EP19: Four Traits of High-Performing CEOs

by | Feb 28, 2023 | Marketing, Podcast, SaaS


Welcome to the In Demand Podcast where we talk about how to reach your first $1 million ARR.

I’m your host, Asia Orangio, founder of DemandMaven, where we work with early stage SaaS companies on reaching their very first growth milestones. Let’s do this.

Today we’re talking about what ultimately makes a high-performing CEO. What does a good CEO look like and what are they doing?

Many founders in the SaaS and software world think that certain CEO advice isn’t relevant to them. However, I think it’s the opposite. CEO advice is more relevant to startup founders as they enter very unknown territory for them as developing leaders. The best way to become a great CEO is to be exposed to many different types of educational knowledge, so you can apply and leverage as much wisdom as possible.

According to Harvard Business Review, there are four things that set successful CEOs apart:

  1. Decide with speed and conviction
  2. Engage for impact
  3. Adapt proactively
  4. Deliver reliably

Make decisions

Decision making is one of those skill sets that, for most of my career, I didn’t think about how well I did it or how quickly.

It actually wasn’t until I was running DemandMaven that I realized I was becoming more and more conservative whenever it came to making decisions. It became much harder for me, and it got to a point for me where I realized this has to improve. I wanted to be able to:

  • Make decisions quickly
  • Trust the decisions I was making

As a CEO, it’s important to make good decisions. And while these decisions don’t have to be perfect, they do have to be fast.

They also need to be made without complete information, which can be really terrifying for anyone who wants to have 100% of the info before making a decision. There’s no way to predict everything. When CEOs don’t make decisions, it blocks everyone from taking action, period.

In fact, perfectionism can be a huge barrier to being CEO. It can hinder a CEO from making quick decisions with conviction.

What’s really fascinating about decision-making as a CEO is that it’s actually better to sometimes make wrong decisions than no decisions at all. At the very least, when you make the wrong decision, you’re making progress by learning how not to do something. You can then move forward with a lot more information. When a CEO stalls a decision and the entire team waits to take action, you’re losing precious time.

One of the top reasons why startups and SaaS companies fail, of course, is due to product market fit, i.e. there’s no real need or demand for what the product is ultimately solving. Or, the company can’t find enough customers. Another common reasons earlier startups fail is by not executing fast enough, which is basically another way of saying not making decisions fast enough. Because in order to take action, decisions need to be made.

CEOs of large companies (let’s say running $50-100 million dollar companies) need to minimize risk as much as possible because there is a lot to lose. But for earlier-staged companies or even bootstrapped companies, there’s very rarely a decision that will completely put you out of business. It’s very rare to find excruciatingly wrong decisions. As long as you learn from mistakes and course correct, you’re almost always going to be fine. This goes back to the decision making process. If you can make decisions quickly and learn from any errors, then you’ll be okay. But if you’re too slow to take action, the company might not be able to keep up in the market.

As the CEO, you’re the leader and deciding things with conviction (even if they end up being wrong) is ultimately healthier for the team so there’s always a clear sense of direction. It’s okay to course correct as a team, but a team without any direction is not going anywhere.

Here are two questions to ask yourself when making a decision:

  1. What is the impact if I get this wrong?
  2. How much will it hold things up if I don’t make a decision on this?

Avoiding making a decision is an avoidant behavior and it’s a very common pitfall as founders transition to CEO.

Here’s the other thing about being a CEO and making decisions: not every decision is for the CEO to make. Ideally, the CEO is surrounded by strong teams of people who support them in their work. Assuming they’re experienced enough, it might make sense for the CEO to strategically pass off decisions to other stakeholders. This is something I’ve been personally transforming internally at DemandMaven.

As the CEO at DemandMaven, I’ve gotten better at fielding questions from the team and understanding when a question is in my realm to answer and make a quick decision, and when it’s an opportunity to guide, coach, and ask thought-provoking questions for the team so that they ultimately arrive at an answer on their own.

