Knowing when you've done enough
Understanding this common leader dilemma
Hello, I’m Suzan. Thank you for reading Suzan’s Fieldnotes — 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.
I love documentaries, especially nature ones with animals. I love watching baby animals grow, love watching their parents teach them how to survive. Predators abound. The fledgling wobbles. They make an error in judgement or they’re unlucky. When a fledgling finds themselves in a precarious situation, I shout at the TV like I’m watching sports. “Swim. Swim faster! Go!” at a duckling trying to escape a predator. Duckling survival rates are 50% at best. Even though I know all or even most of them won’t make adulthood, I still root for them. I want each fledgling to survive.
As with most things in the natural world, it reminds me of leaders who want their own fledglings to thrive —often a new manager or an experienced manger taking a leap into a more senior role like Director or VP. I’ve heard these sentiments from many senior leaders after a fledgling failed.
“I failed him. He didn’t succeed and it was my fault.”
“I finally let that manager go. I knew no amount of effort would have helped them turn it around but I still feel like it didn’t have to end this way. I’ve spent the last three days wondering what I could have done differently.”
“Looking back, everyone knew it wasn’t going to work before I did. I got into “make it work” mode so I missed the signs that the new manager wasn’t going to make it, no matter how hard I worked. I caused everyone stress”
Deep, soul searching conversations follow these admissions. Building capacity in others is some of the most important work leaders do, especially at scaling companies. It’s why many took on a bigger role. Motivating and building capacity in others is arduous work, consuming oodles of a leader’s energy. For most, that effort is worth the cost, except when we can’t find success, no matter how hard we try. There’s a stereotype that leaders easily fire people, that they’re callus about people’s careers. My experience with senior leaders is the opposite. Most don’t long to fire others — in fact more often they move too slowly. Recognizing someone isn’t going to make is one of the hardest moments for leaders, especially for those heavily invested in developing others. If you’re like me, when someone fails I see my leadership as the problem, I try harder. We put all our effort into them until one day we realize they just won’t make it. Even if maybe they could, the cost to others is too great. When we’ve reached this point, the effort vs return ratio is skewed. It’s likely others in the company and even the exec team are putting effort into helping them. It’s become a burden. It’s not good for the person failing either. We’re all panting on the side of the river trying to get that one duckling to survive. We’ve taken our eyes off other predators: the market, an eroding culture, other employers ready to scoop up the rest of our folks.
Like ducklings, not every every new manager or leader will make it. We can't always predict which potential will come to fruition and which will remain unrealized. Sometimes may not be ready, it might not be the right environment for them, you may not be the right person to support them. There are myriad reasons why someone might not succeed in a new role that are outside of your reach. Sometimes you just have to let them go.
Departures and having to dashing career dreams is often deeply painful, triggering uncomfortable emotions. Part of the job of being a leader of people is taking a chance on potential. We forget that not all potential comes to fruition. It’s confusing when that potential founders. We feel out of control, feel helpless. Our own thoughts about failure get tangled up with theirs. We’re responsible for the success of everything and everyone in our area. If someone doesn’t succeed, then We’ve failed too. It feels like a double failure. Someone under your watch failed and because they failed, so did you. It's a failure sandwich with a scoop of confusion. Sometimes the feeling that we didn’t do enough lingers for months.
Nearly every leader I’ve spoken with in the last year has had a manager or leader fail. The questions follow a similar path: Did I do enough? Was there something else I could have done? What did I do wrong and how can I prevent it from happening again?
It’s healthy and important to see if we’re the cause of someone’s lack of performance or toxic attitude. There are times when our behavior can be traced to their demise. More often though, it’s difficult to discern. It’s hard to know what’s within our control and what isn’t. How do you know what's yours and what's theirs? How much of someone else's behavior can you really influence? Where does the boundary between motivation and action lie? Figuring out what part you played isn’t always straight forward. Most leaders work diligently to help a direct report succeed, only moving to separation after exhausting every available path. Lingering feelings of doubt often follow. After all this effort it’s heartbreaking to hear them wonder if there was more they could do, sometimes continuing to question themselves long after.
The question Have I done enough? has a shelf life. Staying there too long leads us down a winding maze trying to find a solution long past the point we know where the exit lies. Doubt can infiltrate, making us lose confidence. There are better ways to spend our time. More productive questions to ask: How do I know when I’ve done enough? When do I know there isn't anything else I can do to change the trajectory of this situation? Having a model gives us a frame of reference and a way to know when we’ve done enough. It saves heart ache and lost hours doubting ourselves. Also help are questions that can help you learn for the next time. Useful questions might include: Did I give enough feedback? Did I do it in a timely enough manner? What did I ignore? Why did I ignore it?
These questions help us find the boundary between what we can control and what we can’t. It helps us know when there isn’t anything else to do to change the trajectory of the situation. We can let go. When we know what enough looks like we can rest easy and focus on helping the rest of the flock thrive.
What else to read
Hiring vs nurturing managers.
Nathan Baschez on why he loves working at startups.
What it really means to be a manager, director, or VP.
How we can learn as a leader.
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.