Think You Know Where You Stand with Your Boss? Think Again.
As an employee, you want to be a good team player.
But sometimes, you also have to take matters into your own hands.
I learned that lesson the hard way.
And honestly?
I wish someone had told me sooner.
So if you're earlier in your career, consider this your head start:
Managing Up Is a Career-Long Practice
Managing up isn’t about being a people-pleaser.
It’s about building a proactive, strategic relationship with your boss,
One that’s good for you and them.
It’s knowing their priorities.
Adapting to their style.
Balancing their needs with your work.
And here’s the catch:
You’re never done learning it.
Managing up is a skill you keep sharpening at every stage of your career.
Two Conversations You Should Start (Today)
1. The Alignment Conversation
You’re not a mind reader.
So get clear on what success actually looks like.
Ask:
“What metrics matter most to leadership?”
“What does good performance look like to you?”
If things feel off?
Use curiosity: “Help me understand what’s driving this priority.”
Pro Tip:
Busy bosses love binary choices: “Would you prefer Option A or B?”
2. The Styles Conversation
Bosses have types. Here’s what to look for:
Commander: Results-driven, fast, blunt.
Cheerleader: Big vision, big energy, big on reputation.
Caretaker: Supportive, consensus-builder, slow to decide.
Controller: Analytical, detail-obsessed, process-first.
Your job?
Flex your style without losing yourself.
Communicate the way they listen best:
(Example: Lead with the bottom line for a Commander.)
What to Do When Things Get Tricky
If your style clashes with theirs:
Flex strategically: meet them where they are, without fawning.
If they’re a micromanager:
Show rough drafts early.
Frame feedback carefully: invite collaboration, not critique.
If they’re volatile or don’t trust easily:
Stay neutral, what I call Rock Mode: calm, clear, no drama.
Frame feedback around their success.
Career Tip You’ll Wish You Knew Earlier
Never assume you know what your boss is thinking, or where you stand.
What you think is clear might not be.
Stay curious.
Keep asking:
“What’s your sense of how things are going?”
“Is there anything I should be doing differently?”
“What would success look like for me over the next few months?”
Assume there’s a gap between your perception and their expectations,
and close it before it becomes a problem.
The Mindset Shift
Managing up isn’t about surviving bad bosses.
It’s about:
Assuming best intent until proven otherwise.
Making your boss’s life easier.
Reducing their cognitive load.
Building mutual respect, not just “doing your job.”
Three Scenarios I Learned From (The Hard Way)
1. The Empowering But Emotionally Unpredictable Boss
Encourages empowerment but melts down, or is emotionally unpredictable.
Wants you to stay "in your lane" but won’t respond when you escalate.
What Works:
Clarify lanes: “Which decisions do you prefer I escalate vs. handle?”
Frame escalations as risk management: “Flagging this for awareness, no action needed.”
Stay neutral. Don’t mirror their emotions.
Watch Out:
Emotional unpredictability will wear you down.
Keep written records of key decisions.
2. The Supportive But Possibly Exit-Oriented Boss
Says supportive things, but behaviour says otherwise.
You sense they might be preparing to push you out.
What Works:
Move key convos into writing: “Following up on our chat…”
Re-anchor with an alignment convo: “Can we confirm priorities for the next quarter?”
Get specific feedback early: “What would you need to see in the next 90 days to feel confident in my work?”
Build visibility with skip-levels and peers.
Watch Out:
Vague feedback and sudden escalations to HR = red flags.
Have a backup career plan ready.
3. The Note-Taking But Non-Follow-Up Boss
They nod, take notes, promise to follow up, and forget.
What Works:
Own the follow-up: “Following up on [topic], here’s what I captured.”
Make decisions easy: binary choices, bullet points.
Create “no response needed” updates to reduce their mental load.
Watch Out:
If their follow-up is always missing, escalate only what’s essential.
Bottom line?
Managing up isn’t extra credit.
It’s a skill set.
A strategy.
And honestly, it's survival.
Learn it early.
Your future self will thank you.
