Calling Those Who Are Ready to Ignite Their Career

Steven Kahan

December 19, 2019

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I invite you to imagine you and I are meeting for a dinner appointment.

It’s a warm evening and we are seated at an outdoor rooftop restaurant overlooking a bright, big city. As the sun sinks into a soft orange glow, and the lights from the buildings illuminate the deepening blue of the streets below, we talk about your college experience. Your face lights up as you tell me about the recognition you received; the camaraderie you experienced with professors, classmates, and friends who challenged your thinking. You express a longing for the structure of the educational framework where success surely comes to those who work hard. And then our conversation shifts to your current job situation.

You inhale deeply. During college, you had imagined so much success and income in your future, but here you are, full knowledge and ready to put it to use, ready to prove yourself—but you’re stuck. You’re stuck in a job where advancement seems long and far away, and your life lacks the richness you desire and expect. You think about your peers, and while there are a few lucky ones who already seem rich and happy (according to their social media posts, anyway), you and most others are still getting by, trying to mitigate risk due to those aforementioned student loans you can no longer defer. You’re hoping for a big break or a lucky streak, or a mentor to take an interest in you and help you to navigate through this career conundrum in which you and other young professionals are caught.

I want to help you discover your own path to becoming a brave leader in a world that you might have previously overlooked or written off as too risky: the tech startup world. While working for a startup might seem riskier than working for a large corporation, the potential rewards far outweigh the risks. And, if you’re smart, you can mitigate the risk.

Have you ever felt stuck in your job? Have you wondered how you will ever reach the level of success you imagined for yourself? You’re not alone. In 2018, amid a robust economy and low unemployment, college graduates struggled to get hired. Upon graduation, 75% didn’t have a job lined up at all. It took the average college graduate almost eight months to find a job—all against a backdrop where the average student loan debt was $41,810. Add to that the fact that in the same year, only 31% of employees in the US and Canada felt engaged at work, and I believe this means we have a serious epidemic on our hands. This epidemic is not new. It nearly infected me.

Many years ago, after graduating college and landing my first job processing claims in a large bureaucratic corporation, I realized that the traditional “safe” path from school to climbing the corporate ladder was not only high risk for my career, it almost felt like a death trap. I dared to question my plan and ask myself, “What if I could earn a great living and love the work I do?” Even though I had no skills or experience in technology, I left my boring, low-paying analog job and went to work for a tech start-up, and it afforded opportunities that would have never been available to me had I remained in a traditional corporate environment. Since then, I have spent more than 30 years building my career within the tech start-up world. From my first start-up job as a marketing representative at Database Design to my current role as CMO of Thycotic, I have been blessed to work for seven tech start-ups. All six of my prior employers have either successfully sold or have gone public, generating more than $3 billion in shareholder value. I’ve had the privilege of working with hundreds of amazingly talented start-up entrepreneurs. I’ve learned about how they think, what they do, and the attitudes they hold that have helped them achieve extraordinary success. My mission is to offer the under-employed, college-educated young person a way out of the deathtrap.

If you carry a huge student loan debt, the reality is that you can’t afford not to work for a start-up. At a big corporation, pay is limited to incremental annual raises according to the company’s well-entrenched salary policies. On the other hand, in working for a start-up, the big payoff comes through stock options. Often, a start-up will offer you a relatively modest starting salary and an opportunity to own a piece of the pie for yourself. This could lead to extremely high compensation later on, assuming the company grows and eventually has a successful exit. I experienced this six times as of this writing, and it’s worked out very well, like millions of dollars well. Working for a start-up won’t just help your bank statement—it will also help you grow professionally at a quicker pace than would be possible at a large corporation. Most start-ups don’t hire with a set idea of your potential or career path. It’s the perfect environment to try on different roles and find your zone of genius, and then move up quickly from there. You can come in at an entry-level position and end up working on big, world-changing projects alongside the founders where your contributions can be seen and noted. At the right start-up, you can quickly stand out and gain more responsibilities and opportunities to advance, both in your position of authority and compensation. Finding exceptional opportunities is only the beginning—you need to be ready to seize them.


“Have you ever felt stuck in your job? Have you wondered how you will ever reach the level of success you imagined for yourself? You’re not alone.”


Beyond tech skills, these companies seek people with all kinds of talents and creativity who have bold ideas and the leadership skills to bring them to fruition. Of course, the best opportunities often come with a side of risk. Most start-ups fail, but even those provide opportunities to ignite your career in the start-up world, and experience vastly different from the traditional corporate norms. You can begin to practice these leadership attributes and entrepreneurial mindsets, and that can propel you to the top and keep you there. These are the traits they don’t teach you in college or in on-the-job training by a corporation’s learning and development team. These are the lost leadership skills that will help you break out from the pack and rise to the top. They will turn your potential for success into reality.They will help you learn the lessons that will empower you to make better decisions and get better outcomes in work and in life itself. In short, forget climbing the corporate ladder. Never before has there been a greater opportunity to rise to the top at great speed. Now is the time to go for it.


