Over the course of my career I have lived and worked in Europe, Asia and the US as a CEO, a general manager with iconic brand corporations, and served on Boards.  Needless to say, I have taken my fair share of risks over the years.  Currently I am on multiple advisory boards for FinTech and AI early stage growth firms, a venture partner with a Fund focused on women founders in technology, and actively support the missions of Women in Cloud (WiC) and the Athena Alliance. Since I am introducing myself, I will happily add that I am also a wife, mother and grandmother.

If you have read any of my earlier blogs, you know I have shared stories of success and failure along my career journey.  This blog focuses on taking high-risk decisions and highlights some of the lessons I have learned, including ones relevant to our current, unprecedented COVID-19 crisis.  

Takeaways

Despite the cliff-hanging experiences I have previously shared, I continue to take risks. In the dynamic, competitive landscape in which we operate, we need to exploit opportunities and rapidly confront threats. I must admit, the decisions related to this pandemic crisis are extraordinary, such as how long to “lock down,” whether it is possible to hold onto jobs, what benefits to provide employees or not, how to handle contract workers, when to re-open work and participate in the community… 

These are some of the questions I explore when taking a typical, non-life threatening, risk.  Yet, as I think about these questions, I realize they are crisis relevant also.

  • Is the potential reward worth the risk?
  • Do we understand the opportunity and/or the impacts of our decision?
  • Do we have a strategy and action plans and back-up contingency plans?
  • Do we have the right team in place and does the team have each other’s back?
  • When things go wrong, is it really time to declare failure or have we just hit the inevitable “messy middles” that one needs to work through? 
  • Are key players (e.g., leadership team, management, direct reports, investors/stakeholders,  Board) really open to a “fail fast” approach or is “success only” the real mandate? 
  • Have I developed a strong bench, so that when I confront an urgent situation and must make an immediate decision and own it, key players will trust my judgement?

These questions vary depending on our current situation, market, industry and options. They change and moreover they can evolve with time. 

Open and Transparent Communications

Despite all efforts, failure or high risk situations can happen. Sometimes due to events out of our control.  Regardless of the reason, open and transparent communications is very often the key to keeping or re-gaining trust and gaining the time needed to turn the situation around and achieve success.  Communications could mean:

  • Keeping the organization updated on the situation, sharing strategy and actions plans, and providing guidance on how to respond to clients and other external queries.
  • Sending communications directly to clients, acknowledging their feedback, and providing assurances that we are working on it and will keep them updated.
  • Providing frequent, on-topic, clear and honest communications to employees through the most commonly used and any new channels.
  • Finding effective ways to get employee and client feedback, and dealing with emotional impacts in addition to the business situation.
  • High visibility and engagement from the top executive leaders is very important, as well as  an effective cascade so more immediate managers can be in alignment with the organization’s philosophy and strategy when talking with their teams.

When taking on a planned high-impact initiative, make the time to gain the buy-in of leadership and key stakeholders.  Determine what are the shared rewards that make the risk worth taking – together.  It is equally critical to have the buy-in and ownership of the working team, whether direct reports, peers or collaborators. This is a continuous process, so if an unexpected crisis happens, there is critical support on which one can rely.  

Accountability 

Success (or surviving failure) involves:

  • Keeping the team continuously engaged, listening to them even if their advice will not result in action, and providing recognition; 
  • Engaging and seeking the advice and buy-in of those above and your peers, as well as finding sponsors and advocates;
  • Taking ownership and accountability for one’s decisions!

Taking risks includes accepting the risk of failure. The question is not if, but how one fails. In Harvard Business Review, James W. Harris the CEO of Seneca Financial Group, wrote: “Skipping out on colleagues when things look grim is the most common failing among super-charged executives. Lying about the true condition of a business is another. Failure is no excuse to chuck ethics out the window.”

Owning my failures has been extremely hard, and yet the lessons learned have led to far more success and skills to deal with ambiguity and the unexpected. My greatest personal success is seeing the people who joined me in taking risks and  rose above any failure that may have happened, move on to achieve their own success.

A wise and experienced executive told me at the very start of my career: “Karen, I am confident you will be successful in your career. As you climb up the ladder, just remember to step around people, not on them. You are sure to meet them again on the way down or in different circumstances. You may not understand this now, but you will.” 

