37:00 Lena: Miles, we've covered a lot of ground on building effective vendor evaluation processes, but I'm curious about the things that commonly go wrong. What are the biggest pitfalls you see organizations fall into, and how can they avoid them?
37:14 Miles: Oh, there are some classic traps that even sophisticated organizations stumble into, Lena. The biggest one I see is what I call "feature creep"—where the evaluation criteria keep expanding as you discover new capabilities in the market. Teams start with a focused set of requirements, but then they see a cool feature in one vendor's demo and suddenly it becomes a must-have for everyone.
37:36 Lena: I can see how that would completely derail your evaluation process. How do you prevent feature creep without being so rigid that you miss genuinely important capabilities?
37:45 Miles: The key is having a change control process for your evaluation criteria. If you discover something that genuinely changes your requirements, you document it, assess its importance against your original objectives, and if you decide to include it, you re-evaluate all vendors against the updated criteria. But you don't just add new requirements on the fly.
1:06 Lena: That makes sense. What's the second biggest pitfall you see?
38:09 Miles: Vendor relationship bias. This happens when your evaluation team gets too comfortable with one vendor's sales team or technical people. Maybe they're more responsive, more helpful, or just more likeable than other vendors. Before you know it, you're unconsciously scoring them more favorably or giving them the benefit of the doubt on borderline criteria.
38:29 Lena: How do you guard against that kind of bias?
38:31 Miles: A few techniques work well. First, rotate who interacts with which vendors when possible. Second, always validate vendor claims independently rather than taking them at face value, no matter how much you trust the source. Third, use structured evaluation processes that don't leave much room for subjective judgment. And finally, have someone on the team play devil's advocate for each vendor.
38:54 Lena: I like that devil's advocate approach. What other pitfalls should people watch out for?
38:59 Miles: Analysis paralysis is a big one. Teams get so focused on gathering perfect information that they never actually make a decision. They keep asking for more data, more demos, more references, more documentation. Meanwhile, the business need that drove the evaluation in the first place isn't getting addressed.
39:17 Lena: How do you balance thoroughness with decisiveness?
39:20 Miles: Set clear deadlines and stick to them. Define upfront what information you need to make a confident decision, and once you have that information, move forward. Perfect information doesn't exist, and waiting for it usually doesn't improve your decision quality significantly.
39:34 Lena: What about on the technical side? Are there common technical evaluation mistakes you see?
1:18 Miles: Absolutely. One of the biggest is over-engineering the evaluation. Teams create elaborate testing scenarios that don't reflect real-world usage patterns. Or they get so focused on edge cases and technical minutiae that they lose sight of whether the solution actually solves their core business problem.
39:59 Lena: So you're saying keep the evaluation realistic and business-focused.
40:04 Miles: Exactly, Lena. Your evaluation should reflect how you'll actually use the solution, not theoretical worst-case scenarios. And another technical pitfall—not involving the right technical resources early enough. Teams will do all their evaluation with security architects and then discover during implementation that the networking team has concerns they never considered.
40:25 Lena: That sounds like a recipe for implementation delays and cost overruns. What about on the commercial side? Any common mistakes there?
40:33 Miles: Oh yes. The biggest one is focusing too heavily on initial license costs without understanding total cost of ownership. Teams get excited about a low-priced solution and then discover hidden costs for professional services, additional modules, or premium support that they actually need.
40:50 Lena: How do you avoid that trap?
40:51 Miles: Build comprehensive cost models that include all anticipated expenses over the expected life of the solution. Don't just look at year one costs—model out three to five years including growth, additional features, support costs, and internal resource requirements. And always ask vendors for detailed cost breakdowns, not just high-level quotes.
41:11 Lena: What about process pitfalls? Are there common ways that evaluation processes themselves break down?
41:19 Miles: Stakeholder misalignment is huge. Teams start an evaluation without getting clear agreement on objectives, criteria, and decision-making authority. Then halfway through the process, someone from finance or legal or a business unit raises concerns that should have been addressed upfront.
41:35 Lena: How do you prevent that kind of late-stage disruption?
41:38 Miles: Invest time in stakeholder alignment before you start the technical evaluation. Get written agreement on objectives, criteria, weights, and the decision process. Make sure everyone who has veto power over the decision is involved in setting the evaluation framework. It's much easier to address concerns upfront than to restart your evaluation because someone feels their priorities weren't considered.
42:00 Lena: Are there any pitfalls specific to security vendor evaluations that might not apply to other types of technology purchases?
42:08 Miles: Security evaluations have some unique challenges. One is the tendency to over-weight compliance checkboxes at the expense of actual security effectiveness. Teams get so focused on whether a vendor has SOC 2 or ISO certifications that they don't adequately assess whether the solution will actually protect their organization.
42:28 Lena: So you need to balance compliance requirements with practical security outcomes.
11:14 Miles: Right. And another security-specific pitfall is not adequately testing integration with existing security tools. Security environments are complex ecosystems, and a solution that works great in isolation might not play well with your SIEM, your identity management system, or your incident response workflows.
42:51 Lena: That integration testing sounds like it could be quite complex. How do you approach that systematically?
42:57 Miles: Map out your security architecture upfront and identify all the integration points that matter. Then test those specific integrations during your evaluation, not just the vendor's generic integration capabilities. And don't rely on vendor claims—actually test the data flows, alert formats, and workflow compatibility.
43:16 Lena: This conversation really highlights how vendor evaluation is as much about avoiding mistakes as it is about identifying the best solution.
24:07 Miles: That's exactly right, Lena. A mediocre evaluation process that avoids major pitfalls will often produce better outcomes than a sophisticated process that falls into common traps. Sometimes the best decision is the one that eliminates the most risk rather than maximizing potential upside.
