Hey Reader,
Let's talk about your boss for a second.
Leaving management training to chance is not a strategy.
But that what most companies do.
Which is why 60% of new managers fail.
Wait. What?
Yeah. Read that again. 60% of new managers fail. *gulp*
And the problem is, your boss is the single most important relationship you have when it comes to reaching your potential, maximizing your impact, your income and your enjoyment in your work.
Is your boss even equipped to do what you need them to do for you?
If you've ever been in a situation where your boss is, shall we say, leading too much or leading too little, you know the feeling.
It's frustrating, demotivating, and downright confusing.
I've been fortunate to have gained experienced reporting to all kinds of different bosses over the years.
So, let's reverse-engineer the problem and figure out what you can do to make sure you're getting effective leadership.
That's right.
Let's fix it without rage quitting, starting a union, or staging a dramatic office rebellion.
Scenario 1: Your boss is way too directive
Your boss is micromanaging, breathing down your neck, and giving you step-by-step instructions on how to find each individual freckle on the back of your hand.
You have the skills and the will to get it done on your own, but they’re treating you like it's your first day on they job.
Yo! Back up!
You feel like they don’t trust you—and every instruction they give feels like a punch to the gut.
Sound familiar?
The first thing to do here is to recognize that your boss might be caught up in “protecting” you or have a deep need to control the outcome.
They actually might think they're helping.
Crazy, right?
Solution: Don’t just sit there fuming.
Proactively show your boss that you’ve got it covered. A simple way to do this is to pre-emptively provide updates.
If you’re about to start something new, outline your plan and ask for feedback (without waiting for them to tell you what to do).
Frame it as “Here’s my plan—I’d love to know if you have any feedback or if you think I’m missing something before I take action.”
You’re showing you’re on top of it, and that you value their guidance—without giving them the chance to step in and take over.
If the micromanagement continues, it might be time for a one-on-one conversation.
You can say something like, “I’ve noticed you’ve been really hands-on with my work lately. I appreciate your guidance, but it's making me second guess my abilities. Am I missing something?”
Scenario 2: Your boss is giving you zero direction
Now, on the other side of the coin, you have the will, but you’re lacking the experience—and your boss is barely giving you any direction.
Like nothin'.
Notta.
Zip.
Zilch.
It’s like being thrown into the deep end with no life raft in sight.
You’re lost.
You’re inefficient.
You’re spinning your wheels.
Solution: First, realize that this situation often arises when your boss has high expectations but doesn't know how much guidance you actually need.
They assume you’ll figure it out on your own—or, worse, they’re afraid of micromanaging you.
*cracks open Goldilocks and the three bears to confirm there is a "just right" option coming up*
You need to ask for more.
I know it’s uncomfortable, but here’s the trick: Be specific about what you need.
Instead of saying, “I need more direction,” say, “I need clarity on [this specific area]. Would it be possible to have some clear milestones, or could you point me toward resources to fill in the gaps?”
This gives them a roadmap for how they can help you, without having to spoon-feed you everything.
But also—take action. Get to work with what you know.
This will not only show your boss that you’re resourceful but also give you more confidence in your ability to figure things out.
Then, circle back with a “Here’s what I’ve accomplished so far; can we review this together to make sure I’m heading in the right direction?”
Here’s the bottom line: You are in control of your career, even if your boss is sometimes a little off-track with their leadership.
Whether they’re being too controlling or too hands-off, it’s up to you to take the initiative.
It might feel uncomfortable at first, but addressing the leadership gap head-on will make you more visible, respected, and in control of your career path.
If you’re ready to level up your leadership, relationship-building, and career impact, these small tweaks will help change everything.
Stay vigilant,
P.S. If you’re struggling with a specific leadership issue (or need more tips on how to handle tricky situations), just hit reply—I’m all ears.
P.P.S. Know somebody who is trying to take more ownership of their career? Press 'forward' on this email and encourage them to sign up to become a Career Vigilante here.
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