It took some time, but I always remembered these words and did, indeed, come to understand them.  When it comes to fighting a crisis like this global pandemic, we clearly must all function together, as one team, up or down the “ladder”.

Karen Cone FORMER CEO, CORPORATE GM, & BOARD DIRECTOR

Karen Cone is the former Microsoft General Manager, Worldwide Financial Services Sector, and CEO and Board Director of the advisory research firm, TowerGroup. She currently serves on multiple advisory boards and is a venture partner for the MastersFund, focused on women founders in technology. Karen has also held senior executive positions with increasing responsibility and scope at IBM, MasterCard and Gartner, where she served on the Gartner International Board. She has lived and worked in the Americas, EMEA & Asia. Karen and her husband, Jeff, have three sons and four grandchildren and currently live in Seattle, Washington.

After almost 20 years at IBM, I accepted an opportunity with Gartner, the leading IT advisory research firm. With a clean slate, I moved rapidly from a research director position to senior vice president and general manager, reporting to the CEO. Of course there were bumps along the way. I expect you have heard of the “fail fast” approach. Well, I have lived “fail fast” and determined that one also needs to “fix faster.” 

“Fail fast, fail often” became a Silicon Valley mantra for start-ups at the height of the dot-com era. Today, as we constantly stretch the edges of the digital world and the boundaries between digital and “brick and mortar” are blurring, “fail fast” has expanded from the start-up world into established businesses. But the business leader who executes on “fail fast” and succeeds in failing is often at risk. Ken Spencer, an innovation thought leader and CEO of Spyder Works wrote an article headlined: “‘Fail fast, fail often’ may be the stupidest business mantra of all time.” Can one “fail fast” without career failure?

The “monkey” is on my back

It was at the turn of the 21st century and e-commerce, dot-com, and the Y2K “bug” were all featured in Gartner research. I was head of Gartner’s technology and IT management research services; we were predicting the explosion of the internet and advising clients on the growing importance of the Web to their businesses and the need to be a player in the rapidly emerging digital world. At senior leadership team meetings, I frequently brought up the widening gap between our research and our limited web reality, and its impact on our credibility with clients. 

I must have been too vocal, because the CEO called me in and told me that I was now the General Manager of gartner.com and the problem was mine to fix.. 

I was blindsided—this was not expected. Like most business and technology leaders at this time, I had no internet experience. My CEO explained that an inside person was needed to lead the effort, someone who knows the business and who the Heads of the disparate acquisitions would trust to also take care of their interests.  Apparently that inside person was me.  So I took a deep breath and started pulling a team together.

We held multiple focus groups both with clients and non-clients who told us what they “hated” about the current gartner.com and research distribution, and shared their visions for the future of our product. This included a website that had contextual search capabilities to filter through the thousands of possibilities and return highly relevant results. We set to work designing a totally unique look and feel for the new gartner.com with ground-breaking functionality.

At Gartner all-company meetings, we promised a new website that would “seduce, sizzle, and stick”. Everyone loved it. I presented the approach to clients at the Gartner Symposium. When I closed my pitch with the words, “We will launch a website that gives you what you never knew you wanted but can’t live without,” I got a standing ovation. My team and I were convinced we had a winner. We were under great pressure from clients, senior management, and the board to launch. So we moved rapidly to get the lightly field-tested product to market. 

Learning the hard way

We launched a leading-edge website in January 2001. We gave our clients just what they asked for. And it bombed—badly! We quickly learned the meaning of the phrase—“give your customers what they ask for, but not too much.”

Usually, this means, “Don’t let your customers drag you down into the traditional and miss the next breakthrough innovation.” In our case, it meant our clients (customers) were not ready for the magnitude of change the new web interface introduced. We began to realize that our testing was focused on ideas rather than actual user experience. Additionally, we discovered that the excellent relevance of results did not compensate for the fact that the search engine was slow. In the Web world, response time is non-negotiable. I had failed and done it fast! Now we needed to fix it fast! 

 “I can do that…”

Thankfully, even when we felt our most confident, we put a contingency plan in place. Prior to the original launch, we were optimistic the new website was what our clients were asking for—yet we also knew that we might need to adapt quickly.

