The only way to think like a leader is to first act: to plunge yourself into new projects and activities, interact with very different kinds of people, and experiment with unfamiliar ways of getting things done.

—Herminia Ibarra, professor and author of Act Like a Leader, Think Like a Leader

Ask a hundred business people what successful leadership looks like, and you'll get a hundred different answers. There might be some overlap, sure, but the truth is that leadership is one of the most difficult traits to define. Thousands of minds have been exhausted in an attempt to capture exactly what it means to be a great leader, and, with so many competing voices offering advice, it's hard to know where to look. In my experience, I've found five basic habits and traits to be a great starting place in my development as a leader. They have helped me quickly go from the ground floor to the C‐suite and I am excited to share them with you now. They are: set clear goals, prioritize them, remain calm during chaos, make fact‐informed gut decisions, and always work to earn your stripes.

Set Clear, Inspiring Goals

No one reaches lofty heights without lofty goals. If you want to lead, then your goals need to inspire you to jump out of bed and give everything your best each morning. For a goal to be truly attainable, whether it be applied to projects and initiatives, health and fitness, relationships, or your career, you must give it this level of enthusiasm.

Far too often, people get stuck in low‐level positions because they let the inertia of a daily workload distract them from their biggest dreams. Without a larger goal to work toward, years slip by, and you run the risk of going nowhere. If you don't set the goal, then by default, your career goal will become merely to get through another day. Don't let this happen to you. Use the opportunity of working with a start‐up to set big goals that inspire you.

With 100% certainty, I would not have achieved anything big or inspiring without first setting the goal and then asking trusted advisors for guidance when I found myself beyond my depth. Everything I have achieved in my career has come from setting clear, specific short‐ and long‐term goals, with an overarching “why” that drives me.

Everything Can't Be a High Priority

Things which matter most must never be at the mercy of things which matter least.

—Johann Wolfgang von Goethe, German writer and statesman

Setting clear goals pays another dividend: it provides the barometer to help you decide what to say yes to and what to say no to. In an intense start‐up environment, it's easy to be overwhelmed by too many goals when they all seem like high priorities. Don't be so busy chasing all the loose dogs that you can't build a fence. Focus your energy on the goals that will solve the biggest problems, create the best results, and propel you the farthest, the fastest.

Early in my career, I had typed up my goals and printed out a long list to keep in front of me. Just looking at it made me anxious and jittery. I didn't know where to start. I asked my manager for help prioritizing. I handed her my list, halfway thinking she would be impressed with my willingness to take on such a huge workload. I thought she would just arrange them in a better order. We spent about 30 minutes discussing them, and during that time, she crossed out about half of my goals. She told me that if I tried to accomplish them all, I would only have a meager pittance of time to spend on each one, and the results would be equally meager. I'd be going an inch in every direction without moving a mile. This lesson in prioritization changed my life.

High performers, as I saw myself to be even at that point of my career, tend to take on massive workloads. This is part of the DNA of hard‐working people, and it's a trait I respect. But it can also create significant stress and lead to burnout over the long haul. I've learned that you can be a high performer without being overwhelmed, if you prioritize your goals. Success isn't about how much you do. Success is about performing the right actions toward the right goals that will create the biggest impact.

The key is to shift your mind‐set. It's not just about doing more than everyone else—which, in highly competitive fields of overachievers, is almost impossible. What will make you stand out is getting better results than everyone else, and the best way to do that is to prioritize. I personally like Sheryl Sandberg's, chief operating officer of Facebook, idea of “ruthless prioritization,” which she defines as “only focusing on the very best ideas. It means figuring out the 10 things on your list and, if you can't do all 10, doing the top two really well.”¹

I've created a framework for ruthlessly prioritizing, and it's been my process for 30 years of executive leadership. I start by creating an annual master list of goals (I hold on to these at the end of every year and occasionally revisit them to see how my goals have changed over the years, and what I accomplished or chose not to accomplish). I break them down into quarterly objectives and weekly goals, and then I stack each goal into one of three buckets: Priority A (do these now), Priority B (do these next), and Priority C (don't waste my time doing these). From there, I break down my A and B goals into daily task lists. Every evening, I set aside time to plan the next day, and I document my top three (only three!) priorities to focus on for the day. This takes discipline and helps me focus on the things that matter most so I don't get caught up in a sea of distractions. The key is to be realistic about what I can accomplish each day. When I get to the office in the dark of an early weekday morning, I concentrate on completing the first priority before moving on to the next one. This is key—you can't just go through the motions of setting goals, you must follow through with action.

