A CEO I work with has been pushing his senior team to think more “entrepreneurially.” He is frustrated that they don’t. He is also, without knowing it, part of the problem.
Most salaried employees are careerists. That is not an insult — it is a description. Their decisions are filtered through a different lens than an entrepreneur’s: what advances the career, protects the position, avoids the wrong kind of visibility. The incentives are different, the risk calculus is different, and no KPI scheme fully closes the gap.
But careerist and entrepreneurial thinking are not mutually exclusive. Some salaried people think and act like owners. The ones who do are markedly different from those who don’t — and the difference shows up in how they handle decisions, spend money, run meetings, and respond to resistance.
If you want your people to be more entrepreneurial, you first need to know where they actually stand. And you need to know where you stand.
The Comparison
The rows below are drawn from real conversations — things actual entrepreneurs and actual careerists have said to me, sometimes within the same week.
Careerist | Entrepreneur |
How does this help grow my career? | How does this help grow my business? |
How can I hit my targets? | How can I add value to customers? |
I want a promotion to a better role. | I want a better lifestyle. |
Who’s gunning for my job? | I need to cultivate next generation leaders. |
How will this expense be viewed by my boss or worse, the finance department? | How will this expense be viewed by my spouse? |
What’s the risk to my career if I do this? Is it worth it? | What’s the risk to my business if I don’t do this? Can I afford not to? |
What do I want my next job to be? | What do I want my business to be like when I take it to the next level? |
How will my boss react? What will my staff say? | How will my customers react? What will the market say? |
Will HR approve this new hire? | I hire the best and pay them accordingly, even if HR disagrees. |
I need to keep costs within budget. | I need to maximize ROI. |
This project has high costs. | This project has high value. |
What can I do to get a raise? | What can I do to generate immediate cash? |
What’s my bonus? | What’s my bottom line? |
It’s safer to stay quiet and blend in. | Success means standing out from the crowd, even if some people won’t like what I say or do. |
I couldn’t possibly even suggest a good idea to my boss when there is a risk she won’t like it. | Always tell me what you think, especially when you believe I might not agree. |
What This Tells You
Read through these and notice your honest reaction — not the reaction you’d like to have, but the one you actually have.
If you identify with three-quarters or more of the entrepreneurial column, you think like an owner, even inside a salaried role. If you’re roughly split, you’re likely a capable operational manager — and there is nothing wrong with that. But if more than half your instincts are in the careerist column, you are not entrepreneurial in the way your CEO probably wants, and no amount of encouragement will change that without a change in how you see your own position.
The same test applies to the people who work for you.
Here is the part that most CEOs miss: you cannot train someone into entrepreneurial thinking. However, you can show the way. You can create conditions that allow it to surface, or you can hire for it directly. But the real leverage is in your own behaviour. When your team watches you defer decisions until consensus appears, when they see you avoid the hard conversation with your own boss, when they notice you signal that safety matters more than momentum — they adjust accordingly. Your behaviour teaches them far more than your words ever will.
Which brings me back to the CEO I mentioned at the start.
He wants his team to be more entrepreneurial. His team is watching what he does. When he avoids a hard conversation with his own boss, when he defers a decision until he has full consensus, when he signals that safety matters more than momentum — they take note. They adjust accordingly. His behavior teaches them more than his words do.
If you want an entrepreneurial team, the first question is not about them.
It is about you.
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