What The Downfall Of My Best Employee Taught Me About Management
A reminder to focus on the effort, not the outcome.
Johnny Cohen | Unsplash My best employee decided to quit — and it taught me a lot about management.
And in her defense, I’d have done the same at that moment. Because things had reached one of those points when the job ceased to offer her the satisfaction and purpose it once did.
She’d gone from strutting around the office with pride to instead wandering around like a guest at the wrong wedding. Once upon a time, she’d been my superstar.
Energetic and enthusiastic — a tenacious fire starter always willing to help. While there had been some doubts about her temperament (she could get a little overwhelmed and snappy when stressed), I felt I could get the best out of her — and I did. For over a year with me and the team, she thrived
But the trouble started when I moved to a new role in the company, and she moved to a different department.
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Her new boss, Steph, is a solid manager. I like and respect her, but I’m not a fan of her hands-off leadership style. I had a sneaky suspicion it would be the same for Jess too. And it’s no secret that bosses matter. The right one can make a hero of anyone. But the wrong one?
Sadly, my fears came true. Despite Jess trying to adapt, it didn’t take long for her to fall out with Steph. And while the details are blurry, both were left feeling disrespected. Jess saw Steph’s actions as unethical; Steph saw Jess as unprofessional. It was a stalemate.
Regardless of who was ‘right’ in their disagreement, Jess decided to get her own back with little protest. The initial fallout had been around attendance.
So, she started calling in sick a little more, normally on Mondays and Fridays. Then she stopped doing the same good job as before, but instead doing the bare minimum. She stopped being proactive.
She stopped taking responsibility for issues early, letting them get bigger and work their way up the chain.
And then she started complaining openly about the company, the managers, and the job she was being asked to do. I tried to intercept. I kept checking in with her, trying to offer different perspectives to help her move on.
But her new perspective about Steph tainted her perspective of the whole company. Me included. Now no longer was she looking to me for support, but as another cog in the machine. Another person was against her.
Inevitably, it wasn’t long before she quit. It’s one of the most frustrating things in the world. Despite tons of support, understanding, compassion, and time, an employee ends up quitting anyway. And it’s on bad terms.
It’s never nice. But be careful. From these moments it’s easy to draw the wrong lessons and make the wrong changes.
If you ever find yourself going above and beyond and still getting stuck by the employee you’re trying to help, here’s how to move forward and grow stronger:
1. Start with the only real metric that matters.
Reflecting on Jess’s departure left me thinking about how we measure success as leaders. Focus on the effort, not the outcome.
Because leadership isn’t about controlling all results (which is impossible). It’s about staying true to the processes that are more likely to get these results. And within this, honoring values that support a team while trying your hardest to get the best out of others.
So detach yourself from outcomes. They rely not on your intentions, decisions, or actions, but instead on other people’s emotions, perceptions, and external influences. You can’t control how things will go, only how hard you try to make them go well.
You’ll probably make mistakes. And yes, with the benefit of hindsight, you probably know how you’d do things differently.
But if you honestly did try your best, take pride in that. And if you didn’t, be honest with yourself about why, take the lessons, and move on.
2. Embrace your emotions
Acknowledging how you feel — be it the inevitable resentment or frustration from things not going to plan — is part of recognizing the effort. It validates your journey through the experience rather than fixating on uncontrollable outcomes.
Don’t suppress things. I’ve learned they’re a necessary part of your growth. Pain can be a great teacher. Let your regrets be the signposts on your path to a better leadership future.
Because we all react differently. And seeing how we respond teaches us about who we are and what we care about.
Ask yourself honestly: What did I do that was positive? When did I show up for this person that they might not realize or know about? When did I put doing the right thing ahead of doing the visibly popular thing?
Reflecting on my time with Jess, I remembered how I would fight her corner in meetings when she wasn’t there. Or when I’d call people out for talking badly or making judgments about her. Or intervene when people would try to excuse their contributions to the situation by putting the blame back on her.
Pretty soon I could feel proud that I did the right thing not because she would know, but because it was the right thing to do.
3. Ask yourself: Is this the only way to see things?
In cognitive behavioral therapy there’s a question you’re encouraged to ask to help you see what you’re experiencing in a different light: Is my perspective the only valid perspective?
