.
  
  
• Ultimately, both sides must be willing to invest in building a solid relationship. Working out communication style differences, appreciating unique backgrounds, and investing to build trust and respect are essential to an effective relationship. Trust your instincts if you feel the possible CEO Whisperer has more than your best interests at heart or is hunting for their next CEO gig.
  

Learning the job of a startup CEO is an intensive personal journey and will require weaving together many threads. Finding the right CEO Whisperer can accelerate the process, although availability and capacity are always challenges. Yet I would be remiss if I did not mention the possibilities of this sort of powerful resource so it is on your radar screen if the right situation presents itself.