What have you been running away from in your role as CEO?

This blog was written by XSeed Capital Partner, Robert Siegel.

Being the CEO of an entrepreneurial venture is unbelievably hard. Not only are odds wildly stacked against one’s success, but unlike in a normal job, the CEO does not have anyone telling him or her what to do. Of course, many people tell the CEO what they should do, but no one tells a CEO where to spend one’s time on a daily or weekly basis where a person is compelled to do what he or she is told.

Fundamentally, a CEO has three responsibilities: 1) Set a vision for the company, 2) Build a great team, and 3) Don’t run out of money. How a CEO accomplishes these things is what often separates a great CEO from an average or poor one.

Managing one’s calendar is one of the hardest things for any CEO to do; since one’s actions have disproportionate impact on the success or failure of the company, knowing where to spend time and where not to waste one’s efforts is critical for a company to have the chance to succeed.

I recently pinged a handful of XSeed’s CEOs and asked them, “What have you been running away from in your role as CEO, but shouldn’t, and why?”  I received many insightful and thoughtful answers.  Broadly speaking, their feedback fell into five buckets:

  • Spend Time Where You Are Weak: One CEO shared how he really enjoys focusing on his product and does not spend enough time out at customers.”  It’s easy as a CEO to justify that the travel time and time away from the office is a hefty cost but there’s nothing like hearing firsthand from customers about how they feel we are serving them and things we can do better.”
  • Grow as Your Company Scales/Build Your Team: The role of a CEO at the founding of a company is different than when a firm is post-Series B. I remember when I ran my first startup how I learned that I needed to change my behaviors as the company evolved. As one of our CEOs said, “As an entrepreneur who thrives on results and execution, moving back from the front-line is difficult but necessary for us to achieve great scale. As a post-Series B company, I need to spend less time doing the work and more time building the organization’s capabilities.”
  • Don’t Avoid Things – Either Large or Small: Several CEOs commented on the importance of not avoiding hard conversations.  Said one, “The CEO’s role is (unfortunately) to have the toughest conversations that no one else wants to have. Those are conversations like: explaining why we need to make a big personnel change, explaining to a strategic partner what isn’t working in the relationship, telling a board member they need to step down, telling the team that they aren’t taking quality serious enough, etc. It’s just the things that every sane person tends to procrastinate about because doing it is so uncomfortable.”

If the CEO won’t have those conversations, usually no one else will either.

Or, as another CEO pointed out, “I frequently find myself running away from making decisions that need to be made, but are not yet pressing. The problem with this approach is that I end up in paralysis through over-analysis. So many decisions are interdependent and when I’m delaying making one, I’m inadvertently increasingly the number of permutations I must think through for every related decision. This causes fatigue and slows down the pace of our organization.”

I’ve often said to our CEOs, “Make mistakes through action as opposed to inaction.” While one wants to be prudent and not rush too quickly through things, taking too long can cause unnecessary delay in long-term execution for a firm.

Or, as one of XSeed’s LPs is fond of saying, “Perfect is the enemy of good.”

  • Always Be Selling: It’s an old saying that others are finally understanding your messaging just at the point that you are sick and tired of saying it. As one CEO commented, “I run from marketing as I feel the product is unique and consistent ROIs are documented, so why do I need to continue and remind people of its value across multiple channels (social media, events, digital campaigns, etc.)? Yet, the brand and ultimately growth is based on this perception created through marketing, especially in the modern era where sales decisions are now often made before even encountering a [customer].”
  • Ask for Help: Being a startup CEO can be brutal. You are constantly struggling with understanding if you are being a visionary or if you are just wrong about things. As the leader sitting at the top of the company, a CEO often feels that he or she is supposed to have all of the answers. Several of our CEOs commented that they need to do a better job of asking for help from others. Said one, “[Not] asking for help is the thing that has probably hurt us the most.  That manifests itself in a bunch of different ways.  I wish I was reaching out to investors more often to help with leads and operational advice. I would be better served to ask for help internally as we wade through new challenges. I hesitate to lean on my professional network unless I feel like I’m providing a fair value exchange (and often I have nothing of value to exchange). The disappointing part of all of this is people are usually more than happy to help if they can – I just need to ask.”

So, what problem are you running away from that you shouldn’t be, and why?