I follow a similar prioritization process for my marketing team's goals. We start with the highest‐level goal for what we're trying to achieve. Using the same example as earlier, our team's number‐one goal might be to contribute a specific amount of revenue to the company's overall revenue goal. Then, using the aforementioned question, we break it down from there. We make sure each person on the marketing team knows his or her role, goals, and what specific tasks to prioritize in order to contribute to our marketing goals and to the company's revenue goal.

And we don't hide our goals and metrics under a bushel. We blast them out on everyone's computer dashboard in real time. We display them on monitors in public spaces throughout the Thycotic offices. We can pull them up on our phones at any moment. We literally create a Management by Objectives (MBO) addendum to the plan, where everyone's quarterly objectives are documented and shared with the whole team, and they regularly report on progress. Everyone in the company can see how the marketing team is contributing to the attainment of revenue on our main priority goals daily, quarterly, and annually. This allows us to adjust as we go, and keeps everyone focused on the highest‐priority goals with no chance of wasting time on fluffy work.

At Thycotic, our senior vice president of international, Simon Azzopardi, has a cool way of keeping the biggest goal in front of his team of employees. His teams cover the Middle East, Europe, Asia, and Africa, and they work with distributors around the world. To keep everyone aligned, he sets the standard for prioritization by holding “True North” sessions and gathering diverse teams together to focus on the most important goal and priority.

He developed his True North process during a 16‐hour flight to Australia years ago. He was sitting in his airplane seat and thinking about his biggest challenge, which was how to keep so many people on his international team motivated and pulling the rope in the same direction. He watched a YouTube video of Stephen Covey standing in front of a room full of executives. Covey told everyone to stand up, close their eyes, and point north. Then they opened their eyes. Everybody was pointing in a different direction. He explained that this lack of direction caused the highest amount of wasted resources in companies because everybody was heading for a different “north.”

This speech inspired Azzopardi to form the solution to his own challenge. Starting the next day, he asked his teams to describe their main goal. “Everybody gave me different answers. I thought it was amazing that we were even mildly successful without being aligned. But how much more successful would we be if we were aligned?”

He implemented his own version of a True North strategy, where everyone on the team is focused on the same goal, and he still uses it to this day. He later found out there was an existing program, but it is different than the one he was inspired to create for his teams at Thycotic.

He starts by defining what True North means for the company, and then the teams and individuals define their own goals and roles within the larger context. Every person on his team carries a small card that is custom for each role, and the cards are updated every year. The front of the card lists the three main areas of focus, and the back of the card expands on the three points. This provides the filter through which the team focuses all of their objectives and activities.

If you want to get promoted, show your value by always moving toward the True North of your company and team goals. It doesn't mean that everything you do every minute has to have a direct tie, but don't let busywork, distractions, or obstacles get in the way of your focused attention on the top goals in front of you. If a senior executive passes an employee in the hall and thinks, “I wonder what that person does?” because it's not clear how the person contributes to the most important priorities, that employee won't last long.

Create Order Out of Chaos

Chaos is part of business, especially among start‐ups that are trying to break through in a constantly changing environment. Since start‐ups are more vulnerable, unbridled chaos can lead to disaster. It's easy to stay focused when everything is copacetic. But when chaos reigns, every employee, not just every senior leader, has an opportunity to step up, lean in, and help to steady the focus on the big picture, revisit the whys, and initiate clear steps forward. It's demonstrating this kind of leadership that can get you noticed and accelerate your path to the C‐suite.

Chaos can take the form of a financial disaster, a lawsuit, a brand failure, or a sudden bad reputation. Or, as in the case of PentaSafe in 2008, it could be a hurricane.

Our company was on the top floor of a downtown building. When Hurricane Ike hit, flooding rose up in the streets below, and the city went dark. All of our people were safe, but our servers were down. We had customers all over the world who relied on our servers to support them in the use of our products. We presumed they would not be aware of or sympathetic to a natural disaster in our city. We knew we couldn't let our customers down and just cozy up in our homes and take a surprise staycation.

Everyone went home, but got online and built out a plan for operating as a team while working remotely. Those of us on the management team navigated the flooded streets and met at our office building, where city officials allowed us temporary access to our top‐floor offices. We walked up the 25 stories in the dark, humid, heat of the stairwell, and making several trips, carried out our most critical servers and equipment.

