Hiring a technology partner is a high-stakes decision. Get it right, and you have a trusted advisor who helps your business move faster. Get it wrong, and you're left with blown budgets, missed deadlines, and software that doesn't work.
After 29 years in this industry — and plenty of time cleaning up other people's messes — I've seen what separates good technology partners from bad ones. Here's what to look for.
They ask more questions than they answer
The first conversation tells you a lot.
A good technology partner wants to understand your business before proposing solutions. They ask about your goals, your constraints, your team, your customers. They want to know what you've already tried and why it didn't work.
A bad one jumps straight to their solution. They're selling what they have, not solving what you need.
Be wary of anyone who proposes a specific technology or approach before they understand your situation. The best partners sometimes tell you that you don't need what you thought you needed — or that someone else would be a better fit.
They've done this before — for businesses like yours
Experience matters, but relevance matters more.
A partner who's built enterprise software for Fortune 500 companies may not be the right fit for your 20-person business. The approaches, tools, and budgets are completely different.
Look for partners who've worked with businesses of similar size and complexity. Ask for references you can actually call. Look at their portfolio for projects that resemble yours.
And ask about failures. Any experienced partner has had projects go sideways. What matters is how they handled it and what they learned.
They explain things in plain language
Technology is complex. Explaining it shouldn't be.
A good partner translates technical concepts into business terms. They help you understand the tradeoffs without drowning you in jargon. When you ask a question, you get an answer you can actually use.
A bad one hides behind complexity. They make you feel stupid for not understanding, or they use jargon to obscure what's really happening. Sometimes this is intentional (making themselves seem indispensable); sometimes it's just poor communication skills. Either way, it's a problem.
You don't need to become a technical expert. But you should be able to understand what's being built, why decisions are being made, and what the implications are for your business.
They have a clear process
Good partners have a way of working. They can explain how they approach projects, what the phases look like, how decisions get made, and how communication works.
Ask about:
- How they scope projects — this matters more than you think
- How they handle change requests — scope always changes; the question is how
- How they communicate progress — regular updates or radio silence?
- How they handle problems — because problems will happen
- What happens after launch — who maintains it?
Vague answers here are a red flag. "We're flexible" often means "we don't have a process."
They're honest about what they don't know
Nobody knows everything. The technology landscape is too broad for any single person or firm to be expert in all of it.
A good partner is honest about the edges of their expertise. They'll tell you when a project isn't in their wheelhouse, or when you need a specialist they can recommend.
A bad one says yes to everything and figures it out later — on your dime.
Ask about projects they've turned down. If the answer is "none," that's concerning.
They talk about your budget like it's real money
Budget conversations reveal a lot.
A good partner wants to understand your budget early — not to extract maximum dollars, but to make sure they're proposing something realistic. They'll tell you if your budget doesn't match your goals, and they'll help you find a path that works. They'll explain what drives costs so you can make informed decisions.
A bad one either avoids the budget conversation entirely (leading to sticker shock later) or immediately asks for more than you mentioned (treating your budget as a starting point for negotiation).
The best partners treat your money like their own. They recommend the right solution, not the most expensive one.
They push back when necessary
You're hiring a partner, not a yes-man.
A good partner will tell you when your idea won't work, when you're overcomplicating something, or when you should buy instead of build. They bring expertise and judgment, not just execution.
A bad one builds exactly what you ask for — even when what you're asking for is wrong. Then, when it doesn't work, it's somehow still your fault for asking wrong.
You want someone who will advocate for the right solution, even when that means disagreeing with you. That's how projects succeed.
They've been around (or plan to be)
Technology projects aren't one-and-done. Software needs maintenance, updates, and evolution. The partner you choose today should be around tomorrow.
Look for stability signals:
- How long have they been in business?
- Do they have long-term client relationships?
- Is there a team, or just one person? (What happens if that person gets sick or quits?)
- Are they financially stable?
This doesn't mean you should only work with big firms — plenty of excellent partners are small operations. But you should understand the risks and plan accordingly.
Red flags to watch for
Based on messes I've seen and sometimes had to clean up:
- No discovery process. They quote without understanding your needs.
- Guaranteed timelines on day one. Nobody can guarantee delivery dates before scoping.
- No discussion of maintenance. They want to build and disappear.
- They own your code. You should own what you pay for.
- Communication disappears. Responsive during sales, absent during delivery.
- They bad-mouth everyone else. Professionals don't need to tear others down.
- Price is the only differentiator. You get what you pay for.
- They promise the moon. Experienced partners know to set realistic expectations.
How to run the evaluation
When you're comparing potential partners:
- Have real conversations. Not just sales pitches — actual discussions about your situation.
- Check references. Call them. Ask what went well and what didn't.
- Request a proposal. See how they structure it, what questions they ask, and how they think about your problem.
- Start small if possible. A small initial project reveals a lot about how someone works.
- Trust your gut. If something feels off, it probably is.
What we bring to the table
Before you start evaluating partners, it helps to understand your own technology landscape. A quick DIY technology audit can help you identify what's working, what isn't, and what you actually need.
At DGK Technologies, we've spent 29 years building software, leading technology teams, and helping businesses make smart technology decisions. We've seen what works and what doesn't.
We're not the right fit for everyone — and we'll tell you if we're not. But for small and medium businesses who need custom development, automation, cloud migrations, or strategic planning, we bring experience, honesty, and a track record of delivery.
We don't disappear after launch. We don't hide behind jargon. We don't build things you don't need.