Navigating an existential crisis in tech: tips from a Silicon Valley executive coach

The emergence of the darker side of A.I. the downturned economy, mass layoffs, and most recently the collapse of Silicon Valley Bank have made the past few weeks especially tumultuous for those working in the tech sector. For over a decade, my work as an executive coach in Silicon Valley has given me visibility into the sorts of quandaries tech leaders face while building products that transform the world in unpredictable ways. Many are facing a new sort of existential stress, as they work to find a way to reconcile how their professional contributions could pose a serious threat to the future of humanity. 

The current mood across the tech ecosystem has shifted away from a once devil-may-care attitude, notably among millennials raised on a diet of ‘move fast and break things’. The Bay Area, known for its youth-forward social climate is widely considered the country’s pulse of progress and tech innovation. My coaching work throughout the tech boom era entailed helping tech workers prepare for eventual burnout, since most were happy to immerse themselves in work with little to no separation of their social lives, only stopping to refuel their mission-driven ideologies with annual trips to Burning Man

The whiplash of recent events in 2023 following the erosive damage caused by the pandemic has led to a jarring new kind of existential stress among the tech crowd. The encroachment of A.I. tools rendering careers obsolete at breakneck speed, the sterilization of creative industries, and evidence that A.I. operates with racially biased, sexist and morally unethical practices has many people deeply fearing what the future holds. 

What exactly is ‘existential stress’ and how does someone manage an existential crisis?

Existential stress occurs as a result of inner conflicting feelings that lead someone to question the meaning and purpose of their life. When we face personally important questions that aren’t easily resolved, we can end up feeling stuck and unsure of how to move forward. This leads to feeling deeply uneasy when we no longer feel rooted in the values and principles that once led our purpose and direction in life. Existential stress may be experienced as a crisis when once effective strategies for managing stress are no longer sufficient and our overall functioning wanes.

If you or someone you know is feeling this way and wondering what to do, here are key signs that you may be experiencing an existential crisis:

Chronic worry. You may be experiencing recurring worries and unsettling fears that you are no longer able to get past, and distract you repeatedly in your daily life.

Loss of motivation. You may be easily overwhelmed or lose direction doing tasks you once completed with effort, and feel a loss of desire or drive that once fueled your work ethic. You may feel disconnected to the purpose of once meaningful tasks, which may leave you feeling like ‘you’ll never catch up.’ 

Low energy. You’ve fallen out of your normal sleep, exercise, and diet routines that historically sustained you, leading to an erosion of your baseline energy. 

Loss of social appetite. You may have less interest in spending time with others you once enjoyed connecting with, due to low energy and mood. With diminished social interactions, we are less apt to consider alternative perspectives and benefit from the restorative nature of social connection

Loss of control. You may feel a lack of control over the future and feel like you can no longer prevent bad things from happening. This can lead to feelings of helplessness, as though your efforts are pointless and/or meaningless.

Anxiety or depression. While it’s normal to experience a range of emotional highs and lows throughout one’s life, you may find yourself struggling with mood symptoms that have reached clinical levels.
Substance abuse and/or self-sabotaging behaviors. You may find yourself relying on substances to avoid thinking or feeling, or falling into habits that are personally harmful as a temporary distraction from feeling lost. 

Seek professional help first. It can be difficult to know where to start when stress levels rise, making it difficult to add anything new to your life. Make time to check in with your primary care physician, share with them any changes you are experiencing in your physical and mental health, as well as any history of diagnoses, and take their advice if they recommend seeing a mental health professional. Adopting the appropriate level of support is the most important step in moving forward successfully, and may require an interdisciplinary approach.

Initiate changing your current patternNewton’s first law of motion states that “every object will remain at rest or in uniform motion unless compelled to change its state by the action of an external force.” The tendency to resist change can put us in a state of inertia. The less physically active we are, the harder it is to move, leading to a cycle of diminishing energy. Adopt healthy sleep and diet habits as a priority, because it can determine your mental health in the same way many other variables do.

Reach out to others. Seeking support from friends and family is crucial when facing existential stress. While it may help to spend time alone to process your feelings, it’s important to not remain isolated for too long. Try seeking out new social opportunities, listen to how others are managing similar stressors. Connecting with others can normalize our experiences and help reduce feelings of isolation.

