How To Become an Executive
Gainsight Chief Operating Officer Allison Pickens Shares Advice for Women Hoping to Reach the C-Suite
When it comes to women's path to the C-suite, lack of representation is just one of many barriers to entry.
Working at a company founded and led by two women, I know I'm lucky to have examples of strong female leadership to look up to.
Most of my peers are not so lucky, and it's certainly the first time I've found myself in this position - it's no wonder why, given that only 6% of CEOs and 25% of executives are women.
I believe strongly in the power of representation - and in the power of stories.
So after chatting with Allison Pickens, Chief Operating Officer at Gainsight, about Customer Success, I couldn't resist the opportunity to ask her about her own path to the C-suite and what she'd recommend to other women hoping to reach C-level roles.
Want to learn how to become an executive? Here are Allison's recommendations.
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What advice would you give to women looking to elevate their careers?
If you're looking to rise in your career, make sure that you're working for someone who you have a lot of respect for and who is not just going to be a friendly boss, but who will advocate for you. You should work for someone who's in your camp, fully recognizes your growth potential, and wants to help you grow over time.
What would you recommend to women interested in taking on a C-level role at some point?
Develop general leadership skills. I think there's a certain set of general leadership skills that apply to any function. For example, you need to learn:
- How to manage a difficult conversation.
- How to communicate with different audiences, whether they be investors with a financial mindset, individual team members, your boss, or peer executives. You have to know how to cater to your audience.
- How to motivate yourself through tough times and develop your own emotional self-awareness and control.
How would you recommend learning these skills?
- Go to a business school that gives you hands-on experience in working on your interpersonal awareness and abilities.
- Read books.
- I've read so many different biographies of leaders throughout history. Biographies help you find examples of situations that might be analogous to what you're going through, so that you can brainstorm ideas for how to get through it.
- Have someone in your network who is a peer coach and can be a sounding board to you during challenging situations.
- Find a peer who can coach you not by giving advice, but by asking thoughtful questions and who you can coach in return so it becomes a reciprocal relationship. You might meet once a month with this person to work through your latest tough situation, and do the same for your partner.
- When you're at the VP level or higher, get an executive coach.
- This is someone who can function much like a peer coach, but is trained on how to do it. They can give you suggestions of tactics that you might pursue and ask you an even more thoughtful set of questions.
- Become an expert on your function by learning as much as you can from other people's experiences.
- You should always look to be the best person for your role. In other words, if your boss were to start a new recruiting search to fill your role right now, would they still pick you? Your answer to that might change over time. It might be that your company has doubled in size and now your role requires a different skill set, so you've got to be able to evolve with your company. Sometimes just staying in the same role as your company changes requires you to promote yourself by upgrading your own skills. You can upgrade your skills by asking detailed questions to more experienced leaders who theoretically could replace you in your job.
What's the hardest lesson you've had to learn as a woman navigating your career and ultimately reaching the C-suite?
The most important thing that I've learned and am continuing to learn is to be authentic to my style no matter what the situation is. I think when you're in an environment where there aren't as many women, or regardless of who you are, where there are not as many people like you, it can be tempting to try to conform to the norm.
That might help you in the short term, but it's going to set you back in the long-term because if you're not true to yourself, you may not end up on the right path for you. You have to stay true to your personal purpose, your personality, and reinforce for yourself on a regular basis that you've got to show up as the best version of you.
Can you share a technique you've used to be a more authentic version of yourself at work?
I think it starts sometimes with the smallest things. Earlier in life, I was in a job where I was virtually the only woman on my team. Although I wasn't fully conscious of it at the beginning, I felt pressured to dress like the men.
Everyone around me wore black or gray pants and a button-down shirt. So I wore black pants and a button-down — basically the women's analog for the male uniform. One day I thought, why am I dressing like this? Certainly that's a fine way for women to dress, but it wasn't my style. I like wearing dresses and bright colors. So I went to a department store and shopped for dresses. I showed up the next day wearing a dress. My boss at the time was a woman, and she also dressed with the standard button-down look. She looked at me and said, "Your dress looks great." Then she went out and bought a few dresses herself! That was incredible validation for me that being yourself is powerful.
It's powerful for you. It's also powerful for other people to see. You will inspire authenticity in other people if you're authentic to yourself.
The outfit example is more superficial, but I think it's important symbolically. An even more substantial example of being yourself in a work environment is expressing your point of view. And especially sharing stories of things that you've experienced. I think it's very important that we have women's voices present in our companies, and even more importantly, in our society. If we can speak up about our perspective in a work environment, I think it will help our companies improve. It will help our society improve as well.
