Great at the Work? Here’s Why Managing Feels Hard

A weird thing happens when you start scaling a solo business: the skills that made you successful can become the exact reason your first hires feel chaotic.

If you’re a solopreneur in the U.S. who’s starting to add contractors, a VA, or your first employee, you’re at the same risk big companies face—creating an accidental manager. That’s the term leadership expert Ashley Herd (former Head of HR at McKinsey, founder of Manager Method) uses for people promoted into management because they were strong individual contributors… not because they were trained to lead.

This matters even if you don’t “manage people” in the corporate sense. The moment you have a freelancer, agency partner, editor, appointment setter, or part-time ops help, you’re managing. And if your business is also experimenting with AI in HR and workforce management—like performance analytics, employee engagement tools, or AI-assisted feedback—you’ll get better results if the human basics are solid.

The real reason top performers struggle as managers

Answer first: Top performers often struggle as managers because the job changes from doing to enabling others to do, and most people never get trained for that shift.

In the podcast conversation that inspired this post, Herd calls out a classic pattern: someone excels in sales (or marketing, or delivery), gets promoted (or in a small business, gets forced into “team lead” mode), and suddenly they’re responsible for delegation, coaching, conflict, motivation, deadlines, and performance.

Here’s the problem: excellence as an individual contributor is not evidence of leadership skill. It’s evidence of individual execution skill.

For solopreneurs, this shows up in subtle ways:

• You hire a contractor to “take it off your plate,” then redo their work at 11 p.m.
• You assume the brief was obvious, then feel annoyed when they deliver something different.
• You avoid giving feedback because it feels awkward, then the same issue repeats.
• You keep hiring “another person” instead of fixing your expectations and process.

There’s a better stance to take: management is a learnable craft, not a personality trait.

Myth to drop now: “If I’m the best at the work, I’ll be the best manager.”

Most companies get this wrong, and plenty of founders do too.

If your identity is built on being the strongest producer, management can feel like you’re losing the thing that made you valuable. Herd points out the trap: managers fear that if they give others credit and responsibility, they’ll become “less needed.”

The opposite is true. Your value shifts upward:

• From producing deliverables → to producing outcomes through others
• From being the idea source → to building the system that generates good ideas
• From “I did it” → to “my team can do it without me watching”

Clear expectations aren’t goals. They’re conversations.

Answer first: Clear expectations work when you define the role, the impact, the standards, and the support—not just the deadline.

Herd frames clear expectations as a conversation, not a line in an onboarding doc.

This is where most solopreneurs stumble, especially when hiring freelancers:

• You communicate what you want (“a landing page”) but not the standards (“must match our tone, include 3 FAQs, be skimmable on mobile”).
• You share the goal (“book 20 calls”) but not the plan assumptions (“we’re targeting healthcare owners, via LinkedIn + email, with a 2-week test”).
• You set a deadline (“Friday”) but not the priorities (“version 1 can be rough, but the headline must be solid”).

A simple expectation framework (steal this)

In your kickoff (or next reset call), cover these five points:

1. Outcome: What does “done and good” look like?
2. Impact: Who is affected if this goes well—or poorly?
3. Standards: Examples, constraints, and “must-haves.”
4. Support: What access, tools, and decisions can they expect from you?
5. Checkpoints: When will you review, and what happens if something’s off?

If you want this to be AI-friendly in your business, translate standards into checklists. That’s where AI workforce management tools can actually help: you can turn “good work” into reusable rubrics and QA steps, then use AI to spot gaps early.

Snippet-worthy rule: If you can’t describe “good” in 3–5 bullet points, you don’t have clear expectations yet.

One-on-ones should not be status updates (and AI won’t fix that)

Answer first: One-on-ones build retention and performance when they focus on obstacles, decisions, and growth—not task recaps.

Herd nails something that’s easy to underestimate: just showing up on time for a one-on-one sends a strong signal that you care.

For a solopreneur, one-on-ones can feel like overhead. But if you’re running even a small remote team, they’re often the difference between:

• silent confusion vs. early problem detection
• “looks fine” work vs. aligned work
• short contractor relationships vs. long-term partnerships

Try this 30-minute one-on-one agenda

Keep it consistent. Consistency builds psychological safety.

