INBOX INSIGHTS, August 20, 2025: Common Leadership Mistakes, AI Beauty Standards - Trust Insights Marketing Analytics Consulting

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INBOX INSIGHTS: Common Leadership Mistakes, AI Beauty Standards (2025-08-20)

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A Common Leadership Mistake

Earlier this year, I watched a CEO confidently tell the company at the all-hands meeting that their AI strategy was “handled” because his IT director was “looking into it.” Three weeks later, that same IT director quit, taking with him all the knowledge of what they were actually trying to build.

This reminded me of a project I completely botched early in my career. I was leading a major process overhaul and decided to “empower” my team by assigning different pieces to different departments and then stepping back to “let them do their thing.” Marketing handled the communication strategy, Operations tackled the workflow changes, and Finance managed the budget implications.

I thought I was being a great delegator. Turns out, I was just being absent.

Six weeks later, we had three beautiful solutions that didn’t work together, a confused workforce, and a budget that nobody could explain. The problem wasn’t my team (they were brilliant). The problem was that I had abdicated leadership instead of actually leading. It’s a very common leadership mistake.

Here’s the Thing About Strategic Initiatives: They Need Strategic Leadership

When you’re facing a complex challenge (whether it’s AI implementation, digital transformation, or any major change), your brain immediately starts sorting it into departmental buckets. Technology stuff goes to IT, people stuff goes to HR, money stuff goes to Finance.

But here’s what that CEO (and maybe you) are missing: Major strategic initiatives aren’t departmental projects. They’re fundamental shifts in how your business operates.

When you say “my [department] is looking at it,” what you’re really saying is:

“I do not understand this well enough to lead it.”
“Someone else can figure out how this changes our entire business model.”
“I’m comfortable making significant decisions about things I don’t understand.”

None of these are particularly confidence-inspiring leadership positions.

What Real Strategic Leadership Actually Looks Like

Leading a major initiative doesn’t mean you need to become an expert in every technical detail (though a basic understanding wouldn’t hurt). It means you need to understand how this change will fundamentally impact:

Your customers’ expectations: How will their experience change, and are you prepared for that?
Your competitive landscape: What advantages or vulnerabilities does this create?
Your workforce: Which roles will change, which skills will matter, and how will you help people adapt?
Your operations: What processes need to evolve, and what new capabilities do you need?

This isn’t stuff you can assign to a department and hope for the best. This is “the future of your entire business” stuff.

The Questions You Should Be Asking (Instead of Delegating)

When a leader tells me their [insert department here] is “handling” a strategic initiative, I ask them these questions:

What specific business problems are you solving? (Not “we need to modernize” – actual problems with actual costs attached)
How will you measure success? (And please be specific – “better efficiency” isn’t a measurement)
What resources and capabilities do you need that you don’t currently have?
How will this change your customer experience? (Because it will, whether you plan for it or not)
What could go wrong, and how will you handle it? (Spoiler: Things will go wrong)

If you can’t answer these questions, you’re not leading. You’re just hoping someone else will figure it out for you.

Your Team Needs You to Lead, Not Disappear

Here’s something that might surprise you: Your departments actually want you involved. They’re probably frustrated that you keep asking them to “make [big strategic thing] happen” without giving them business context, strategic direction, or cross-functional coordination.

It’s like asking different people to plan different parts of a cross-country road trip without telling them the route, budget, or timeline. They can research their individual pieces all day, but they can’t make strategic decisions about your business without you.

Your departments can execute brilliantly within their expertise. They cannot (and should not) decide without you:

Which business priorities to tackle first
How to coordinate across departments
What trade-offs you’re willing to make
How to communicate changes to stakeholders
What risks you’re willing to accept

Those are leadership decisions. Your decisions.

Three Things You Can Do Tomorrow

1. Schedule a “big picture” session with all involved departments. Make sure everyone understands not only their piece, but how all the pieces fit together and why.

2. Identify the specific business outcome you’re trying to achieve. Not the process you want to improve – the actual business result that matters to customers, employees, or shareholders.

3. Ask each department what they need from you to be successful. I guarantee the answer isn’t “just leave us alone to figure it out.”

