Hey Leader,
Not everyone on your team wants to climb the corporate ladder. And guess what? That does not mean they lack ambition.
I know. For some of you, that might be hard to hear.
Especially if you are the kind of leader who has spent your entire career working toward the next opportunity, the next promotion, the next level of success.
But here is something I want you to consider.
Just because someone does not define success the way you do does not mean they are any less successful.
Let me give you an example.
Imagine you are sitting down for a one-on-one with one of your most dependable employees.
This person delivers results. They meet their deadlines. They show up, do excellent work, and rarely need to be reminded of anything.
You ask them a question we have all heard a thousand times.
“Where do you see yourself in five years?”
And they say, “Honestly? Right here.”
Now, be honest.
What is your first reaction?
Do you start wondering why they are not more ambitious? Do you immediately begin thinking about how to motivate them?
Well, what if I told you that you might be trying to solve a problem that does not exist?
The Leadership Mistake We Need to Talk About
Recently, I had the opportunity to reconnect with my friend Vanessa Van Edwards at the Global Leadership Summit.
Vanessa is a bestselling author, the founder of Science of People, and someone who has spent years studying human behavior and communication.
Her new book, Conversation, came out this week and there is a concept in it that I think every leader needs to understand.
Through her research, Vanessa identified five common story archetypes that influence how people see themselves and approach life.
One of those archetypes is called the Contented Pragmatist.
These are people who find satisfaction in what they already have. They value stability, meaningful routines, and enjoying the life they have built.
They are not necessarily looking for dramatic change.
And here is what I find so interesting.
Some of the very qualities that make these people excellent employees are the same qualities leaders sometimes mistake for a lack of ambition.
Think about that.
You have someone who is dependable, consistent, and genuinely happy doing excellent work.
And because they do not want your job, you think something is wrong.
Leaders, we have to do better than that.
What Science Tells Us About Being Satisfied
There is research that helps explain this.
A 2002 study led by a psychologist at Swarthmore College examined the difference between people who constantly search for the best possible option and those who are comfortable choosing something that meets their needs.
The researchers found that people who consistently pursued the best possible option tended to report lower happiness and life satisfaction than those who were comfortable with a good-enough choice.
Now, that does not mean we should stop striving for excellence.
You know me better than that!
But it does remind us of something important.
Wanting more and being satisfied are not the same thing as being successful and unsuccessful.
And as leaders, we have to stop treating them that way.
You see, one of the biggest mistakes we make in leadership is assuming that everyone is motivated by the same things that motivate us.
Maybe you are motivated by recognition, promotions, increased responsibility, or the opportunity to lead a larger team.
Wonderful!
But the person sitting across from you might value stability, flexibility, meaningful work, or having more time with their family.
Neither perspective is automatically wrong.
The problem begins when you assume your definition of success should be theirs.
Here Is Where It Gets Interesting
Vanessa makes another important point about Contented Pragmatists.
While many are genuinely satisfied with their lives, some may settle too quickly because they do not fully recognize their own potential.
And that distinction matters.
Because there is a BIG difference between someone who is happy where they are and someone who does not believe they deserve more.
One is contentment.
The other may be a lack of confidence.
And if you are not paying attention, you can easily mistake one for the other.
So how do you know the difference?
You have a conversation.
Not a conversation where you spend the entire time explaining what you think their career should look like.
A conversation where you actually get curious about what matters to them.
This is exactly why I teach the A.L.L.Y. Leadership Model.
Because leading people who are not like you starts with understanding that they may not think like you, communicate like you, or want the same things you want.
And that is okay.
How to Lead Someone Who Defines Success Differently
The next time you sit down with someone on your team, I want you to put the A.L.L.Y. framework into practice.
A: ASK
Instead of automatically asking where they want to be in five years, try asking:
“What does success look like for you right now?”
Or:
“What parts of your work give you the greatest satisfaction?”
Notice the difference?
You are not telling them what they should want. You are giving them an opportunity to tell you what matters.
L: LISTEN
And I mean really listen.
Not listening while mentally preparing your next piece of career advice.
Pay attention to what they say and what they do not say.
Are they genuinely satisfied? Do they feel valued? Are they interested in growing their skills without necessarily changing their position?
You cannot know until you listen.
L: LEARN
Now take what you have heard and use it to understand the person in front of you.
Maybe they want more responsibility but not a management position.
Maybe they love their work and want to become even better at it.
Or maybe they have stopped pursuing opportunities because nobody has ever helped them recognize their potential.
Your job is to learn the difference.
Y: YOU TAKE ACTION
This is where leadership actually happens.
If someone is happy in their role, recognize the value they bring. Give them opportunities to continue developing without forcing them onto a career path they do not want.
If someone is holding themselves back because they lack confidence, help them see what you see.
Tell them specifically what they do well. Show them opportunities they might not have considered.
And then give them the freedom to decide.
Remember, your job is not to make everyone want what you want. Your job is to help people succeed based on what matters to them.
Your Leadership Challenge This Week
I want you to think about someone on your team who consistently delivers great results but rarely asks for more.
Maybe you have assumed they are not motivated.
Maybe you have been trying to encourage them to pursue a promotion they have never expressed interest in.
Or maybe you have simply overlooked them because they seem perfectly happy where they are.
This week, I want you to have a different conversation with that person.
Ask them what success looks like for them.
Listen to their answer without trying to change it.
Learn what motivates them.
And then take action to support their goals, not just the goals you think they should have.
Because here is the bottom line.
Great leadership is not about creating a team full of people who think like you. It is about learning how to lead people who do not.
And sometimes, the best thing you can do for a high-performing employee is stop trying to change what already works.
Now, I would love to hear from you.
Have you ever mistaken someone’s contentment for a lack of ambition?
Share your experience in the comments. I think this is a conversation more leaders need to have.
One More Thing Before You Go
If this topic resonates with you, I highly recommend checking out my friend Vanessa Van Edwards’ new book, Conversation.
She explores all five story archetypes and shares nine Power Questions designed to help us have more meaningful conversations.
Two of my favorites are surprisingly simple:
“Have any fun plans coming up?”
“What do you love to talk about?”
Simple questions. But think about how much you could learn about someone just by asking them and genuinely listening to their answers.
And as I always say, never underestimate the power of a conversation.
Your Ally,
Stephanie