There is no shortage of leadership advice out there. Books, podcasts, frameworks. Everyone has a “playbook.”
Most of it sounds great. Some of it even works.
But the lessons that actually stick tend to come from real moments, real people, and a few situations you would not volunteer to repeat.
Here are five that have stayed with me throughout my career:
1. Leave doors open
Early in my career, I worked for a leader I would not describe as the easiest relationship at the time.
But we stayed respectful. We stayed professional. No dramatic exits. No “one last email” you regret five minutes later.
Fast forward nearly 15 years later, and we are still in touch. He has been one of the first calls I make before every career transition, offering guidance at moments that mattered most.
It is a small world. Smaller than you think.
I recently heard a story about someone who was let go because they were not well liked. Years later, she ended up working at one of that company’s biggest customers.
Now imagine that dynamic.
The same people who once made that decision, now sitting across the table, hoping to continue to win the business.
And if anything goes sideways, guess who carries the reputation risk.
You never know where people will land or how the story comes back around.
And yes, there are rare exceptions. If someone is truly toxic or treats people poorly, distance is necessary. But even then, how you exit still matters.
This lesson actually started long before my career.
My dad told me that when he left a major law firm to start his own, he made a point to speak highly of where he came from. No negativity. No tearing it down. Just respect.
Down the line, that same firm referred him one of the largest cases he ever received. That stuck with me.
Be thoughtful. Be professional. Take the high road. It pays better than the alternative.
And it goes both ways.
Be thoughtful about how you treat people on their way out, too. I have seen situations where transitions were met with frustration or tension. Those moments leave a lasting impression, and they matter just as much.
If there is one piece of advice I would give to anyone earlier in their career, it is this:
Be classy on your way out the door.
Go above and beyond, even after you give notice. Leave with professionalism. Keep the door open.
Careers are a marathon, not a sprint.
2. “I don’t know, but I’ll figure it out” is a superpower
There is a moment in every role where you are handed something you have never done before.
The temptation is to sound confident. Maybe a little too confident.
Resist that.
“I don’t know, but I’ll figure it out” is one of the most credible things you can say.
It signals ownership, curiosity, and just enough humility to be trusted.
Also, you usually do figure it out. And when you do, you remember it forever.
3. Not everyone will like you and that is okay
This one takes a minute to accept.
You can be prepared, thoughtful, and well intentioned, and still not be everyone’s favorite person in the room.
That is not a failure. That is math.
What matters more is understanding the landscape:
- Who influences decisions
- Where alignment exists
- Where it does not
You do not need universal approval. You need awareness and the ability to navigate it without losing your mind.
4. Find the good in people, even when it takes effort
I worked with someone at USAA who never had a bad word to say about anyone.
Even the people others might complain about. Especially them.
She always found something positive. Something to build on.
I have learned over the years that constant complaining is not a strategy. It is just noise.
Focusing on strengths and solutions tends to get you a lot further. And makes you someone people actually want to work with.
5. There are always two sides to a story
In leadership, you are often asked to make decisions quickly and with incomplete information.
Quick is easy. Right takes a little more work.
The best leaders I have worked with pause. They ask questions. They listen to both sides before forming an opinion.
Because most situations are not as simple as they first appear. And reacting too quickly is a great way to be confidently wrong.
Final Thought
None of these lessons came from a textbook.
They came from conversations, missteps, observations, and a few moments where you think, “well, I will not do that again.”
How you show up matters just as much as what you deliver.
People remember both.