#37 The Good, Bad & Ugly of Lonely Leadership

THAT MOMENT WHEN YOU HEAR

• “Of course it's lonely at the top! Nobody gets how pressurising it is to make these big decisions that could sink the ship.”

• “There’s nobody else I can to turn to at work for help - I’m paid to be the smartest person in the room right? Everyone else in the office gets to say ‘I don’t know’, complain and criticise - except me.”

• “I spend so much of my waking hours at work…my wife definitely doesn’t like it…I don’t like it…I’ve missed my kids’ events…I don’t have close friends beyond work friends anymore - but that’s just the way it is, right? Someone has to take the hit, someone has to do the work.”

• “I’m afraid if I tell people at work the stress I am feeling, they will no longer know how to relate to me or respect me. What kind of leader confesses they don’t know what they are doing?”

…you’re in the Good, Bad & Ugly of Lonely Leadership

😇 THE GOOD THING is more leaders recognise that social connection is healthy, too much loneliness is toxic and we need different social spaces for different connections.

During the peak pandemic year of 2020, US Surgeon General Dr. Vivek Murthy called attention to what he believed was a public health crisis in America.

It was not Covid-19 he was calling attention to - but Covid’s impact on the invisible epidemic called loneliness.

Murthy argued that prolonged disconnection from other people increases

• our risk of premature death by >60% (comparable to smoking 15 cigarettes daily)

• our risk of heart disease by 29%

• our risk of stroke by 32%

He was so concerned about loneliness’ impact on physical, mental and emotional health that his Surgeon General’s Advisory on Our Epidemic of Loneliness and Isolation recommended that all leaders, communities and organisations take immediate action to help their people form more human connections.

What is Loneliness? It’s an uncomfortable emotion we experience when there is a persistent “mismatch between the quantity and quality of the social relationships that we have, and those that we want.” (Perlman and Peplau)

Being persistently lonely gets us into a chronic stress state because we are not built to live in a state of perpetual existential unease. We are biologically and neurologically built to seek social connection.

Given the amount of waking hours we all spend on work and at work, loneliness in the workplace is every leader’s concern. Because if the place people are giving most of their energy and time to fails to provide them the “quantity and quality of social relationships they want” at work, we are adding to that public health crisis Murthy warned about.

So what can leaders do to decrease loneliness at work?

Don’t let distraction, disconnection and detachment characterise your work relationships. Remember, people are hardwired to function best when we relate to them with healthy attention, affection or attachment.

• Remember, we are neurologically designed to seek security, safety and belonging from others. Anything less adds to psychological and physical stress. When talking, we can give our full attention to each other rather than being distracted by tasks. We can also offer clear signs of affection or affirmation that warm up even a tough conversation rather than only emotional coldness that chills any attempts to connect. We can learn to secure and attach to each other even as we disagree strongly rather than detaching, distancing and making each other more insecure.

Don’t just stick to supporting relationships at one level. Remember, people need healthy relationships at the 1-1, group and collective level.

There are 3 levels of loneliness that require connection to 3 specific social spaces.

• Intimate loneliness – perceived lack of meaningful 1-1 relationships

• Relational loneliness – perceived lack of quality friendships

• Collective loneliness – perceived lack of belonging to a community

To resolve loneliness, support connection in 3 social spaces:

• Inner core: This is our most intimate, tiny circle of 5 loved ones who will drop everything for you when things collapse. (e.g. your partner, best friend, beloved parent etc.).
  

• Sympathy group: This is the next circle of 15 people (including your inner circle, maximum 50 people) who are your good quality friendships at work and beyond.

• Active network: This is our outermost circle of 150 to 1500 people: casual acquaintances from work, school or community groups. You aren’t necessarily “friends” but you get a sense of belonging to a “community” or “tribe” sharing common interests, values, or goals.

Vivek Murthy explained in his book Together that all 3 social spaces must be filled with quality relationships for us to experience a persistent sense of social connection and thriving.

• An undeveloped Inner Core = intimate loneliness: Even if you have a stable community or meaningful friendships, you can feel lonely because you long for close confidantes to be there in crisis.

  So, Leaders, encourage yourself and others to make time for priority connections with their Inner Core outside of work. This is where we must go to ease their emotional loneliness.
  

• An undeveloped Sympathy Group = relational loneliness: Even if you have a loving inner circle or stable community, you can feel lonely because you hunger for good friendships.

