Shortcutting a deal devil-may-care

We all get lucky sometimes -  you’ve got a client who’s ready to sign, the finish line is in sight, and you’re eager to close the deal. Much faster than you anticipated but the client’s pain is real and you’ve just been hitting the right spots from the get go. But then, there’s that little voice in the back of your mind reminding you about the one person you haven’t talked to or that one use case out of ten that’s still uncovered. Coincidentally, the stakeholder you didn’t involve will usually be involved 99% of the time once your client project starts. And about that use case… the other 9 went so smooth, you will hardly be departing over the “missing one”. So what’s to do? 

After all, a signature is a signature, right? That commission sure looks juicy that much faster appearing on your bank account than intended. But, shortcuts can be deceptiving. While it might feel like a quick win, skipping over crucial stakeholders is like building a house without a foundation - things might hold up at first, but eventually, the cracks will start to show.

The Risk: Shortcuts Lead to Long-Term Problems

Yes, it all depends on the situation. Your client is a small company able to communicate fast and adapt to situations like “one project member has not formally been addressed yet”, go for it. Even better, you find yourself in a situation where closing the deal might only be possible through a sales cycle off the usual playbook track while this opportunity might even disappear if you wait too long: “But we have to spend our budget this month otherwise there’ll be no next budget…” 

In any case you’ll have to make the decision whether it’s worth making that extra effort or let sleeping dogs lie. Selling to clients with an established department setting and fixed project parts in implementation projects, taking the shortcut may seem like a fast track to victory, but it’s more like stepping into quicksand. Studies show that up to 70% of software projects fail due to poor preparation and lack of stakeholder involvement. Once the project is underway, all or just some of those unconsulted stakeholders might emerge, potentially throwing wrenches into the implementation. Suddenly, your client feels like they’re on a sinking ship, overwhelmed by issues that could’ve been addressed early on. Cue the frustration, delays, and a massive hit to your credibility. Moreover, your Customer Success team might not be that happy as well.

Short Customer Lifetime Value

Here’s where it gets worse: a client who feels blindsided by implementation issues is more likely to churn. When your SaaS company is steadily hitting that 5% churn rate or lower that is considered “healthy”, all good. Your sales team has gotten a grip on the balance between pushing deals to close fast (enough) and letting those few that were maybe bound to fail anyways fall off the cliff. Again, in those situations when the deal size is considerate and you do expect or even count on that client to grow its install base with you, premature churn will become a real problem. They’ll remember the pain of that botched rollout and be far less open to future business. That means you’ll miss out on upsell and cross-sell opportunities, turning what could have been a long-term partnership into a brief, bumpy ride.

The Power of Thorough Preparation

In any case, life is a … Well, can be cruel. Just as you’re about to seal the devil-may-care deal, already rubbing your hands and planning to buy a round at the pub, that one missing use case and the overlooked stakeholder rear their heads, suddenly throwing a wrench into the process. The shortcut didn’t stick, and now the deal is on shaky ground. The voice that was formerly quiet and unobtrusive becomes a smug little boy, crossed arms and rolling his eyes while answering the question from the outset: “I told you so…”

This is where the power of thorough preparation shines. By including all stakeholders and addressing every requirement upfront, you not only keep the deal on track but also position yourself as a trusted partner, not just another vendor. Establishing this as your routine you’ll feel that you’re actually in control of deals, able to push and shape them with a beneficial outcome for your company that results in reliable revenue. Moreover, this approach builds trust, and as the relationship deepens, new client use cases often emerge, revealing further upsell opportunities. When you take the time to cover all bases, you not only close deals faster but also lay the groundwork for a lasting, mutually beneficial partnership.

Key Takeaways