Further Resources

The Art of Managing Up: What Portrait Artists Know About Supervision

My mate's daughter is a portrait artist. Real one, not the caricature type you see at markets. She spends weeks studying faces, understanding bone structure, capturing not just what someone looks like but who they are beneath the surface.

Last month, watching her work on a commission, something clicked. The way she observed her subject, adjusted her approach based on their personality, managed their expectations whilst delivering something they didn't even know they wanted—it's exactly what the best supervisors do with their own managers.

We've got supervision all wrong in Australia. We train people to manage down brilliantly—how to motivate teams, delegate tasks, give feedback. But we barely mention the art of managing up, which is arguably more critical for a supervisor's success than anything else they'll learn.

Think about it. Your ability to influence upwards determines your budget approvals, team resources, strategic direction, and career trajectory. Yet most supervisory training courses focus entirely on the people below you on the org chart.

Portrait artists understand something we've forgotten in corporate Australia: your subject (in this case, your manager) has needs, fears, blind spots, and preferred communication styles that must be decoded before you can create something meaningful together.

The Observation Phase

Every portrait begins with observation. Artists don't just glance at their subject and start painting. They study lighting, angles, expressions. They notice the way someone's eyes crinkle when they're genuinely amused versus when they're performing politeness.

Your manager is no different. They've got tells. Karen from Finance always drums her fingers when she's about to reject a proposal. David in Operations speaks faster when he's uncertain about a decision. Sarah the Regional Manager asks three specific questions when she's already made up her mind and just wants confirmation.

I spent five years missing these signals completely. Would walk into meetings with perfectly logical proposals, data-backed recommendations, everything a rational person should want to hear. Got shot down repeatedly.

The breakthrough came during a restructure in 2018. My manager, usually decisive and direct, kept postponing our one-on-ones. Started noticing he'd glance at his phone constantly during team meetings, something he never did before. The drumming fingers. The rapid-fire questions that didn't quite connect to what we were discussing.

Turns out he was fielding calls from head office about redundancies. Not something he could share, but something that completely changed how he evaluated every request that crossed his desk.

Once I started reading the room properly, my success rate with upward influence improved by about 70%. Conservative estimate.

Understanding the Canvas

Artists know that every surface behaves differently. Oil on canvas versus watercolour on paper requires completely different techniques. Same pigment, different results.

Your manager's "canvas" is their current context. Are they under pressure from their own boss? Dealing with budget cuts? Fighting for resources across multiple departments? Recently promoted and feeling imposter syndrome? Been in the role for years and starting to phone it in?

Most supervisors present the same way regardless of context. Bad move.

When my current manager started eighteen months ago, she came from a completely different industry. Banking background, suddenly overseeing manufacturing operations. Brilliant woman, but she was drowning in technical details and afraid to admit it.

Instead of overwhelming her with process improvements and efficiency metrics, I started framing everything in terms she understood. ROI calculations. Risk management. Compliance implications. Same ideas, different language.

The other supervisors kept presenting in engineering speak. Guess whose projects got approved?

Context isn't just about your manager's background. It's about timing, organisational politics, external pressures. I know supervisors who save their biggest requests for Friday afternoons because their manager is generally more relaxed heading into weekends. Others who have learned never to approach certain topics during budget season.

The Sketching Process

Portrait artists don't jump straight to final details. They sketch first. Rough outlines, basic proportions, checking composition before committing to permanent strokes.

With managers, this means testing ideas informally before formal proposals. Corridor conversations. "Quick question about something I've been thinking about." Casual mentions during existing meetings.

This isn't manipulation—it's smart communication. You're giving both parties a chance to explore concepts without the pressure of immediate decisions.

Here's what drives me mental: supervisors who ambush their managers with fully-formed, detailed proposals in scheduled meetings. No warning, no context-setting, just boom—here's my seventeen-point plan for transforming our customer service approach.

Your manager's sitting there trying to process completely new information whilst simultaneously evaluating feasibility, budget implications, stakeholder reactions, implementation challenges. Of course they're going to default to "let me think about it" or "that's interesting but not right now."

Smart supervisors plant seeds weeks before they need decisions.

Working with Light and Shadow

Every portrait has areas of light and shadow. Artists use both deliberately to create depth and dimension.

Your manager has bright spots—areas where they're confident, knowledgeable, passionate. They also have shadow areas—skills gaps, knowledge blind spots, topics that make them uncomfortable.

The mistake most supervisors make is trying to eliminate the shadows. Pointing out what their manager doesn't know. Highlighting gaps in their understanding. Basically holding up a spotlight to every weakness.

Artists do the opposite. They work with existing light sources, enhance natural highlights, use shadows to create depth rather than trying to eliminate them.

When I realised my current manager struggled with technical project details, I didn't create elaborate explanations trying to bring her up to speed. Instead, I focused on the strategic implications she did understand and positioned myself as her trusted technical interpreter.

She gets to stay in her strength zone. I get to be genuinely valuable. Win-win.

The Revision Process

Here's something that separates amateur artists from professionals: willingness to revise. Professionals expect multiple drafts. They're not attached to their first attempt.

Most supervisors pitch ideas once, get pushback, and either give up or become defensive. They take revision requests as personal criticism rather than collaborative refinement.

I've had proposals rejected four times before finding the right angle. Same core idea, different presentation each time. The breakthrough usually comes when I stop thinking about what I want to communicate and start thinking about what they need to hear.

That manufacturing efficiency project I mentioned? First pitch focused on productivity gains. Rejected—too risky during uncertain times. Second pitch emphasised cost reduction. Rejected—budget already allocated elsewhere. Third pitch framed it as risk mitigation for compliance issues. Approved immediately.

Same project. Different light.

The Final Portrait

The best portrait artists deliver something their clients didn't know they wanted but recognise immediately as perfect.

This is the gold standard for supervisor-manager relationships. You're not just executing their vision—you're enhancing it. Adding details they hadn't considered. Bringing technical expertise to their strategic thinking.

When done well, business supervising skills become less about managing people below you and more about amplifying the effectiveness of people above you. You become indispensable not because you're irreplaceable, but because you make everyone around you better at their jobs.

The portrait artist analogy breaks down eventually, of course. Your manager isn't a static subject—they're growing, changing, responding to new pressures. The organisational landscape shifts constantly. What worked last quarter might not work next quarter.

But the core principle holds: observation, understanding, adaptation, revision. These aren't soft skills or nice-to-haves. They're the fundamental toolkit for any supervisor who wants to move beyond simply managing their immediate team.

Most importantly, this approach transforms the supervisor-manager relationship from transactional to collaborative. Instead of simply reporting up and delegating down, you become a strategic partner in achieving shared objectives.

And that, more than any technical skill or management framework, is what separates good supervisors from great ones.

It's also what gets you promoted faster than your peers, but that's probably obvious by now.

Our Favourite Blogs: Growth Network Insights | Training Matrix Resources