Practice self-expression. Pent up emotions can rob us of vital energy and focus. Find ways to process and express what you’re going through. Seek out opportunities that allow you to be creative, connect with your inner experience, and process it through writing, artwork, or any simple, routine task that soothes you.

Practice gratitude. When we experience ongoing stress, everything begins to blur together and falls under a negative light. Build the habit of noticing what you normally ignore, and have learned to take for granted. Look outside of your bubble, beyond your station in life as a reminder of how much you can appreciate about your current existence.

Focus on what you can control. Feeling a newfound loss of control is a core part of existential stress. Focus on what you can control to ground yourself in reality.  Remind yourself there will always be elements of life you can’t control, let alone predict. Fixating on those things reduces our ability to pay attention to the parts of our life we can influence with forethought and effort.

Practice mindfulness and meditation. Developing a restorative mindfulness practice like meditation can open a gateway to much needed relaxation. Giving yourself this mental ‘downtime’ works to restore mental agility and improves your ability to respond to stressors. 

Redefine your life’s purpose. Our existential concerns are often born out of feeling a loss of direction, leading to fears that we’re no longer on the right path. Take time to revisit your values, and if necessary develop new strategies for decision-making. It’s a good reminder we never stop changing, so our habits may need updating if we are to remain focused on what’s most important to us.

Assuming positive intent- the secret weapon to surviving the holiday season.

The holidays are coming, or as people in the tech industry like say ‘seasonality‘ is approaching. During this time of year most of us will face a series of negotiations and decisions with people across our professional and personal lives. Conversations will unfold with co-workers and loved ones as we work to sync calendars, discuss budgets for spending, solidify holiday plans, and account for the differing needs of others during the busiest time of year. When differences of opinions arise, the urge to ‘be right’ is an irresistible response that heightens our emotions and can fuel conflict with others. (To every family member of mine reading this bear with me as I illuminate the small yet significant insights you’ve inspired over the years. Thank you for being my experimental group! Signed, Dr. Know-It-All.)

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‘Assuming positive intent‘ can help us move past our need to ‘be right’ and ‘win the debate’ and instead, cultivate a conversation where both parties are invested in finding effective solutions.  While the following tips won’t necessarily ‘feel right’ or reinforce your hard-won identity as a debate champion, it will help you avoid the emotional drain of gridlocking with others committed to their point of view.

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How to ‘assume positive intent’

The act of trying something new with a lightness of heart can be referred to as a ‘lark’. How to assume positive intent when conflict arises with others using my L.A.R.K. approach:

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  • Listen for their story. When we hear an opinion from someone that contradicts our understanding of a situation, we tend to stop listening because we become preoccupied with changing their mind until they agree with us. When we stop listening, we not only signal to the other person we aren’t interested in understanding them, we literally cut ourselves off from hearing critical information that could help lead to a mutually agreeable solution.
  • Acknowledge their point of view. Our tendency is to jump to conclusions when someone does something differently than we would, and assume the worst. Because humans are hardwired to perceive threat in instances of conflict, we focus on finding ulterior motives in those who disagree with us. Make a genuine effort to understand the premise of their opinion based on the information they have, and acknowledge their right to see things differently than you do.
  • Respect their difference. When we assume another person is misinformed, wrong or has malicious intentions, our tone of voice and non-verbal micro-expressions can turn negative. This can be read by others as an unwillingness to respect differences of opinion. Guard against communicating unintentional disrespect by modeling the response you would like to receive from others when it’s your turn to share your opinion.
  • Kindness cultivates generosity. Now when you feel yourself gunning to ‘prove your rightness’, take a step back and remember that when you preoccupy yourself with changing someone’s mind, you are reducing the likelihood of them responding with generosity, and increasing the likelihood of them responding with animosity when it’s time to generate possible solutions. Your job is to listen, acknowledge, respect, and convey kindness before moving on to explore possible solutions that could be mutually agreed upon.

