The Vendor Merry-Go-Round
Before I get into this, let's look at some research data:
87% of senior leaders struggle to balance innovation with risk management, according to Forrester Consulting — and under that pressure, most default to instinct and familiarity over structured evaluation.
Only 6% of executives are satisfied with their organization's innovation performance, according to McKinsey's Global Innovation Survey.
81% of buyers express dissatisfaction with the provider they ultimately chose, according to Forrester's State of Business Buying research across 16,000+ global buyers.
We keep picking the same names and getting the same results.
The enterprise software marketplace has never been noisier. AI tools, workflow platforms, data layers, integration frameworks — thousands of vendors competing for attention across every category. For anyone accountable for strategy execution, it's genuinely overwhelming. The landscape changes faster than any evaluation cycle can keep up with.
So what do decision-makers do? They default to the name they recognize. Salesforce. Microsoft. Oracle. Monday.com. Airtable. Asana. The darlings. Not because those tools have been rigorously evaluated against actual operational requirements — but because nobody ever got fired for buying IBM. The brand absorbs the blame if things go sideways. It feels defensible.
The problem is that "defensible" and "right" are not the same decision.
When organizations default to scale over fit, they pay enterprise premiums for tools built for generic use cases, then spend months configuring them to approximate what their business actually needs. The transformation strategy stalls. The ROI never materializes. Eighteen months later, someone's in a conference room asking what went wrong.
There's a second failure mode that doesn't get named enough: the delegation problem. Executives who don't have bandwidth to evaluate vendors delegate that work — and the people they delegate to aren't always qualified to do it. You need evaluators who understand the tools they're assessing well enough to stress-test vendors' claims. Without that technical and operational fluency, the process is theater. Add confirmation bias toward familiar tools, shortcuts driven by laziness, and diligence reports that look like analysis but aren't, and the decision that lands on an executive's desk has already been filtered into something that protects the evaluator rather than the organization.
Purpose-built, category-defining tools — the ones that would actually move the needle — never make it past the first screen. They lose to familiarity. And the organizations that dismissed them fall behind the ones willing to look harder.
There's also a structural risk hiding inside "safe" decisions that almost nobody is pricing in: vendor control. In August 2026, Bending Spoons announced a definitive agreement to acquire Airtable. Contract language moves fast in this kind of portfolio — sometimes faster than customers can react. Organizations that built workflows on Airtable and never negotiated change-of-control protections into their agreements are now exposed. This is exactly the kind of leverage available when working with niche, purpose-built vendors — you can negotiate MSA terms that protect against acquisition-driven pricing changes, feature deprecation, and shifting terms. You rarely get that conversation with a platform that already owns the market.
3 Concrete Actions to Protect Your Innovation Process
1. The senior executive must take the final vendor meeting. After the diligence is done, the person accountable for the strategy's success — not a delegate, not a committee — needs to sit across from the principal at the vendor and hear it directly. Not a sales rep.
2. Qualify the evaluators before you trust the evaluation. If the people running vendor selection cannot articulate the specific operational problem the tool needs to solve — and demonstrate they understand how the tools they're assessing actually work — they're not qualified to run the process. Fix that before you shortlist anyone. Bad diligence handed upward becomes bad decisions handed downward.
3. Require criteria-first evaluation, not brand-first shortlisting. Build the requirements map from the people who live the workflows before you look at a single logo. Define what fit means in business terms. Then evaluate against it — not against name recognition, analyst placement, or whoever just raised a Series C.
The safe bet isn't safe. It's just familiar. And in a market moving this fast, familiarity is exactly how transformation strategies fail.
