Chief Executive Officer and His Colossal Mistake

Dear Yogesh,

I’m the COO of a medium-sized, mostly India-based specialty product business. For years, my role was execution while our CEO was the visionary. Our business was straightforward, but after we expanded into services and opened a few storefronts—against my advice—things have started to spiral.

Our CEO expects the executive team to figure things out, but I’ve realized our CFO and the person leading IT are completely out of their depth. The CFO lacks experience with the complexities of services and payroll, while our tech lead keeps suggesting software platforms that don’t integrate, costing us more than expected. We’re overspending, and it feels like we’re in freefall, but my CEO refuses to get into the details.

I feel stuck. I can’t solve all the problems alone, and though we had a solid business, I’m frustrated with how the CEO’s decisions have upended everything. He dismissed my concerns about the lack of infrastructure before expanding, and now he seems less reasonable every day.

Part of me just wants to walk away, but I’d lose equity, and at the rate things are going, that won’t be much anyway. The CEO and I were once friends, but that relationship seems to be falling apart. I’m not sure if this can be salvaged. Any thoughts?

— Fateh Singh

Dear Fateh Singh,

I’m sorry to hear you’re going through this—it’s not easy to be in your shoes. While you may not be the first to face this kind of challenge, it doesn’t make it any less frustrating or painful.

I think you already know what you need to do, and reading the following will just help confirm it. There are a few key issues here, and while some are more fixable than others, it’s important to understand them clearly:

1. Your team lacks the necessary skills to handle the new areas of the business (this can be addressed, though not quickly).
2. There wasn’t enough planning or the right resources in place for this expansion (unfortunately, this is history now, and we can’t change the past).
3. Your CEO seems to have abandoned responsibility, possibly due to stress or poor judgment (it seems like you’ve already made attempts to address this, but it’s unlikely you can change his mindset).
4. The relationship between you and the CEO seems strained (this might be repairable over time, but it could also be beyond repair).
5. You have a lean operation with no other executives to support you (if there are other competent leaders in the company, now is the time to lean on them).
6. Your anger and frustration are clouding your judgment (this is something you can control, and the sooner you regain your focus, the better).

Does that resonate?

I think your first priority should be to calm yourself down. You need clarity to make a crucial decision: Is this worth fighting for? Take time to decompress—whether through meditation, exercise, or simply disconnecting from the situation. Get a good night’s rest, and come back to this with a clearer mind.

Once you’ve gained perspective, ask yourself if you’re willing to tackle the situation head-on and turn things around. If your answer is a hard “no,” then it’s time to walk away. But if you feel like you might still have the energy to fix this, decide exactly what you’re willing to do and for how long. Timeframes matter; if you commit to a limited period, it helps you stay focused without feeling trapped by the long-term unknown.

Next, accept the situation for what it is—anger and blame won’t help you fix anything. Yes, your CEO’s decisions have contributed to this mess, but focusing on the blame isn’t productive.

You might also consider negotiating a clear reward for yourself if you manage to turn things around—perhaps a bonus or an agreement with your CEO on what success looks like. That could help motivate you to dive in and fix things.

Here’s a practical way to approach the challenge if you decide to stay in the game:

1. Get help—reach out to a trusted advisor or mentor for guidance.
2. Hire expertise—whether it’s a consultant or someone with experience in the areas you’re lacking, this will be an immediate boost.
3. Make a plan—outline what needs to be done, and in what order. Identify what can be delayed, and focus on the critical issues first.
4. Tackle the big problems one by one, starting with the most urgent.
5. If all of this feels overwhelming, then perhaps this situation is beyond repair or you no longer care enough to fix it.

Once you strip away the emotions, you’ll be better able to assess the situation logically and determine if it’s worth continuing or if it’s time to step away.

At this point, you should be feeling one of two things: “I can do this” or “I need to get out.” Trust yourself to make the right call.

I wish you the clarity to make your decision, and the courage to follow through on whatever choice you make.

Yogesh