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Indra Nooyi, the CEO of PepsiCo, describes learning to assume positive intent as the best advice she’s ever received:

My father was an absolutely wonderful human being. From him I learned to always assume positive intent. Whatever anybody says or does, assume positive intent. You will be amazed at how your whole approach to a person or problem becomes very different. When you assume negative intent, you’re angry. If you take away that anger and assume positive intent, you will be amazed. Your emotional quotient goes up because you are no longer almost random in your response. You don’t get defensive. You don’t scream. You are trying to understand and listen because at your basic core you are saying, “Maybe they are saying something to me that I’m not hearing.” So “assume positive intent” has been a huge piece of advice for me.

Recognizing a different opinion doesn’t mean you are admitting fault, that your point of view is inferior, or that your opinion should have less value than others. Rather, assuming positive intent gives the other person the benefit of the doubt in order to set the best possible tone for generating solutions. It doesn’t mean you agree with their opinion, but it does allow you to see with more clarity where bridges could exist.

So when your co-founder, team mate or significant other holds an opinion that is entirely different than yours, aim to identify their operating system before trying to change it!

Give yourself the command “Tools > Clear History” to rid your mind of cutter that obstructs your ability to listen with less judgement. While we may never truly ‘know’ another person’s underlying motivation  behind their point of view, we can aim to convey a willingness to respect their difference.  Our mutual bandwidth for problem-solving is increased when we assume positive intent, so all parties gain more data points to generate viable solutions.

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What “Crazy Rich Asians” tells us about the current struggle women face in work, love and family

The box office hit Crazy Rich Asians has proven to be a massive success, with a $34 million domestic haul over five days, with estimates projecting an eventual domestic take of more than $100 million.  The film stretches beyond it’s rom-com roots, showcasing female leads exploring the complexities of Asian cultural identity, as well as the current struggle women everywhere face in work, love and family.

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The film entertains with an array of well-developed female characters facing what modern women everywhere are still fighting for – the ability to compete fairly to achieve a high level of professional success, personal self-worth beyond unattainable standards of beauty, egalitarian romantic relationships based on mutual respect, and a family life that allows for motherhood without total self-sacrifice of personal aspirations.  The New York Times recently published back-to-back pieces on these very dilemmas: Costs of Motherhood Rise, Catching Women Off-Guard, How Sexism Follows Women From Cradle to Workplace capturing how far behind American society is in providing equal opportunities for women to balance work and family engagements compared to their male counterparts.

Crazy Rich Asians’ myriad of honest storylines capture women fighting to defy oppressive gender stereotypes, using brilliant strategy to seize control of their future, as well women complicit in their own oppression, scorning others for not having ‘corrective’ plastic surgery, wielding power against women for not being born into wealth and class, and hurling misogynistic insults like ‘gold digger’ to provoke conflict and pain.

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Crazy Rich Asians brings thoughtful attention to the intersectionality of Asian culture and gender identity in light of major life milestones women aspire towards, including professional, marital and family developments.

I continue to be inspired by the diverse mix of Asian women I’ve come to know though my coaching practice in the San Francisco Bay Area. Supporting them through their pivotal life transitions has given me a deep appreciation for their unique experiences as Asian American women striving to achieve work/life balance in Silicon Valley.  Inclusive stories like those depicted in Crazy Rich Asians create an enriching opportunity for us to dissect, discuss and plan for success through all the challenges they may face.

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Decoding my personal truth: how to figure out what to do with my life (and still ideally pay my bills!)

These days, people are increasingly using executive coaching for the purpose of ‘figuring out what to do with my life’ (and ideally still be able to afford living in the Bay Area!)  From high-ranking executives at globally successful companies, to startup founders who’ve sold their company and are now free to roam, to Bay Area transplants who’ve grown disenchanted with the tech scene- all have entered my practice ready to decode their personal truth, find their greater purpose, and build a personally meaningful roadmap toward their version of success.

“A man should look for what is, and not for what he thinks should be.”  Albert Einstein

Our personal truth serves as our unique roadmap, helping us navigate toward a future created with purpose.  Every day we make choices that steer us on our personal path- our inner beliefs, preferences, sense of right and wrong all come together to drive the direction we take in life.  In his book Unapologetically You, behavioral science academic and author Steve Maraboli advises us of the importance of this position: “Live your truth. Express your love. Share your enthusiasm. Take action towards your dreams. Walk your talk. Dance and sing to your music. Embrace your blessings. Make today worth remembering.”  

