UC All-Stars: Leaders Reveal Their Biggest Business Mistakes

All of the leaders featured in the inaugural UC All-Stars series are undoubtedly successful in their fields.

But, that’s not to say there haven’t been some hiccups along the way.

• UC Leaders Awards applications are open! Nominate yourself or a fellow leader now

As part of our inaugural UC All-Stars series, we asked more than 50 UC Leaders to name the biggest business mistake they’ve made and what they learned from it.

Below is a snapshot of some of their answers. You can view their complete answers to these questions and more in UC All-Stars or click a leader’s name to view their full profile.

The shared mistakes among these industry leaders span from career transitions made too late to prioritising personal pride over seeking help when needed.

Others have learned the hard way about the perils of inadequate team onboarding and the repercussions of overestimating market readiness.

Career Moves

Ilya Bukshteyn, Vice President of Microsoft Teams Calling and Devices at Microsoft, focused on the aspects that have driven career progression decisions.

He states: “I have in the past made job / role changes motivated primarily by a desire for career advancement, and my learning from those has been that really the most important thing for me is who I work for, and how aligned I am with that person’s values, priorities, and leadership style.”

Graham Walsh, Director of Global Technical Sales and Alliances at Neat, highlighted a pivotal career move that didn’t go as planned.

He said: “Leaving the UC industry to try something different. I learned that I should focus on what I did great at and evolve myself in that industry.”

Zeus Kerravala, Founder and Chief Analyst at ZK Research, reflected on a particularly decision in his career.

“I can’t think of any mistakes I’ve made in my career per se; my only regret was staying at Yankee Group too long,” he said.

“The ship was clearly sinking, and I had been thinking of splitting out on my own for some time. I could have done that earlier but things have worked out fine so perhaps that was meant to be.”

Irwin Lazar, President and Principal Analyst, Metrigy, shares a significant learning moment from his career. He says: “Taking a job in an organization that thought we could ‘fix’ token ring rather than migrate to Ethernet. I learned very quickly that absent coherent support from senior management, an IT plan is doomed to fail.”

Early Career Choices

Several All-Stars highlighted situations from their early career.

Patrick Kelley, Distinguished Architect at Zoom, reflected on the challenges of seeking help when he was starting out.

“Being too proud to ask for help early in my career,” he said.

“My ego always got in the way. I always wanted to be the best and smartest in everything. That isn’t possible.

“Once I learned I don’t have to know the solution 100 percent of time I just have to know how to ‘GET’ the solution, my career became much more enjoyable and productive. Know how to get results and that doesn’t mean knowing the answer, it means knowing the right people that can get you the answer.”

Graham Fruin, Senior Research Analyst at IDC, talked about the pressures of early career expectations.

“Stressing myself out that I needed to learn every single aspect of all companies involved in the market and thinking I was a lot worse than everyone else because I didn’t have that knowledge,” he said.

“Learning that nobody has a full picture and to focus on what is important helped me become a better analyst.”

Tim Banting, Practice Leader – Digital Workplace at Omdia, recounted an early mistake in data presentation.

“Early in my career, I made a mistake by providing senior executives with raw data instead of actionable insights,” he explained.

• What is UC All-Stars?
• UC All-Stars: Leaders Name Their Biggest Challenges of 2024
• UC All-Stars: Leaders Choose Their Business Heroes
• UC All-Stars: Leaders Name the Biggest Tech of 2024

“When I shared data regarding our competitor, one of the executives responded by saying that they weren’t concerned about the competitor because it would take years for them to reach the same market share that our company had at the time.

“This experience taught me an important lesson that as a competitive intelligence professional, it is crucial to present data in a way that C-level executives can understand it without any misinterpretation due to their biased perspectives.”

Melissa Swartz, Technology Consultant, Swartz Consulting, LLC, discussed her early career missteps in a corporate environment.

She said: “After college I worked for a large, bureaucratic phone company. I was young and idealistic and thought that success in that environment would be based on achievement and merit, so I worked on producing results instead of cultivating a network of people who could help me advance.

