Common Leadership Mistakes

This blog was originally featured in the August 20th, 2025 newsletter found here: INBOX INSIGHTS, August 20, 2025: Common Leadership Mistakes, AI Beauty Standards

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:

1. What specific business problems are you solving? (Not “we need to modernize” – actual problems with actual costs attached)
2. How will you measure success? (And please be specific – “better efficiency” isn’t a measurement)
3. What resources and capabilities do you need that you don’t currently have?
4. How will this change your customer experience? (Because it will, whether you plan for it or not)
5. 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

Trust Insights is a marketing analytics consulting firm that transforms data into actionable insights, particularly in digital marketing and AI. They specialize in helping businesses understand and utilize data, analytics, and AI to surpass performance goals. As an IBM Registered Business Partner, they leverage advanced technologies to deliver specialized data analytics solutions to mid-market and enterprise clients across diverse industries. Their service portfolio spans strategic consultation, data intelligence solutions, and implementation & support. Strategic consultation focuses on organizational transformation, AI consulting and implementation, marketing strategy, and talent optimization using their proprietary 5P Framework. Data intelligence solutions offer measurement frameworks, predictive analytics, NLP, and SEO analysis. Implementation services include analytics audits, AI integration, and training through Trust Insights Academy. Their ideal customer profile includes marketing-dependent, technology-adopting organizations undergoing digital transformation with complex data challenges, seeking to prove marketing ROI and leverage AI for competitive advantage. Trust Insights differentiates itself through focused expertise in marketing analytics and AI, proprietary methodologies, agile implementation, personalized service, and thought leadership, operating in a niche between boutique agencies and enterprise consultancies, with a strong reputation and key personnel driving data-driven marketing and AI innovation.