What makes a great leader? Try asking your team how you could fail

By Dennis Clemente

Being your company’s intrapreneur or leader, you have to ask your team, “Tell me all the things that could go wrong?!” 

As a leader, do you think you can ask your team this question–“Tell me all the things that could go wrong?”–and expect to get real answers? That startling question is from the best-seller, “Decisive,” by Chip and Dan Heath, and it’s the same question asked at the NY Intrapreneur meetup on the Upper East Side last May 14.

So many tech meetups these days are all about pitching, showcasing us great works that come from creating products that promise to make all our lives easier.

In this meetup founded by Debbie Madden, also a CEO at Cyrus Innovation, the panel of guests from Coach, Ogilvy & Mather, Simon & Schuster and Kaplan Test Prep showed how they are willing to be candid.

They talked about work and the disruptions, ugly or not, that occur in collaborations, in how we organize ourselves, motivate one another and combine talents to meet challenges. So where other events shun sensitive questions, this meetup was open, incisive, and even conspiratorial, with all the biases we have as baggage.

For example, it may be surprising to hear people admit to having “self-interests,” but here is one example. “I want to work with the same team. That’s the fight I will fight,” said the reflective Ken Judy, VP Technology of Simon & Schuster Digital.

NY Intrapreneur's panel of speakers
NY Intrapreneur’s panel of speakers

There’s a certain grain of truth in that statement. Indeed, working with the same team who trust its leader as much as its members has some advantages—it saves time and effort, because Judy declared, “No one gives trust; it could take a year or more,” as he emphasized the gravity of what we face in any new project: distrust.

Judy was at one time executive manager and software developer who managed development and product at Oxygen Media (NBC-Universal), and was a product manager and agile coach at NYSE Euronext Advanced Trading Solutions.

As the moderator, Madden set the analytical tone of the meetup with questions that allowed the leaders to discuss their role as their company’s intrapreneur.

For entrepreneurial ideas to take off, Ilio Krumins-Beens, executive director, Agile Practices at Kaplan Test Prep said it’s important for the disconnected software and business team to connect, if it means changing processes. I spend time using agile technology with key influencers.”

Krumins-Beens has been working with teams to deliver software and web applications for over 15 years in a range of industries–government, media, tech startup, and education. He is a passionate agilist who has presented at several Agile/Lean conferences since 2007.

For the two women in the panel, time is key.

For Kathleen Gareiss, managing director of Digital Delivery at Ogilvy & Mather, having a timeline (to follow) is crucial, because “ideation can take long.”

Danielle Schmelkin, VP-Business Intelligence and Data Management at Coach, agreed. “Time is always a factor,” elaborating on how meeting deadlines is always a challenge. She is a proponent of “passion (being) one ingredient and relationship is another” to entrepreneurial success.

Gareiss is a digital native with more than 15 years of experience working in the interactive industry. The focus of her interactive career has been on producing new, large-scale platforms and global implementations. She works within a company to standardize and “operationalize” the processes needed to deliver these digital experiences.

“The outcome of the day is important for me,” Gareiss declared.

Schmelkin, for her part, is responsible for all of the technologies associated with transforming data into critical business information. Prior to joining Coach, Shemlkin held key positions at Barnes & Noble, Inc., where she was most recently VP of Business Intelligence, responsible for creating and implementing a business intelligence platform for the entire enterprise. She was also CTO during the launch of the nook, Barnes & Noble’s digital reading platform.

“We should always work toward a goal,” Schmelkin said. “Guide the company where they can go or not. (But know) there are concepts they will not be ready for.”

Answering that, Judy said, “You have to throw (some) ideas away. Not all ideas can be (executed).”

As a parting shot, each one offered their set of beliefs about what someone just starting can bring to the company they work for.

Gareiss answered first, saying good “writing” tops her list, as well as “being a sponge all the time.” Shemelkin thinks demonstrated “leadership and communication skills” are vital.

Krumins-Beens, for his part, said it’s important to “trust your idea and to not let anyone dissuade you when you get a ‘no.’ You don’t want a string of jobs. You want a career.”

Judy said with a crack in his voice, “Don’t take too much for yourself, though. Routinely collaborate. Work hard with humility.”

The meetup was organized by Madden, who founded NY Intrapreneur in 2012 to enable rich conversations about innovation within the NYC tech community. She is also speaks and writes on enterprise and startup trends.

Publishing, marketing teams face Agile challenge: deadline dates

By Dennis Clemente

If you’re looking to improve your scale or capability, there’s nothing like having some Agile thinking in place. For the uninitiated, it could simply mean having a workflow with sticky notes on a white board that categorizes tasks as “to be done.” “in process” and “finished.” But it’s more than that for two teams at the Agile for Non-Software Team meetup hosted and organized by Lori Masuda last April 9 at Kaplan Test Prep.

At the meetup, the two Kaplan teams that were paired with editorial and marketing staff presented the result of their Scrumban and Lean practices in a panel discussion that allowed for the “sharing of the good, the bad and the future.”

The toughest challenge for both teams proved to be meeting deadline dates.


One team was tasked to write the LSAT (Law School Admission Test) Premier, while another, Grad Marketing, worked on improving its own processes in both managing general tasks and fulfilling requests for marketing collaterals.

In the past, it was not unusual for the LSAT team to write a book with one author. This time, the LSAT team faced the challenge of collaborating with a large group of people where not all the great feedback can be incorporated instantly; that hefty book is like the yellow pages of old where the process of completing it can test the most patient of stakeholders and authors.

The marketing team, for its part, had a “black-box” process with many submissions but no clear way of prioritizing all the requests. They wanted transparency and collaboration with their stakeholders.

Both teams implemented daily scrum meetings and visual task boards. For the LSAT team, they implemented the Demos and Sprint Planning. For the marketing group, they streamlined retros and single product owners.

Masuda listed the following challenges presented by the panel:

1. Managing deadline dates. How to address deadline dates with shifting priorities
2. Planning/estimating/team capacity. How to adjust to unavoidable guess work
3. Commitment level. How to make everyone commit 100%
4. Work-in-progress concerns. How guidelines work but hard for everyone to stick with on a regular basis

When everyone can’t be together, it seems Agile thinking beats huddling in front of a computer, as it resulted in something that should inspire the rest of us:
1. Increased transparency
2. Increased collaboration and
3. Better communication and alignment with business

Since most of the participants worked remotely, a challenge for many, they discovered how Google Hangout was heaven sent.