“I learned that, in a large organization, politics outweigh performance. Eventually, I left the company and started my own consulting business, taking those political lessons with me that provide insight when working with client organizations.”

Fredrick Shears, Global Head of IT at CT Group, recounts an early career blunder that taught him the value of caution.

“Very early on in my career, when I started work on an internal IT helpdesk,” he said.

“I accidentally emailed a vendor a list of all staff credentials. Fair to say it didn’t go down very well.

“Luckily my colleague was a wizz with powershell and changed all of the passwords in a matter of minutes. I learnt to re-read every email and attachment I sent, something which I still do to this day!”

Start-up Struggles

Some of our All-Stars highlighted challenges and mistakes that stemmed from working in young businesses.

Development Architect Tom Morgan highlighted the importance of maintaining boundaries between personal and professional life.

“I once did some work for a friend who was just going into business,” he explained.

“I never got paid and lost a friendship over it. I learnt to have very clear boundaries between personal and work lives and be very clear about your expectations.”

Nigel Dunn, Vice President of EMEA North at Jabra, reflected on the lessons learned from a pioneering business venture.

“I have made so many mistakes to pick one would be belittling to how I’ve learned in business and in life,” he said.

“With two friends, I started a business that was a forerunner of being able to download and buy software that we take for granted today on the internet, our idea was releasing software from a catalogue on a CD on a try and buy basis. We were ahead of our time and my mistake was to try to disrupt a market that hadn’t yet established itself (it was on Sun micros and Unix) when the market was too small on popular software to be disrupted.

“However, it taught me to always have a vision of where you want something to go and to keep the plans simple and understandable. That way, everyone can clearly see their part in it and you get maximum participation to achieve your goals. It also taught me that assumptions are not as good as facts.”

Technology Analyst and Strategist Kevin Kieller had a similar story.

“I started in the technology space writing video games for the VIC-20 and Commodore 64,” he said.

“I then migrated to creating custom business applications. Along the way I tried my hand at creating several products. When I failed, it was because I became enamored with my own ideas and did not line up an initial customer (or customers) to validate that I was solving a real problem, that someone would be willing to pay to address.

“I don’t code in my job these days, but ensuring and validating that shiny new technology solutions, detailed analysis work, articles, or webinars have a clearly defined audience that perceives real measurable value in your offering is an important lesson I learned.

“I often ask myself three questions: ‘who will this serve?’, ‘what value will this deliver?’, ‘how will the value be measured/proven?'”

Team Building

Steve Osler, CEO and Co-Founder at Wildix, reflected on early hiring and onboarding mistakes.

He shares: “The biggest business mistake I made early on was two-fold when it came to hiring and onboarding our team members for international expansion,” he said.

“First, in our rush to enter new markets, I did not have a rigorous enough selection process and ended up bringing on people who ultimately lacked the independence, flexibility and problem-solving mindset needed for startup success.

“Secondly, when we did find the right people, I realised that I hadn’t adequately equipped them for success. In particular, working remotely in these new territories required more than just competence; it needed autonomy, comprehensive training, and sufficient resources.

“By unintentionally constraining talented people, they were not able to apply their full capabilities or make quick decisions locally. These challenges have been instrumental in reshaping my leadership philosophy and Wildix’s approach to team building.”

Alan Masarek, CEO at Avaya, also underscored the significance of team building in his career.

He said: “I’ve been fortunate to lead multiple organizations over the course of my 40-year career.

“My biggest mistakes and greatest accomplishments have both centered on my ability to hire and retain great talent and build successful, highly performant teams.”

Stijn Nijhuis, CEO of Enreach, discussed the importance of stakeholder engagement in project management.

He said: “In the past there have been cases where we have invested significant resources in R&D projects that we believed in, but we did not sufficiently check the dependencies and enthusiasm of other stakeholders.

“What I have learnt from this is to make sure we keep certain projects smaller in scope and more simple, allowing us to test the market much sooner.”