I work with largely millennial workforces, which means I’m frequently asked to decode the “why” behind everything the generation does.
I am asked by leadership why millennials are so averse to risk, unwilling to stretch themselves, and happy where they are.
Often, I hear, “I just think young employees today have a serious confidence problem. They need my permission for everything. Otherwise, they won’t push themselves!”
The theory goes that these millennials lack focus, drive, and an ability to think for themselves because they have low self-esteem. But, in the same breath, I’ll also hear this generation is entitled, stuck-up, and thinks it’s smarter than everyone else.
What gives?
Part of it is a story of cross-generational tension as old as time, along with socioeconomic and psychosocial factors that I would need hundreds of pages to fully address, and part of it is that self-esteem is at play, just not in the way my leaders think.
It’s not that millennials have low self-esteem or high self-esteem, but more than any generation except Generation Z, they’re the most likely to have contingent self-esteem.
As Susan David defines in Emotional Agility: Get Unstuck, Embrace Change, and Thrive in Work and Life, contingent self-esteem is simply “the belief that…worth must be earned.”
In other words, those who experience contingent self-esteem require the direct or indirect approval of others to determine how they value themselves.
I should qualify here that someone’s self-esteem, which is their confidence in themselves or their own abilities, is not a fixed constant.
This idea dates to psychologist William James’s work on self-consciousness in Principles of Psychology, which posits that our changing relationships to ourselves, our thoughts, and our circumstances impact our self-image.
However, the idea that self-esteem might change from one day to the next, depending on how closely people match up against their values or their ideal visions of themselves, is not the same as contingent self-esteem.
Regular self-esteem might momentarily change depending on good or bad experiences; contingent self-esteem is constantly fluctuating based on outside perception. Consequently, those with contingent self-esteem will often strive for the positive feelings associated with success and avoid the negative feelings associated with failure.
So, what does contingent self-esteem look like in real life?
The example that comes to mind for many is body image. When ‘ideal’ representations of beauty are showcased through media, we are prone to making comparisons between ourselves and that ideal, with our self-worth eventually being tied to how close or far away we are from that ideal. This can lead people to take extreme measures, like developing eating disorders or over-exercising at dangerous levels.
But contingent self-esteem shows up at work, too.
In many of the companies I work with, team members struggle with contingent self-esteem because of the environments they came from and how expectations were set.
Think about it this way. Let’s say your parents told you since you were very young that it was your job to get into college, preferably an elite one. Growing up, you spent your weeknights and weekends with math tutors, SAT instructors, debate coaches, and tennis pros to prepare for applying for that elite college. Finally, you get in, and are told exactly what you need to do to get A’s, win prizes, and generally be liked. But then you graduate.
At work, gold stars aren’t routinely doled out, no one is standing over your shoulder telling you how you’re doing or even what you should be doing, and now you work alongside equally or more talented, intelligent, and skilled peers!
What happens to you? How do you know your worth?
You start to guess. You hold onto compliments and affirmations, which teach you to repeat those actions, the ones that made others see you as valuable. Any time you get in trouble or make a mistake, you remember and avoid the activity. If you can’t avoid it, you sink into despair, resentment, or even inaction.
This is how we get to the phenomenon I described in the beginning: a generation of employees who execute effectively, but struggle to take risks, always look to you for permission to do their work, and often come off as more complacent than ambitious.
Millennial workers are not complacent; they’re afraid of losing their very fragile grasp on their own sense of self-worth.
As someone who has lived through this, it is very scary. The instability of not knowing how you feel about yourself until you are validated or invalidated by someone else results in a lot of hard-to-understand behaviors for everyone involved.
I brought up contingent self-esteem to a client recently, and a light went off for him. He said he clearly understood not only his employees, but also his college-aged children for the first time.
And then, he said, “Alida, you’re my Millennial Whisperer. Now that we know what the problem is, go fix it.”
As much as I weirdly love the idea of talking to an upstart Product Manager as if she is a majestic yet stubborn chestnut mare with the once-in-a-lifetime chance to win the big race, I know that “Alida’s going to fix it” is probably not the best solution.
Granted, I see success with learning initiatives and coaching sessions where I sit down with employees, explain contingent self-esteem, and teach them tools and techniques for developing a more stable sense of self-worth. Fear-setting exercises where we break down the worst that could happen versus the best in structured models can often be transformational for employees…in the short-term.
I can address this problem in my client companies up to a point. It helps them to have an impartial external force who can shed light on why employees don’t need permission to take risks, while also enabling personal development that can lead them to a more grounded sense of being overall.