But what if we aren’t sure of what we are meant to do, and our greater purpose seems unclear?  How do we ‘know’ what’s right for us?

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Disenchantment A new Netflix toon with a title that captures the sentiment of many.

How can we be sure of ‘what’s best’ when we make choices for our future?  Some people feel a deep sense of conviction about their life’s purpose- “I was born to make music. I was born to build.  I was born to heal.”  Other people don’t feel this depth of clarity, and take aim for their future by solving tangible problems first- they develop a range of practices, skills and resources to prevent commonly avoided hardships like sickness, injury, poverty, social isolation.  Others feel satisfied knowing they’ve contributed to offsetting the needs of their family, community, or are embodying their religious tenets faithfully.  Even with recognizable success, some people may still wonder if they they’ve adequately challenged themselves to fulfill their personal destiny or greater purpose in life.  How can we ‘know’ if we’ve made the right choices for ourselves? At some point, a person’s experience of happiness and purpose comes back to personal taste, or preference for achievement.

Cultural expectations, opinions of people we admire, and social influences related to the times further shape our notions of what an ideal, purpose-driven, meaningful life looks like.  How have outside influences shaped your assumptions about what you should do with your life?  Without awareness of what’s driving your thoughts, feelings and behaviors it’s easy to get stuck in the habit of chasing goals without fully understanding if it’s personally important to do so. We can distract ourselves by measuring outcomes in size, volume, impact, or accumulation as a marker to indicate the degree of our success.  We may even learn to rely on these outcomes to tell us how satisfied we should feel.   

Three Exercises for discovering personal truth-  how do you ‘know’ yourself?

Cognitive psychology is the scientific study of the mind as an information processor- cognitive psychologists seek to understand human perception- the process of how we experience our emotions, how we develop mental representations, and derive genuine fulfillment from our experiences.  

Bring to mind some of your favorite moments in your past.  When you think about places, recreations, or experiences that you enjoy for the sake of the pleasure they gives you- try to uncover the why behind the attraction, or the feeling they’ve given you.  Identify your preferences in the following areas, simply based on your experience of them: how do you ‘know’ you like them?

  • areas in nature (cliffs, beaches, snowy mountains, open fields, woods, etc)
  • Sounds of specific musical instruments, musical genres, or eras of music
  • Social activities at a party (group games, exploratory dinner conversations, group cooking, dancing, people watching, etc)

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Discovering truth in Silicon Valley

2. Can you identify how external influences or mental representations play a role in how you developed these preferences? 

  • Consider how your family, social circles, workplace or local communities have shaped your understanding of how to best spend your time.
  • How does the narrative you’ve adopted about your personality style (e.g. loner, leader, helper) shape your predictions of trying new experiences and how you’ll feel about them?

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3.  Imagine moving to a society where areas of achievement, compensation for work and the social status of various roles were completely different than what we know them to be now.

  • Can you imagine choosing a role/occupation (a collection of responsibilities and activities) without knowing how this society thought of it?
  • What would you be doing? (Starting an original project? Building a team after evaluating competencies in people? Leading growth?)
  • How much of your attraction to these elements are because you’re familiar and/or been successful in doing these things in the past?  
  • If you found out there was one additional responsibility within this role/occupation that you were apprehensive to take on, what would that be?

These exercises are meant to help you uncover and tap into your personal truth, creating a guiding force for making choices in the big picture of your life path.  Be patient with yourself, track the evolution of your thoughts, feelings and insights throughout the process.  You’re on your way to ‘knowing’ yourself better than ever before.