  
  So, Leaders, encourage yourself and others to keep regular face-to-face contact, help each other with personal projects, and provide emotional support - at work and outside of work. This is where we can go to ease our social loneliness.

• An undeveloped Active Network = collective loneliness: Even if you have a loving inner circle and meaningful friendships, you can feel lonely because you want to find some larger sense of community.
  
  So, Leaders, support yourself and others to volunteer for a Greater Good goal or connect with like-minded tribes at work and outside of work. This is where we can go to ease our existential loneliness.

The good news is this also lifts some pressure off for those of us who find ourselves in someone’s social spaces and gives us clarity of whether we are the best suited to take care of this person’s particular level of loneliness.
 
An intimate partner need not feel pressured to care for all the causes we care for.
An acquaintance need not feel pressured to listen to our most intimate sharings.
A wider community need not feel pressured to be close friends with everyone.

Supporting each other to ease our loneliness is a good thing to do.

Supporting each other to go to the specific, more appropriate circles to ease our particular type of loneliness may be an even better thing to do.

🤬 THE BAD THING is we often forget the person “at the top” is very vulnerable to loneliness. This is not a personal predicament - but a systemic and predictable condition.

For all the advice I gave above for leaders to support their people to find connections, my worry is for leaders themselves.

The saying “It’s lonely at the top” is all too true.

Barry Oshry - a pioneer in human systems thinking - has some sharp observations based on his ground research about why leaders at the top consistently feel lonely.

Oshry argues that “top”, “middle”, “bottom” are not titles but persistent conditions that all of us will face from situation to situation, from system to system.

• The position of the Top = anyone functioning as the Developer of the organisational system or work situation. (e.g. you hold ultimate responsibility for the morale and output of your project team)
  

• The position of the Bottom = anyone functioning as the Fixer of the organisational system or work situation (e.g. you are on the receiving end of decisions from ‘above’ and have to fix or execute accordingly)
  

• The position of the Middle = anyone functioning as the Integrator of the organisational system or work situation (e.g. you are balancing between requests/pressures from the Bottom vs. the Top)

In other words, you don’t have to have the namecard and corner office “LEADER” to suffer the loneliness of “being at the top”. You will suffer it as long as you are positioned as “the top” relative to others in an organisational system or work project situation.

So why do leaders at the Top feel predictably and systematically lonely?

• The job scope of Tops is always about creating a stronger system where everyone involved is aware of dangers and opportunities and are using their full potential to ensure the system’s survival and development.

• And the situation of the Tops is always about managing environmental complexity while making decisions for the system: So Tops handle a daily bombardment of incoming data, diverse perspectives and different changes from the environment that impacts the system.

• But the reflex of most Tops tends towards Sucking Up Responsibility: When problems hit, many well-intentioned, skillful and sincere Tops cope sensibly at first by taking responsibility. But the more critical the issue, the more they may feel pressure to take on more responsibility than others. They even take over or take away responsibility from others.

• This reflex to Suck Up Responsibility gets particularly unhealthy if they are rooted in deep personal and cultural fears: a personal fear of looking weak, stupid or needy; a professional belief that leadership is about sacrificial carrying of burdens or command & control; cultural beliefs about leaders needing to be stoic, silent and invulnerable.

• But as the Tops keep Sucking Up Responsibility, Tops get overwhelmed and lonely from labouring by themselves. They develop unhealthy thoughts about being fundamentally alone, different or better than others. They feel unsupported - even while they are surrounded by people who want to support them but aren’t given space or permission to support them or people who have given up figuring out how to support them. The more they take over other people’s responsibilities, the more they reinforce unhelpful beliefs that only the Tops are responsible and only the Tops are capable. This disempowers people, robs their opportunities to grow and diminishes the system’s ability to perform.(Oshry’s cartoon of this experience is below)

  

• At their most unhealthy, Tops develop a “This is Mine. That is Yours. Don’t meddle with Me” mentality towards everyone (even fellow Tops). They harden their boundaries of responsibility into thickly walled Silos. This makes them get aggressively and territorially lonelier: The longer they work in silos, the less aware and less involved they are in what’s happening in other people’s territory. As their walls grow more impenetrable, they have less empathy for others’ issues and concerns. Continuing to hold their strong views and manage their complex burdens behind their armoured walls leave themselves and others feeling unseen, unheard and misunderstood - and profoundly lonely. (Oshry’s cartoon of this experience is below)

😈 THE UGLY THING is we assume that loneliness is just the price leaders must pay for success - and surely their rich rewards ought to soothe the sting. But this lack of empathy isolates the “lonely leader” further - potentially endangering themselves and others.

