It's 7 pm on a Thursday.

Sarah is reviewing the third draft of a campaign brief from Emily, her junior marketing manager.

It's... fine. Technically correct. All the boxes checked. The timeline makes sense. The budget is reasonable.

But it's missing the strategic thinking.

The positioning talks about features, not the customer problem. The targeting is too broad. The success metrics focus on activity (impressions, clicks) instead of business impact (pipeline, revenue).

Sarah opens her email to send feedback. Her fingers hover over the keyboard.

She's about to type: "Change section 2 to focus on ROI instead of features. The CTA needs to be more urgent. And the timeline doesn't account for review cycles."

Then she stops.

Because she's done this before.

With Emily. With three other junior team members. Every single week for the past year.

She sends detailed feedback. They make the changes exactly as specified. The work gets done. The campaign launches.

And nobody learns anything.

Emily gets better at following Sarah's instructions. But not at thinking strategically.

She gets better at executing Sarah's vision. But not at developing her own.

The realization hits:

Sarah isn't developing leaders. She's creating order-takers who can't function without her input.

Every time she tells them exactly what to do, she's reinforcing dependence.

Every time she fixes their work instead of coaching them through it, she's guaranteeing they'll need her to fix the next one too.

She's the bottleneck. And she's the one creating it.

Sarah deletes the email.

She schedules a 30-minute call with Emily for tomorrow morning.

Not to give feedback. To coach.

That was 18 months ago.

Today, Emily runs campaigns with minimal oversight. She thinks strategically about positioning, audience, and business impact. She solves problems independently. She's ready for promotion to senior manager.

The difference wasn't talent. Emily was always capable.

The difference was that Sarah stopped managing and started coaching.

Why Most Marketing Leaders Default to Managing (Not Coaching)

Here's the pattern Sarah sees everywhere:

Brilliant individual contributors get promoted into leadership because they're exceptional at doing the work.

So when their team struggles, they default to what they know: doing the work themselves, or telling people exactly how to do it.

Managing looks like this:

• "Here's exactly what I need you to do."
• "Change this section to say X."
• "No, not like that—like this."
• "You know what, let me just do it myself. It'll be faster."

And it creates:

• Order-takers who wait for instructions
• Dependence (they can't move forward without you)
• A bottleneck (everything requires your input)
• Junior staff who never develop strategic thinking

The brutal truth?

Managing feels productive. You get immediate results. The work gets done correctly. You maintain control.

But you're not scaling. You're just working harder.

Why do leaders choose managing over coaching?

Because it's faster. Short-term, at least. Just tell them what to do. Get it done. Move on. Coaching takes 30 minutes now to save 2 hours later—but "later" feels less urgent than "now."

Because it feels safer. You control the output. Less risk of mistakes. Coaching means letting them struggle, which feels uncomfortable.

Because it's what they know. Nobody taught them how to coach. They learned by being managed. So they replicate what they experienced.

Because it feels helpful. "I'm being a good manager by giving clear direction!" Actually, you're preventing growth.

The cost?

Sarah at 7pm on a Thursday. Again. Reviewing work that should have been done right the first time.

For the 500th time this year.

Because her team can't make strategic decisions without her.

Because she trained them not to.

The Fundamental Shift: From Doing Their Thinking to Helping Them Think

The mindset change is everything.

Managing asks: "How do I get this person to execute my solution?"

Coaching asks: "How do I help this person develop their own solution?"

It's a complete reframe of your role.

Here's what it looks like in practice:

The Old Approach (Managing)

Emily brings Sarah the campaign brief draft.

Sarah reads it. Mentally fixes all the problems.

Sarah: "The positioning is off. Change section 2 to focus on ROI instead of features. This CTA is too weak—make it more urgent. And the timeline doesn't account for review cycles. Fix those and send me the next draft."

Emily: Makes the exact changes Sarah specified.

Result: The campaign brief is good. Emily learned to execute Sarah's thinking. Emily will need Sarah to fix the next brief too.

The New Approach (Coaching)

Emily brings Sarah the campaign brief draft.

Sarah: "Before I read it, walk me through your thinking. What's the core problem this campaign is solving for the customer?"

Emily: Explains her thinking—focused on product features and capabilities.

Sarah: "Okay. Now when you read section 2, is it addressing that customer problem, or is it talking about our features?"

