Clear-Eyed Optimism

A strong entrepreneur will be able to develop and project confident optimism about the opportunity they choose to pursue. Yet, it is critical also to be clear-eyed about the risks and hurdles that must be overcome to accomplish the dream.

Investors, team members, and early customers are all looking to a founding startup CEO for passion, enthusiasm, vision, and confidence. The founding CEO is the face of the startup. They must be able to craft a vision and a story that encourages others to get excited and join in. To embody this leadership role successfully, the CEO must be able to be both deeply knowledgeable about their chosen opportunity so that they can answer the many questions about the layers of details and be passionately convinced themselves about the potential. They must believe to be authentic in persuading others to believe.

However, it is possible to take their conviction too far. Drinking one’s own Kool-Aid (meaning to wholeheartedly and without reservation believe in one’s vision and the perceived potential high rewards) can be dangerous. While a strong leader needs to be able to articulately cast an optimistic vision of the future, as a CEO, it is imperative to also stay grounded in the reality that all startups are risky and achieving success requires many factors to break in your preferred direction. Building a successful startup is always, always, always hard – much harder than it looks from afar. Sometimes, despite optimism and passion, all the puzzle pieces fail to come together.

Solving the myriad problems that will emerge during the journey of a startup from ideation through inception to ultimate growth and profitability requires anticipating and perceiving those problems and figuring out practical solutions that fit the startup’s stage of development and available resources. In other words, in addition to maintaining their optimism, the CEO must be clear-eyed and grounded in the reality of the struggle. Otherwise, the potential for being sideswiped or unexpectedly crushed goes up exponentially.

So, how does a CEO balance sharing their passion and delivering an optimistic vision while simultaneously paying attention to and addressing the difficulties, downsides, risks, and setbacks? Here are some strategies I have found helpful:

• Constantly evolve that optimistic vision – Successfully leading a startup does mean crafting a continually evolving vision of how the company can grow into a great success. You must be able to weave together and defend all the elements required to build a successful business to inspire others to join in and support your efforts. Unfortunately, if you showcase your doubts, it can really scare others. This reality creates tremendous pressure to continuously project that positive, forward-looking image to build the confidence of others in your leadership. Doing this aspect of leading a startup is essential.
  
  
• Connect with other CEOs as mentors and mutual confidants – The reality is, however, that you will have doubts, questions, skill gaps, and weaknesses. While you cannot publicly process all of that, it is critical that you seek out others who will understand the complexity and demands of a startup CEO’s role so you have a safe space to trade insights and support. From my experience, the best resources for this are fellow active or former CEOs who “get” what a CEO’s world looks like and understand the complex demands you are facing. Today, I find that the greatest help I can give to those first-time CEOs I am mentoring is to be an understanding encourager and someone who can relate to and provide suggestions on addressing some of the hard decisions we all sometimes face. I have found that colleagues and family members are often supportive but unable to relate, so while they have a role to play, finding peers is often critical to getting good, honest feedback on the day’s issues.
  
  
• Actively seek out the pessimistic views and look for the problems – Few people want to tell you that your “baby” is ugly, so sometimes negative feedback is delivered wrapped in soft clothes. Yet you must actively seek out and listen for the nuggets of truth implied by confused potential customers, skeptical potential investors, risk-adverse potential partners, and many others. You have to step back and consider the macro trends and emerging competitive factors that are changing the environment around your startup’s opportunity. It is just so important to be wise about whether the timing, competition, customer needs, technology under development, and other factors are still lining up for success or if something critical has changed. Sometimes, there are shifts that you need to detect as early as possible because they mean that your chances of success have dipped to levels where you have to consider how long you will keep going and if it makes sense to keep draining everyone’s time and resources for a diminishing chance of success.
  
  
• Sometimes, you have to call it – The headwinds on a startup can be tremendous. Every startup I have been involved in has gone through near-death periods when we had to consider whether it was time to call it. Sometimes, despite the naysayers and skeptics, we found a way through and achieved the hoped-for success. Sometimes, I looked hard at the future and the trajectory of our key success factors and had to conclude that we were not going to be able to pull it off and that we should make the hard call to stop. When you are in the middle of the race, it can be tough to see around the next turn accurately. Still, it is the job of the startup CEO to consider all of the information available and chart the course forward, even if that means pulling up your horse and stopping instead of continuing to drive forward. You must decide what the best path is for all of the stakeholders. This is one of the essential jobs of a good CEO.

Most of those involved in a startup contribute but are fundamentally relying on others (often the CEO, who is best positioned to have all the relevant details if they are doing their job well) to make the critical go/no go decisions. A “go” means accurately seeing what will undergird a successful run and conveying that optimistic vision so others can enthusiastically follow and contribute. A “no go” requires always maintaining an open mind that sees the evolving situation and its implications with clarity so that if the tides turn against you, you can either find a way to navigate through the crisis or, if that is not possible, make the hard choice to wind down with integrity.