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Millennial men ask “Is it ever ok to approach women in public?” How to meet women in the age of #metoo

Downtown San Francisco during the work week is always swarming with millennials in clothing styles meant to convey ‘simple, smart and purposeful’ yet for many, dating life is proving to be anything but that.  The millennial clients that I coach through professional and personal life goals came of age in a time when digital technology had already changed how people communicate, disrupting social rules of dating among other mainstays of modern society.  Thirty-nine percent of Millennials admit to interacting more with their phones than the actual people in their lives, making them even less likely to to talk to strangers without clear cause in their everyday comings and goings.  Many millennial men who’ve achieved professional success are now ready to marry, but are realizing the strategies they used to find casual sex partners aren’t cutting it for finding ‘the one‘.  With no time to sift through dating profiles or spend nights in bars, these guys are engaging coaching to develop proactive dating strategies that set them up for success in their daily activities.

“I want to meet a really smart woman, much smarter than me!  Someone who is passionate about pursuing her goals, driven by values that we both share.  I want to be attracted to her mind more than anything! But she should want to be healthy and fit and enjoy being sexually active for us to be truly compatible.  Financial independence is important too, since living here is so expensive.  Is that too much to ask?”

That’s Silicon Valley in a nutshell, and honestly that’s not even a tall order compared to what my high-achieving female clients have on their marital check-list.  So while online dating has been effective for solving most people’s casual sex needs, it feels agonizingly inefficient to most people ready to meet someone marriage-worthy, especially with personal brand consciousness and FOMO influencing millennials’ major life decision-making process.  I encourage my single clients to attend curated social events or engage in recreational activities with a male/female ratio that benefits them, increasing the odds they meet people of similar caliber who share mutual interests.  I ask them to take the approach“if I had to solve this problem in the next two weeks, how would I do it?  What can I do to get started today?” which gives people a sense of urgency and gets them ready to apply practical solutions in the here and now.

After mapping out a few actionable plans with a male client, he earnestly asked “is it ever ok to just approach a woman in public these days? You know without coming across as desperate or creepy.” Admittedly I was taken aback by this question – I was struck by the difficult task of overcoming social anxiety they’ve spent less time addressing thanks to technology, while leveraging enough social finesse to engage others in a respectful and compelling way.  Many millennial aged men understandably prefer to play it safe in unclear circumstances, or risk coming across like a cheesy pick-up artist (PUA).  Have millennials come to rely exclusively on dating apps, social introductions, singles bars and events that serve the function of bars to form romantic connections?  Has the heterosexual male to female ‘cold call’ approach become totally obsolete?  Like the evolutionary equivalent of the human appendix, wisdom teeth or tonsils, once useful in our dark past but at best should remain dormant or at worst may trigger pain and suffering? Fox Monkey GIF by Animation Domination High-Def-downsized_large

Once upon a time men were far more likely to approach women in public outside of well-defined social circumstances, when our society was more deeply rooted in the notion that ‘masculine persistence wins the heart.’  American media largely produced by men has been dominated by storylines that convey if a woman responds to a man’s advances with disinterest, she can be persuaded to change her mind through a combination of charm, wit, and low-key psychological warfare.  This dynamic calls for female passivity, contributing to how women are treated as ‘fair game for romantic pursuits’ in public spaces.  The time of reckoning for gender inequality has come with the #metoo movement, an activist-led eruption of female empowerment that has become a global phenomenon, upending the longstanding tolerance of objectification and abuse of women for the purpose of male sexual gratification.  Though gender equality across all realms has a long way to go, it is still possible for men to safely and respectfully engage women in public by learning to read social cues with greater sensitivity.  It will likely not be easy or feel comfortable.  As I said to my male client “approaching a woman in public is graduate-school level game– we’re working on social skill mastery at the kindergarten level- first things first.”  (My clients are sturdy and know I don’t dish out what I know they can’t take!)

If you want to approach a woman in public but are unsure of how to proceed, take the time to read the situation closely.  This may take time you don’t want to spare- but keep in mind, a rushed approach increases the chance of a failed mission.

