Diane Flynn is CEO and cofounder of Reboot Accel, a suite of in-person and online programs that help women return to work by getting them current, connected, and confident. The idea for Reboot was born from her own experience returning to the workforce after a sixteen year pause. Once in her role as Chief Marketing Officer for GSVlabs, Flynn fielded queries from other women about how to make the move back to work. Recognizing a need, she launched Reboot Accel, which has served over 750 women in 8 different cities, resulting in new paths and jobs for over 82 percent of them. In 2018, Reboot will continue to host Accelerators, and is working with dozens of companies to help them source this talent pool.
By Kristina Van Dyke
You founded Reboot Accel as a result of returning to work yourself after a break. Can you tell us about your career prior to your pause?
I went to Stanford, worked at the Boston Consulting Group in Chicago for a few years and then got my MBA from Harvard. I then spent a decade at Electronic Arts in California, running sales, marketing, and business development for the educational software division. I absolutely loved my job and never thought I would pause my career. But I had toddlers at home and both my husband and I traveled extensively for work, so I ended up pausing my career to be with my three children. I spent 16 wonderful years with them and I still felt very busy. I volunteered at school, our church, and served as an advisor at the Stanford Children’s Hospital. Then, about three years ago, I had an opportunity to come back as chief marketing officer at a tech company, an incubator.
Tell us about your transition back into the formal work sector.
I was reluctant to return full-time and initially agreed to work 25 hours a week. But I found that I loved having this piece of my life back, getting dressed for work in the morning and going to the office, and working with various generations. After about a month, the CEO encouraged me to join the team full-time, which I did.
How had you and the work environment changed over 16 years?
I had three observations coming back after a 16 year pause. First, while I felt confident in my strategic skills, as well as marketing and branding experience, I did not have the technology skill set required to succeed in today’s work environment. I didn’t have a LinkedIn profile or the 500 connections and you need to have a professional presence. I didn’t understand social media as a business tool, and I needed to learn Slack, Skype, Google Hangouts, Zoom, collaborative calendars, and among many other tech tools. The workplace had totally changed.
My second observation was that a growth mindset enabled me to get up to speed quite quickly. I asked a lot of questions, did Google searches, watched YouTube videos and figured it out.
My third observation was that as I shared with women in my community that I went back to work, many of them expressed interest in returning as well, but they had no idea where to start.
What was motivating them to go back to work?
Many were experiencing life changes like kids going to college, divorce, widowhood — and with that, many suggested a loss of a sense of purpose. They felt they had much to offer, but didn’t feel current with today’s workplace technologies, they felt disconnected from their networks, and most of all, they lacked confidence. They asked: “Who would hire me? What do I have to offer?” Meanwhile, I’m thinking, I would hire almost all of these women! They have been running families and volunteer organizations. They are sharp, motivated, talented, and know how to “get things done”. That was the genesis of Reboot Accel. I didn’t do any research about the market for this idea or competition. I just went for it – I had access to a training center at work, a passion for teaching technology, and most importantly, a founding team of women who subscribed to the mission.
Can we talk more about the confidence piece? It’s incredible to see how quickly that erodes and prevents re-entry into the formal work sector.
Impostor syndrome is a major factor. Women will not apply for jobs unless they think they can meet all of the job specifications, whereas a man will apply if he thinks he can do 60 percent of it. The more time that we’re home disengaged from paid work, the quicker our confidence erodes.
I see this lack of confidence across the board. Whether you’ve been out for 6 months or 20 years and whether you have no college education or a graduate degree, it doesn’t seem to matter. It translates to everyone.
How intractable is this lack of confidence?
We are developing some exciting data on the fact that it can be overcome fairly quickly. Most women who enter our one week immersion program give themselves scores of one or two [out of 5] at the beginning of the week, and fours and fives at the end. We believe this confidence boost comes from demystifying today’s office technologies and by helping them see how much they have to offer in terms of soft skills, judgment, maturity, connections, wisdom, and negotiation – things that are enhanced during a pause, not diminished. And then there is being in community with like minded women, seeing that you’re not alone, and meeting women who have successfully re-launched.
