Leadership is Lonely

There are times along a startup CEO’s journey that are profoundly lonely. It is the nature of the role.

While having co-founders increases a startup’s chances of survival and building a team is an essential step along a successful startup’s path, the role of startup CEO can be lonely.

It often feels like the only ones who can understand a startup CEO’s perspective are other startup CEOs. There is a burden of responsibility and a breadth of perspective that is unique to the role itself. In a very real sense, you do not have the support of a boss for when decisions get murky and difficult. Your team looks to you to balance the most critical priorities facing the startup.

While a startup CEO needs to pay attention to essentially everything in the startup, some of the areas that the CEO must attend to can by nature be pretty solitary journeys. For example, a CEO takes the lead on the following essential areas:

Investor Management

Investors are betting on the horse (the company) and the jockey (the CEO). To succeed in securing an investment, the CEO must establish a trust-based relationship and then build on that relationship with effective communications. Many major investors will call periodically to chat. There may be post-Board meeting executive sessions with pointed questions and feedback for the CEO. Those conversations can be quite tricky – and often, the CEO is on-the-spot on their own to address investor concerns. From an investor’s perspective, ultimately, the CEO is responsible for everything that happens in the startup, good or bad. The CEO either causes, enables, or fails to execute to accomplish the startup’s goals with every resource the startup has available. It is a lonely responsibility to be in the chair where the buck stops.

Strategic Decisions

While many may have input, the CEO is ultimately on the hook to make the final call on the high-potential startup’s critical strategic decisions. Deciding how much to invest in what activities to efficiently achieve the startup’s vision involves constant identification and synthesis of many factors, both known and those still emerging. It could involve balancing between spending fast enough to develop momentum and wisely enough to have the resources to react to the inevitable setbacks. Or, how to create strategic relationships that add value without creating unwanted entanglements. Sometimes there are wrenching decisions and tradeoffs that must be made. I remember nights spent awake wrestling with how to prioritize conflicting interests, deciding on the least bad path to take, and picking up the phone to just deal with the major issue at hand.

People Management

Leading a company means building and leading a team. It is simply impossible to scale a high-potential company as a one-person show.  Teams are composed of people. Recruiting, compensating fairly, and motivating people according to their unique needs requires insight and finesse. As the team grows, managing people challenges becomes an ever-increasing part of the CEO’s job. While identifying people problems often becomes easier with experience, addressing them effectively with clarity, grace, tact, and confidentiality while managing those who remain is always a challenge. When those people problems emerge in the CEO’s inner circle, figuring out how to sort through the complex tradeoffs to make the best decision for the company is terribly hard – and can be some of the loneliest decisions for the CEO.  

The common thread in these essential areas is that they demand the comprehensive point-of-view that only the CEO naturally has, and they often involve difficult tradeoffs between competing options.  Sometimes a partner-team member can provide input, but ultimately the hardest decisions often land in the CEO’s lap for the final call.  The fuzzy, contradictory, or high-stake ones put the CEO in that lonely spot. If you do not wish to stand in that spot, then find another role to occupy.

To learn to navigate these tempestuous seas, I can only offer a few tips.

• Personality matters. Do you have the personality that is willing to take that ultimate responsibility?
• Continuing to grow and learn as fast as you can provides the raw material for sound decision-making. Often, you have to take ideas from various places and adapt them to your specific circumstances. While you can and should always glean new insights from many places, I do not believe there is a class, accelerator, or degree program that will teach you the job of startup CEO. Much of what you need to know, you will have to teach yourself on-the-job.
• Mentors and peer accountability partners are an invaluable source of new insight into the complicated decisions I need to make as CEO. Regular coffees, lunches, or texts with CEO-peers/mentors can provide knowledgeable, confidential sounding boards that are just far enough removed from my day-to-day to understand the CEO point-of-view and help me craft a nuanced path. Over the years, I have cultivated mutually supportive peer CEO relationships to give both of us the support we need.
• A supportive spouse or friend who cares about you as an individual can provide that dollop of emotional support when you are staring alone into the void. A strong faith can help put the world into a manageable perspective.

When someone asks me about becoming a startup CEO, I always try to talk them out of it. Most of my C-level leaders tell me at one point or another that they would never want my job. For those of us for whom the role fits well, know that there will be lonely times in the journey, but that is one of the costs of leadership.