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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Millennials tech twist on engagement, weddings and parenthood

While millennials are still getting married at much lower rates than previous generations, some are finally beginning to grow and up, entering the world of marital engagements, wedding planning, and parenthood. True to form, their choices reflect advancements that set them apart from Gen-Xers, who were the first to utilize technology to chronicle their love stories on websites like theknot.com, build wedding registries online, gift personalized CDs with digitally remastered music as wedding favors, show spliced video montages of the bride and groom’s childhood at wedding receptions, and research honeymoons on websites like tripadvisor.com. As a card carrying member of generation X, I can proudly say we thought we were so cutting edge! Our kids were the first to be born with smartphones and tablets in their hands, and we posted their baby pictures on our social media pages and texted them to their grandparents. But time nor technology stands still, and Gen-Y has begun to put their own tech twist on engagements, weddings and baby plans. As someone who works with a high volume of with millennials in the San Francisco Bay Area, I have taken note of the following trends:

Their romantic relationships have an online life of their own. As the saying goes, no one really knows what happens behind closed doors, but in the personal lives of millennials, we can certainly take a look at their online activity to see what they’d like us to believe about their relationship status and history. The internet has become their forum of choice for chronicling romantic highs and lows, functioning as a means to gain public support, air grievances, compete for attention, and display markers of success (not to mention deleting away failures.) From public playlists on Spotify, hashtags on Twitter and Instagram, Pinterest boards and Facebook’s ‘Relationship Status’ updates, Gen-Y leaves little to the imagination when it comes to sharing their stories of romance.

They crowd source their decisions when it comes to navigating relationships. Millennials are used to solving problems fast, arriving at optimal solutions with the least resistance possible. Millennials have been groomed to work in competency-based teams, and this concept is frequently used for managing their personal lives too. They prefer to avoid conflict, and are more comfortable than previous generations relying on others to help them make decisions. Jeff Snipes, CEO of Ninth House, a provider of online education, including optimizing team effectiveness, says a hierarchical, leader-oriented team was more appropriate for earlier generations: “Traditionally if you worked up the ranks for twenty years and all the employees were local then you could know all the functions of the workplace. Then you could lead by barking orders. But today everything moves too fast and the breadth of competency necessary to do something is too vast.” When faced with life-changing decisions about relationship commitment or endings, Gen-Y seeks the opinions of their team of friends, family and experts to help them navigate and solve problems. When problems are deemed too private to share, websites like popular sites like Whisper and Secret are put to use by millennials as a way to air their private thoughts, share their hidden behaviors and ask for advice completely anonymously, so there is no threat to their carefully constructed online image.

Their engagement stories, weddings and honeymoons reflect their brilliance and investment in personal branding. While previous generations aimed to establish their worth and reputation through self-improvement, author Dan Schawbel of Me 2.0: Build a Powerful Brand to Achieve Career Success points out that Gen-Y has discovered that in the dawn of the internet, admiration and success comes from self-packaging through a carefully concocted personal brand. From the days of Myspace to Tumblr, millennials have grown up managing their self image like celebrity publicists. Gen-Y has turned self-portraits into a way of life- ‘selfies’ have become one of the internet’s top forms of self-expression. Their overall online presence has been a way to uniquely distinguish themselves from everyone else, and they are highly invested in making their relationship milestones ideally memorable as part of their personal brand. Whether they capture and share these milestones via Snapchat’s Our Story, Instagram, Twitter, Facebook, or personal blogs, millennials are sure to control how the world sees their love stories unfold through brand management. One San Francisco Bay area millennial shared with me she got engaged via FaceTime, since her long-distance boyfriend was living in abroad and couldn’t wait to pop the question. To his credit, her (now fiance) also created an iMovie that he shared with her, depicting him staged in funny scenarios accompanied by a personalized musical score that specially captured their romantic history.

They’re comfortable resisting tradition, understanding that ‘following the rules’ doesn’t necessarily bring ‘happily ever after.’ Author Paul Hudson of Elite Daily, The Voice of Generation Y observes that millennials are far less likely than past generations to buy into the notion that marriage is the gateway to a future of stability and happiness. Harry Benson, research director at the Marriage Foundation, describes the strong link between parental divorce and a reluctance to get married. “If your parents split up then most people are more likely to be quite skeptical about the value of marriage,” he explains. “So as there’s rising divorce rates, you can imagine how when the next generation appears, people will be more dubious about marriage.” Bobby Duffy, leading market researcher on generational analysis, says there are also far more financial pressures on millennials than previous generations. They have more educational debt in a less stable economic climate, and face an incredibly buoyant housing market. According to CNNMoney, twenty-somethings are transitioning into adult life at a more gradual pace, opting to cohabitate and co-parent without traditional marriage at a much higher rate than previous generations.

They anticipate their babies’ future in a world where technological identity matters. One website says it all:awesomebabyname.com, a new online tool that allows parents to choose a name for their child based on website domain availability. Yes people, this is happening. I heard it first a few months ago when a pregnant patient of mine found out she was having a girl, the first thing she and her cohabiting boyfriend/expecting father-to-be did was buy website domains and establish email accounts in her name. Of course, now there’s an app for that! “It’s important to give your children a fighting chance of having good SEO (Search Engine Optimization) in the 21st century,” says Finnbar Taylor, who created this website together with Karen X. Cheng. “We use search engines all day long to answer our questions and find things, including people. Imagine being called John Smith and trying to get a ranking on Google search. It’s important to give your child a unique name so that people, like potential employers, will be able to find them easily in the future.”

Granted, millennials are still in their 20’s, a time when it’s still developmentally common to be preoccupied with self-image, and an idealized future that looks different than previous generations. The question is, as Gen-Y ages, which of these trends, if any, will change?