Once you’ve been hired at the start-up, you won’t just float to the top. It’s requires a lot of effort to swim to the surface. You’ll be competing against everyone else in the startup world for leadership positions, and the fact is, many of them will have similar skill sets. To stand out from the crowd, you’ll need to find new ways to set yourself apart, and one of the best ways to do that is to develop and display strong leadership attributes. Leadership is a multifaceted skill that takes time and effort to learn. To really stand out, you need to develop your ability to ask more questions, take more risks, make tough decisions, and come up with great ideas and execute on them.

Just as start-ups must create products and services to differentiate themselves in the marketplace where they are competing with bigger and better-funded companies, you must differentiate yourself from the herd of people who want the higher jobs that you are after. A start-up company’s differentiators include the products, services, distribution, brand image, or specialization that they offer. Here’s what it looks like when you apply those concepts to your career: Your product is your performance. Your service is how you deliver superior solutions and build relationships. Your distribution is how you communicate and share your performance. Your (personal) brand is the experience others have when they interact with you. And your specialization is your deep knowledge in one main area that helps you deliver your product better than others. In my many years making personnel decisions, I’ve noticed that the employees who get hired and move up are the ones that make everyone else realize they are the best at what they do. Even employees with the least amount of experience can move up ahead of those with seniority by showing their leadership skills.


“Once you’ve been hired at the start-up, you won’t just float to the top. It requires a lot of effort to swim to the surface.”


Following are six specific ways you can separate yourself from the herd:

  1. Take initiative. Are there important tasks on your manager’s to-do list? Take on a project that no one wants to tackle, but must get done.
  2. Build relationships across the company. People who get big things done are people who know others who can help.
  3. Show your love for the company. Surprisingly, not enough people go out of their way to show their commitment to a company and its values and goals.
  4. Build your skills. As you grow your knowledge in the area where you want to move up, you will become an invaluable asset.
  5. Go the extra mile. Ultimately, the one quality most under your control is your effort. If you slack off, it shows, and you’ll be canned. But if you push yourself and go further than anyone else, that will show and help you move up in the company.
  6. Sharpen your communication skills. Even a poorly written email message will reflect poorly on your skills, so keep it sharp, always.

It’s worth noting that a big opportunity to differentiate yourself is when you help to differentiate your company in the market. It’s a double-dip of differentiation—you can improve both your own standing and your company’s standing. A great example of this came during my time at PentaSafe. When I joined, we were a small, private cybersecurity firm competing against three much larger public companies. The thing was, we were all selling essentially the same product: vulnerability assessment and intrusion detection.

We needed a way to differentiate ourselves, and because of our limited resources, we would never be able to do that with the technology alone. The other companies had much larger and more impressive R&D departments. So, I took a look at our company and a look at the field, and what I realized was that while the other firms focused on the technology alone, nobody was looking at the other side of the security equation: the people and the policies.

We had this project that one of our creative engineers was working on. We weren’t sure we’d take it to market. It was a tool that allowed companies to assess how well their employees understand the security policies, which is huge, because most employees don’t know these policies at all. Usually, they get a huge dump of papers, sign them without reading them, and forget about it.

We went ahead and brought the product to market and we used that as a main differentiator. It allowed us to sell ourselves as the only company that addressed all three factors in the security equation: the technology, the policies, and the people.


“Just as start-ups must create products and services to differentiate themselves in the marketplace where they are competing with bigger and better-funded companies, you must differentiate yourself … ”


The funny thing is, we hardly sold any of the new tools that would assess how well employees understood the policies. On that level, it would look like a failure, but the fact that we had the tool got us into the door at many firms. Once we were in the door, we were able to sell them on our main product and win business away from our larger competitors. So, in that way, it was a great success. We didn’t stop there. Along with two team members, Chris Pick and Todd Tucker, I pushed on that competitive advantage. The three of us developed a community we called “the Human Firewall Council.” We gathered thousands of people from all over the world together in one place to talk about cybersecurity. The council really took off. Chris and Todd, after PentaSafe was acquired and we all cashed out in a big way, both went on to work for another firm, APPTIO. There, they implemented the same sort of council and expanded on and improved the idea. This initiative helped them achieve success and move into executive leadership positions.

Let’s break down some of the lessons here, because there are a couple. The first is that, whether you’re a company or an individual, if you want to succeed, you need to find an area where you stand out. The second lesson is that many times, you can achieve both of these goals at once. When you discover a vital innovation that helps the company stand out and act on it, you will stand out in turn, and then you can leverage your newfound expertise to launch successfully in new ventures.