It’s always psychologically risky for leaders to lower their walls to reveal what they are struggling with. Many do face incredulous critics from fellow Tops as well as their Middle, Ground when they do try to connect with others about the struggles they go through as a “Top” managing complexity.

When DBS CEO Piyush Gupta opened up publicly about how he suffered massive anxiety at 40 closing down a dot com he led while trying to find jobs for 100 ex-employees, many comments on social media were unsympathetic:

Comments like the one above show the 2 big assumptions we have about leaders that prevents “them” from connecting with “us”:

• Unhelpful Assumption #1: The leader’s job is to lead - so just lead. We don’t want to hear about your weakness. If you’re that weak, maybe you shouldn’t be a leader.

• Unhelpful Assumption #2: The privileges (wealth, fame, titles etc.) you leaders are rewarded with should be sufficient to shield or soothe you from any struggles - so you have nothing to complain about.

Unhelpful Assumption #1 dehumanises leaders, seeing them as a job position and not a human being. If we want our workplaces, organisations and systems to be more human, we get there by encouraging our leaders to be more in touch with their humanity - not less.

Unhelpful Assumption #2 is understandable but untrue. Wealth, fame, titles etc. tangible privileges cannot shield us from human pains or soothe the psychological and emotional suffering caused by being detached from meaningful connection with others. You cannot buy a sense of authentic connection - if you did, you’d always question it’s authenticity. If there aren’t intentional interventions made, someone’s privileges can become their golden cage where both the one in the cage and the one outside the cage assumes they cannot connect in any meaningful human way.

But why should we care if leaders get more lonely and disconnected?

1. The more disconnected leaders are from others, the narrower is their view of themselves and the world. This stunts their own growth and the growth of people they lead. When we connect with people, we learn to include their worlds into our sense of Self. Engaging with each others’ differences and commonalities helps us expand our assumptions of who we could be, who we want to be, who we need to become. Disconnected leaders withdraw into themselves and bring their followers alongside, creating echo chambers that further narrow and stagnate their worldviews. 

2. Disconnected leaders get deeply anxious inside - and anxiety is a contagious emotion. High performing leaders can hide their loneliness and anxiety for a long time while still doing great work. However, subtle signs of discomfort will eventually leak out and affect their performance. Their underlying anxieties can also infect other leaders and people in palpable ways. Everybody can feel uneasy as well as if they too are on the edge and unable to connect with others about what’s going on - mirroring their leader’s experience.

3. The most chronically disconnected leaders can become dysfunctional Lone Wolves who endanger themselves, others and the systems they are in charge of. Sometimes chronically lonely leaders may indulge in risky behaviours or make risky decisions that border on self-destruction or destruction of others. But Lone Wolf leaders are so disconnected that they can no longer be communicated with, comforted or confronted in a healthy way. So their behaviours continue unabated or enabled.
   
   Psychologists refer to this as social-distance: where you keep the majority of people far enough away from your personal world in order to maintain an illusion of success.

   After a Lone Wolf leader has self-destructed, people surrounding them might reflect: “She was a private person” or “We worked for years with him but never quite knew him.” or “They kept to themselves. Nobody could get close.”

🌸 THE BEAUTIFUL THING is you can start connecting with people to ease your loneliness today. It’s not about quantity but quality. Not about frequency but consistency. Not about intensity but authenticity.

Fear not, introverts. It’s never been about how many people you know or how frequently you have to talk to them.

Focus on quality not quantity:
You can be less lonely if you build a handful of healthy, intentional relationships in those 3 social spaces: nurturing 5 loved ones, 10 close friends and volunteering/joining 1 community cause group (that will eventually link you to 50+ friendly acquaintances) is a good start.

Focus on consistency not frequency:
Find a rhythm that makes most sense for the relationship you want to nurture: loved ones need more daily and weekly connection; close friends need more weekly or monthly connection; friendly acquaintances can do with monthly, quarterly or annual meetups. Dial down the frequency for relationships that don’t need that much time and energy from you.