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HOW TO’S:

  • Make sure this woman is not wearing a wedding ring.  This is an easily avoidable rookie mistake!  Practice discreetly checking out left hands in various situations so you can be ready to quickly assess when it matters.
  • Respect women’s time.  Does it look like the woman is in a perceptible hurry?  Is she engaged in an activity that she’d probably prefer not to have interrupted?  If she’s busy working on a laptop she probably won’t welcome small talk- wait until it’s obvious she’s taking a break to speak to her.  Is the woman clearly relaxing, enjoying a meal by herself or having some personal downtime?  If she responds with only a fleeting or absent smile, minimal verbal response or eye contact, take the hint and keep it moving.  Persistence in the face of a minimal response is only going to feel uncomfortable and annoying to her.
  • Pay attention to eye contact.  Has the woman made purposeful, positive eye contact with you at least a few times?  Catching a woman’s eye once might be accidental, twice might be her checking to see if you are still looking at her.  Women naturally check their surroundings for their own safety, and women find they need to keep an eye out for guys who might be staring, stalker style.  Your job is to make sure you come across as friendly and safe– if you’re so nervous you can’t smile in the split second you catch a woman’s eye, you might not be ready to approach a woman in this manner.  Practice talking to women you don’t know in social settings where people are clearly expected to mingle so you develop a sense of how to accurately read non-verbal cues.

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  • Drop the idea that channeling alpha male confidence will lead to a positive outcome.  Guys are really attached to the idea that exuding cool confidence is what women want.  It’s refreshing and much more likable if you can manage to be yourself and talk with a woman like she’s a person not an object to win over.  Better to be awkward and able to laugh at yourself if the situation calls for it!  Take it from a woman- we’re often just as concerned with first impressions, and you’ll make it much easier for her to respond to you if open with something genuine and friendly.

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  • Ask her opinion about something related to the shared situation you’re both in, and be sure to listen and show appreciation for her response.  This is simple enough to do, especially if she’s in nearby proximity.  Respond with something of equal tone, and if possible include an opportunity for her to keep the conversation going.
  • Get out of your comfort zone, and use light-hearted humor to break the ice.  Authentic self-deprecation and self-declared inexperience is an easy way to gain a moment of sympathy from women.  Women are natural care-takers, teachers and experts in many, many things!  Guys, if you put yourself in a situation where there are women who are excellent at something, you will stand out not only because you’re willing to risk looking foolish, but also because you’re interested in something they clearly enjoy.  This only works if you demonstrate a genuine interest in learning.  If you keep at it long enough, women will likely take pity on you and offer some support.  I’ve seen it happen a million times before!

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Adopting these strategies aren’t meant to guarantee that you’ll get a date after perfecting them, but can work to start an engaging conversation that could potentially reveal a reason to stay in touch with a woman as result.  Good luck out there, and you’re welcome!

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Millennial managers leading startups: their generation’s new face of management.

According to Pew Research center the millennial generation (born 1983 – 2000) now number 75.4 million, surpassing the 74.9 million Baby Boomers (born 1946 – 1964) and Generation X’ers (born 1965 – 1984).  More than one-in-three American workers today are millennials, and have become the largest share of the American workforce.

In today’s current work climate, it’s not enough for millennial-aged managers to focus on productivity for their company’s success.  Employees who share their generational employment outlook expect them to drive the company’s mission with clarity and inspiration, embody a leadership style that supports their work/life balance and self-care routine, and provide opportunities for them to do work that fulfills their passion for making a positive, meaningful impact.  Millennials widely embrace thought leaders like Simon Sinek who encourage them to marry their values and intentions to their work endeavors for lasting fulfillment in their life.  Amid these formidable expectations, it’s easy for a manager who understands the values of the millennial generation to feel conflicted about how to drive productivity while still supporting her employees work paradigms.

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Any manager who leads without a strong sense of direction is destined to fall short of their targeted goals.  A millennial manager I coach in the venture capital space suggested I write an article based on the headway we’ve made in developing her leadership approach to managing her millennial-aged team.  The following Q & A is based on questions she and other millennial managers have expertly hashed out through their leadership coaching work.

“How can I screen potential candidates during the hiring process to reveal their true work ethic?  The nature of our work is deadline driven, and it’s hard to know who will prioritize work objectives over personal objectives.”