Emily: Reads it. Realizes the disconnect.

Sarah: "What would make it stronger?"

Emily: "I should probably focus on the business outcome they care about... ROI, not just the features that deliver it."

Sarah: "Exactly. Why ROI specifically for this audience?"

Emily: Explains the strategic reasoning—CFOs care about financial impact, not technical capabilities.

Sarah: "Good. Now look at the CTA with that same lens. If you're a CFO who just read about ROI impact, what action would compel you?"

Emily: Realizes the CTA is generic. Proposes something more specific and urgent.

Sarah: "Better. Now walk me through the timeline..."

Result: The campaign brief is good. Emily learned to think strategically about customer problems, positioning, and calls to action. Emily can apply this thinking framework to the next brief herself—without Sarah.

Both approaches produce a good brief.

Only one approach develops strategic capability.

The Questions That Change Everything

Instead of telling them what to do, ask questions that force them to think:

Strategic alignment:

• "What's the core problem we're solving for the customer?"
• "How does this connect to our Q4 revenue goals?"
• "If you had to explain this to the CFO, what would you say?"

Options and tradeoffs:

• "What other approaches did you consider?"
• "What's the risk if we do it this way?"
• "What would need to be true for this to work?"

Quality and standards:

• "Is this our best work, or just good enough?"
• "If you had another week, what would you improve?"
• "Would you put your name on this and send it to the CEO?"

Customer perspective:

• "Put yourself in the customer's shoes—what would you think?"
• "What question are they going to have that we're not answering?"
• "Is this obviously better than them doing nothing?"

The magic?

You're not telling them what's wrong. You're giving them the framework to diagnose it themselves.

After 5-6 coaching conversations using these questions, something shifts. They start asking themselves these questions before they bring you work.

That's when the multiplier effect kicks in.

The Coaching Framework: Three Parts, 30 Minutes

Every coaching conversation follows the same basic structure.

Part 1: Make Them Do the Thinking First (5 minutes)

Before you read their work. Before you offer any input. Before you identify problems.

Ask: "Walk me through your thinking."

"What were you trying to achieve?"

"What decisions did you make and why?"

Why this matters:

You're forcing them to articulate their reasoning. Most strategic thinking actually happens when you have to explain your choices out loud.

If they can't articulate their thinking? That's the real problem—not the execution.

Example:

Junior marketer brings you a social media content plan.

Don't: Immediately spot the 12 problems and tell them what to fix.

Do: "Before I look at this, tell me—who's the primary audience and why did you prioritize LinkedIn over other channels?"

If they can explain the reasoning clearly, great. They thought it through, even if the execution needs work.

If they stumble? Now you know where the coaching needs to focus.

Part 2: Ask Questions That Reveal Gaps (15 minutes)

Don't point out what's missing.

Ask questions that make them discover it.

Use the question categories above to systematically work through their thinking:

• Strategic alignment
• Options and tradeoffs
• Quality standards
• Customer perspective

The pattern: You ask a question. They answer. Their own answer reveals the gap they missed.

"How does this connect to our revenue goals?"

"Um... I'm not sure it does directly..."

Now they see the problem. You didn't tell them. They discovered it.

"So what would you need to change to create that connection?"

Let them propose the solution.

Part 3: Let Them Propose the Solution (10 minutes)

After they've identified what's missing or weak, resist the urge to give them the answer.

Instead:

"So what would you change?"

"How would you approach this differently?"

"What's your recommendation?"

Even if their first answer isn't perfect:

"Okay, why that approach? What else could work?"

Keep asking until they arrive at a solid solution themselves.

The 80% Rule:

If their solution is 80% as good as yours, let them run with it.

They'll learn more from executing a B+ solution they created than an A+ solution you handed them.

And in 6 months, they'll be creating A+ solutions themselves.

When do you step in with direction?

If their solution would cause serious damage—major financial loss, legal risk, brand disaster—then yes, be directive.

But 90% of the time? It's not actually high stakes. Let them learn.

Five Coaching Techniques That Actually Work

Technique #1: The "If You Were Me" Question

When to use it: Junior staff brings you a decision they want you to make.

Instead of deciding: "If you were in my role, what would you decide and why?"

What it does: Forces them to think like a leader. Consider tradeoffs. Make hard calls. Take ownership of the recommendation.