Reboot Accel started in Silicon Valley but is expanding to cities across the nation. In California, your organization seems tech-focused. Is that the case elsewhere?
No matter what role you hold in any part of the country, today’s workplace is very technical. You have to have a certain suite of skills and understanding of today’s office technologies. If you look at roles like HR, legal, finance, marketing, all of them have a strong tech component now. If you’re in sales, you have to know how to work with CRM [Customer Relationship Management] systems. In marketing, you have to understand search engine optimization, social media, and digital marketing metrics. The legal profession requires working with certain collaborative tools. I’m impressed by how many women with engineering or computer science degrees are interested in returning to tech roles. The process of discernment or answering the question “what is my purpose and how do I want to spend my time?” is ubiquitous.
Reboot Accel creates opportunities for returners to meet with companies or their representatives in Silicon Valley. What respective discoveries occur at those events?
We give host companies opportunities to showcase their culture and discuss ways they support women. We also host HR panels with heads of talent, and respond to specific specific questions about how to handle the pause on the resume, how to address possible ageism, as well as how to negotiate your salary. I love that the hiring managers get to actually meet these women, since they’re typically very impressed by what returners can offer.
Another great opportunity for this discovery to be made is through “returnships,” or internships for returners, which allow an individual and a company a chance to get to know each other for a defined period of time. It also lets the returner grow confidence about her skillset and fit. We have hosted “returnships” within Reboot Accel with great success. We create a clearly defined project that allows a returner to up skill and, talk about recent tangible results in an interview setting.
The gig economy, project-based work, and volunteer opportunities all seem to represent opportunities for women to keep themselves in the game without necessarily committing to full time work, especially during periods where family and other demands prevent it. Can you talk about this changing dynamic in the work world?
When I left my job in the late ’90s, I felt I had two choices: all in or all out. My daughters are in their twenties and I bet they will never fully pause their careers because of the variety of flexible work options now available. If I had had the option to stay partially in the game, I would have. I know many other women would have as well.
There just wasn’t a flexible, work-at-home option when I paused my career. Now there are so many more opportunities. Those going through ReBoot Accel are all seeking different levels of fulfillment. For some, it’s financial stability. For others, it’s connection with a like-minded community. Some are seeking to return part-time, while others are interested in full-time roles. Still others are looking to do something entrepreneurial, perhaps even something with social impact. We’ve started an entrepreneurial bootcamp to meet that demand.
What are the downsides of this more flexible approach to work?
An Intuit report [page 21] suggest that 40 percent of all jobs will be flex by 2020. While the gig economy is exciting from a personal or family life perspective, I think it is going to pose serious challenges from a financial and long-term planning perspective. I believe people will have to work longer [in age] than they have in the past and will have less security with regard to healthcare and retirement funds.
What has been more challenging than you anticipated in helping women return to work?
I’ve been surprised at just how stubborn the bias against this demographic of returners is. Our women face a triple bias: gender, age, and the pause itself. I see progress every time one of these women breaks through and is hired, does great work, and convinces another employer of this demographic’s value. While those in Diversity and Inclusion within companies are readily convinced of the value returners offer, the hiring manager is often slower to warm. Change is happening; I would just like to see it happen faster.
As Reboot evolves, what new kinds of training are you adding to the curriculum?
We are paying more attention to the power of language. We’ve found that a lot of women will get an interview and then have a hard time effectively communicating their skills and talents. I’ve given a talk called, “Upping your Language Game: 14 Ways Women Undermine Their Impact and Influence,” not only in the Reboot Accel context, but also increasingly in venues like my kid’s school, universities, and even for women’s initiatives at companies. We also have curriculum focused on contract negotiation, personal branding, and office etiquette. There is a growing interest in the topic of multiple generations working together. The workplace and culture are changing rapidly, and women seek feedback and coaching on how to most effectively express their ideas and contribute their talent.