We moved all of the equipment to a dry location with power, and our IT team got them all reconnected and fired up so our customer support could go on. While many Houston companies shut down during that week, we barely skipped a beat and kept on providing the same level of support that our customers expected. It came down to creating order out of chaos. In the midst of the fury, we had a communication process in place so we could build a game plan. We focused on a set of priorities and put our customers at the top of the list.

In another case of mitigating chaos, a hacker launched a DDoS (distributed denial of service) attack that took down our website right at the end of a quarter when we were trying to hit our sales numbers. Again, calmness ruled the day and we assessed the situation, understood what we needed to do, and created priorities. The employees who demonstrated calm, cool, collectedness came across as those who would be able to lead with a steady hand and a plan when they had a chance to move up to a leadership role.

You can't control your competitors' moves, nefarious people, or the weather. You can, however, have the right principles in place (individually, as a team, and as a company) so you can handle potential chaos in an orderly way.

This doesn't mean overanalyzing everything that could go wrong to the point of fear and overwhelm. That's counterproductive—if you get stuck thinking about everything that might not work out, you'll never be able to get anything done. Instead, focus on these six ways to build your propensity for creating order out of chaos, and stand out as a potential leader:

1. Embrace the chaos. While some people shy away from it, great leaders lean in. They realize that turbulence is part of flying, and you have to fly through it.
2. Focus on the destination. Chaos is distracting and noisy. Maintain clarity around where you are headed. When kids are learning to ride a bike, they quickly realize that they have to look up ahead. If they stare at their spinning front tire, they will soon crash, and the crying won't be pretty.
3. Focus on the must‐haves, not on the should‐haves. Establish order in the most critical and largest areas first.
4. Be the model. No matter what position you currently hold, or the level of instability around you, you can demonstrate your leadership with a clear purpose, determination, and a sense of calm.
5. Communicate professionally. Take a deep breath before you speak, and don't allow your emotions to get the best of you. Others will notice what you say and your body language, even in the midst of chaos.
6. Properly manage expectations. People naturally want to take action to quickly eliminate chaos. Resist that temptation. Sometimes, fast action only exacerbates the crisis. You won't be able to resolve every crisis instantly or in one fell swoop, and make sure that you and your team are aware it is a process.

Make Fact‐Informed Gut Decisions

Steve Jobs was famous for bucking conventional wisdom and following his gut, his intuition—and obviously, he scored astronomical wins. But, you and I are not Jobs, so for us terrestrial types, I recommend a more balanced decision‐making leadership style that I call “fact‐informed gut decisions.” Data must drive decisions because it's the concrete, proven evidence of a logical, rational set of facts. At the same time, you need to embrace a bit of Jobs's cavalier energy and listen to what's gurgling in your gut. Part of a start‐up's competitive edge comes from its ability to move fast, and this often means acting on an opportunity before you have all the data, or before the data has caught up with reality. Getting too mired in analysis paralysis can negate an important advantage.

One of the times I listened to my gut, and it paid huge dividends, was when I was one of the leaders of Thycotic, a cybersecurity start‐up that existed before cloud‐based security solutions were popular. The CEO and I were deliberating on exactly if and when our company would take the giant step to the cloud as a solution for IT security. We analyzed all the facts about the cloud and interviewed customers to determine their comfort level with the idea. The data we got didn't support the switch—it showed that most customers didn't trust the cloud enough to handle all of their proprietary information. The data indicated that eventually, though not right away, the cloud would be popular and profitable, and we should wait three to five years before getting into the game.

But there was this voice in our gut, whispering, You have a wide‐open competitive window; do it immediately.

We listened, and became one of the first companies to offer cloud‐based cybersecurity solutions. That first‐mover advantage put us in a great position to capitalize when the cloud took off in popularity, and our revenues skyrocketed.

This reminds me of an observation made by Jack Welch, the former chairman and CEO of General Electric, who said, “The best executive today is the executive that can see around that corner. [They can see] what's coming. Not when you're in the tunnel, and the train is coming right at you. Anybody can make change then. The job is to change before that's necessary, and it's the hardest thing in the world.”²

To become known as a good decision‐maker (and therefore a good leader), you need a great nose for the hard facts and a trusty gut. It's okay to trust your instincts—they're a big part of how you got to where you are, and will continue to define your life. But, whenever possible, do your best to support it with data.