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8 (Virtual) Diversity Conferences to Attend in 2021
Diversity Reboot 2021: The One Hundred Day Kickoff
<p><strong>When</strong>: February 1-5, 2021</p><p><strong>Where</strong>: Virtual</p><p><strong>Price to register:</strong> Free!</p><p><strong>Where to register: </strong><a href="https://summit.powertofly.com/" target="_blank">Here</a></p><p>We had to include our own Diversity Reboot on our list of the best diversity and inclusion events to attend in 2021 because we know firsthand how the quality of 100+ expert speakers, the enthusiasm of 10,000 participants, and the cutting-edge tech that enables meaningful virtual networking and job fairs combine to create a truly epic five-day experience. This year, the theme 100 Day Kickoff harnesses the energy of the new government's first 100 days in office to help jump-start personal and professional plans to build more diverse and inclusive workplaces. </p><p>Following the February summit, we'll have a monthly series of smaller virtual summits on topics spanning everything from returnships to LGBTQ+ advocacy, so be sure to stay tuned for updates!<br></p>The Future of Diversity, Equity and Inclusion 2021
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<p><strong>When</strong>: March 8-12, 2021</p><p><strong>Where</strong>: Virtual</p><p><strong>Price to register: </strong>$820</p><p><strong>Where to register:</strong> <a href="https://cvent.me/ZQ4BbE" target="_blank">Here</a></p><p>The Forum on Workplace Inclusion's 33rd annual conference includes 12 session tracks, from DEI Strategy to Social Responsibility, along with 59 workshops and daily networking sessions. This year's theme focuses on one question: "What will it take to start a workplace revolution that moves us from talk to action?"</p>Diversity: How Employers Can Match Words With Deeds
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<p><strong>When:</strong> August 18, 2021</p><p><strong>Where: </strong>Virtual</p><p><strong>Price to register: </strong>$195</p><p><strong>Where to register:</strong> <a href="https://www.hci.org/conferences/2021-virtual-conference-hire-diversity-equity-and-inclusion-august-18-2021" target="_blank">Here</a></p><p>This conference put on by the Human Capital Institute is one of 12 virtual conferences that HCI has planned for 2021. This one focuses on fair and inclusive talent acquisition, including how to attract diverse talent, implement inclusive hiring practices, and addressing bias in employee selection. Other conferences will focus on optimizing talent strategy, engaging employees, and developing your workforce.</p>Virtual Grace Hopper Celebration 2021
<p><strong>When:</strong> September 26-29, 2021</p><p><strong>Where:</strong> Virtual, broadcast from Chicago, Illinois</p><p><strong>Price to register:</strong> Was $799 for regular access to the virtual conference in 2020; 2021 pricing hasn't yet been announced</p><p><strong>Where to register:</strong> <a href="https://ghc.anitab.org/attend/registration/" target="_blank">Here</a>, though 2021 registration wasn't live at the time of writing</p><p>Grace Hopper might be the best-known conference for women in tech. Through keynote presentations, networking sessions, job fairs, and community-building activities, vGHC reached over 30,000 women for their 2020 conference and are expecting even more in 2021! While not a conference focused exclusively on diversity and inclusion, many speakers plan to focus their talks on creating environments for women to thrive in the male-dominated tech field.</p>Inclusion 2021
<p><strong>When:</strong> October 25-27, 2021</p><p><strong>Where:</strong> Virtual and in person in Austin, Texas as of now</p><p><strong>Price to register:</strong> Hasn't yet been announced</p><p><strong>Where to register: </strong><a href="https://conferences.shrm.org/inclusion" target="_blank">Here</a>, though 2021 registration wasn't live at the time of writing</p><p>The Society for Human Resource Management's biggest conference of the year saw 1,200 DEI leaders participate last year; SHRM hopes to see even more come to learn, be inspired, and to walk away with a playbook of implementable strategies to create truly inclusive workplace cultures.</p>AfroTech 2021
<p><strong></strong><strong>When:</strong> November 8-13, 2021</p><p><strong>Where:</strong> Virtual</p><p><strong>Price to register:</strong> Early bird pricing is $149 for individuals and $249 for corporate attendees; regular pricing hasn't yet been announced</p><p><strong>Where to register:</strong> <a href="https://experience.afrotech.com/" target="_blank">Here</a></p><p>AfroTech is a conference hosted by Blavity, a tech media platform for Black millennials. It focuses on emerging tech trends, connecting Black talent with top tech recruiters, and providing networking and educational opportunities, with an overall goal of building a strong Black tech community. Over 10,000 people participated in 2020. While the conference isn't focused specifically on DEI, its main audience of Black tech talent is an important one to understand and to engage at work and beyond, and several speakers plan to focus on issues of race and inclusion at work. </p>Finding Her Sport: Being Part of the Team in a Startup Environment
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Tips to Prepare for Your Interview at SoftwareONE
Nina Unger, Talent Acquisition Specialist at SoftwareONE gave us a behind-the-scenes look at SoftwareONE's Application process, culture, and values.
Learn about the company and how you can make your application stand out!
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