The Bottom Line

Major strategic initiatives are going to impact your business whether you lead them or not. The question is: Do you want to be the leader who guided that transformation strategically, or the one who woke up one day to discover their company had been changed by forces they didn’t understand or direct?

Your departments can execute amazing work. But they can’t replace your leadership.

So stop hiding behind “my [department] is looking at it” and start actually leading. Your future self (and your stakeholders) will thank you.

What’s one strategic initiative you’ve been tempted to “delegate and disappear” from? Reply to this email or join our free Slack group, Analytics for Marketers.

– Katie Robbert, CEO

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Last time on So What? The Marketing Analytics and Insights Livestream, we revisited the basics of prompt engineering. Catch the episode replay here!

This week on So What?, we’ll be taking a look at AI bias and how to test for it. Are you following our YouTube channel? If not, click/tap here to follow us!

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In this week’s Data Diaries, let’s do something really different and review an AI guide. Which guide? We’re going to specifically examine Dove’s Real Beauty Prompt Playbook.

This 72 page guide is intended for creators – anyone using any kind of image generation AI – to generate better, more inclusive, more accurate, less biased imagery (particularly of women) in a thoughtful manner.

The guide first starts out highlighting the biases in AI image generation models, something we’ve highlighted in our own materials. When asked to generate an image of a beautiful woman absent other qualifiers, the Bulimia Project found:

37% of the images included blonde hair (the actual population size in the USA of women with blonde hair is 4% via beauty brand Olaplex)
30% of the images included brown eyes
53% of the images included olive skin

In a study from March 2024 on AI-generated images of women, women were depicted in occupational portraits between 23-42% of the time, significantly lower that identical prompts with men, who were shown in occupational depictions 58-77% of the time by the same models.

What’s fascinating is that even though Dove has pledged to not use AI generated images of women in their publications and content, the prompting guide is a tacit acknowledgement that lots and lots of people will. Its intent, which is outstanding, is to persuade us to be more thoughtful in how we prompt, with guiding questions like (page 22):

Can I effectively communicate with AI using the correct vocabulary to foster inclusivity?
- This will help to evaluate my progressive biases and their root causes, but also my true values of beauty.
How does society influence my perception of beauty? Who do I personally find beautiful and why?
Is the person that I generated closer to a model or the beautiful range of people I see in all areas of my life?
Does the AI-generated person have sexualized characteristics?
Who is going to feel represented by the image I generated?
Am I making the world a more inclusive place with my AI representation?
What’s the purpose of my image? Is it for inspiration, showcasing a specific trait, conveying a mood, or representing a specific demographic?
Do I have any preconceived notions about this group or characteristic that would be helpful to check?
- E.g. a beautiful face = white skin, big eyes & straight nose.

The rest of the guide is a workbook and workshop in generating thoughtful, mindful images of real people, taking into account our latent biases and teaching not only what not to do, but what to do, what language and vocabulary to use to obtain useful, balanced results from AI image generation.

As I’ve often paraphrased from the Captain America movie, AI is an amplifier – it takes the good and makes it better, and it takes the bad and makes it worse. While this guide won’t influence people who have biases about beauty they willfully choose to reinforce, this guide is useful and helpful to people who want to route around and reduce their biases as they use AI. One of the four pillars of responsible AI is respect for our fellow humans, and Dove’s guide is a very helpful one to have on hand.

Almost every AI course is the same, conceptually. They show you how to prompt, how to set things up – the cooking equivalents of how to use a blender or how to cook a dish. These are foundation skills, and while they’re good and important, you know what’s missing from all of them? How do you run a restaurant successfully? That’s the big miss. We’re so focused on the how that we completely lose sight of the why and the what.

This is why our new course, the AI-Ready Strategist, is different. It’s not a collection of prompting techniques or a set of recipes; it’s about why we do things with AI. AI strategy has nothing to do with prompting or the shiny object of the day — it has everything to do with extracting value from AI and avoiding preventable disasters. This course is for everyone in a decision-making capacity because it answers the questions almost every AI hype artist ignores: Why are you even considering AI in the first place? What will you do with it? If your AI strategy is the equivalent of obsessing over blenders while your steakhouse goes out of business, this is the course to get you back on course.

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