A silent dissenter won't respond to "What are your concerns?". Instead, "soft-float" several potential objections, like giving them a multiple-choice question (e.g., "Is it our integrations, our pricing, or something else?"). This lowers the barrier for them to engage and allows them to latch onto a specific point, revealing their true apprehension.

During due diligence, the most revealing portfolio company reference checks involve asking CEOs leading questions. Frame inquiries to suggest the private equity sponsor is taking undue credit for successes. This tactic encourages frankness and uncovers the true dynamics of value creation and deal sourcing.

Use one-on-one breakout meetings to gather intel you can't get in a group setting. Ask directly about competitors, pricing, and evaluation status. The private, trusted environment makes stakeholders more likely to share candid details, effectively turning them into your internal informant on the deal.

When Irembo's new payment product's main customer was an internal platform generating 99% of revenue, they mandated weekly external customer interviews for the new PM. This created a crucial counterbalance, ensuring the product was built for the market, not just its powerful internal stakeholder.

To truly understand a prospect's decision-making process, ask for more than you expect to get, such as requesting to be part of their internal evaluation meeting. Even a "no" often prompts them to reveal more about their process, criteria, and stakeholders than a standard discovery question would.

Buyers won't openly state their career risks, such as getting fired for a failed project. To uncover these fears, ask: 'What does success look like for you three months after this is deployed?' Their answer reveals their key success criteria, which are directly tied to their biggest perceived risks.

To avoid sounding pushy when asking critical questions about a deal's viability, frame them as necessary steps to ensure the customer's success post-implementation. This shifts the intent from closing a deal to building a successful partnership, encouraging open answers.

Instead of an immediate post-close review, conduct retrospectives 6-12 months later. The true quality of due diligence and strategic fit can only be assessed after operating the business for a period. This delay provides deeper insights into what was missed or correctly identified, leading to more meaningful process improvements.

To prevent knowledge gaps between deal execution and integration, IFS makes the same internal expert responsible for a specific workstream (e.g., product, GTM) during commercial diligence and the subsequent integration phase, creating end-to-end accountability.