AI isn’t legacy tech: it’s new, fast-moving, and still evolving. That gives SMBs a real advantage—everyone’s learning in real time; and by choosing the right AI partner, smaller teams can move just as quickly as larger ones. Today, AI technology is becoming a core driver of smarter, faster, and more efficient operations—from streamlining internal workflows to delivering more personalized customer experiences. When applied strategically, it can boost productivity, reduce costs, and help your business stay competitive in a rapidly evolving market.
Successful AI adoption isn’t about how technical your team is; it’s about choosing an AI partner who can translate potential into real business value. The best technology partners don’t just name-drop tools like Microsoft Copilot and walk away. They take the time to understand your goals, guide you through implementation, and stick around to ensure the AI actually works for your team.
Unfortunately, that level of support isn’t always easy to find: while 74% of SMBs rely on technology partners for IT management, cybersecurity, and operational efficiency, most say those same partners fall short when it comes to AI. In fact, 85% of respondents to a recent Propulsion survey said their technology partner had recommended an AI tool—but in most cases, that guidance rarely went beyond a casual suggestion. There was no help with onboarding, no integration support, and no plan for measuring impact.
“Our technology partner is not in this space at all. They do basic IT management, but they’re not helping us figure out AI opportunities. If we wanted this, we’d need a totally new type of provider.”
- Director of IT Operations, financial services industry
That disconnect is exactly why SMBs need to ask better questions—not just about the tools being recommended, but about the guidance and support that come with them—especially when AIadoption still feels uncertain or overwhelming. When choosing an AI partner, look for one who acts as an extension of your strategy, your operations, and your team.
As you evaluate potential partners—whether they’re SaaS vendors, IT consultants, or broader technology solution providers—use the following questions to assess not only the AI solution itself, but also the quality of the partnership behind it:
1. What business challenges can you help us solve with AI?
AI is not one-size-fits-all. The right partner won’t just push a flashy solution; they’ll start by learning how your business actually works. What are your short- and long-term strategic business objectives and priorities? What are your biggest bottlenecks? Where do your teams spend too much time on low-value tasks? Which parts of your operations are ripe for improvement but too complex to tackle manually? A good partner will take the time to understand these dynamics and map AI capabilities to specific, high-impact AI use cases that support your goals—not just generic industry benchmarks.
Maybe you’re trying to reduce response times in customer support, or automate routine finance or HR processes. Maybe you’re trying to make sense of large volumes of customer data to uncover trends and opportunities. A strong technology partner should come to the table with a point of view—one grounded in experience and tailored to the realities of your business.
Your AI partner should also be able to show proof. Ask for real examples of how similar businesses—ideally other SMBs—have successfully used their AI solutions to improve outcomes. What changed? How long did it take to see results? What did adoption look like? If a partner can’t tie their recommendations to real-world performance or measurable ROI, that’s a red flag. You’re not just buying software—you’re choosing an AI partner who should be accountable for those outcomes.
2. How will you ensure AI is secure and compliant for our business?
AI systems are only as trustworthy as the data practices behind them, and a single breach or misstep can have outsized consequences. From customer records and financial statements to internal emails and HR data, AI often touches sensitive information across your organization. If your technology partner can’t ensure that data is handled securely and responsibly, the risks quickly outweigh the rewards. Here’s what to ask:
How will you help us choose the right AI tools that meet our compliance and security requirements? Different AI tools come with very different risk profiles, depending on how they access your data, where that data lives, and what protections are built-in. A strong partner should help you navigate those nuances—comparing Copilot v. Copilot Pro v. Microsoft365 Copilot, for example—and explain:
● Where the data is processed (locally v. cloud)
● What data is shared with the AI provider (if any)
● Whether your organization’s data is used to train models
● What admin controls are available to restrict access or limit scope
● Which regulatory frameworks each tool supports out of the box (HIPAA, GDPR, CCPA, etc.)
This kind of upfront guidance ensures you’re not only choosing an AI solution that works—but one that keeps your data safe and your business compliant.
What safeguards are in place for how AI interacts with our data? It’s not enough to ask whether your data is “secure.” You need to know exactly how it will be:
● Collected: What data is being used, and how is it selected?
● Stored: Where is it hosted? Is it encrypted at rest and in transit?
● Accessed: How does the AI retrieve the data? Are user permissions in place to prevent overreach?