One great example of this was when we needed to re-package how we do retainers here at DemandMaven. We were running into a problem where we would sell a retainer but it was work that only I could deliver on the team, which is a problem, because as CEO, I’m not the best person to execute on a retainer. I consider myself a SaaS marketing ghost: I’m there when summoned, but for the most part, I’m ideally just quality control. So when we kept running into this problem, I ultimately brought the problem to the team and they decided for me. It was awesome. We ended up walking away with a far better understanding of what was required from a retainer perspective. Moral of the story: CEOs don’t have to make every single decision. Sometimes, the teams they rely on can help.

Engage for impact

Engaging for impact is ultimately about moving towards your growth goal effectively, getting everyone on board with the decisions, and moving in the same unified direction with team buy-in. It also means understanding what the problems are and having the right people on board to address those challenges. As a whole, engaging for impact is making sure all of these pieces of the puzzle are aligned so that the company can achieve what they’re hoping to achieve.

In order to do this well, CEOs have to be really good at communicating with the team. Whether your team is just a few people or way bigger, it’s still important. When communicating with the team, it can be helpful to remind people time and time again. You have to be good at communicating ideas to other people. For example, at DemandMaven, I often communicate to the team: here’s where we’re going, here’s your part in this, and ultimately, it’s a matter of depending on your team to contribute in order for the goal to be achieved. A key part of getting the team on board is communicating all of this in the first place.

And last before we move on, it’s important when engaging for impact that CEOs don’t avoid conflict. When CEOs can dive in head-first into the problems, they’re going to eliminate roadblocks much quicker than a CEO who avoids them. In the book Traction by Gino Wickman, he recommends creating an actual database where you track problems. For example, what roadblocks are consistency slowing down your team? The CEO can and should spend time reducing those problems as much as possible to give the team a much better experience as they execute. These could be challenges related to culture, hiring, team, or even technical workflow issues.

Adapt proactively 

One of the roles of CEO is to spend their time on thought-provoking information and insights that they can use to influence the company. For example, as the CEO of DemandMaven, I’ve been keeping a very close eye on the impending economic downturn because it might greatly impact my clients who are VC-funded, as well as my own business. It’s my role as CEO to understand how this greater market shift will change things and how we might need to adapt proactively as a result.

The best way for a CEO to keep tabs on their market is to conduct objective structured research.

Another example where this comes up is customer research. We perform detailed customer research for clients here at DemandMaven and we’ve seen with clients at times that their target customer base can have one JTBD profile one year and potentially have a shift by the next year. CEOs that are regularly researching not only the market, but also their core audience, can ultimately adapt much more proactively.

Deliver reliably 

As CEO, it’s your role to unpack and figure out: where does performance fall apart? Where can we take responsibility and hold ourselves accountable, while also giving ourselves grace and compassion for not being perfect?

Here’s what I’ve learned in my career:

In order to deliver reliably, you don’t have to win every single time. This was something that gave me a lot of anxiety in my own career. There are inevitably times when we get things wrong. To deliver reliably, it’s okay to sometimes get it wrong as long as you always learn. The learning is the win. It’s the opportunity for growth. It’s not something to be shameful about, it’s ultimately what helps us become stronger performers and ultimately stronger leaders. That’s considered a win to me.

Before ending the episode, I want to provide a few book recommendations:

How to Decide by Annie Duke – honestly, this book has a little bit of a surprise therapy in it. Be prepared for re-evaluating not just how you decide at work, but also how you decide personally and in general.

Traction by Gino Wickman – this is helpful for any CEO or leader

And last, I would love for you to pause and think:

  • What could you work on or improve, even if you’re not a CEO or founder yet?
  • How could you be a better CEO of your life?
  • Are you engaging with the right tools, people, and resources?
  • Are you as organized and effective as you want to be?
  • Are you adapting to change?

I hope this brings a few things to mind. Alright, thanks again for listening. I’ll see you next time ✨

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