Several years ago, I interviewed Doug Dennerline, CEO of Betterworks and former CEO of Webex, in an interview originally published in Thrive Global. Here is an excerpt from our conversation:
Adam: What is something about you that would surprise people?
Doug: I have four children and the first three are girls. I have spent my career supporting and mentoring women. Many of them have gone on to be great leaders, which is very satisfying. I was responsible for helping to drive gender diversity globally while I was a leader at Cisco. So I’m very invested in equality in the workforce.
Adam: How did you get here? What experiences, failures, setbacks, or challenges have been most instrumental to your growth?
Doug: The long story short is that I spent 25 years as a sales leader before I became the CEO of Webex after its acquisition by Cisco. I’ve been running SaaS companies ever since, including serving as President of SuccessFactors and serving as the CEO of Webex after its acquisition by Cisco.
It was a challenge to lead Webex (the inventor and market leader in web meetings) post the acquisition. Webex was a $525M SaaS company and was now part of a $45B networking company. Securing the budget to expand Webex to meet the challenges of handing the 16,000 Cisco sales reps the Web application was difficult. At the time, Cisco didn’t really understand the SaaS business. The team and I had to work diligently to justify the budget to meet the exploding demand. In the end, we prevailed. However, I learned an important lesson in patience and perseverance. In order to build software that meets the needs of today’s more agile processes, you have to stay competitive, and continuously be open to learning, pivoting, and adjusting.
Adam: What are your hobbies and how have they shaped you as a leader?
Doug: I grew up playing sports – football, basketball, baseball, track, tennis, etc. I enjoyed and learned the most from playing football. You don’t win in football if you operate as 11 individuals. You only win in football if you play as a team. Another important lesson from football is you can gain lots of yards and lose the game. You have to learn how to score points to win!
Adam: In your experience, what are the defining qualities of an effective leader?
Doug: A truly effective leader will prioritize building a culture of feedback in their workplace. If you can do that, I believe any company will be set up for success because your workforce will be aligned with your top priorities. Your employees will feel invested in and understand the roadmap for their professional development.
I also continuously work to empower my teams. I prioritize hiring experienced, motivated, smart leaders, challenging them to strive to reach new levels. I want my teams to make the most of a feedback culture and share their opinions so they can problem-solve as a team. I’m also a big believer in radical candor – it’s the only way to truly know how your company is running. I don’t believe in lines and spend time doing skip-level meetings each week. I tell everyone, we can’t fix what we don’t know is broken. Tell us what’s not working!
Adam: Who are the greatest leaders you have been around and what did you learn from them?
Doug: I learned a lot from John Chambers during my time at Cisco. He has a stretch mentality that has served me well in my career. He’s highly transparent and his favorite place is in front of a customer and that’s my favorite place too. John Doerr, who serves as a Betterworks board member (and was an early investor), is a believer in what we do at Betterworks. He is another great leader who has worked tirelessly to champion OKR’s and better performance management processes for his career; something we all must continue to work toward, no matter the industry.
Adam: How can leaders and aspiring leaders take their leadership skills to the next level?
Doug: I mentioned it earlier but radical candor coupled with emphasizing a culture of feedback will absolutely help you lead with integrity, and ensure that you’re getting the best work out of your teams. Additionally, take on cross-functional assignments so you can experience other leaders and functions. It will allow you to experience and see what works and what doesn’t work. It also will help you think outside of your functional responsibilities.
Adam: What is your best advice on building, managing, and leading teams?
Doug: I have three:
1) Nurture an environment that supports transparent feedback:
Successful teams are built on trust. People need to feel psychological safety within their work teams and know that they can speak freely with their managers – both about work and life in general.
2) Make the performance management process as transparent as possible:
How an employee’s performance will be evaluated and how their career will be developed are important aspects of the employee experience and overall corporate culture. All employees should be trained on how to employ transparent goal setting and progress tracking. Regular conversations with their manager including feedback and career development ensure everyone will be off to the right start.
3) Prioritize proper management training and learning:
We’ve all heard the adage that people don’t quit bad jobs, they quit bad managers. All managers should be trained on how to manage performance in order to properly prioritize their people, align on the necessary company-wide strategy, and prioritize results that serve both their organization and teams. Learning and refining should be an ongoing process that is encouraged and supported by managers and leaders.
Adam: What is the single best piece of advice you have ever received?
Doug: When you want to make a statement and show what you know, turn the statement into a question. You will learn more that way and people will know that you are listening versus being quick to judge and giving direction.
Adam: How can anyone pay it forward?
Doug: Take the time to mentor up-and-coming leaders. I’ve always prioritized an open-door policy at my workplaces, and I honor that practice. My teams have all been encouraged to reach out to me with questions, and I work to help people learn and grow wherever I can. I hope that by modeling this, I’ve encouraged other leaders, both new and tenured, to do the same.
Adam Mendler is an entrepreneur, writer, speaker, educator, and nationally recognized authority on leadership. Adam is the creator and host of the business and leadership podcast Thirty Minute Mentors, where he goes one-on-one with America’s most successful people – Fortune 500 CEOs, founders of household name companies, Hall of Fame and Olympic gold medal-winning athletes, political and military leaders – for intimate half-hour conversations each week. A top leadership speaker, Adam draws upon his insights building and leading businesses and interviewing hundreds of America’s top leaders as a top keynote speaker to businesses, universities, and non-profit organizations. Adam has written extensively on leadership and related topics, having authored over 70 articles published in major media outlets including Forbes, Inc. and HuffPost, and has conducted more than 500 one on one interviews with America’s top leaders through his collective media projects. Adam teaches graduate-level courses on leadership at UCLA and is an advisor to numerous companies and leaders. A Los Angeles native, Adam is a lifelong Angels fan and an avid backgammon player.
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