Deidre is a serial entrepreneur who has founded and led several companies, including Workboard. Her last company, PSS Systems, created a new market category and inspired deep customer loyalty from Global 1000 companies including ExxonMobil, Citigroup, Travelers, Novartis, Wells Fargo and others. It was acquired by IBM in late 2010; at IBM, Deidre ran the high-growth Information Lifecycle Governance (ILG) business, improving information economics for enterprise customers. She has 16 patents and has published dozens of articles.
How has your life experience made you the leader you are today?
There are some key experiences that form my behavior and beliefs as a leader. Team sports growing up taught me the joy and value of winning and losing together. With three brothers, I grew up playing as hard as I could and without perceiving a gender barrier. I didn't come from a place of abundance, which fostered the drive and grit to keep rising. As self-perceived underdog, I always felt I needed to catch up which evolved into being a voracious learner. And I've had significant personal setbacks, which taught me that humility and tenacity are a brilliant combination.
How has your previous employment experience aided your position at Workboard?
The idea for Workboard came directly from my experience leading a large, growing business at IBM. With team and customers in virtually every time zone and myriad distractions, I realized my ability to focus the team on big goals and to sustain alignment and goal achievement would be central to success. But the effort required for alignment and goal focus took as much as 20 hours a week - that was time that could have gone to growth and achievement but probably should have gone to sleep and a more balanced life! I couldn't find a simple, elegant tool that linked people with goals, priorities, work and feedback. We launched Workboard to fill that gap for 169 million managers stretched too thin for greatness.
What have the highlights and challenges been during your tenure at Workboard?
The big challenges are classic entrepreneurial ones; making high-impact decisions without a lot of evidence or historical data. You have to be able to tolerate a lot of uncertainty and operate with a level of fearlessness that isn't typical in later stages or a larger company.
The highlight of work is always talking to customers - people who rely on Workboard, achieve great results more sustainably and who take the time to tell us how much of a difference we make for them. Nothing inspires me more.
How can we move beyond 'to do' lists and actively achieve the goals that our organisations need?
We need to sustainably, consistently integrate and align our to do lists with our goals. Breaking goals down into actions is essential to achieving them, and working a list is a great technique -- when the right things are on the list! Research shows that organizations fail to achieve goals for a couple of reasons:
•Only 7% of people actually know what they need to do to achieve goals, while 76% of people work from a to do list - clearly the right things aren't on the list.
•Goals are irrelevant to people in the course of their work. They're abstract and intangible, forgotten as soon as they're communicated, or both.
•Managers fail to hold people accountable; 50% of managers shy away from constructive or course correcting feedback because they don't want to be the bad guy. This short-term interest in popularity really backfires over the course of a few years and a career.
Managers' fundamental job is to communicate goals, triage priorities to sustain alignment to goal, make sure the right work gets done, report progress upline and give the team feedback on their work. Unfortunately, business has become increasingly complex while tools for managers haven't changed since Microsoft Office was introduced in 1990.
Most managers don't have the capacity to continuously link goals, priorities, work and feedback very well - the research shows just how big the gap is. 86% of executives (Deloitte Human Capital Trends Report 2014) cite lack of leadership skill and management pipeline as their greatest talent issue, because this gap shows up in profits and costs. It's critical to give front line managers more capacity to lead and keep the all-important linkage between goals, real-time priorities, work, reporting and feedback.
How do you maintain a work/life balance?
I'm very lucky because I get a huge amount of energy and satisfaction from work; it makes me happy to focus on invention, iteration, engaging customers and team members and solving complex problems. I suppose for some people, that makes me unbalanced but for me it's more about a sense of wellbeing and vitality than balance per se. I've been committed to yoga, cycling and mindfulness for a decade, which helps me stay well and move closer to fearless.
What do you think is the biggest issue for women in the workplace?
It's hard to boil it down to a single issue, but I think the perception that all successful people must look, act and behave a certain way is the greatest limitation on talent and achievement for women and for companies. When our mental model for what a "contributor" looks like is constrained, contributions are constrained as well. Issues of equal pay, the opportunity to rise, the bias on voice tone, and the aggressive man vs. bitchy woman conundrum all stem from the narrowest view of what successful, contributing humans look and sound like.
How has mentorship made a difference in your professional and personal life?
I've had five mentors who shaped my world and self view. The first catalyzed my desire to excel for the sake of excellence. The second helped me believe I could achieve great things in business and showed me what an entrepreneur looked like. The third coached and coaxed me to reach for it and brushed me off when I fell in the process. The fourth pushed me to build a business model and strategy depth and gave me a clearer picture of how others experience leaders. The fifth helped me become more centered and compassionate, and helped me start meditation practice.
Which other female leaders do you admire and why?
IBM CEO Ginny Rommety for leading through a cathartic, extremely challenging phase. I love her view that "growth and comfort do not co-exist" and her clear ability to get comfortable being uncomfortable. Indra Nooyi, CEO at Pepsi, for her candor about the complexity of integrating job and family. Amy Jain and Daniella Yacobovsky at Baublebar for their supply chain brilliance and ability to create tremendous customer-brand connection without retail stores. Elizabeth Holmes, Theranos CEO, for her sheer fearlessness and determination. It's epitomized by her absence of a back up plan. She says, "The minute you have a backup plan, you've admitted you're not going to succeed." Most people can't fly without a net.
What do you want Workboard to accomplish in the next year?
Grow our customer community 10x and become the obvious go-to tool for rising leaders everywhere.