Even if you disagree with their final recommendation, you now understand their reasoning. And you can coach on the gaps in their thinking rather than just overriding them.

Technique #2: The "What Would Make This Great?" Question

When to use it: Their work is fine, but not excellent. Solid B work.

Instead of: "Here's what's missing..."

Ask: "This is solid. But if you wanted to make this great instead of good, what would you add?"

What it does: They know it's not quite there. But they couldn't articulate what's missing. This question forces them to identify the gap themselves and raise their own quality bar.

Technique #3: The Red Team Exercise

When to use it: They're confident about a strategy or plan. Maybe too confident.

The exercise: "Okay, now I want you to argue against your own plan. What's the strongest case for NOT doing this?"

What it does: Develops critical thinking. Identifies blind spots. Forces them to consider downsides, risks, and alternative perspectives.

Strategic thinkers can argue both sides. This teaches them how.

Technique #4: The "Show Me Your Work" Approach

When to use it: You suspect they haven't thought it through deeply enough.

Instead of: Pointing out everything they missed.

Ask: "Walk me through your research process. What data did you look at? What did you learn? What surprised you?"

What it does: Either they can show their work (great—they did think it through deeply) or they can't (which reveals the real problem: lack of rigor in the process).

Teaching them the process matters more than fixing this one output.

Technique #5: The Reflection Question

After they complete any significant project:

"What worked? What would you do differently next time? What did you learn?"

Don't skip this step.

Learning doesn't happen during execution. It happens during reflection.

By forcing them to articulate lessons learned, you're turning experience into expertise.

When to Coach vs. When to Direct

Coaching isn't always the right approach. Sometimes you need to be directive.

Direct when:

1. True emergency. The website is down. Campaign launches in 2 hours. CEO needs this now. No time for coaching—just tell them what to do.

2. They lack foundational knowledge. If they don't understand basic concepts (what's CTR? how does attribution work?), teach first, coach later. Coaching assumes baseline competence.

3. High-stakes, zero tolerance for error. Board presentation. Earnings call. Major customer pitch. This isn't the time to let them learn by making mistakes.

4. They're brand new (first 30 days). First month = teach them how things work here. Give clear direction. Build foundation. Month 2+ = shift to coaching.

Coach when:

1. They have baseline skills. They know how to do the work. You're developing their strategic thinking.

2. There's time to iterate. Not an emergency. You can afford to let them struggle and learn.

3. Stakes are manageable. Mistakes won't cause serious damage. Learning opportunity is worth the risk.

4. You want to develop judgment. Goal isn't just this one output. It's building their capability for the next 100 outputs.

5. You're the bottleneck. If you're constantly reviewing, fixing, redoing—that's a sign you need to coach more, manage less.

The ratio over time:

First 90 days: 80% directive, 20% coaching

After 6 months: 50/50 split

After 1 year: 20% directive, 80% coaching

After 2 years: 90% coaching, 10% directive

As they develop, you shift from doing their thinking to helping them think.

What Changes After 6 Months of Coaching

Remember Emily from the opening?

Here's what changed after Sarah shifted from managing to coaching:

Months 1-2:

Coaching conversations took 30-45 minutes. Sarah questioned whether it was worth the time investment. Emily's work improved, but slowly. Sarah was tempted to go back to just telling her what to do.

Months 3-4:

Emily started anticipating Sarah's questions. She'd bring more thought-through work. "Here's my draft, and here's why I made these decisions..." Coaching time dropped to 20-25 minutes per conversation.

Months 5-6:

Emily's first drafts were consistently 80-90% there. Sarah's input shifted from "think about this differently" to "have you considered this edge case?" The strategic thinking was there.

Today (18 months later):

Emily runs campaigns independently. Sarah reviews final work, not drafts. She provides strategic input on positioning and approach, but Emily handles execution autonomously.

Time investment: 15 minutes per week, down from 5-10 hours.

The multiplier effect:

Sarah used this coaching approach with four junior team members over 18 months.

