The Red Flags I Never Ignore (And Neither Should You)

Hey there,

Last week, I turned down what looked like a perfect engagement on paper.

The company was in my sweet spot. The technical challenges were interesting. The budget was there.

But something felt off.

After 20+ years in technology leadership, I've learned to trust my gut when it comes to red flags. More importantly, I've learned that saying "no" to the wrong opportunities is just as crucial as saying "yes" to the right ones.

Here are the warning signs that make me walk away, no matter how attractive the opportunity:

1. Misaligned Expectations

   • They want a full-time CTO's availability at a fractional price

   • They expect immediate transformation without organizational change

   • They're not willing to invest in necessary resources

2. Cultural Red Flags

   • High turnover in technical roles

   • Blame-focused leadership

   • Resistance to transparency

3. Strategic Misalignment

   • No clear vision or constantly shifting priorities

   • Unwillingness to address root causes

   • Short-term thinking at the expense of sustainability

4. Communication Issues

   • Difficulty getting straight answers about current state

   • Resistance to direct conversations about challenges

   • Hidden agendas or politics

In one recent case, I spotted a major red flag during the discovery call. The CEO kept referring to their previous three CTOs as "incompetent" and "not strategic enough."

One CTO might be a bad fit. Two might be unfortunate. But three? That's a pattern that speaks to deeper organizational issues.

I gracefully declined that opportunity. Three months later, I heard they'd churned through two more technical leaders.

Remember: Your reputation is your most valuable asset as a fractional CTO. Every engagement either builds or erodes it. Choose wisely.

The hardest part? Often these red flags come wrapped in very attractive packages. Big budgets. Exciting technology. Prestigious brands.

But I've never regretted walking away from a toxic situation. I have regretted trying to "make it work" despite clear warning signs.

What red flags have you learned to watch for? What's your litmus test for determining if an opportunity is worth pursuing?

To great client relationships,
Lior

Lior Weinstein 
Founder & Head Coach, CTOx