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.
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.
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.
It's been six years since Sarah Cooper graced us with her 10 Tricks to Appear Smart in Meetings. But how on earth can we appear smart in our new virtual world, in which for many of us, going to work is just sitting in one long series of probably-not-necessary Zoom meetings?
1. Dial in.<p>Dialing in rather than joining via the link instantly boosts your credibility. Who calls into Zoom meetings? People who are still busy and important enough to be leaving their houses! But you needn't actually be one of those people, or even more than a foot away from your computer to pull off this maneuver. (Remember, this article is called *seeming* smart, not being smart.)</p><p><strong></strong><em>Bonus: </em>If it's a large meeting at which attendance will be taken, the person running the meeting will inevitably ask, "Who's calling in from 443-322-2121?" That's when you raise your metaphorical hand, jump off mute, and say "[Your name] here. Really looking forward to hearing your perspective on [meeting topic]." And voila! You've stolen the meeting spotlight.</p>
2. Don't come on camera—ever.<img lazy-loadable="true" src="https://assets.rebelmouse.io/eyJhbGciOiJIUzI1NiIsInR5cCI6IkpXVCJ9.eyJpbWFnZSI6Imh0dHBzOi8vYXNzZXRzLnJibC5tcy8yMzQ0ODU5OS9vcmlnaW4ucG5nIiwiZXhwaXJlc19hdCI6MTYzNjMwNjI3OX0.4fLyq2CvkZAJ7n_03esZepY37mOdyGdDdTEUYt5XEU0/img.png?width=980" id="bc7e6" class="rm-shortcode" data-rm-shortcode-id="fbbf21cc5d8c863b30654ae6993b04f5" data-rm-shortcode-name="rebelmouse-image" /><p><br></p><p>Much like the "dial in," this technique works because it makes you appear aloof. If <em>The Crown has </em>taught me anything, it's that the key to maintaining a sense of mystique and prestige is to keep people at arm's length—and if you absolutely <em>must</em> touch them, wear a glove.</p>
3. Only communicate via chat.<p>Once you've mastered the art of staying off camera, you can level up by communicating exclusively via the chat box. Don't come off mute at all, even if the speaker asks your opinion. You are the elusive chatter and you will not be forced into actually participating in said meeting.</p>
4. Ask to share your screen.<p>Being aloof is great, but it's all about balance. Sprinkling in some active participation will really shock and impress your colleagues if you catch them off guard, so save this technique for when you've strategically <em>not </em>participated in a string of meetings.</p><p>Spend a few minutes prior to the meeting prepping a few inspirational slides with words like "synergy," "optimization," and "redefining 'culture'", or spend a few minutes poking around in Google Analytics. </p><p>Then wait for the opportune moment to say, "Can I just share my screen for a moment? I have some really interesting data I'd like to share...." and BAM — brilliance established.</p>
5. Show off your Zoom-saviness.<p>Try saying, "You know you can mute people, right?" to the host when they beg whoever's got the lawn mower and crying baby in the background to put themselves on mute for the nth time.<br></p>
6. Create an alter ego.<p>This tactic requires commitment, but the pay off is certainly worth it. Join the Zoom meeting from your normal account + name, and then join it again on a second device from an alias. Have your alter-ego ask some probing or stat-based questions in the chat and have the answers ready ahead of time. It should work something like this:</p><p style="margin-left: 20px;"><strong>Your alter ego Charlene</strong><strong>:</strong> "Does anyone know what percentage conversion rates increased by in Q2?"</p><p style="margin-left: 20px;"><strong>Real you</strong>: *doesn't miss a beat* "It looks like Charlene has a question in the chat. That would be 36%."</p><div>Never mind that no one on your team knows who Charlene is or why she's at this meeting, they'll be too blown away by your brilliance to notice. (Bonus points if you use this strategy in conjunction with techniques 1, 2, 3 or 4!)</div>
7. Place an obscure object in your background that exudes intelligence.<img lazy-loadable="true" src="https://assets.rebelmouse.io/eyJhbGciOiJIUzI1NiIsInR5cCI6IkpXVCJ9.eyJpbWFnZSI6Imh0dHBzOi8vYXNzZXRzLnJibC5tcy8yMzQ0ODYxOC9vcmlnaW4ucG5nIiwiZXhwaXJlc19hdCI6MTYwNzk5Njg2Mn0.V9_-3Ij3v_QndseqlrXRt5Nn39EJ97-itjls5zzYPf8/img.png?width=980" id="a369d" class="rm-shortcode" data-rm-shortcode-id="604a2f04b53c2e3bc801bfa5256f367b" data-rm-shortcode-name="rebelmouse-image" /><p><br></p><p>We're talking a telescope, or perhaps a hardcover copy of <em>War & Peace </em>(no one need know that its only purpose in your life is as a makeshift yoga block).</p><p>If you don't have any suitable props at your disposal, do not despair: download some screenshots of Sheldon's apartment from <em>Big Bang Theory </em>or the chalkboard in <em>Good Will Hunting </em>and use those as a virtual background.</p>
8. Ask "Is this really the best course of action given the current climate?"<p>Economic collapse, COVID, racism… No need to specify whether you're referring to one or all of the above; just sit back and watch your boss squirm amidst the ambiguity.</p><p>This strategy pairs very well with techniques 2 and 3. You can prep additional vague-but-probing questions ahead of time and pepper them into the chat box throughout the meeting:</p><ul><li>How will this scale?</li><li>Do we really have the bandwidth for this right now?</li><li>What's the value-add here?</li></ul>
9. Remind everyone that you have a paid Zoom account.<p>"Oh, it looks like we're getting the 40-minute warning. I have a paid account, do you want to switch to my room?" It's helpful, with just a touch of condescension. Everyone knows condescending people are smart. And everyone knows that people with paid Zoom accounts are super important.</p>
10. Tell everyone you have a hard stop.<p>When pressed for details, share your philosophy on "work-from-home" balance and how committed you are to getting up once an hour to walk to your refrigerator.</p>
11. Ask the screensharer/host to "pull something up" for everyone.<p>Ask the presenter to navigate to a screen that only you know how to navigate well. Laugh maniacally while they suffer from crippling performance anxiety. Let them struggle for as long as is tolerable before saying, "Oh you know what? I can just share my screen if you want. That would probably be easier." BAM you're the hero. Don't worry, no one will even pause to consider that you could have proposed this course of action from the start.</p>
12. Say Zoom fatigue as many times as possible.<p>If you're too tired to employ any of the other strategies, just say "I know everyone is experiencing a lot of Zoom fatigue, so we can keep this meeting short." Then hang up as quickly as possible. Meeting averted! </p><p>After all, there's no better way to demonstrate your intelligence in a virtual meeting than to demonstrate why it wasn't really necessary in the first place. </p>
I sat in front of my CEO to discuss several complaints of racism. I was new to my role as a Culture Director. I was nervous about his reaction to the complaints. But I also knew he strongly supported developing this new department; I knew that he would take the right steps. So I was shocked when I heard him say sheepishly, "I don't know, Noelle...all of this stuff about racism. I just don't see it. I don't even see color. I'm pretty much color blind."
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