Blog by Ben Greenberg, VP of Corporate Development at IT Solutions
If you’re considering exiting your business or are navigating the challenges of growing your MSP, we invite you to connect with Ben.

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As someone who’s witnessed countless MSP owners navigate the M&A process, I’ve noticed sellers often overlook critical questions to help understand if a buyer may be the right partner for them. Here are five questions I suggest every MSP seller should ask a prospective buyer, and why the answers matter.

 
 

1. What Is Your Long-Term Vision for the Business?

Too often, sellers get caught up in the numbers and overlook the bigger picture. This question is a litmus test for the buyer’s depth of understanding and commitment to building value. A buyer who can clearly articulate plans for organic growth, investments in people and systems, and an appreciation for company culture is far more likely to be a good steward of your business.

If the answer feels vague or purely financial, it’s a red flag. Look for signs that the buyer understands the road ahead: Will they invest in developing talent? Are they planning to expand service offerings or geographic reach? Do they value innovation in an ever-changing MSP world? This question also provides insight into cultural alignment, which can make or break a successful integration.

 
 

2. What Is the Timeline for the M&A Process, and How Successful Have You Been at Sticking to It?

Ask the buyer to outline their typical M&A process, including major milestones, due diligence phases, and closing dates. More importantly, ask them how often they’ve actually met these timelines in previous deals.

If a buyer routinely misses deadlines or glosses over the details, sellers should proceed with caution. Delays can cost you money, create uncertainty for staff and clients, and signal deeper issues with the buyer’s organizational abilities. A qualified Buyer will have clear processes and a proven track record of executing as promised and within 60 days post Letter of Intent (LOI).

 
 

3. What Do Your Post-Close Communication and Integration Plans Look Like?

Successful deals don’t end at closing; they begin there. Sellers should press buyers for a comprehensive communication and integration strategy that starts well before the ink dries. Ask about a dedicated integration team and ensure a focus on both client and employee success.

Furthermore, ask the buyer how they plan to inform and engage your employees and clients post-close. Are they proactive in addressing concerns? The best integration plans are transparent and empathetic—focused not only on operational efficiency but also on cultural cohesion and retention.

 
 

4. How Will the Deal Be Funded and Structured?

The structure of your deal has direct implications on risk, complexity, and your ultimate payout. Sellers should insist on clarity regarding funding sources (cash, debt, equity, seller notes) and deal structure (asset or stock purchase, earnouts, holdbacks, etc.).

Complex funding mechanisms or uncertain sources create risk. The best deals minimize risk and maximize simplicity. It’s always best to review with an experienced M&A attorney prior to signing a Letter of Intent (LOI).

 
 

5. What Is Your Track Record?

Finally, history is often the best predictor of future behavior. Ask the buyer to describe their track record from several angles:

• Deal Completion: How often have they closed deals on the terms initially proposed under the LOI?
• Employee Retention: What are their development opportunities and how do they foster a positive culture post-acquisition?
• Client Retention: How do clients fare after the deal, and what type of support do they receive?
• Seller Satisfaction: How do sellers feel after selling to the prospective buyer? Ask for references to meet with, prior to signing an LOI

By asking these five questions, sellers can better assess a buyer’s intentions, capabilities, and suitability. Remember, the right buyer will welcome your questions and provide honest, thoughtful answers. When sellers and buyers start from honest conversations, it opens the door to partnerships that go beyond the deal and deliver lasting value. With ITS as your trusted advisor, you gain the IT insight and strategy to strengthen decisions, accelerate integration, and set your partnership up for long-term success. Let’s explore how we can support your next move.

Unlocking growth through M&A presents unique opportunities and challenges. Whether you’re planning your next acquisition or considering selling your business, we’re here to help your MSP thrive.