5 Questions Every Business Leader Should Ask

Before Picking a Technology Partner

Choosing the right technology partner isn’t just a technical decision. It’s a business one. The stakes are high, the contracts are long, and the ripple effects (good or bad) touch every part of your organization.

At Deliver Digital, we’ve been brought in too many times after the fact. When the project is stuck, the internal team is frustrated, and the vendor is nowhere to be found. In almost every case, the problem didn’t start with the implementation. It started with the selection.

Most leaders focus on features, price, and pitch decks. But those rarely predict the success of a partnership. What does? Clear expectations. Aligned incentives. A team that understands your business, not just your backlog.

Here are five questions we use to help clients pressure-test their potential partners before they commit.

1. What does success look like for us?

Too often, “success” is defined after the project has already started—or worse, when it’s over. That’s a problem. You need a shared definition of success before the first kickoff call. That definition should include:

• Business outcomes (e.g., increased lead conversion, faster onboarding, reduced churn)

• Operational improvements (e.g., fewer manual handoffs, clearer reporting, reduced vendor sprawl)

• Cultural alignment (e.g., stronger internal buy-in, leadership trust in IT)

If your partner can’t articulate your success in business terms—not just technical outputs—they’re not ready to lead.

Pro tip: Ask them to define success without using buzz words like “digital transformation,” “scalability,” or “innovation.” If they can’t explain the win in your language (not theirs) they’re selling you a trend, not a result.

2. Who's really going to do the work?

Sales teams win the deal. Delivery teams make or break it. We've seen this pattern dozens of times: a charismatic account exec sells a vision, then hands it off to junior delivery staff with no context. You end up project-managing your own implementation.

Key things to ask:

• Will we meet our delivery team before signing?

• How do you ensure consistency between sales and delivery?

• Who has final say when strategy and scope collide?

Great partners commit to continuity. They introduce you to the team early, they document decisions obsessively, and they don’t make you guess who’s accountable.

Pro tip: Ask who they’d assign if the contract were double in scope or size. If the A-team only shows up for bigger logos, you’re not a priority; you’re filler.

3. What happens when things go sideways?

Every implementation hits friction. That’s not a failure, it’s reality. What matters is how your partner shows up when things go wrong.

We always ask vendors to walk us through their most recent project failure. Not the sanitized version—the messy one. What went wrong? Who noticed it? How did they respond? Did the client re-engage with them afterward?

A good partner has:

• A defined escalation path with direct contacts

• Experience navigating scope shifts and internal politics

• The confidence to raise issues early—even if it makes them look bad in the short term

Pro tip: Ask what they lost by owning a mistake. Did they kill a phase, lose margin, reset with the client? Partners who’ve never absorbed a loss probably haven’t earned your trust yet.

4. How does this partner work with others?

Your tech stack isn’t a solo act. CRM, ERP, MSP, digital experience layers: they all connect. Or, at least, they should.

Yet we’ve seen too many vendors refuse to collaborate, blaming others when things break. That’s a governance failure in the making.

Here’s what we want to see:

• Proof of previous work in a mixed-vendor environment

• A willingness to adapt to your existing ecosystem, not force theirs

• Use of shared PM tools, reporting frameworks, and rituals

Pro tip: Ask how they handled a conflict when another vendor dropped the ball. If their answer is finger-pointing or “we weren’t responsible for that,” expect the same when your project gets complicated.

5. What will ongoing governance really look like?

Most vendors treat go-live like the finish line. That’s a mistake. In our experience, the 6-12 months after launch is when your ROI either accelerates or erodes. Governance isn’t a report. It’s a rhythm.

Ask about:

• Post-launch engagement: What cadence do they propose for check-ins, metric reviews, and roadmap adjustments?

• Scorecards: How do they measure their own performance?

• Change management: How do they ensure internal adoption sticks?

Too many vendors say “we’ll be there for the long haul” but disappear as soon as phase one is paid. The right partner builds governance into the contract—and into the culture.

Pro tip: Ask what governance looks like when things aren’t going well. If they can’t describe a tough quarterly business review where the numbers were off and the execs were frustrated, they’re managing optics, not outcomes.

These five questions won’t guarantee success. But they’ll help you avoid the most common causes of failure: unclear expectations, shallow relationships, and mismatched incentives.

At Deliver Digital, we build these questions into every discovery session. We don’t just ask them—we help you interpret the answers, so you can move forward with confidence.
If you’re evaluating a tech partner—or worried about one already on the books—we’re here to help. Book your free call with our founder, Keith, today!

FAQ

• 1. What should I look for in a technology partner beyond price and features?

  Prioritize alignment with business outcomes, team continuity, governance discipline, and collaboration experience. Tools come and go—relationships last.

• 2. How do I evaluate whether a vendor’s team will stay consistent post-sale?

  Ask to meet delivery leads before signing. Request bios, past client references, and transparency on team structure and turnover.

• 3. What is vendor scorecarding and how does it work?

  A vendor scorecard is a governance tool that tracks partner performance against defined KPIs—like uptime, support responsiveness, feature delivery, and internal adoption. It helps shift accountability from anecdotal to actionable.

• 4. How do I manage overlapping vendors without creating chaos?

  Start with ecosystem mapping: who’s responsible for what, how they’re connected, and what handoffs exist. A strong partner will proactively align with others instead of operating in a silo.

• 5. What’s the most common red flag in partner selection?

  Overpromising. If a vendor says yes to everything or avoids tough conversations during pre-sales, they’ll likely do the same under pressure.

• 6. When is the right time to engage Deliver Digital?

  Ideally before selection begins. But we also help mid-project—when leaders realize what they bought isn’t what they needed. Either way, our goal is clarity, not complexity.