Result:

• 15-20 hours per week freed up (no more constant review cycles)
• Team makes better strategic decisions independently
• Junior staff ready for promotion (built bench strength)
• Sarah can focus on executive strategy instead of execution review

The math:

30 minutes of coaching per conversation × 4 conversations per person = 2 hours invested upfront per team member

2 hours of review time eliminated per week per person × 26 weeks = 52 hours saved per person

ROI: 26x return on time invested

And that's just time savings. The real value: a team that can think strategically. A team that can scale. A team that doesn't need you to be the bottleneck.

What her team says now:

"She asks questions that make me think harder, instead of just telling me what to do."

"I feel like I'm actually developing as a marketer, not just completing tasks."

"I can make decisions and move forward without waiting for her input on everything."

That's the difference between managing and coaching.

The Common Coaching Mistakes (And How to Avoid Them)

Mistake #1: Fake Coaching

What it looks like: "What do you think you should do?" They answer. "Actually, here's what I think you should do..." and you override them with your answer anyway.

Why it fails: You asked coaching questions but still gave a directive answer. They learn you don't actually want their input—you just want them to guess what you're thinking.

Fix: If you ask for their recommendation, respect it. Either approve their approach or ask more questions to help them refine it. Don't fake-ask and then override.

Mistake #2: Coaching at the Wrong Time

What it looks like: Campaign launches tomorrow. They bring you work that needs significant fixes. You say, "What do you think you should change?"

Why it fails: This is an emergency. There's no time to coach. They need clear direction right now.

Fix: Be directive in the moment. Get it done. Then schedule a coaching conversation after the crisis: "Let's debrief this next week—what would you do differently next time?"

Mistake #3: The Never-Ending Question Loop

What it looks like: You keep asking questions but never help them arrive at an answer. They're frustrated, confused, and spinning.

Why it fails: Coaching without structure is just being unhelpful. Socratic method without purpose is torture.

Fix: Use the three-part framework. Make them think → Ask questions that reveal gaps → Let them propose solution. Then either approve or guide them to a better answer. Don't leave them hanging.

Mistake #4: Coaching Everything (Including Trivial Decisions)

What it looks like: "You used blue in this email header. Walk me through your color choice reasoning and how it connects to our brand strategy..."

Why it fails: Not everything deserves strategic analysis. Some decisions are just executional. Coaching trivial stuff wastes time and irritates people.

Fix: Coach on strategic decisions (positioning, audience, approach, business impact). Be directive on tactical details (font choices, minor wording tweaks, formatting).

Mistake #5: Giving Up Too Early

What it looks like: "I tried coaching for two weeks. It wasn't working fast enough. Back to managing."

Why it fails: Behavior change takes 2-3 months minimum. They're unlearning dependence on you. That takes time.

Fix: Commit to 90 days. Track progress week by week. Adjust your technique based on what's working. But don't give up after three conversations.

The Choice

You have two options as a marketing leader.

Option 1: Keep managing.

Tell your team exactly what to do. Fix their work when it's not right. Make their decisions for them. Control the output.

You'll get immediate results. The work will get done your way. You'll maintain quality.

And you'll work 60 hours a week forever.

Because they need you to think for them. Because you trained them to need you.

Option 2: Start coaching.

Ask questions instead of giving answers. Let them struggle through problems. Help them develop strategic thinking instead of just following your directions.

It'll feel slower at first. You'll have to resist the urge to just tell them what to do. You'll watch them make mistakes you could have prevented.

It'll be uncomfortable.

And in 6 months, you'll have a team that thinks independently. That makes strategic decisions without you. That can lead.

You'll get 15-20 hours per week back. Hours you can use for actual strategy instead of reviewing drafts and fixing execution.

Sarah's choice:

That Thursday night at 7pm, 18 months ago, when she deleted that feedback email and scheduled a coaching call with Emily instead—that was the turning point.

Not just for Emily. For Sarah.

Because coaching isn't really about developing your team.

It's about multiplying your impact.

Stop being the bottleneck in your organization.

Start building problem solvers who can think strategically without you.

The 30 minutes you invest in coaching today eliminates the 2 hours you'll spend reviewing and reworking tomorrow.

And builds a team that can scale without you.

That's the choice.

What are you going to do with your Thursday night at 7pm?

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Ready to shift from managing to coaching?

Download our Coaching Conversation Toolkit—the complete framework with 25 coaching questions organized by situation, the 3-part conversation structure, and a 90-day coaching plan to transform how you develop your team.

Because the best leaders don't create followers.

They create more leaders.

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