• 5 minutes: Wins + what’s working
• 10 minutes: Blockers + what they need from you
• 10 minutes: Decisions + tradeoffs (where you give context)
• 5 minutes: Growth (skills, responsibility, what they want more/less of)

To avoid turning the whole thing into a status report, use a shared doc (or your PM tool) where updates live asynchronously.

Where AI fits (without making it weird)

If you’re using AI in HR and workforce management, keep it supportive, not performative:

• AI can summarize project notes and surface “open loops” before the meeting.
• AI can draft a one-on-one agenda based on tasks, messages, and deadlines.
• AI can help you spot recurring blockers (late reviews, unclear briefs, changing priorities).

But don’t outsource the human part. Trust isn’t automated.

Feedback that doesn’t trigger defensiveness: Pause → Consider → Act

Answer first: Great feedback lands when you slow down, check your motives, and focus on helping the person win.

Herd’s feedback framework—Pause → Consider → Act—is practical because it addresses what actually goes wrong: managers react fast, get emotional, and make it about themselves.

Pause

Don’t deliver feedback at peak irritation. Take a beat. Even 60 seconds helps.

Consider

Ask: What’s my real goal?

If your goal is to vent, you’ll sound like a critic. If your goal is to improve performance, you’ll sound like a coach.

Also consider what you don’t know yet. Go in with questions:

• “What got in the way of hitting the deadline?”
• “What assumptions did you make from the brief?”
• “What would you do differently next time?”

Act

Deliver the feedback clearly, then co-create the next step.

A simple script that works:

• Observation: “The email sequence went out with broken personalization fields.”
• Impact: “That hurts reply rates and trust.”
• Expectation: “We need a QA step before launch—every time.”
• Support: “I’ll provide a checklist and we’ll test together once.”
• Next step: “Can you add QA to your process and show me the updated workflow by Wednesday?”

Use AI to draft the words, not the intent

If feedback feels awkward, AI can help you translate your rough thoughts into professional language. Just don’t use it to avoid the conversation.

Here’s a prompt I’ve found useful:

Rewrite this feedback to be clear, kind, and specific. Keep it in my voice (direct, not corny). Include: observation, impact, expectation, next step.

Manage like a coach: “What would you do?”

Answer first: Coaching creates independent decision-makers, which is the only sustainable way to scale.

A moment from the conversation stands out because it’s so simple: when someone asks, “What should I do?” respond with, “I don’t know—what would you do?”

That one line changes the relationship.

• It signals trust.
• It builds judgment.
• It prevents you from becoming the bottleneck.

For solopreneurs, being the bottleneck is the silent killer of growth. Not because you’re lazy—because you’re overloaded.

A coaching stance also helps you use AI better. If AI drafts options, your team learns to evaluate options, not wait for commands. That’s how you build a business that can run while you market, sell, or take an actual weekend.

A tiny action that boosts motivation: tell people why you chose them

Answer first: Saying “here’s why we hired you” builds identity, commitment, and trust from day one.

Herd shares a tactic more leaders should use: tell new hires (or current team members) why they were chosen.

Not generic praise—specific reasons:

• “You’re fast, but you don’t cut corners.”
• “Your writing has that rare mix of clarity and warmth.”
• “You asked better questions than anyone else.”

This is especially powerful in January.

A lot of contractors and employees reassess work after the holidays (and after year-end burnout). If your retention strategy is “pay on time and hope,” you’ll lose good people. A two-minute message about why they matter is cheap and effective.

Practical next steps for solopreneurs hiring in 2026

Answer first: If you’re about to hire, fix expectations, meeting cadence, and feedback habits before adding headcount.

Use this checklist before you bring on your next freelancer or first employee:

1. Write the “done and good” checklist (3–7 bullets).
2. Set a one-on-one rhythm (weekly for new hires; biweekly once stable).
3. Create one feedback template (observation → impact → expectation → next step).
4. Decide what AI will do (summaries, drafts, dashboards) and what it won’t (trust, accountability, hard conversations).
5. Tell them why you hired them—even if they’ve been with you for months.

If this hits a nerve, that’s a good sign. It usually means you’re close to the next stage of growth.

Your question to sit with: If you hired one more person next month, would your current management habits make them better—or burn them out?