Optimizing due diligence with digital tools and AI
The third episode of our Building Your Digital M&A Engine webinar series took on one of the most complex—and critical—stages of the deal lifecycle: due diligence.
Led by Charles Cautley, Chief Product Officer at Midaxo, and Kendra Mills, Customer Success Manager, this session walked through how leading M&A teams are using digital platforms and AI to streamline diligence, improve collaboration, and avoid the pitfalls that often derail deal success.
Missed the live session? Watch the on-demand recording here.
Common diligence pitfalls—and how to avoid them
Early in the session, participants were polled on the most common pitfalls they see in diligence. The top answers?
- Over-optimism about deal potential
- Value leakage over time
- Information overload and rushing the process
Charles and Kendra noted that without a digital system to guide cross-functional collaboration, these risks multiply—especially when diligence work is scattered across emails, spreadsheets, and data rooms.
A digitized M&A platform helps teams:
- Centralize all documents, issues, and communications in one secure place
- Maintain visibility and accountability across every functional workstream
- Apply consistent best practices and checklists from one deal to the next
Where AI adds the most value
While AI can’t replace human judgment, it’s transforming how teams handle the most time-consuming parts of diligence.
According to live poll results, the most widely adopted use cases today are:
- Document analysis and summarization – accelerating review and flagging risks
- Drafting and validating communications – reducing manual rework and improving consistency
With Midaxo’s built-in AI assistant, “Madi,” deal teams can:
- Ask natural-language questions about projects or documents (“What are the open risks?”)
- Automatically identify missing data for decision-making
- Summarize and extract key insights from diligence documents
- Update deal scores or project data based on new findings
This means diligence leaders can focus more on analysis and decision-making, and less on administrative work.
Making repeatable, accurate diligence the default
Charles summarized the value succinctly:
“Ultimately, it’s about simplicity, efficiency, and repeatability—making diligence more consistent and reducing the risk of missed issues.”
With Midaxo, teams can build and reuse best-practice templates, automate notifications and task ownership, and collaborate seamlessly with internal and external users. Every action, change, and AI interaction is logged for full traceability.
What’s next
Join us for the next installment in this series on October 22nd—Episode 4: Delivering the Value – PMI and Synergy Tracking.
And if you missed the session on how AI and digitization can simplify your diligence process—and set your team up for smoother integration and value realization, you can watch the full webinar on demand here.