Focus on authenticity not intensity:
You don’t need to be vulnerable and intense with everybody but you can practice authenticity to build connection.

To keep your practice of authenticity simple, think of it in 3 levels for now:

• Think of Level 1 Authenticity as something true but too vague, too bland or too “huh?” for someone to connect with (eg: “I ate chicken rice the other day.”)

• Think of Level 2 Authenticity as something true, a bit emotionally vulnerable enough for a friendly acquaintance to intentionally connect with (eg: “I was thinking about whether to enrol myself in a postgraduate psychology programme. It feels really intimidating though. I don’t feel confident I can tackle that on top of my daily work.”)

• Think of Level 3 Authenticity as something true but potentially too emotionally vulnerable for even a friend to know how to connect with appropriately or intentionally (eg: “I have been processing so much childhood trauma these last few years. When I was 5, my mother….”)
  
  The most disconnected and lonely way to exist in the world is to conduct all your interactions only at Level 1 or to aim your Level 2-3 interactions at the wrong people.
  
  With your Sympathy group and Active Network,
  practice Level 2 more often than Level 1. Never Level 3. 
  
  With your Inner Circle, practice Level 2 often. Occasionally when needed, Level 3. (This level can be overwhelming even for your Inner Circle so it may be good to also bring that level of conversation to a professional who is more skilled at supporting you.)

PRACTICE THIS

6 things you can do to create meaningful and authentic connection at work

1. Reflect on who fills up your 3 Social Spaces + who else you may need: Categorise the people in your life into the 3 social spaces — inner circle, sympathy group, and active network. Where is the gap of good quality relationships that you are facing? Which social space seems underdeveloped? How connected do you feel to your spaces right now and how much more connected would you like to be? How can you make it easier for yourself to connect with the ones that matter more to you?
   

2. Make space in the calendar for meaningful connections: A schedule packed with multiple meetings and conversations that are more about task and less about meaningful connections is a recipe for creating loneliness. Depending on where is the loneliness coming from (intimate, relational, collective), organise time and space to go to the appropriate social spaces (Inner Circle, Sympathy Group, Active Network) to form healthy connections there.

3. Join horse-shoes, not circles: Friendly groups are those that literally and figuratively create a bit of open space for someone new to step in and connect with them. It is socially hard for many of us to intrude upon what looks on the outside like a closed little friend-group. If you are on the outside looking in, always look for people or groups that are willing to be that horse-shoe for you. If you are daring, you can even create a horse-shoe for others to join. (eg: a Lunch and Learn with an online course you bought that’s open to all every Friday at the pantry)

4. Stop doing Covert Avoidance. Convey what you find interesting or delightful about them. This is when you show up physically but are avoiding and checked out mentally. You could turn up for team lunch and be thinking about emails, putting self-protective headphones in your ears, playing it cool while you wait for someone to approach you. This does not make people feel sure if you want to connect. Share one simple thing that you find interesting or delightful about them is a great way to connect (eg: “I really liked your presentation last Friday by the way.” “Hey, I heard you are working on the Port Authority job, I’d love to hear more.”)

5. Show up for something a few times over a period of time (not just a one-time guest appearance): Trust and connection is easier to build if people are being exposed to you regularly over a few sessions. If there isn’t a current regular thing that people at work do together, create something sensible that people can show up daily (eg: team lunch), weekly (eg: team sharing) or monthly for (eg: team learning).
   

6. Whenever you’re ready, share something at Level 2 Authenticity.

Thanks for reading!
There are 3 more ways I can support you:

1. Get me to support your team/organisation’s change efforts: 

My team and I can work with you on people dynamics that are getting you stuck. I help my clients by strategising, training & coaching key personnel and facillitating neccessary conversations.

Email [email protected]
or fill in this form on our website.

2. ​Come for our public training courses in change leadership skills

I want to help you build a foundational set of skills you need to work on changes you are longing to see.

• Facilitating Conversations For Change

• Facilitating Conversations For Diversity, Inclusion & Belonging

• Leading Effectively as Middle Managers

• Facilitating Psychological Safety For Team Health & Organisational Effectiveness

3. Keep reading and listening to what I am learning

• Subscribe to my Good, Bad, Ugly newsletter on LinkedIn, go here or email/web

• Listen to my podcast Finding Common Ground

Take care of yourselves & the ones you love,
I’ll see you next Friday,

Shiao