However, the answer to contingent self-esteem is secure attachment, and that needs to come from the company and its leaders.
Susan David breaks down secure attachment as:
“This idea that I, in all my glory, as well as my stinkiness and imperfection, am loved and accepted — allows [you] not only to take risks in the world but also take risks with [your] own emotions. Knowing [you] will not be invalidated, rejected, punished, or shamed for feeling whatever [you] feel, you can test out sadness, happiness, or anger and figure out how to manage or respond to each of those emotions in turn.”
While David is talking about what parents can do for their children in this example, I think the principles apply.
I’m not asking company leaders to tell their employees they love them and they will be loved no matter what they do. But, I am asking them to create the space for their employees to take risks in the first place and consistently show them that this behavior is rewarded, not punished. This usually means being explicit and transparent about what matters to you, what you expect, and what will happen.
So, what does creating the conditions for secure attachment look like?
I think it breaks down into three parts.
One of my companies is known for blunt, no-nonsense feedback that often makes new employees feel defensive, threatened, and challenged when they don’t have cultural context. To address this problem, they made a simple shift. They started the onboarding process by explicitly telling employees how communication works at the company and why.
They say something along the lines of:
“We hired you because we know you can do this job, and we believe in you. Whatever happens here, we think you’re awesome. We cut the small talk and give harsh feedback because we think you deserve to be here, which means we don’t need to spend upfront time easing you in. We’re already working on solutions with you.”
While some employees might not like this approach or feel intimidated by it, at least they know what it is. The result is that when they are challenged or told they’re wrong, it doesn’t automatically make them feel worthless. They don’t feel pushed into silence, disingenuous agreeableness or fear. They feel secure that they can take risks and make mistakes; even if their choices blow up, the other people in the room are rooting for them regardless.
Feedback that is specific, personal, and actionable is more likely to be taken, but what matters most when it comes to establishing security is whether the feedback targets the person, or their actions.
“You are disorganized” or “You are a doer, not a strategist” are value judgments that tell people they are fundamentally bad in some way.
Feedback like, “When you started this project, you didn’t take steps to organize your priorities” or “I think you approached this like a checklist instead of an opportunity to set a larger vision for the department, which meant the scope of thinking was too narrow” doesn’t tell them they are inherently good or bad, but that their behavior — which is psychologically much easier to change than “who they fundamentally are” — needs to shift.
Whenever I go into companies to do diversity, equity, and inclusion or culture assessments, one of my go-to questions is, “What behaviors do you reward and what behaviors do you punish?” The answer tells me what the underlying culture of the organization really is.
While employees aren’t usually asking this question, they are on the receiving end of their company’s implicit system of rewards and punishments.
Employees with contingent self-esteem who don’t feel a sense of secure attachment are always looking for cues to what will earn a pat on the back versus a slap on the wrist. That means leaders must be very clear about what matters.
For example, if you want employees to be more risk-taking, don’t harshly punish them when they do take risks and fail. I see this happen in my client companies all the time.
Leaders will ask employees to think outside the box, but when a customer comes back unhappy or a new bug shows up in a demo, that attitude changes. The employee who took the risk gets publicly reprimanded, pulled off the project, or shifted into another kind of role. This immediately signals to the employee — and all the employees making social comparisons to him — that the risk is way greater than the reward and therefore not worth taking.
You can’t ask everyone to be everything. Risk-taking comes with higher rates of short-term failure. Self-managing usually involves more mistakes because of trial-and-error. Taking ownership for the first time means a higher chance of falling short on responsibilities because of lack of experience.
Before I even started Ethos, I met with a good friend to help address some issues she was facing in her own company’s culture. At the end of the conversation, I reminded her of something I still stand by today.
“As a leader, it is not your job to be your employee’s life coach.”
By no means am I asking leaders to sit down with their employees and help them do the tough emotional work that comes with navigating their own relationships to themselves. You’re not there to be their biggest confidence booster or part-time therapist. Those are not the right roles to play.
What I am asking, though, is that you understand your employees: how they think, how they have been socialized, and what assumptions they brought to work with them. Then, with this knowledge, put structures in place around expectations, feedback, and communication that help them improve and grow.
Just like you would expect to train a new employee how to build systems or manage new processes, plan to train them in how to navigate what is likely a very foreign environment loaded with opportunities to reinforce false assumptions and tie their worth to external impressions that don’t actually matter.
