Great at the Work? Don’t Auto-Promote Yourself to Manager

A weird thing happens when a solopreneur starts to grow: the exact habits that made you effective alone can start sabotaging you with a team.

You move fast. You “just handle it.” You keep quality high by doing the hard parts yourself. Then you hire a VA, a contractor, maybe a junior marketer—and suddenly your week fills up with clarifying, correcting, re-explaining, and firefighting. You’re still doing the work and now you’re managing humans.

This post sits inside our AI in Human Resources & Workforce Management series because the most common scaling mistake I see isn’t a bad tool choice—it’s role confusion. As Ashley Herd (founder of Manager Method, former Head of HR at McKinsey) put it on the Duct Tape Marketing Podcast: a lot of managers are “accidental.” Solopreneurs become accidental managers too—except you promoted yourself.

The “accidental manager” problem hits solopreneurs first

Key point: Being a strong individual contributor is not the same skill as leading other people’s performance.

When you’re solo, your output is a direct function of your time and skill. When you hire, your output becomes a function of:

• The clarity of your expectations
• The quality of your communication
• Your ability to coach (not command)
• Your willingness to give feedback early
• The systems you build so work doesn’t live in your head

Most founders assume management is “common sense.” It isn’t. And the penalty for learning it late is brutal: missed deadlines, churned contractors, inconsistent brand execution, and stalled lead flow.

If you’re in the USA and hiring in Q1 (a common “new year, new goals” push), this matters even more. Contractors are juggling multiple clients, and your ability to run tight one-on-ones and set clear outcomes is the difference between “easy growth” and “constant replacement.”

Clear expectations are a conversation, not a task list

Key point: “Clear expectations” isn’t “I told them the goal.” It’s alignment on impact, tradeoffs, and support.

Ashley Herd’s framing is simple and useful: clear expectations require more than a number or a deliverable. They require context.

Here’s what that looks like for a solopreneur hiring help with marketing.

The expectations ladder (use this for any role)

Instead of saying: “Publish two blog posts a week,” walk through this ladder:

1. Outcome: What does success change in the business?
   • “These posts should generate qualified email signups and support sales calls.”
2. Quality bar: What does “good” look like?
   • “Match our voice, include examples, no fluff, and follow our SEO brief.”
3. Constraints: What must be true?
   • “No external links. Don’t mention client names. Use our offers only.”
4. Process: How will work move?
   • “Draft → internal review → revisions → publish. Two revision rounds max.”
5. Support: What help do they get?
   • “You’ll have access to past posts, a keyword list, and a style guide.”

Solopreneurs often stop at #1 or #2. Then they wonder why execution drifts.

Use AI to make expectations explicit (without turning robotic)

This is where AI in workforce management earns its keep. Use AI to:

• Turn your “messy” brain dump into a role scorecard
• Generate a checklist for recurring deliverables
• Draft a one-page “definition of done” for common tasks (blog post, email campaign, landing page)

The goal isn’t to outsource judgment to AI. It’s to stop outsourcing clarity to luck.

One-on-ones that don’t turn into status-report purgatory

Key point: One-on-ones are retention tools and performance tools—if you stop treating them like a weekly interrogation.

Herd called out something many team members experience: managers skip one-on-ones, show up late, or cram them into a status update. The signal that sends is loud: “You’re not important enough to plan for.”

For a solopreneur, the signal is often accidental. You’re not trying to be dismissive—you’re overloaded.

A simple 25-minute agenda that works with contractors and employees

Use a shared doc (Google Doc/Notion) where both of you add bullets during the week.

1. 5 min: Wins + progress
   • What shipped? What moved? What got blocked?
2. 10 min: Decisions + tradeoffs
   • What needs your input? What should they decide?
3. 5 min: Growth + friction
   • What’s confusing? What’s annoying? What’s slowing them down?
4. 5 min: Next-week priorities
   • Confirm the top 1–3 outcomes, not 12 tasks.

If you want one line that changes your management style, steal this from the podcast discussion:

Ask “What would you do?” before you answer.

It forces ownership upward (in a good way). It also prevents you from training your team to be dependent.

Where AI fits in one-on-ones

In the HR tech world, AI note-takers and meeting summaries can get controversial. My stance: use AI to capture action items, not to police people.

Practical uses:

• Auto-summarize decisions and owners
• Extract action items into a task manager
• Spot recurring blockers across weeks (“waiting on approvals” shows up 6 times)

Avoid: “sentiment scoring” or anything that feels like surveillance. Trust dies fast.

Feedback without the ego: Pause → Consider → Act

Key point: Most feedback failures come from fear—fear of awkwardness, conflict, or being disliked.

Herd’s Pause → Consider → Act framework is useful because it fights the two biggest manager traps:

• Reacting in the moment
• Avoiding the conversation entirely

Pause

Take a beat. Don’t send the spicy Slack message. Don’t “fix it yourself” at midnight.

Consider

Ask: what’s the outcome you want?

• Do you want them to learn, or do you want to vent?
• Are you correcting a pattern or a one-off?
• Did you actually define the expectation, or are you assuming they “should know”?

This is also where you check your ego. A lot of founders avoid feedback because it’s uncomfortable. That’s self-focused. The employee or contractor pays the price.

Act

Deliver feedback with specificity:

• “When the email went out without the final CTA…” (observable)
• “…we lost a day of signups and had to resend…” (impact)
• “…next time, use the pre-send checklist and tag me for approval by 2 pm.” (next step)

Also: give positive feedback more often than you think you need to. Many people rarely hear what they’re doing right—especially contractors.

The coaching mindset: how to scale without cloning yourself

Key point: A manager’s job is to multiply output, not become the bottleneck.

The podcast made a great point using sports: the best coaches aren’t always the best players. In business, top performers often become managers and struggle because they expect everyone to operate like them.

Solopreneurs have the same issue—except the “top performer” is you.

Here’s the shift:

• Boss mindset: “Do it my way.”
• Coach mindset: “Here’s the outcome. Show me your approach. I’ll help you improve it.”

That’s how you hire specialists (writers, media buyers, ops managers) without trying to turn them into mini-you.

A hiring move that builds instant trust

One of Herd’s simplest suggestions is also one of the most ignored:

Tell people why you hired them.

Not “excited to have you.” Specific reasons:

• “Your writing samples showed strong structure and zero fluff.”
• “You asked sharp questions about attribution and pipeline.”
• “Your portfolio proved you can ship without hand-holding.”

This matters because it creates identity and direction on day one. People lean into what you name.

People Also Ask: solopreneur management + AI in HR

Why do great employees (or founders) struggle as managers?

Because execution skill and leadership skill are different. Managers succeed through clarity, coaching, feedback, and systems—not personal heroics.

What are the first HR processes a solopreneur should implement?

Start with:

• A role scorecard (outcomes, quality bar, process)
• A weekly one-on-one cadence
• A feedback system (what gets reviewed, how often, by whom)
• A simple onboarding checklist

AI can help draft and standardize these quickly.

What’s a responsible way to use AI in workforce management for a small business?

Use AI to reduce admin burden—job descriptions, onboarding docs, meeting summaries, and performance checklists. Avoid surveillance-style uses that erode trust.

Your next step: don’t “wing” the management role

Most solopreneurs don’t fail at hiring because they picked the wrong person. They fail because they never built the management muscles that make a good person effective.

If you take one action this week, make it this: write a one-page expectations doc for your next hire or contractor deliverable, then run one one-on-one using the agenda above. You’ll feel the difference immediately.

The bigger question is the one you’ll keep facing as you scale: Are you building a business that runs on your talent—or a team that can deliver without you being the constant translator?