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When asked the question, “What advice would you give to professionals about to take on the CEO role for the first time?”, a good number of CEOs focus on the importance of establishing two-way honesty and transparency, building a business for the long haul, listening more than you speak, choosing and committing to a leadership model, and knowing what you are getting into, among other insightful ones.
Here are some more tips for an aspiring CEO from some experts in the field:
• Scott Abel, Founder & CEO, Spiceworks (CEO experience: Nearly 9 years): “Be open and honest with your employees. Truly be approachable. Build a culture where people are comfortable coming to you and telling you bad news. When startups go perfectly they’re hard – and they never go perfectly. We shouldn’t do anything that makes them harder. The more open and honest you are with your team about how you’re doing – with product traction, sales, and money in the bank – the more honest they’ll be with you about what’s working and what’s not inside your company.”
Dean Drako, President, CEO & Founder of Eagle Eye Networks (CEO experience: 22 years): “Build for success, not for an exit. You can be open to selling the company, but planning for it as your goal is a flawed strategy as it detracts from your customer focus. Most acquirers are interested in a successful company. Build one. Measure results and adapt quickly. Smaller companies can change and move fast – use that to your advantage.”
• Thomas Ebling, President, CEO & Chairman of the Board, Demandware (CEO experience: 14 years): “Always remember this old adage: ‘You have two ears and one mouth for a reason.’ It is really important to avoid rushing to judgment; spend time listening and learning from people already at the company. I’ve always found that your new team will often have the answers to the challenges that led to the CEO transition, but they just weren’t being heard.”
• Gregory S. Gilmore, CEO, Planview (CEO experience: Less than one year): “Don’t be an accidental leader. In other words, be intentional about your leadership model. So many times CEOs end up in the chair but don’t follow a model of leadership. If you are not providing the leadership your organization needs, people will seek it elsewhere, undermining your influence and credibility. You cannot allow that to happen. There are lots of resources available on leadership, but here’s what people miss: No model will work well unless you apply your specific talents and gifts – as well as your weaknesses and shortcomings – to it. This requires a clear assessment of your leadership abilities. Culture is an important aspect of the organization. You have to be intentional in driving and permeating the culture you want your company to have. You do this by taking every opportunity to instill the value system you have established in your organization. You reveal and reinforce your value system by how you handle crises, incentives, recognition, and many other factors. All those things are critically important. As a CEO you must be willing and able to embrace ambiguity. CEOs must understand that there is always some part of the job that they can’t control. Even if you take a command and control approach, you will not be able to regulate everything and may end up alienating your employees and other constituents. Those who cannot embrace ambiguity end up being demoralized and damaging the very culture they are trying to create.”
• Alan S. Knitowski, Chairman & CEO, Phunware (CEO experience: 8 years): “The best advice that I can provide for a first-time CEO is to really, really understand what you are getting yourself in to before you say ‘yes.’ This is not only about ensuring that you are ready to accept the reality that you will be ‘on’ 24x7x365 from the day that you start until the day that you stop, but also that your family will be front and center to those most impacted when the inevitable intrusions of your business take priority over everything else in your life. You need to have complete alignment at home with the realities of what you are going to be doing, and the sacrifices that will need to be collectively made by all of those involved and impacted. There are absolutely no free lunches in being a first-time CEO, for either you or your family, and you have to realize that your learning curve and the impositions of your business on your life should not be underestimated. Finally, you should realize that you have to be the visionary, the evangelist, the brand ambassador, the operator and the fundraiser all in one. The glass needs to be half full, not half empty, and you need eternal optimism in your goal and quest to achieve the impossible. You will consistently have less resources, less money and less maturity than your peers, so you will need to make up for it with aggression, confidence, work, planning, commitment and a tireless pursuit of excellence in every facet of your business. But enjoy it, because it is the most amazing and rewarding experience in business life.”
• Mark McClain, CEO & Founder, SailPoint (CEO experience: 14 years): “Learn the difference between organizational health and organizational strategy. In business school, they teach you that the focus needs to be on organizational strategy. I’m completely on board with the thesis Patrick Lencioni puts forth in his book The Advantage: While strategy is important, organizational health is an even more critical long-term advantage. Organizational health is more about making a company effective by creating a unified leadership team, aligning goals and having a clear purpose, and then communicating that vision to everyone within the organization. Just like we all do with our own physical health, we have regular company check-ups to ensure our company is healthy from the inside out. That way we can effect change before it affects us. I believe this is one of the primary reasons we’ve been able to attract and keep some of the best people in the industry, while fostering innovation and building exceptional customer relationships.”
• Brian Tervo, President & CEO of North American Operations for TIE Kinetix (CEO experience: 6 years): “Understand that you do not know everything about the business no matter how much of a subject matter expert you may be. Build out a team of various disciplines that challenge each other to come up with the best idea, not just people who agree with your every word. Start with a communications survey to get a real picture of how your employees communicate and where they put their trust. Operate with total transparency (and hold yourself to the highest moral and ethical standards!).”

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