There is too much at stake today to overlook the facts, and they've never been more accessible than now. With a few clicks on business intelligence tools, you can collect raw data and perform an analysis to help you interpret and contextualize it. Facts improve the speed and efficiency by which you can predict outcomes. They give you a clearer picture of the situation and help you understand what's working and what isn't. They can help you understand what specific tactics drive the most revenue, why sales are up or down, and if your customers are happy or not. Armed with this intellectual information and layered with your own intuition, you can reliably make the best decisions.

We've already discussed how you can improve your researching and data analytical skills. You might be asking: how can I improve my intuition? It's possible, but tricky. The first part of this process we've already covered—strive to do your diligence and have as many facts/metrics at your disposal as possible. Then, get outside opinions from people you trust so that you're making more intelligent, educated guesses, instead of just shooting from the hip. After that, the real growth comes in reflection. Once you've seen how each decision you've made plays out, review them. What were the outcomes? How did the factors leading up to the decision affect the outcomes? Were the results predicted by the data? What surprised you? Was the decision the right one? Was there a better course of action you could have taken?

You don't want to get caught beating yourself up for making a wrong call. Instead, use these questions to learn from what you did, then take the lesson and put the rest behind you. If you do this enough and are honest enough with how you evaluate yourself, you'll build up your intuition and it will help you make better fact‐based gut calls in the future.

Earn Your Stripes

In the military, you don't get stripes on your uniform without hard work that puts everything on the line. The same thing holds true in a start‐up. You have to earn your stripes, every day, especially if you want to be promoted. Being seen as a valuable asset is not automatically bestowed upon anyone, even if you arrive with heaps of success, a resume stuffed with experience, and a vast collection of knowledge.

This holds true for me, too. When I join a new company, I never feel worthy of my title until I get a few major wins. Even then, I never feel 100% comfortable, and, if I catch myself getting too relaxed in my position, I create discomfort for myself. This motivates me to keep working hard and proving my worth to my teammates, and I suggest you adopt this perspective, too.

For example, when I first came on with PentaSafe, Doug Erwin invited me over to his house for a private meeting, where the executive team told me the challenges that the company faced. Essentially, we weren't differentiated enough in the market. I set a goal to overhaul the company's branding, positioning, website, and marketing materials—in the first 100 days. Since then, this has become my calling card and how I earn my stripes whenever I start at a new company. Just as the first 100 days of a presidency are some of the most important, I think your first 100 days at a new job are the most important. It will set the tone for the rest of your time at the company, and show everyone around you what sort of worker you are and what to expect.

So, I got this team I didn't know at all, and I came in and said, “We're changing everything.” They thought I was crazy—that there was no way we would be able to pull off all that I wanted to accomplish in the first 100 days. I pushed them, hard, and it turned out that not a single one of them broke under the pressure. They all were dedicated and talented individuals, and when I pushed them, instead of stumbling, they ran faster.

At the end of the 100 days, we had a kickoff meeting for the next quarter and upper management gave me an hour to present what we had done. As part of the presentation, one of the guys on my team had created a video that explained how the new logo we'd created encapsulated the company's mission. I'd never seen it before, and the video was so incredible that it literally almost brought the audience to tears (including me).

When I finished presenting all of the work that we had done, the entire auditorium stood up and applauded. My team all came onstage and took off their nice button‐down shirts. Underneath, they were all wearing T‐shirts with logos that looked like the “Survivor” logo but it read: “I Survived a Quarter with Kahan.” The attendees kept applauding my team and me, and, in that moment I realized two things: my team and I had earned our stripes and the trust of the company, and I knew that the company was aligned, united in its mission, and ready to charge forward. Five years later, we navigated a lucrative exit. If you attack every situation like it's an opportunity to display your worth, work ethic, and creativity, it will pay dividends for your career and the company.

Be aware that it's impossible for you to earn your stripes if you lack clarity on what's expected of you. The most important thing you can do is to set clear expectations with your manager and co‐workers. Successful people make sure that expectations are mutually agreed upon at the outset of their employment, of their projects, and of their objectives. They revisit expectations periodically with key stakeholders to ensure they are aligned. When expectations are mismatched, like it or not, your boss normally gets the final say. So if you're not in sync with your boss about expectations, you may never figure out what it takes to succeed within your organization and team. Also discuss with your boss what their expectations are for you in this role.

Along the same lines, a great way to stand out and show initiative is to go to your boss and say: “Tell me what I need to do to earn my stripes here.” It will immediately put you on their radar as someone who is dedicated and eager to provide your best work. The key is to listen to the answer and actually follow through. When you do that, you'll put yourself at the front of the pack when the executive team is looking for new leaders.