How to hire them:  Work ethic fit is critical to a company’s success, because a candidate with mismatched work ethic will negatively impact productivity, disengage other employees, and create inefficiencies for the rest of the team.  Early stage startup culture has influenced new hire expectations – it’s not unusual for employees at startups to serve in multiple roles to sustain rapid company growth periods.  Experienced millennial managers ask potential hires to share how they’ve handled shifting workflow and multiple role responsibilities in prior positions.  “Can you tell me about a time when you’ve asked a manager for guidance on how to prioritize your workload?  Particularly when you’ve thought meeting a deadline was going to be difficult or impossible because of the high volume and pace of the workload.”  This gives hiring managers a chance to learn if the person has experience identifying and solving workflow prioritization with others. By being transparent about their company’s work style and pace, and sharing specific examples of how team members typically ‘get shit done’ they reduce the the risk of hiring a poor fit for their company culture.  Millennial managers recognize the need to reconcile workload with self-care routines, and have learned to ask revealing questions like “How do you deal with burn out or work fatigue?  How have you managed times when you’ve had conflicts with team members?  What are your expectations for personal time off, working overtime, or through holidays?”

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Experts in psychological personality assessment use tactical questions like this to measure what they refer to as ‘faking good’, to detect a person’s willingness to be forthcoming or tendency to present themselves in an unrealistically positive light.  If given multiple opportunities, can a potential hire share a well-rounded work history that naturally includes unmet challenges, times of burn out, and how they’ve learned from those experiences?  Or are they consistently defensive and unwilling to acknowledge when they’ve been challenged or experienced conflicts at work?  Millennial managers seek to hire people who are willing to be direct and forthcoming, understanding this communication style lends itself to effective problem-solving with others.

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“What can I do to inspire my team members to take initiative in their own professional development?”

Millennial startup founders-turned managers understand the desire for personally meaningful work as a motivating principal behind professional development.  Based on this core value, millennial managers can inspire their employees to invest in their own development by encouraging them to cultivate their personal vision of career growth and success.  Managers seeking to inspire their employees ask “What do you enjoy most about their role?  What would you like to eventually do more of, and less of in your career path?”  By understanding what personally motivates someone, what is most rewarding, and how they’d like to see their professional opportunities take shape, a manager can provide support based on that particular vision.   Further, supporting employees in this way and holding them accountable for progress in their role performance will resonate on a deeper, more meaningful level.

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“How can I set the standard for work ethic with my team?  My employees get overwhelmed by deadlines, and it seems to be influenced by low self confidence and their desire to protect their work/life balance.” 

How to drive high performing employees:  When managers find they have an employee struggling to meet deadlines, the situation can put everyone on the defense.   The dilemma of many millennial managers in startups is that most if not all of the employees are highly valued for their unique abilities and everyone’s individual contributions are critical to company progress.  Further, the time and resources it takes to replace an employee and the risk of destabilizing team morale makes opting to solve the problem a frugal first approach.  While some employees may be failing to complete work as a result of prioritizing personal time, others may be failing to meet work expectations for other reasons.

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Through coaching, a millennial startup founder I support resolved how to effectively manage one of her highest-performing employees who’d begun struggling to meet his production deadlines.  After processing her emotions and generating a communication action plan, she began by conveying her high regard for his contributions to the company’s success, giving examples and recognizing his overall growth.  She listened to his perspective about why his productivity had declined without jumping to conclusions, with the intent to support him in finding a resolution that fit both of their needs.  This encouraged him to share openly about what his challenges and mental roadblocks were, and what changes could lead to a return to consistently high productivity.  This inquiry-led communication style led to both of them making a shift in thinking about how he could best operate in his role without compromising future leadership opportunities, provided new ways for him to contribute to deadline completion, fostering a solution-focused dynamic between them as manager and employee.

Many of the millennial managers I’ve supported have found inspiration for their managerial style based on the wisdom of their favorite leaders in tech, turning up their employee productivity and balancing idealism with practicality by:

  • making changes to the types of work an employee is responsible for completing (e.g. shifting an employee from working autonomously on projects to working in a support role to others)
  • providing alternative options for employees’ work evaluations based on their preference (e.g. brief periodic check-ins to ‘debug’ work progress rather than a longer final project critique)
  • building a work culture that encourages employees to take part in decision-making in how they solve problems rather than dictating how problems get solved

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