● Processed: Is the data being used for model training? Is it visible to third-party vendors or human reviewers?
AI-specific safeguards should include things like differential privacy, context-aware access restrictions, AI activity logging, and admin-level visibility into what the model is doing with your data.
Your partner should offer concrete, transparent answers to these questions—not just general assurances. Third-party audits or certifications (like SOC 2 Type II, ISO 27001, or FedRAMP, depending on your industry) provide extra peace of mind that their approach is robust and regularly validated.
Additional features to look for:
● Data anonymization or masking for sensitive fields
● Audit logs specific to AI activity (e.g., who triggered which prompt, what data was accessed)
● Custom access controls to limit visibility and usage by team, department, or geography
Security and compliance aren’t nice-to-haves—they’re foundational. And in the age of AI, they’re not just IT concerns; they’re board-level risks and essential trust signals. The right partner will offer both the tools and the transparency to help you deploy AI responsibly from day one.
3. Can your AI solution integrate with the systems we already use?
One of the fastest ways to derail an AI initiative is friction. If a new tool doesn’t integrate with your existing tech stack—whether it’s your CRM, ERP, accounting platform, modern work tools (e.g., Microsoft 365), or internal knowledge base—it won’t just create extra work. It can lead to broken workflows, data silos, and frustrated teams who end up abandoning the tool altogether.
Ask every potential partner how their solution fits into your current ecosystem. Can it connect to your systems via APIs or offer out-of-the-box integrations with tools you already rely on? Or will your team be forced to juggle exports, build custom connectors, or manually sync data across platforms? The more seamlessly an AI solution plugs into your stack, the faster your team will start seeing value—and the more likely they are to actually adopt it.
Integration isn’t just about convenience. It’s about continuity, usability, and long-term impact. A tool that’s easy to adopt today is far more likely to stick around tomorrow. (Bonus points if your partner has experience working with your exact systems or within your industry. Familiarity with vertical-specific tools or legacy platforms can dramatically reduce onboarding time and ensure fewer surprises down the line.)
4. How will you support our employees as they start using AI?
Your employees don’t need to be AI experts or prompt engineers, but they do need to feel comfortable using the tools you put in front of them. Without the right support, even the most powerful AI solutions can become shelfware. Adoption is earned through thoughtful onboarding, hands-on training, and clear communication—not just about how the tools work how they’re meant to be used in alignment with your organization’s AI usage policies. One of the most helpful places to start is with prompting—learning how to ask AI the right questions to get reliable, useful results.
A strong partner understands that introducing AI means changing behavior, and that change takes guidance. They’ll help your team not just use AI, but use it well and with confidence. That means translating technical features into everyday use cases, addressing common questions early, and making help accessible when people need it.
Ask potential partners what kind of employee enablement they offer:
● Live onboarding sessions to walkthrough features and workflows?
● On-demand video tutorials or searchable knowledge bases?
● In-app guidance and contextual tooltips for just-in-time support?
● Access to customer success teams for more complex questions or team-specific scenarios?
● Ongoing training and support?
Look for a partner who treats education as part of the product—not just a bonus or afterthought. The easier it is for your employees to learn and apply the tools, the faster you’ll see ROI on your AI investment.
5. What are the costs, and how flexible is your offering?
AI adoption should feel like a smart investment, not a risky gamble. That starts with financial clarity. Be upfront about your budget and make sure your prospective partner is just as transparent in return. Ask for a clear breakdown of pricing—especially when it comes to usage-based fees, data volume thresholds, per-seat licenses, or feature tiers that might unlock only after you’ve already committed.
Don’t just ask about cost—ask about control. Can you pilot the solution before scaling? Are there flexible contract terms that let you grow over time instead of locking you into an enterprise plan from day one? Can you scale features, seats, or integrations incrementally as your team’s needs evolve?
Questions to ask prospective partners include:
● Do you offer usage-based pricing, and how are those rates calculated?
● Are there any data volume caps or overage fees we should plan for?
● What’s your typical contract length, and are there options for month-to-month or shorter-term engagements?
● Are all features available from the start, or are some gated behind higher-tier plans?
● What kind of onboarding and support is included in the base price?
The best partners understand that SMBs operate under tighter budgets and shifting priorities. They’ll collaborate with you to build a pricing and implementation plan that aligns with where you are now, and where you want to go. And they’ll never push tools or features you don’t need just to hit a sales target.
