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Five questions to ask before choosing who to work with

August 8, 2026·1 min read
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Five questions to ask before choosing who to work with

Choosing who to work with is mostly about asking the right questions early. Here are the five we'd ask in your position - and the answers you should expect to hear.

1. What does the process look like?

A clear, step-by-step answer is a good sign. Vagueness here usually means surprises later.

2. What will it cost - and what could change that?

Fixed where possible, transparent where not. You want to hear about the edge cases before they happen.

3. How long will it take?

Honest timelines beat optimistic ones. Ask what could delay things and how you'll be kept informed.

4. Who exactly will I be dealing with?

Names, not departments. Knowing your point of contact makes everything smoother.

5. What happens if something goes wrong?

Everyone makes mistakes; the difference is how they're handled. Look for a straight answer about guarantees, fixes and follow-up.

Want to put us to the test? Ask us any of these - we'd be glad to answer.

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Comments (2)

O
Owen Hughes Sep 7, 2026 at 11:09 AM
Do you have a version of this for smaller teams? Most of what I read assumes forty people and three managers.
T
Thennick Advisory Sep 8, 2026 at 11:15 AM
Sending you something by email. Short answer: the same five questions, half the meetings.
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