I recently got to chat with Harry Stebbings on the 20 Minute VC Podcast, covering a range of topics including:

  • How what it takes to be a great CEO has changed over the last 30 years
  • Whether “management upscaling is the most important role a CEO can do
  • How “the old school CEO approach is upside down and backward?”
  • What the fundamentals are to ensure your executive team are aligned and working in tandem
  • Why transparency across the organization is fundamental to both efficiency and culture?
  • Why cloud companies have to be customer-centric like never before

If you’d like to check out the full episode, that can be downloaded here. I also wanted to share a few key highlights from my conversation with Harry in the following Q&A four part blog series. If you haven’t already gotten a chance to read my first and second post, be sure to read that before starting part three below!

Harry: We talked a lot previously about the term “culture.” What does that really mean to you at its core?

Rob:  Harry, I think there are a number of key factors that contribute to a winning company culture. What I’ve learned over the years is that the most important thing is to have an inspired, solid mission.

As the CEO, I know that it can be very difficult to pull the organization together and set the tone for this culture that we’ve been trying to define here.

That really comes down to making sure everybody has a sense of ownership; those key traits of an organization turn coworkers into being teammates.

Culture really comes down to how you get teams to communicate, embrace the overall goals, and come together with plans.

One of our values at Sage Intacct is, “Kindness always; no jerks here.”

People will have different ways of approaching a particular initiative. You want them to bring forth those experiences to maximize the overall planning as you go forward. Depending on the way someone brings forth those experiences, it could turn a difficult discussion into a terrible discussion. That’s where we train people about how to bring forth their ideas in a conducive manner. Not attack others, not put others down but to make sure that we’re building on each of the experiences as we determine the right outcome.

Harry:  If that’s the right structure then to really get that optimal culture, I’m intrigued, where do you think many go wrong in that desire to create this high‑performance company culture?

Rob: I think that one of the pressures that you have in Silicon Valley, and with organizations even outside of Silicon Valley, is that there’s so many things to do that a CEO could stay very tactically focused on execution. We keep trying to move the needle day by day by day. There are always so many things to do, and you’re usually up against bigger competitors, so you have to be agile.

You have to be able to adjust to what’s going on in the market day by day by day. If you don’t create the framework we discussed up front about what’s the overall mission, why is it inspiring, what are the goals, and then setting up the objectives… that day‑to‑day agile approach actually can get you into trouble.

As Yogi Berra said, “When you get to the fork in the road, take it.” You may end up somewhere you didn’t expect to be.

Check out the final post of this series next Thursday!