6. How will this AI solution drive meaningful business outcomes?
AI shouldn’t just make your internal operations more efficient; it should also help you achieve the outcomes that matter most to your business. That might mean improving customer satisfaction, yes—but it could also mean driving more revenue, reducing churn, accelerating sales cycles, or increasing marketing efficiency.
A strong technology partner will help you draw a clear line between the AI they’re offering and the outcomes you’re trying to achieve. Can the tool shorten time-to-resolution in customer support? Can it help your team deliver more targeted campaigns, close deals faster, or retain high-risk accounts with proactive outreach? Can it improve onboarding or reduce time to value for new customers?
These aren’t nice-to-haves—they’re business drivers. In today’s competitive landscape, speed, personalization, and insight aren't just customer expectations; they’re the foundation of growth and differentiation. If your AI tools can’t help you move the needle on outcomes that matter, they may be adding complexity instead of clarity.
Questions to ask your prospective technology partner:
● How will this solution support our top business priorities (e.g., growth, retention, efficiency)?
● Can it help reduce friction in our support process or sales pipeline?
● Will it enable personalization in marketing, onboarding, or product usage?
● How do you measure improvements in business impact—not just activity?
● Do you have benchmarks or case studies tied to tangible results?
Look for partners who optimize for outcomes—not just process. Efficiency matters, but measurable impact matters more. The best AI solutions support real growth across functions—from customer experience to sales to marketing—and the right partner will help you deliver on all of them.
7. Who will manage AI as our needs evolve?
AI isn’t a “set it and forget it” solution. Like any powerful system, it evolves alongside your business—responding to new goals, changing data, shifting workflows, and external market pressures. What serves your needs today may need to be reconfigured or scaled differently six months from now. That’s why it’s essential to understand who’s responsible for managing and optimizing AI over time.
Some tools require ongoing tuning—whether it’s refining prompts, retraining models with new data, or adjusting how the tool fits into your evolving tech stack. Others need to be re-evaluated as new features become available or priorities shift. A strong partner will anticipate these needs and proactively guide you through them.
Ask your potential partner whether they provide:
● Regular performance check-ins to review what’s working and what needs adjusting
● Access to technical experts who can help optimize your implementation over time
● Change management support as your team grows or adopts new tools
● Feature rollout guidance to make sure you’re leveraging improvements as they’re released
You’ll also want to know: Is there a dedicated account manager or customer success lead who knows your business? Or will you be routed through general support every time something changes?
8. How will you help us measure the success of our AI initiatives?
Data-driven decisions start with tracking the right outcomes. But when it comes to AI, success isn’t always obvious—it might look like time saved, smarter decisions, fewer manual tasks, or a better customer experience. That’s why it’s critical to work with a partner who can help you define what success means for your business, and then give you the tools and benchmarks to track it over time.
A strong AI partner will build success metrics into the rollout process, helping you establish baselines before implementation and set realistic, meaningful KPIs tied to your goals. Whether you’re aiming for operational efficiency, revenue growth, or improved customer engagement, your partner should show you how AI will move the needle—and how you’ll know when it does.
Questions to ask your prospective partner:
● What metrics do you typically recommend for tracking AI success?
● Do you offer dashboards or reporting tools to monitor performance in real time?
● Will you help us establish pre-AI baselines so we can measure true impact?
● How do you track and communicate long-term ROI?
The ROI of AI isn’t always about top-line growth. It might be that your team now saves 20 hours a week, that support tickets are resolved twice as fast, or that customers are rating their experience more positively. Whatever success looks like, your partner should help you define it, document it, and continuously improve toward it.
The bottom line: choosing an AI partner who’s in it with you
AI doesn’t need to be complicated, intimidating, or out-of-reach. With the right partner, it can be a low-friction, high-impact addition to your business operations—solving real problems, supporting your team, and scaling with you over time.
These eight questions aren’t just a checklist for vetting vendors; they’re a roadmap for choosing an AI partner who’s ready to deliver real results. They’re a way to uncover whether a partner is fluent not just in AI, but in your business—ready to share in your challenges, champion your goals, and help you turn potential into performance.
At Propulsion, we help small and mid-sized businesses integrate AI in ways that are secure, practical, and aligned with your goals. If you’re exploring AI and want a strategic partner—not just a service provider—get in touch with our team for an assessment.
