Hiring a technology partner is one of the bigger decisions a family business owner makes. The right partner can modernize your operations and support you for years. The wrong one can leave you with a half-finished project, software you don’t control, and a bill you didn’t expect. These ten questions will help you tell the difference before you sign.
1. Who will actually do the work?
Ask to meet the people who will run your project day to day. If the people in the sales meeting won’t be on the project, you should know that up front.
2. Have you worked with businesses like ours?
Experience with family-owned and owner-led companies matters. Ask for examples at your size and in similar situations, not just in your industry.
3. How will you learn how our business works?
A good partner asks a lot of questions before proposing solutions. Be wary of anyone who recommends specific software in the first meeting.
4. How do your recommendations tie to revenue, cost, or risk?
Every major recommendation should come with a plain-English business case. If a partner can’t explain why something is worth the money, it probably isn’t.
5. What does a small first step look like?
Look for a partner who can start with a contained, fixed-fee engagement, such as a strategy sprint or a single high-value project, so you can judge the relationship before making a large commitment. See How to Modernize an Older Business Without Disrupting Operations.
6. Who owns the code, the data, and the accounts?
You should. Get it in writing, along with documentation and access to every system. Read Do You Own Your Software? for what to check.
7. How will you get our people to use it?
New systems fail when employees don’t adopt them. Ask how the partner handles training, rollout, and the long-time staff who will be most affected.
8. Who is accountable if something goes wrong?
If the project involves design, development, marketing, and hosting, find out whether one firm is responsible for all of it or whether you’ll be coordinating several vendors yourself.
9. What happens after launch?
Ask about ongoing support, security updates, and response times, and whether the team that built your system will still be available in three to five years.
10. How will we communicate?
Agree on who your main contact is, how often you’ll get updates, and how decisions get made. Clear communication prevents most project problems.
Red flags when hiring a technology partner
- Proposals full of jargon with no clear business outcome
- Pressure to commit to a large, long project before any smaller proof of value
- Vague answers about who owns the code or what happens after launch
- A different team showing up once the contract is signed
How One80 Group answers these questions
We built One80 Group around these answers: the senior people you meet do the work, you own what we build, recommendations are tied to business results, and we stay accountable from strategy through long-term support. You can see some of the organizations our team has worked with.
Talk it through with a senior advisor
One80 Group is a technology partner for family businesses from first idea to $200M. Book a free 15-minute consultation and we’ll give you a plain-English view of your best next step.