From the start, we held all-team meetings every week. During these meetings, we would challenge the team to brainstorm solutions to our most difficult requirements, the potential showstoppers. My favorite words to hear were when someone would call out: “I can do that…” So once again, we called the team together and explained what we needed to fix fast! This included “dumbing down” the user interface and changing it to something much more familiar. However, the far more complicated challenge was to significantly reduce the response time of the search engine, while keeping relevance. 

As soon as we presented the problem, conversations spread throughout the large room. The team was thinking out loud. They owned the challenge. We waited… And then we heard the magic words, “I can do that…” And we did. We embraced our failure, learned from it, and moved on to focus on the fix. Three months later, in April 2001, we launched the second version of gartner.com. And it was a great success. 

I surely prefer success, yet I must admit I did learn life-changing lessons from failure.  Some are specific to this scenario, like the incredible risks associated with short-cutting critical success factors, such as user experience.  Or, the fact that the “best” solution may not be the right solution.  Or, listening to your customers, but not too much. More profoundly, I recognized that if one looks to survive a “Fail Fast” risk, having the Team and key Stakeholders with you is essential to “Fix Faster.”

Karen Cone FORMER CEO, CORPORATE GM, & BOARD DIRECTOR

Karen Cone is the former Microsoft General Manager, Worldwide Financial Services Sector, and CEO and Board Director of the advisory research firm, TowerGroup. She currently serves on multiple advisory boards and is a venture partner for the MastersFund, focused on women founders in technology. Karen has also held senior executive positions with increasing responsibility and scope at IBM, MasterCard and Gartner, where she served on the Gartner International Board. She has lived and worked in the Americas, EMEA & Asia. Karen and her husband, Jeff, have three sons and four grandchildren and currently live in Seattle, Washington.


My journey to the C-Suite and the boardroom has been successful. It was, however, more rocky and slower than many of my male counterparts of equal (or even lesser) competency. I learned many lessons along the way and I am sharing them with you, in hopes they will help others along their own career journey. Here is one of them.

How honest feedback changed my trajectory?

I spent the first half of my career at IBM. It was challenging in a good way and I was continuously learning and growing. I held exceptionally diverse roles from international sales to regional staff to global account marketing manager to country product manager and corporate head of software business practices. I had assignments in the US, France, Russia, Japan, and China. It wasn’t easy, as during this time I also brought three children into the world and was raising them with my husband. Nonetheless, I continued to progress and move up the ladder, until I didn’t. In hindsight, one could say I hit the glass ceiling and did not know what had happened.

I was a second-line manager and one level below “executive.” My performance ratings were top notch. All that said, I was going into my sixth year at the same level with no apparent prospects of promotion, while male colleagues with performance results less than mine were moving into the executive ranks. I worked incredibly hard and consistently delivered. I was confused. I knew I must be doing something wrong, but did not know what. 

The director of my group was promoted and was replaced by a woman executive —for the purpose of this story, let’s call her Carolyn. After only six weeks, the new director decided unexpectedly to move on from IBM. As Carolyn prepared to depart, I requested a meeting. I realized that this manager who had observed me for many weeks could provide some blunt feedback with no conflicting agenda. I asked Carolyn for insights as to why my career had stalled. 

Carolyn was certainly blunt. She said the issue was not my performance, it was excellent. Instead, it was the image I projected while getting the job done that was blocking my rise into the executive ranks. Apparently, as I strived to meet all deadlines in a complete manner, I came across as someone always in a rush and, thus, not in control. My focus was on what still needed to be done, rather than taking time to acknowledge and celebrate what was already accomplished. This gave my colleagues and management, mostly men, the opportunity to take credit for these accomplishments without recognizing my leading role. Most importantly, Carolyn said I was perceived as a high performing “worker bee”. I did not project the executive presence required for a senior leadership position. My direct reports recognized me as a leader, but key stakeholders impacting my career did not. 

It was like a bucket of freezing cold water had been dumped on me. I was both shocked and grateful. Grateful that Carolyn had been so open with me. Shocked at the truth of what she said. And disappointed in my lack of self-awareness. I felt the need to try harder, as women often do. Nevertheless, it was clear that my glass ceiling was as much of my own making as it was due to a male-dominated work environment. It was time to reinvent myself and my image. 

