The Shoulds
How not to let them take over your brain
Hello, I’m Suzan. Thank you for reading Observations and Annotations — a newsletter exploring leadership, psychology and organizational dynamics through real life stories. I try to make this one of the best emails you get this week. It’s one of my favorite things to write. If you enjoy the content, please like and share it.
Leaders should…
Be perfect. When we tell others it’s ok to make mistakes we really mean it. When we’re the ones making the mistakes? We dwell on them, wear them like a suit of shame. Leaders shouldn’t make mistakes is a quiet refrain so woven into the fabric of our mind, we stop noticing it. People’s careers and the business are on the line, getting it right is just what’s required.
Always know the answer. Even if we’ve never encountered it before or the situation is rapidly changing. This is why we were hired, right? If we don’t know well, why are we here? Do we even deserve this position?
Reach for empathy at all times. Even when others don’t have it for us. Even with tremendous pressure and sky high stakes. Even when it’s hard to find empathy for ourselves. Even when we’re burning out and struggling with our own well-being. Even though we’re human and make mistakes too.
Meet myriad demands. Create robust processes, resolve conflicts quickly, develop the team’s capacity, create policies that support the team’s well-being, meet company goals, hire a solid team.
Not work too hard. Stay up until 1 AM to finish that performance review but don’t let them know that you did. Be a good example to the team by finding balance, despite all the demands.
Never lose our cool. Never shed tears, show uncensored displays of vulnerability even when others yell at us, blame us for things outside our control. We tell ourselves we need to keep our emotions in check even when we’re working well beyond our capacity just trying to keep up. Keep up the facade even when our personal lives are falling apart.
Be confident. Be strong. Never express doubt. Never have doubt. Take on the hard stuff to relieve the team. Never show an ounce of fear or lack of confidence. The best leaders are stoic and tough.
Not be too confident. Don’t get that ego involved. Have humility. Be vulnerable, but the right kind of vulnerable.
Give, give, give but never receive. It would be selfish and unleaderly-like. We must be self-contained units, acting in service of others but never needing support or advice.
Hold ourselves accountable. Look to ourselves as the problem in a situation. Try harder again and again. Adjust ourselves to meet other’s needs no matter what.
Get deliverables done. But always be available for the team and never skimp on 1:1s even if it means your deliverable work begins at 8pm after a full day of meetings.
Do any of these rumble through your head? I felt many of these as an executive. When leading others expectations pile up. Even when the shoulds start externally we quickly internalize them making them our own. Worse, we pile on more internal expectations. These shoulds are often confusing and unrealistic, constraining our behavior in unnatural ways. Some feel like contradictions for example, imbue confidence but don’t go to far into your ego, demonstrate that you’re open to the team’s suggestions. It’s easy to get lost in the maze of contradictions and shoulds. Trying to navigate them is like having a side gig on top of our day job. It’s not that we should act opposite to these shoulds. I will never argue for self-interest or being indifferent to the needs of others. We do need to have empathy, stay level-headed, provide answers, and hold ourselves accountable for our actions, the ripples they create. And—there’s a balance.
We can’t always act as our best selves. There’s competing priorities that make us feel stretched beyond our limits. We run into unrealistic demands. Even as a leader having multiple intersections can make it harder to push back against external expectations. Placing extra expectations on ourselves adds unnecessary strain. Having grace for ourselves when we can’t be our best can help us find our equilibrium faster. We’re human, not superheroes. We don’t need to be super human or confinded to a narrow set of “leader” behaviors. We just need to do our best and when we miss, take the lessons for next time. We can’t wholescale change who we are or the expectations of others but we can shift our own internal environment to make our experience of leadership as less fraught.
What are the “shoulds” running through your head? Maybe it’s time to tame them.
What else to read
How one exec designed a system to help him focus and stay balanced.
The fallacy of “what gets measured gets managed”.
The internal causes of burnout.
Kindness as an antidote to loneliness.
Written by Suzan Bond, a leadership coach and former COO. Based in Brooklyn. You can find me elsewhere on Twitter and Medium. Comments or questions about leadership or scaling startups? Send me a note.