Most of us who’ve worked at a small company know this moment: You’re two years in, basically running entire departments, but your title is still something vague like “marketing coordinator.” There’s no org chart on the wall because there are only twelve of you. The CEO sits ten feet away but has no idea what a promotion would even look like because they’re too busy keeping the lights on.
So what do you do when you want to advance but there’s literally nowhere to advance to or any plan for advancement at all? Such was the frustration of an Optimism Library subscriber who wrote in this question: “My company doesn’t have clear promotion criteria. How do I navigate this ambiguity and still position myself for advancement?”
We brought it to Simon to get his take on navigating career growth when your company treats promotion paths like jazz improvisation rather than corporate ladders.
Simon’s response was direct: Ask for clarity. But how you ask makes all the difference.
“This is very common in smaller companies,” Simon said. “Bigger companies, because they’re corporate, they tend to be a little more organized for this kind of thing.” In contrast, “entrepreneurial ventures are kind of like, woohoo!, right?”
He added that personality and relationships often factor into these decisions: “Sometimes it is and sometimes it isn’t” fair—but that’s the reality.
The Assumption Problem
“One of the worst things you can do if there’s ambiguity is assume that it’s somebody else’s responsibility,” Simon said. The dangerous part? Your boss might think everything is perfectly clear.
Simon has been on the other side of this confusion: “I’ve definitely been guilty of this, you know, where I’ve been the leader of a team, and I think everything is crystal clear.”
Then reality hits at year-end: “I’m missing key information. I promote one person but not another. I give bonuses to some but not others, and everyone’s like, ‘What?’ I’m thinking, ‘You knew this was coming, right?’ But they’re like, ‘We had no idea.'”
The Solution Script
Instead of criticizing the company’s lack of structure, Simon suggests positioning your request as asking for help:
“Hey boss, I need help, right? I want to be the best version of myself. I want to outperform. I want to do right by this company. I want to hit all of my goals, all the goals you have for me, and it will really help me if you and I could spend a little time and actually write down what your expectations are of me, if we can have that discussion so that I can give you everything you expect of me and more.”
The key elements:
- Ask for help
- Focus on excellence (not just promotion)
- Take ownership of performance
- Create written documentation
This perspective changes the conversation from confrontation to collaboration.
Alternative Approach
Simon offers another version that acknowledges your boss’s existing expectations:
“I need your help. I know you have expectations of me. I know you have expectations of us. It would be really helpful so that I meet all of your expectations, that I can find out what’s in your mind and put it on paper so that I can give you what you want and more.”
This script:
- Validates that expectations exist
- Positions you as eager to exceed them
- Creates concrete documentation
- Benefits both parties
“So ask for help, instead of complaining about what’s wrong,” Simon said. When faced with organizational ambiguity, the person who creates structure often benefits most from it.
Facing a challenge at work? Maybe Simon can help. As an Optimism Library subscriber, you’re invited to our exclusive quarterly Live Q&A sessions where you can ask Simon your questions directly.