You might think that the most successful start-up CEOs with stellar track records, huge social influencer platforms, and millions in the bank are the ones doing all the talking in a meeting. But it’s the opposite: they ask thoughtful questions and listen for responses. They realize that the right questions inspire reflection, and that reflection inspires action. If you want to move up to the C-suite, cultivate this skill.

I learned this lesson early. At one of my first start-up positions,I earned a reputation as someone who delivered, so the leadership asked me to take on a new function, well outside of my previous experience. I wanted desperately to impress my new manager, so at each meeting with him, I barfed-up a nonstop barrage of plans and solutions. He just listened quietly, and I left each meeting congratulating myself on how smart and clever I was.

Even though my team got impressive results, my relationship with my manager soured. I couldn’t understand why. Then one day, a mentor of mine asked how I was doing. I told him I was down because my manager and I weren’t working together well, and I couldn’t figure out why. What else would this mentor do, but ask a bunch of questions? After listening to my responses, he said, “Ask your manager more of the right questions instead of telling him all the answers.”

In those days, I carried a notebook wherever I went. My mentor gestured to it and told me to write a small question mark at the top of every page to remind myself what to do.

I took his advice. It worked like magic. Turns out my manager had wanted me to ask for his priorities and feedback so he could collaborate with my team and me. Our relationship improved, and so did our team’s results.

I see the same tendency to try to act like an expert all the time in young, confident professionals. It never works—it’s the rough equivalent of getting “INEXPERIENCED” tattooed on your forehead. If you want to impress, especially when you’re young, focus more on asking smart questions than on telling people what you know. It will show you have the maturity to realize how much you don’t know, and are eager to deepen your knowledge. This will make your supervisors and peers trust you and want to give you more challenging projects and responsibility.

It takes effort to overcome the urge to have all the answers or “be right,” but it’s essential for success, especially in the start-up world. In The Book of Beautiful Questions, published in 2018, innovation expert Warren Berger quotes the venture capitalist Christopher Schroeder, who says, “he uses the following question to remind himself to keep an open mind: Would I rather be right … or would I rather understand? If you’re adamant about being right,” Schroeder says,“ you lock yourself in your own echo chamber—and that can cause you to make bad decisions.”

In a large company with established processes, it’s easy for an employee to do only what they’re told, without asking questions. But in a start-up environment, where the company’s processes are being developed, it’s critical to ask intelligent and useful questions to comprehend the big picture and find additional creative solutions. Not only will it make you stand out as thoughtful, but it will also make you better at your job.

The same concept applies when talking to customers. I’ve received hundreds of sales calls during my career. Most of the salespeople can express their value proposition, but only a handful ask me questions. Those salespeople who don’t ask questions forget the most important aspect of sales: listening. How can they pitch a product to me, if they don’t even know what problems I’m currently dealing with? Maybe I have a problem that I don’t even realize I have yet. Sure, they can tell me they see a problem, but I’m far more likely to believe it if I say it myself. The salespeople who ask the most intelligent questions, those that make me realize the gaps in my solutions, are almost always the ones I end up buying from.

The big takeaway from this isn’t just to ask more questions. It’s to ask more thoughtful, higher-quality questions. There’s nothing more annoying than someone who asks questions just to ask them, or who asks questions about something that’s already been covered.


“The big takeaway from this isn’t just to ask more questions. It’s to ask more thoughtful, higher-quality questions.”


If you want to learn how to ask good questions, there’s no better teacher than Socrates. According to his method, you start with an open-ended, challenging question. Then, follow it up by asking “Why?” After much discussion, you might land on some sort of an answer. Then, you ask more questions about that answer, examining the solution you came up with.

Of course, unlike in philosophy—in business, you must act, so at a certain point you need to pause the process of reevaluation to implement a solution. After that, however, you still should continue to ask questions regarding your solution, and refine your thinking.

While this might seem intellectualized and esoteric, it applies to business as well. For example, instead of asking, “Are our customers satisfied?” ask questions like, “How can we help our customers experience greater satisfaction?” “What is the purpose of this function?” and “How can we better support customer success?” From there, it’s a matter of finding the best answer and coming up with a set of actionable items. Then, carry out those actions but don’t let the process stop there. Once you have results, continue to interrogate what happened, asking questions like, “Why did that occur?” With those sorts of questions, you can refine the steps you took even further.

There is, however, one question that is more important than any other in any decisionmaking scenario, personal or professional. Asking this question can lead to a deeper understanding, better decisions, and more brilliant outcomes. Those who ask this question are seen as more strategic and forward-thinking, and those are traits that zoom leaders to the top. The question: What’s next? Simple, isn’t it? Try it and see the results for yourself.

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