To Lonely Startup CEOs: Give This to Your Significant Other

September 17, 2010

If you are are the CEO or founder of an expansion stage technology company, pass this post to your significant other. If you have a significant other (boyfriend, girlfriend, husband, wife, life partner) who is the CEO of an expansion stage technology company, then read this post, because it is for you.

As the significant other of a expansion stage CEO, you probably have a roller coaster of emotions that comes along with the relationship. You have probably found that your lonely CEO is an extremely exciting and passionate person, and you have also found that your mate is stretched too thin, a bit obsessive with work, and is tired a lot of the time. This all comes as a package, but there are several things that you can do to help your lonely CEO improve the situation. You have influence over the situation and you can experience more of the highs of the relationship with your impressive CEO while experiencing fewer of the lows. This post is all about what you can do to help both your lonely CEO and yourself at the same time.

The Experience of the Significant Other of a Lonely CEO

Let me explain the situation as I have seen it play out. Your lonely CEO got an idea a while back and started thinking more and more about the idea, and started to talk to people about it. Over time, the idea grew to a point that your significant other gained some level of clarity on the idea and the idea stuck to a point where she started thinking about it all the time. It was like a movie, playing over and over in his/her head, each time edited and getting better with each iteration. At some point your lonely CEO started sharing the movie with others and got their edits. Over time, you lonely CEO fell in love with the “movie” and needed to turn the vision into reality. If your lonely CEO is like most, this is where it all began. The movie took control and your CEO had to make it a reality.

If you ask your significant other today why he/she is doing what they are doing, you might hear an answer that is something like “because I had to;” that is if your lonely CEO is being completely honest (some people invent more analytical or rational reasons, but “because I had to” is at the core for most).

Then, as your lonely CEO started telling more people about the movie (a.k.a. vision), he/she started inspiring others and getting more edits to the movie. This made the vision even better and started to become a shared vision with multiple people. Some of the people got inspired and couldn’t help but participate in the idea.

So the journey of realizing the vision began. Luckily (unluckily?), your lonely CEO was optimistic and did not completely know all of the challenges ahead or all of the bumps in the road. As your CEO and management team executed, lots and lots of problems arose and the management team managed to figure out ways to address them. Eventually, they got to a point that the customers really liked the product and more customers bought it. Over time, the product got better and more and more customers started purchasing it.

As new customers arrived, the number of new issues went up proportionately. Your lonely CEO hired more people, but the new employees made the number of issues go up, not down. It is an overwhelming time for your CEO and the team is stretched, but managing to handle it.

As the company entered the expansion stage, your lonely CEO became one of the loneliest people in the world. Essentially, the customers grew in number, the employees grew in number, and the number of issues and the skills required to address the issues exploded. The management teams at the company became saturated with issues and the overload became even more intense for your CEO, where all of the unresolved issues ultimately landed. This made your mate overwhelmed and lonely.

From your perspective, you have probably seen your lonely CEO less and less and also see a much more tired person during these shorter and shorter windows.

The Team of the Lonely CEO

I wrote about the lonely CEO, what the lonely CEO can do to improve the situation, what the management team can do to improve the situation, what the Board of Directors can do to improve the situation, and what the Venture Capitalist can do to improve the situation.

Now, here is what you, as the significant other of the lonely CEO, can do to improve the situation for both you and your mate.

You are probably probably the single best person to help your mate, as you are in a unique position of understanding, trust, and objectivity that no other person has. You have one of the most unique and talented people in the world as your mate and, while your lonely CEO will always be driven, there are several adjustments that you can help make that will make things better over time, as I discuss below.

Addressing the Situation

First, really try to understand your lonely CEO’s specific situation. You can get some generic insights here, but try going out to a quiet dinner, feeding your mate a couple great alcoholic beverages and asking about the situation may really help your understanding. Just talking about it will help, but the key is to try to get to the two or three issues that keep your lonely CEO up at night. (note: if this doesn’t get a conversation started, try more alcohol… but take a cab home!)

Once you do this, and after the effects of the alcohol wear off, you should try to help your mate with the following items.

Ask your mate what the long term goals are for the company.

…just the next year or so. If you don’t get a crisp answer with less than a handful of clear goals, suggest to your mate that clarifying the goals for both your CEO and for the management team would be a really good thing.

What is your mate doing that he/she should not be doing as the CEO.

Focus is one of the most important things that a CEO can do, but most try to do too much and get stretched too thin. They also work on many issues and activities that they should be delegating, but they are used to doing it themselves and need some ongoing nudges to pass the work to other people, or to eliminate the work by focusing on fewer clear goals.

If the longer term goals for the company are clear and shared by the management team, then the issues that keep your mate up at night are people-related at their core* from the CEO’s perspective (want more awareness and sales leads? It is a people issue at its core. Want more sales? A people issue too. Specific issue in a department? It is ultimately a people issue). Identify the person or people that will help resolve the 2-3 major issues that keep your mate up at night. Start with an issue and ask why the issue exists. Then keep asking why (while trying not to be too annoying).

Try to get to the bottom of whether the people issue is management team, board, or investor related as identifying the core will help to identify possible ways to address them.

Help your mate figure out one thing that he/she will do differently (for now).

It probably boils down to clarifying goals, focusing more, or addressing a specific people issue (hiring a person, or working through a problem or opportunity with one or more people). Note that there are probably lots of things that your lonely CEO can do, but take them one at a time as this is a long-term effort.

Unfortunately, this is not a single event, but rather an approach that you need to keep taking repeatedly if you really want to have an impact. The questions are valuable to your lonely CEO, as they help to clarify what to do to improve the situation. You are not really solving the problem, but rather helping your CEO solve the problem through your questions and repeating the questions regularly (weekly, monthly or quarterly, depending on your relationship and inclination). This can really help clarify the ongoing changes.

Over time, if the situation does not improve for your lonely CEO, it may be time for your mate to “pull the ripcord”. Not everyone is really passionate or really good at being a CEO and many CEOs of early stage companies are not as passionate about the work when the company gets into the expansion stage, where the work becomes more about clarifying the goals, getting the right people, and getting the people to work together well to realize the goals.

Your CEO may be happier hiring a new CEO and taking a more specialized role in the company or, perhaps, moving to a new earlier stage company. This gets pretty tricky because there are a lot of emotions involved, but the real test is asking the question, “are you as passionate about what you are doing as you were last year or two years ago?” Then ask “why or why not?” The answer to the question may be telling.

My general sense is that giving the questions a go will shed some light on the situation and at least make your understanding of the situation better, and make your lonely CEO at least feel less lonely as a result of your support. I suspect that your lonely CEO will find that your questions lead to answers and, ultimately, actions that help your lonely CEO.

Good luck with it and let me know how it goes!

*Note: If the goals are clear and shared by the management team, then the issues from the perspective of the CEO are people issues. That’s because the CEO should generally not be addressing the specific issue directly, but rather working through someone else to address the issue, thereby making the issue a people issue from the CEO’s perspective. The CEO should be addressing the people issue and that person should be addressing the issue more directly. Clearly, the CEO has work to do to address the people issue and might help the person address the issue directly for development purposes, but the core issue remains a people issue.

Founder & Partner

As the founder of OpenView, Scott focuses on distinctive business models and products that uniquely address a meaningful market pain point. This includes a broad interest in application and infrastructure companies, and businesses that are addressing the next generation of technology, including SaaS, cloud computing, mobile platforms, storage, networking, IT tools, and development tools.