Lessons learned in executive presence

That said, the perception of others creates a reality that is difficult, though not impossible, to change.  The very next morning, I stopped rushing. I immediately realized that I needed to walk into meetings calmly with my head high, not looking down at my papers or what today would be my laptop or smartphone. I needed to come across as confident and in control. Gathering my courage, I began to change some of my behaviors, including:

  • Discussing what was done and not apologizing for what was not done
  • Speaking up in meetings without asking permission first
  • Replacing “I hope this meets your needs” with “I am confident this will meet your needs”
  • Avoiding phrases like: “try to, hope, feel, perhaps you could…”
  • Finding opportunities to share soundbites on successes, without being boastful
  • Gaining support of key stakeholders in advance of meetings

There is one critical behavior that I practiced then and continue to this day — ensuring that the successes of the team, as well as the individuals on the team and our collaborators, are recognized and promoted. I firmly believe this is an essential part of leadership excellence. It drives achievement and benefits the organization as a whole.

So how did I fare with my “re-invention”? It made a difference. My voice carried more clout and the outcomes were impactful. That said, I realized that changing the perception many stakeholders held of me would take considerable time with an uncertain outcome. I concluded that this was an unacceptable risk and that my time was better served elsewhere, so I successfully moved my “re-invented self” to a new opportunity. 

At times one is so consumed by the need to succeed that we ignore the successes we have achieved. I hope my story helps you understand the need to step back and look at everything you have accomplished and course correct to accomplish more. Stay tuned for more!

Karen Cone FORMER CEO, CORPORATE GM, & BOARD DIRECTOR

Karen Cone is the former Microsoft General Manager, Worldwide Financial Services Sector, and CEO and Board Director of the advisory research firm, TowerGroup. She currently serves on multiple advisory boards and is a venture partner for the MastersFund, focused on women founders in technology. Karen has also held senior executive positions with increasing responsibility and scope at IBM, MasterCard and Gartner, where she served on the Gartner International Board. She has lived and worked in the Americas, Europe & Asia. Karen and her husband, Jeff, have three sons and four grandchildren and currently live in Seattle, Washington.

Women in Cloud is announcing the following finalists for the #CloudInnovateHERxDigital Pitch Challenge, and we are proud to present their solutions

Special congratulations to our 11 finalists that will be pitching their solutions on May 1.

  • SIPPIO enables Microsoft Teams with calling capabilities globally, allowing a user to work from anywhere, anytime at an economical price point without a committed contract, hardware or maintenance. Customers can opt in/out, up/down and be free of traditional phone systems.
  • Agtools is a SaaS Ag and Food supply chain platform offering real-time data and intelligence to farmers and buyers of over 513 fruits and vegetables helping them manage market volatility, increase profitability and reduce the world’s 4,900 daily truckloads in USA and 62,300 daily truckloads in the world in food waste.
  • BackpackEMR is transforming medical aid from temporary, short-term solutions into high-quality, long-term healthcare.
  • B’zT is an award-winning innovative fashion that creates child protection through apparel combined with tracking technology.
  • illuxi Intelligence is a cloud based, hosting and content delivering platform. We also produce, advise and support clients using our business intelligence tools for their content delivery.
  • Velaku is a workplace communications and content management solution that transforms the employee experience by revolutionizing how employees find, share and consume content directly in the flow of work.
  • The PositivityTech intelligent platform empowers organizations to treat complaints not as a drain on business resources, but as a critical source of information and insight that can create business impact.
  • Rainbow Secure Note – rSecureNote is a digital vault for Enterprise and Business Professionals to store, manage their digital assets (data, files), Business Workflows powered by Rainbow Password and Smart Multi-factor Technology.
  • Pagomed is an all-in-one solution which helps doctors charge their invoices and keep track of their income.
  • Argyle is your coordinated BIM model in 1:1 registered Augmented Reality for robust, easy field verification and QA.
  • Drbot.health precision-matches patients with the right healthcare providers, using artificial intelligence, to decrease clinical misdiagnosis

With this pitch challenge, we wanted to go one step forward and give our audience a chance to choose their  best solution among the lot. We are very happy to announce that, among the above finalists, the audience will get to vote for a solution they believe is revolutionary during the #CloudInnovateHERxDigital Pitch Challenge on 1 May, 2020. Click here to register to attend and have your chance to vote! The popular category winner is in for exciting rewards such as $1,000 in Azure Credits, an invitation to join UN Delegation, two complimentary tickets to WiC Annual Summit, and access to travel discounts up to 65% off.

