I have loved getting to know venture capitalists from all over the country during my time fundraising for my company QuotaDeck and probably will be back at it again next year for our series A round. One thing I love when talking to VCs is hearing about their experiences and background.

I was able to dive in deep with one VC who I have become friends with, Jason Portnoy or Subtraction Capital who lead me down his path of experience of working with some amazing Chief Executive Officers as a senior team member (during his operating roles) or as a board member and/or advisor (during his tenure as an investor). Being a CEO is a unique role that very few people on the planet get to experience. Hopefully some of these tips will help you make the most of that experience while you lead yourself and your company toward success.

1. Don't have all the answers

When you are building your company, there are a lot of decisions to be made. You do not need to have all of the answers. One of the most valuable things you can do as a leader is to create a culture where the right answers present themselves as quickly as possible and can be acted on as efficiently as possible. This means your business can't be so cluttered with noise and distractions that your employees can't hear the subtle signals the company is sending them about what it needs to scale and be successful. Be ruthless about subtracting things that are distractions for you and your top managers. Then have them use this approach with their direct reports, and so on. Done purposefully, your company will soon have very few distractions standing in the way of it's inherent success.

2. Take good care of yourself physically and emotionally

Your job is demanding and your physical animal needs to be healthy for you to think clearly. Eat well. Get a lot of sleep. Get some exercise. Pulling all nighters doesn't make you important, it makes you tired - and tired CEOs are not operating at peak mental capacity. For emotional health, Jason is a big advocate of hiring an Executive Coach or a Life Coach. CEOs bear enormous amounts of responsibility and pressure and typically have few people with whom they can share intimately enough to work through their thoughts. A trusted and objective outsider can help you process the normal emotional swings that come with starting your own company or leading a large organization.

3. Learn from The Five Dysfunctions of a Team

There are several key, yet subtle takeaways from this book that helped me immensely in my senior operating roles. One that seems to always come up in conversations and make an impression is just how short the list of responsibilities is for a CEO. These responsibilities are to:

  • Hire a great team,
  • Set the corporate vision, and
  • Lead and manage your team toward that vision

Jason says he typically advise CEOs to get themselves on a path where they aren't doing anything at their company except those three things. To be clear, this is not an easy list. If you are only doing these three things exceptionally well, you will find that they will soak up almost all of your time.

4. Communicate with your stakeholders

Sharing information on a regular cadence is the best way to build strong relationships with your stakeholders (employees, investors, key business partners, etc.). Your constituents should be advocates for your company, helping you source deals, recruit new team members and think through business strategy, and they can't do that if they don't have information. These communications should not be novels. You don't have time to write that and they don't have time to read it. A short monthly email with the following items is usually enough:

  • Reporting on basic metrics/financials and progress toward goals,
  • Framing of key company initiatives and strategy thinking, and
  • Rough plans for the next few months.

There is high correlation in Jason's venture portfolio between the quality, consistency and transparency (good news and bad) of company updates and the performance of the companies. They think there are several reasons for why this behavior is an indicator of success. One possible explanation is that writing updates forces CEOs to periodically take a step back and crystalize their thinking about their business more objectively, and holds them more accountable to goals which they've stated publicly.

5. Embrace your position as an inside-outsider

You are both an insider (as the chief executive) and an outsider (as a board member). You bridge the gap between the inside of the company and the outside world. Embrace this position. It is unique to you as CEO, so you have to take advantage of it. Get out of the office and circulate in the world. Not only does this increase the visibility of your company (you are the chief spokesperson), it takes you out of the day-to-day routine and helps you gain valuable knowledge and perspective that you can then assimilate into the company to help it learn, adapt and grow.

Published on: Oct 29, 2015
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