10 Big Mistakes to Avoid in an Acquisition

M&A Can Be Tough on CTOs - Here’s How to Handle Things Better

For any CTO that’s been through an acquisition you know that they can be one of the hardest things you’ve ever done. Today I break down 10 critical mistakes for CTOs to avoid during mergers, acquisitions and bolt-ons.

Cheers & let’s dive in! 🦈

Bobby

Mergers, acquisitions and bolt-ons are notoriously tough on CTOs.

The pressure 😤 to integrate two or more different product and engineering organizations, systems, products and processes can feel overwhelming.

You’re expected to move quickly, preserve talent, integrate systems, and ensure nothing breaks while navigating cultural landmines and competing priorities.

In fact the hard truth is that even when mergers look good on paper, they often fail in execution.

But for a CTO, failure isn’t just a financial thing, it’s organizational, cultural, and can be deeply personal. How you manage the first year after a merger can define your entire legacy.

Having executed on M&A myself and advised dozens of CTOs navigate M&A activities, here are the 10 most common failure modes to avoid.

1. No Single Culture Wins

One of the biggest traps is trying to preserve one team’s culture over the other.

The temptation is strong: your “original” team probably feels like the good guys, and their way of working feels familiar. But mergers are not about preservation they’re about change.

The reality is that no single culture survives intact. If you cling to the old ways, whether yours or theirs, you risk alienating at least half the team and stalling progress.

Instead, accept early that the combined culture will be different. And it will likely evolve multiple times before it stabilizes.

Your role is to guide & cultivate a transformation toward a stronger culture, not to preserve what once was.

2. Focus on Customer Use Cases Rather Than Tech

There’s a reflexive urge to immediately combine platforms, codebases, and systems. It feels like progress. But it’s often the wrong thing to do.

What matters most in an acquisition is usually customer value. The event is your golden opportunity to reassess what both companies are building — and why.

Instead of asking, “How do we integrate this system?” ask, “Which customer use cases actually drive growth?”

Be ruthless about which systems to keep, combine, or sunset — but let that decision be guided by business value, not technical elegance.

You don’t get many chances to pause and re-prioritize. This is one of them.

3. Waiting to Make Changes is Best

Everyone wants to show fast progress once the acquisition deal is done.

Boards are watching. And executives want results. But rash decisions made in the first 90 days can be costly and hard to undo.

Resist the pressure to move overly quickly.

The smartest CTOs use the early phase of a merger to observe deeply. They learn how each team operates, understand the product-market fit of each business unit, and uncover the underlying power structures before making any bold moves.

Yes, some things will need quick action — but treat most decisions like chess, not checkers. Take the longer term view.

4. Don’t Standardize Too Early

Acquisitions often bring with them the desire to impose standards quickly (to create order from chaos).

Common tools, unified processes, aligned org charts — it all sounds good. And yes, eventually, you’ll need consistency.

But early standardization can backfire. Why?

Because you don’t yet know what “good” looks like in the new organization.

Pushing one team’s way of working onto the other can create resentment, cause talent to leave, and lock you into processes that don’t scale.

Let standards emerge organically, instead.

Observe what’s working across teams. Support grassroots standardization where it’s already happening. You’ll get better buy-in and better results.

5. One Tech Team is Always Stronger

Let’s be honest: in nearly every merger, acquisition or bolt-on, one tech team is going to be stronger than the other.

Your goal should be to not to create false balance.

The worst thing a CTO can do is pretend that both sides are equal when they’re not. It slows decision-making and creates artificial power struggles.

Instead, lean decisively into the stronger team.

Let them lead where it makes sense. Use their strengths to lift up the rest of the organization. Trying to equalize everything will only slow you down and create friction.

This doesn’t mean you ignore the weaker team — but be honest about where leadership and momentum truly reside.

6. Talent Retention Isn’t As Important as Leaders Think

Mergers and acquisitions often trigger panic about retaining top talent.

Leaders bend over backward to keep people, offer retention bonuses, or make organizational compromises to avoid attrition.

Yes, losing key players hurts. But what actually matters more is the strength of your recruiting engine.

Mergers create churn — accept it.

You’ll lose people. You’ll gain others. Some of your “top performers” won’t survive the new culture, and that’s okay.

Focus on building a strong, resilient hiring function that can replenish and upgrade your team over time.

Your goal isn’t to prevent all losses — it’s to make sure the company keeps getting stronger.

7. You’ll Miss A Lot…So Learning Fast is Key

No matter how careful you are, you’re going to make mistakes.

You’ll misread dynamics. You’ll back the wrong leaders. You’ll push initiatives that don’t land.

That’s normal.

The key is not perfection, it’s learning fast.

The best CTOs treat mergers & acquisitions as high-speed learning environments. They set up feedback loops. They talk to teams constantly. They course-correct quickly and without ego.

They make micro-adjustments EVERY week.

If you’re going to survive a multi-year merger process, you need to build a muscle for rapid learning.

Perfection is the enemy. Speed of adjustment is your ally.

8. Seek to Build a Smaller Tech Team

Acquisitions and bolt-ons often start with the assumption that bigger is better. Two companies, two engineering teams — double the power, right?

Wrong.

Great mergers often lead to smaller, more focused, and more talented teams.

You may find that you don’t need two teams doing the same thing. You might discover that consolidating functions creates more leverage. You may also need to eliminate redundancy to meet cost targets.

Don’t be afraid to build a smaller, tighter organization post-merger.

If it’s well-aligned, diverse in skills, and high in talent density, it will outperform a bloated one every time.

9. Fixing Technical Debt Can Wreck You

Here’s a trap I’ve seen destroy engineering teams during MA&: someone gets the idea that now is the time to fix all the accumulated tech debt in 1 or both companies.

Seems logical, right? You’re already doing integrations, might as well clean things up.

But that’s a dangerous move.

Tech debt cleanups are costly, distracting, and rarely deliver immediate value.

During a merger, your focus should be on stabilizing systems, serving customers, and generating momentum, not embarking on massive refactors.

Fix what’s critical. Postpone what’s not. And don’t let technical idealism derail your merger.

10. Mergers & Acquisitions Never End for a CTO

Here’s the truth no one tells you: the merger may last your entire tenure.

If you’re the CTO for 3 to 7 years post-merger, the integration work — cultural, technical, organizational — may be ongoing that entire time.

Sure, the biggest waves hit in year one. But the ripple effects continue for years.

New systems emerge. New leaders rise. Old decisions resurface. Culture evolves in fits and starts.

Your mindset should be long-term.

Treat the merger not as a project with a clean end, but as an enduring stream of work that needs constant tending.

If you embrace that reality, you’ll lead with more patience, more wisdom, and more impact.

Closing Thoughts

M&A can feel like the most high-stakes puzzle you’ll ever face as a CTO.

But if you avoid these 10 failure modes — and focus on culture, customer value, patience, and adaptation — you’ll not only survive it… you’ll come out the other side with a stronger, faster, more resilient organization.

And maybe even a little bit of your sanity intact. 😃

By the way, if you need any help on this feel free to reach out any time at: bobby@technocratic.io.

And in the meantime, keep the shark swimming! 🦈