Most boards hire a management company once or twice in a decade — which means most boards interview badly. The company across the table does this every week. The questions below are the ones that predict what year two actually looks like, because they force specifics instead of sales language.
About the money
1. What exactly is in the monthly financial package? You want a specific list: balance sheet, budget-versus-actual, bank reconciliations, accounts payable and receivable, delinquency aging, and reserve activity. If the answer is "a summary report," the detail is being withheld.
2. How are operating and reserve funds segregated? Massachusetts associations should expect separate accounts, dual controls on reserve transfers, and written board authorization for any reserve use.
3. What is billable beyond the base fee? Ask for the schedule of extras — meetings beyond a set number, postage, legal coordination, project management. The honest answer is a document. The dishonest answer is "not much."
About attention
4. How many associations does each manager handle? This is the single best predictor of service quality. A manager with a huge portfolio is a dispatcher, no matter what the brochure says. At Dahlia, portfolios are intentionally limited so boards get a manager who knows the community's history.
5. Who answers the phone when our manager is out? Every company has a backup plan. Good ones can name the person and explain the handoff. Ask what happens on the third day of a vacation, not the first.
6. Can we speak to a current client of similar size? A refusal is a complete answer.
About emergencies
7. What happens when a unit reports an active leak at 11 p.m.? Listen for: intake line, dispatch authority, documentation, next-morning board notification. You want a process, not reassurance.
8. When does the board get called versus informed? A good manager knows the difference between "act now, report immediately" and "needs board authorization." That judgment call is most of the job.
About transitions and records
9. What does your standard transition plan look like? A serious company describes record inventories, fund transfer coordination, vendor continuity, and owner communication as a sequence with owners and dates.
10. How do you handle inherited problems — unpaid vendor balances, incomplete records? You are testing honesty here. The right answer acknowledges that inherited messes are normal and describes a documented process: verify, communicate, prioritize, keep the board informed. See handling inherited vendor balances and our case study of a difficult transition.
11. What won't you do? Every company has limits — portfolio sizes, property types, service areas. A company with no limits has no focus.
12. What would make you resign from an account? This question does more than any other to surface character.
Scoring the answers
Bring this list to the interview and write down the answers during it. Specifics beat polish. A company that answers twelve questions with numbers and documents will manage your money the same way — which is the entire point.
Ready to compare answers? These will help:
From Our Case Files
See How We Handle Situations Like This
Documented case studies from real Massachusetts and Rhode Island associations — difficult transitions, financial reconstruction, and emergency response.
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