If I could do it again: Confessions of digital business executives

In every defeat is a lesson showing you how to win the victory next time.

Robert Collier

For this issue, we asked four of the smartest, most successful business leaders we’ve worked with to share their greatest e-business mistakes and what they learned from them, so that others might become more expert in the telling. While each of their stories was unique, the truths that emerged are universal.

“You can’t be all things to all people.”

Martin Clifford is a successful serial entrepreneur and venture capitalist. He is currently the CEO of in Chicago; the fastest-growing company in one the fastest-growing categories on the Internet.

The biggest mistake in my e-business career was with social networking start-up We started in 2005 addressing a need among young professionals for career guidance and contacts. Sort of a Facebook/LinkedIn hybrid before those sites took off. We were all inexperienced in the space – social networking was new – and we had no golden rules to follow.

Our investors expected immediate viral growth, which didn’t happen, so we started the process of ‘change.’ We tried one thing after another; each change moving us further away from our original concept. We added more and more functionality. We over-complicated. We moved away from addressing a known need to looking for one. Then we started to back-fit problems into our solution, burning significant cash along the way.

We made a lot of mistakes with, but I also learned a lot and developed the following rules for success, which have served me well at Sittercity:

  • Less is more. Keep it simple, from strategy to product to marketing.
  • Know your customer inside and out.
  • Build from a small customer base, prove what works, and grow carefully from there following a disciplined cycle of iterate, test and measure.
  • Incentivize your team (they’re not doing it for you).
  • Trust your instincts.

“Letting your org chart dictate how you serve customers is a recipe for disaster.”

Tim Peter is managing director of online marketing and operations at The Leading Hotels of the World and a tireless generator of business insights via his blog and Twitter. He has 10 years in the hotel industry, and 14 in e-commerce and Internet product management.

My story revolves around a product launch for a former employer. My boss felt that we didn’t need to involve a particular group in the launch of the product. There were a number of ‘territorial’ issues going on and he didn’t want to concede any ground to his rival. I had my doubts about the wisdom of this approach, but didn’t want to rock the boat, so I kept my mouth shut.

Unfortunately, I was proved right. Shortly after launching the product, we learned that it negatively impacted an important customer group and had to make major changes quickly. Getting the right people involved up front would have made a world of difference.

E-commerce projects touch most parts of an organization and often affect customers and constituents beyond just the e-commerce team. It’s hugely important that all parts of the organization understand what’s going on so they can raise concerns and help you address potential issues up front.

My lesson: Start with your customer and align your team around their needs. Get the egos out of the room by moving the focus from internal politics and personalities to the needs of your customers. By focusing on serving the customer best, the entire organization succeeds.

“Being right is one thing. Proving it is another.”

Dan Leeds is managing director of product at NYSE Euronext, where he is working to ensure that tomorrow’s New York Stock Exchange is as indispensable to the global economy as yesterday’s was. In past lives, Dan held product and customer experience leadership roles at iVillage, and Citibank.

Sun Tsu said the fight outcome is determined before the first blow is struck. And like warfare, every project is either be doomed or enabled for success before it starts.

I’ve let timelines be dictated to me that were impossible. I’ve let project scopes grow beyond what was feasible. I’ve allowed myself to be pushed into situations where I knew I didn’t have the resources to deliver.

Failing to persuade leadership to make the right tradeoffs ahead of time was the problem. No amount of professional instincts could sell it. So I finally turned to detailed analysis. Work effort/resources ($) = time.

In one watershed moment for me, I was engaged in a scope session with a client. After discussing project goals, he asked me to ballpark a timeline. I braced myself and said, ‘Eight months.’ The response was immediate: ‘How can it take so long?’

I knew that generalities wouldn’t work, so I played my new card: “There are several ways we could play this out. We could break it up into phases. We could add resources, or we could trim scope.” He agreed to give me a few days to model these scenarios. We showed that by spending some extra money, we could accelerate the timeline by two months. We also modeled a phased program that took longer for full completion, but got us to market sooner. In the end, he chose the eight-month program.

Now I spend a good deal of time calculating scenarios and creating options. It doesn’t always work – there are some people who are beyond even this method – but it does give you a fighting chance at success.

“If you have to choose between technical skills and industry knowledge, choose technical skills every time.”

Shari Gottheim is assistant VP of U.S. business at MetLife, where she oversees the firm’s business-to-business programs online. Prior to MetLife, she was a consultant with Accenture and Braincraft Technologies in New York, where she had the opportunity to learn from and assist many leading brands.

Within the past year, I had the opportunity to hire for a couple of key positions on my team. Given the amount of work being asked of our organization, we had no time for gaps in our staff. One of the roles I needed to hire was a business analyst to write requirements. I was faced with a choice: Hire based on insurance industry knowledge or hire based on professional competencies such as project management, relationship-building and asking the right questions.

If I hired on industry expertise, I wouldn’t have to get the person up to speed on how our products worked and how users interact with them online. If I hired based on technical competencies, the person would need to learn our business. I hired based on insurance expertise.

What quickly became apparent is it’s easier to teach someone the particulars of a product or industry than it is to teach them professional skills that can take a career to develop. The next person I hired , I looked for solid professional skills and judgment rather than industry expertise. The approach is sometimes more important than the answer.