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What I Learned in My First 100 Days as CEO

strategic objectives ceo people

Top 5 Takeaways from a First-Timer

Earlier this year, I made one of those career moves that can make even the most polished professional slightly queasy.

I decided to accept a job as CEO.

Fortunately, I was no stranger to leading people. I’d founded and grown my own businesses and served at the VP level for well over a decade. Still . . . taking on the mantle of chief executive felt like a different ballgame. And it was.

These are still early days in my tenure as CEO of Khorus Software. Nevertheless, a few realities about being a first-time CEO struck me during my first 100 days in the role. Here are five of them.

1. Time becomes more precious than ever.

Once my title changed on LinkedIn, and especially after the press release about my new role went out, people came out of the woodwork to talk to me. Tons of well-intentioned friends and colleagues wanted to help introduce me to great contacts — TODAY.

I completely expected marketing and sales professionals to want to talk to me: they want to sell me something. But I underestimated how much time I would spend meeting with people I felt obligated to meet with because someone made the referral.

To be clear: If I could rewind to Day 1, I’d still take every one of those meetings. Many have and will be beneficial. I’m deeply grateful to everyone who has offered their connections and expertise.

But all those meetings had to be balanced with equally important duties like:

  • Immersion in our product and service offerings
  • Getting to know the team as people and professionals
  • Learning from customers
  • Fully grasping the operations side of the business and all its moving parts
  • Developing strategy and objectives for the company

In these first months, drinking from the firehose would’ve been a luxury. I was drinking straight from the hydrant.

I’m still working on how to manage it all, but I can say that never in my life has prioritization been more important.

2. Building trust is a slow process.

When I became CEO of Khorus, I took over for veteran tech CEO Joel Trammell, who founded the company. Joel developed Khorus out of deep expertise and passion for helping leaders align their organizations and execute strategy (and only stepped aside as CEO when called to lead Black Box Network Services).

In many ways, Joel is the CEO’s CEO, and the team he assembled at Khorus trusted him deeply. Now I was stepping in as a first-timer. It took some time to bond with the team, learn what they know and how they work, and build their trust in me.

My guiding principle was to build what Joel calls the three Cs: competence, credibility, caring. I’m still working on it, but understanding these ingredients of trust has helped.

I also had to build trust with external people, which presented a different kind of challenge. Most people expected me to immediately be able to answer very detailed questions. In a few cases, I had to be honest and say: I’m not sure. I’ll get back to you on that.

3. Do yourself a favor: Find a great guide.

When I stepped into Joel’s shoes, he gave me a huge advantage in that he literally wrote the book on how to be an effective CEO. I knew exactly what responsibilities he and the board felt I was responsible for because it was laid out right there.

I was also extremely fortunate to have Joel on hand during the transition. Once you become CEO, you don’t have a traditional boss (besides the board), and getting feedback and guidance is difficult.

CEO loneliness is a real phenomenon. One survey found that half of all CEOs reported feeling lonely, and more than 60% believed it hindered their performance.

Now that I’m here, I can see why. Despite all those meetings, it can feel isolating to be at the helm of an organization. Seek out support from people who’ve been there, whether it’s:

Consensus is rare.

Like every team in human history, ours at Khorus has disagreements. Good-faith, positive disagreements — but disagreements nonetheless.

I’ve always been a decisive person. Making calls and then pursuing the plan comes naturally to me. The CEO Genome Project has found that people described as “decisive” were 12 times more likely to be high-performing CEOs, and I think most people would describe me that way. I had that going for me.

However, being decisive isn’t so easy when you have ultimate responsibility for the whole organization.

I found myself wondering: Will I anger or demotivate this person because they don’t agree with the decision I’m about to make?

I have had to remind myself that no decision I make will please everyone, whether it’s updating our core values (that one really happened) or deciding how to allocate our development resources (that one has happened many times already).

As another great CEO guide, Ben Horowitz, has said:

“In my experience as CEO, I found that the most important decisions tested my courage far more than my intelligence.”

After these first 100 days, I agree with that statement. The hardest part hasn’t been deciding what to do — it’s been hearing out varying perspectives and making a decision even though I know we’ll never reach full consensus.

5. A great system makes a difference.

As I mentioned, the demands on my time have been intense in the months since I became CEO. I sometimes find myself slipping into fire-fighting mode. The most recent, urgent-seeming thing is what gets my attention.

In those moments, focusing on the system has pulled me back and helped me re-prioritize.

What do I mean by “the system”? I mean the consistent set of processes and actions you design to help you achieve your objectives as CEO.

At the department level, systems are usually clearer. Before Khorus, I led a Customer Success department. I knew the metrics I needed to focus on. I had software that helped me and my teams track our work. There were countless resources to rely on as I built expertise in that domain.

The CEO role, on the other hand, is a generalist position. At worst, it can feel like a cross-functional mishmash. You’re responsible for every part of the business, but there’s no blueprint for how to run the whole thing cohesively.

Again, I lucked out here. At Khorus, our product is just such a system for CEOs, who traditionally lack software that helps them lead effectively. Of course, no software is required to build a good leadership system, but my Khorus-driven one looks something like this:

1. Beginning of quarter
  • Establish 5–7 strategic objectives for company.
  • Work with each member of leadership team to set specific goals/KPIs that support those strategic objectives.
2. Operations meeting each Monday
  • Revisit strategic objectives with the team.
  • Gather insight and predictions on how supporting team/goals are going.
  • Create action items when execution roadblocks arise.
3. End of quarter
  • Close out strategic objectives as Achieved or Not Achieved.
  • Debrief on lessons learned (important background for establishing new strategic objectives).
  • Deliver one-on-one feedback to leadership team.

This cadence, simple as it may seem on the surface, has become ingrained in how I lead. It not only clarifies what success looks like for the team — it also keeps everyone focused on priorities and puts me in touch with what’s going on in the organization.

Without it, I’d feel lost.

In the grand scheme of things, my CEO career so far is a blip on the calendar. However, it’s already felt like a long journey — one that teaches me something new every day.

By Carolyn Jenkins

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