When we’re feeling negative, we can easily slip into narrow thought patterns. We accept as a given that our perspective is the only one, narrowing our thinking so we can only see things through this lens.
But there is always a way to reframe things from a different angle. People experience their lives through the window of their perception. This is based on myriad influences, from their upbringing, politics, relationships, beliefs, and a whole cornucopia of things you cannot control.
They may be carrying resentments, insecurities, personality traits, and prejudices that all color their view in a way you don’t realize. Consequently, this might have clouded their ability to reflect on or appreciate your support. Not for a lack of trying, but because their lived experience has led them to this.
One person’s meddling is another person’s helping. If there’s evidence for one, there’s probably evidence for the other. Try to find counterpoints for each of the negatives so you can maintain a more balanced perspective on things. And from that, draw the lessons to help you grow.
4. Reflect on your approach
Nothing you ever do, good or bad, comes without the added benefit of lessons. But not all lessons are created equal. If you don’t pay attention, you could learn the wrong ones.
When you face an employee who leaves you feeling like you didn’t help, remember to reflect on what you did to help, how you tailored your approach to fit them, and what skills or experience you brought to the interaction that were beneficial.
But also recognize your limits. You can’t do it all. You can’t help everyone. Did you help? Did you overstretch yourself and take on more than you should or could?
I wanted to help Jess. I thought that with my input I could help things. But I’ve come to realize that as I was only half-involved, I was never going to be able to fully resolve it.
And it’s not my place to. It was for Jess and Steph to work it out. I could be available and willing, but ultimately it’s down to them to figure out a way forward.
Your intentions might have been admirable, and you may truly have wanted to help. But did you help? Be honest with yourself so you can do better next time.
5. Take stock of your values
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Even if you don’t think you have any values, you do. They are connected to the little beliefs that you have somewhere, perhaps deeply, in your mind. When you face a challenging situation, it helps to reflect on what role your values play in your actions.
If you have some you are aware of, look for how you upheld them in your interactions with this employee.
If you aren’t aware of or haven’t thought about your core values, try reverse engineering instead. What values seem to come up again and again? What does that tell you about what you think is important, and how you approach the job?
I’ve worked in education for the last decade and a half. I’ve been a coach for many years and have always been in or around leadership positions. Through all of these is a core belief: people can develop. I am a big believer in human potential and the power of helping others unlock their talents. This can sometimes mean I’m slow to recognize a lost cause. Or I might put too much pressure on others to develop when they’re quite happy where they’re at. Knowing these things about myself, I’m better prepared to adapt to people in the future.
Learning about yourself is one of the highest-value things you can do. While it might make sense to learn about people around you for obvious reasons, learning about yourself pays off the longest. Because nobody will be in your life as long as you will. The better you know you, the better your life will be.
6. Treat the situation as a case study for how to do better next time.
What did you learn about yourself? What did it show you about these types of personalities/people/employees? At the end of the day, did you treat them with care and fairness?
Channel this energy into your personal growth, otherwise you run the risk of it manifesting in negative, destructive ways. And these can become self-fulfilling prophecies.
What you focus on expands. So focus on growth, not your flaws. And let go of their misrepresentation. It’ll live on only as long as you keep it alive.
The fact of the matter is you can’t control your own story. Whatever you do, part of it is always created by others. If you want to change this perception, start creating more evidence that’s contrary. If you don’t feel it’s truly you, then you’ll have plenty of other situations to call on that counteract it.
And if the real reason it’s hurt so much is you deep down suspect they might be right, that’s a lesson for you. Your insecurities shine a light on where you could and perhaps should improve.
Denying them won’t fix them. Embracing them, and the lessons they offer, will. You won’t get it right every day. You can’t. It’s called trial and error, not trial and right every time.
Each interaction, each fallout, each win — they’re all opportunities to learn, improve, and grow. The best you can do is stick to your values, take lessons from your experiences, and prepare yourself mentally for what might happen so you can make peace with it if and when it does.
But also, cut yourself some slack. Accept who you are. Even if you might improve, you need to be able to respect yourself for where you are, right now, today. Do not wait for some potential future you because the present is all we’re ever promised. Act accordingly.
Tobias is a writer, leadership coach, and corporate executive. He's had articles featured in Medium and Business Insider, as well as many other sites, and has been working in and around leadership for the best part of two decades.