The #CloudInnovateHER Pitch Challenge which was designed to help women tech entrepreneurs across global markets develop, showcase and win enterprise customers. This competition was designed to provide economic access and industry visibility to women tech entrepreneurs while also giving them an opportunity to present technologies that create a sustainable impact in today’s world.

The digital pitch challenge event will kick off with a special keynote by Giovanna Mingarelli, CEO & Co-Founder of M&C Consulting on “Navigating Market Opportunities in the Midst of COVID-19”. Following that, our distinguished panel of judges will listen to each 2 minute pitch and ask questions to learn more about each solution before voting for the overall winner.

Our virtual pitch challenge is breaking the geographical barrier during the Covid-19 era while incorporating new-age technology like AirMeet. AirMeet is designed with a focus on large events to be hosted online with a special focus on community networking capabilities at small “roundtables” and a “backstage” experience. The event is supported by International Association of Microsoft Channel Partners, M12 – Microsoft’s Venture Fund, EQUALS Global Partnership, Founders LIVE, Verbinden, Alley, New Tech Northwest, AirMeet, Speaker Engage, Headstart Network, and Meylah. This is a chance to win $5,000 in cash and cloud credits, along with invitations to be a part of the United Nations delegation and much more.

This pitch challenge gives opportunities for women around the world to showcase their cloud solutions to industry leaders and cloud experts. Women in Cloud’s mission is to help bridge the access gap through this pitch challenge and help women technology entrepreneurs reach their goal and contribute to economic growth.

Our community is stronger now than ever before. The year 2020 started off as an exciting era with our third annual Women in Cloud Summit with tremendous hope for the future. But now we have hit a bump on the road with the rise of the COVID19 pandemic. However, we at Women in Cloud are determined to keep working towards our mission to help women entrepreneurs create $1 billion in economic opportunity by 2030!

At the Women in Cloud Summit 2020 we launched our inaugural #CloudInnovateHER Pitch Challenge which was designed to help women tech entrepreneurs across global markets develop, showcase and win enterprise customers. This competition was designed to provide economic access and industry visibility to women tech entrepreneurs while also giving them an opportunity to present technologies that create a sustainable impact in today’s world. The positive response from the community has now pushed us to launch #CloudInnovateHERxDigital. 

Yes! We come bearing some exciting news for all the quarantined female technology entrepreneurs from around the world. Women in Cloud is taking #CloudInnovateHER digital and will allow everybody to showcase their enterprise ready cloud solution to the world on the most powerful platform in the world: the internet. 

How do you enter?

Well, it is quite simple. Women-led companies developing an enterprise-ready cloud solution that’s earned less than $10 million in the past 12 months qualify to enter. Enter your business pitch or encourage others who qualify to enter. Solutions will be evaluated for originality, market feasibility, and use of cloud and AI solutions. Deadline to enter – April 24, 2020. Click Here to Apply

Why should you enter?

Women in Cloud is a network of over 1500+ industry leaders, policy makers and innovationists who are always looking for the next best solution available. This pitch challenge could provide your company access to the markets as well as the unique Women in Cloud Microsoft Accelerator program designed to further enhance the knowledge and techniques of an entrepreneur in the technology industry.  

This is a chance for startups and companies to compete on a global scale for a share of $5,000 in cash and cloud credits and we are more than excited to bring this chance to your doorstep. 
Click here to apply now and join our Women in Cloud Network and embark the journey of building an inclusive tech economy. 

Join the Digital Event and Vote for Your Favorite Pitch!

Join us on Friday, May 1 at 12pm PST to see the live webinar of the pitch challenge. We will feature 10 finalists that will showcase their solutions to a panel of esteemed judges. The community will be invited to learn more about the companies and vote for their favorite pitch to win the People’s Choice award, which will be announced the following week on May 8. Register to attend #CloudInnovateHERxDigital today!