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Limiting Loneliness: A Self-Help Guide for Executive Extroverts

  • 19 May 2021

It’s widely accepted that executive leadership today depends on outstanding people skills. In our experience as leadership advisors, skills such as collaboration, influencing, motivation and inspiration become more important as people climb the corporate ranks. At the same time, it can be lonely at the top. As executives assume positions of increasing seniority, their peer set falls away, leaving fewer confidantes and sounding boards. These two truths combine to give rise to the plight many executives are facing around the world: their ability to inspire greatness in others has elevated them to leadership positions, but as a result, they have lost some of the comradery that has contributed to their personal satisfaction. What’s a poor executive extrovert to do? 

These problems have become more acute in an age of isolation in which working from home has deconstructed many of the traditional ways people interacted – office socials, business lunches, and water cooler conversations. Busy executives often find that Zoom coffee chats with no specific agenda are the first thing to get crowded off their calendar, and back-to-back meetings are no longer interspersed with in-person collisions on the way to the restroom or coffee pot.  It is even more important that extroverted executives find constructive ways to build interaction into their day-to-day realities.

We offer three strategies to executives who find themselves wishing they could bounce ideas around with others more regularly or who are yearning for the days when they were surrounded by thought partners. These strategies are rooted in the fact that support is all around you, if you just know when, where, and how to ask for it. You might find you’re not as lonely as you think!

1.    Help Others Help You: Lean on Others Productively

Eight little words are a central foundation for effective engagement: “When can I get 10 minutes with you?” They allow you to get the interaction you need while minimizing negative side effects for those around you. Extroverts often benefit from talking through issues to process them. However, they may feel selfish asking for time from their executive peers, whose calendars are already busy. This problem is exacerbated for those in the top roles. Surrounded only by subordinates, an executive might be loath to ask a report if he or she expects the report will feel duty-bound to oblige but may secretly harbor resentment for the interruption. However, this phrase allows your chosen sparring partner to meet you on terms that work for them, selecting a moment and context in which they can make themselves available without distraction or mental discord, thereby minimizing the risk of your outreach interrupting or annoying your colleagues.

Of course, this card can only be played so many times, and we recommend using this tactic for moments when you really need meaningful engagement with a specific colleague on a time-sensitive topic. There may be other times when you are excited or moved by something and find yourself bursting with an urge to share it. Fortunately, technology offers plenty of platforms for “one-way sharing” to scratch that itch.  Email or group chats are a useful forum when you are excited or proud about something, particularly if you take the opportunity to highlight others’ success, for example: “Team, just wanted to share this great feedback I got from Client X, she is delighted with the work we did on Project Y; huge thanks to Cecilia who drove a ton of the legwork for that!” If you don’t already have one, consider setting up a dedicated WhatsApp Group with your colleagues for non-work-oriented messages, including sharing jokes, pictures, or interesting articles. This helps streamline official channels by keeping them focused on work-related topics, while creating a platform for sharing other parts of your life. This can have the benefit of deepening work relationships, but also allows participants to choose the frequency and forum for their engagement. 

2.    Pay it Forward: Choose Your “Victim” Wisely

If you are itching to discuss an idea, you may look to your closest colleagues and conclude that they would see this as a chore. They may be extremely busy, or they may have dealt with the same issue a hundred times before. But don’t forget the adage that “one person’s trash is another person’s treasure.” If your usual suspects are unavailable or not inclined to share your energy, consider whether there is someone else who might be willing, or even eager, to do so. Did one of your clients get a big promotion? Instead of calling one of your peers, consider telling your executive assistant, who has probably exchanged hundreds of emails with the client over time. Are you thinking through how to approach a tough situation with a client? Consider asking that up-and-coming manager on your team, who is working on advancing her client management skills, and turn a brainstorm into a teaching moment. 
As you have climbed the corporate ladder, you may have come to see a myriad of things as burdens which would be viewed by others as major opportunities. More broadly, there are probably plenty of people on your team who would appreciate extra time with you, even (or especially) if it’s spent helping you think through a problem. Lean on these people productively, and you may be able to contribute to their development while also satisfying your own need for engagement. 

3.    Be Your Own Confidante: Talk to Yourself with Flair

If there is no one available to talk to, there are several ways you can engage productively with yourself to create similar – or possibly better – outcomes. Dictation can help you process your reactions following a meeting or conversation, while also codifying your thoughts for future use. If you wrap up a discussion and find yourself with an urge to tell someone about it, turn on your phone’s talk-to-text feature and share your thoughts with Siri. Even better, put on some headphones and do your dictating while you go for a walk. No one will know that you’re not talking on a Bluetooth headset! This strategy can also be valuable if you are being harder on yourself than you would be on anyone else; if you talk about your problem the way you would talk to a friend, you can also listen to yourself in the same vein. Not only will you have the chance to process your reactions, but you may identify a blind spot, and your phone will capture notes which could be highly useful down the road.   

You can take this strategy to the next level with journaling. There are myriad journaling techniques which can help with processing issues or challenges in ways that mimic the interaction you enjoy with others. For example, Carl Jung’s technique1 of active imagination involves translating your unconscious into images or even personifying them as entities . You can use this technique to play out a dialogue in the pages of your notebook, allowing pieces of your brain to hash out the debate you might enjoy having with other people. This further allows you to push the boundaries of your own thinking, challenging yourself to adopt a specific viewpoint, to stretch your comfort zone or activate various elements of your personality. For example, if you view yourself as overly practical and have a development goal to devote more mindshare to big picture vision, you can journal a conversation that “Practical You” might have with “Visionary You,” and in so doing, experiment with wearing a different hat than your default one. How lonely can you be when you’re surrounded by all those voices in your head?

Lonely No More

If you are an executive extrovert, you may feel lonely at the top, as many of the social structures you depended on have fallen away on your journey up the corporate ladder. But many of those structures have not fallen far, and some may have been replaced by other opportunities. You are probably still surrounded by people who will be happy to engage with you, as long as you do it in a way that works for them, or by leaning on “one-way sharing” when that will do the trick. There are likely a host of people who would enjoy talking something through with you and may even be able to learn something from the opportunity, if you think carefully about where to look. And you can always look inward for a chance to keep yourself company, while potentially learning some things along the way. Your social prowess helped get you where you are, so don’t feel you need to relinquish it now. If you funnel it in new directions, your extroversion can continue to be a source of energy in almost any context.


[1] Hoerni, Ulrich; Fischer, Thomas; Kaufmann, Bettina, eds. (2019). The Art of C.G. Jung. W. W. Norton & Company. p. 260.

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