The Health Check Question Bank

The questions that surface drift before the client does

A health check works because of who it asks. Not the client, who is the last to admit a relationship is cooling, but you, who already senses it and just hasn't written it down. The questions below are organized by the twelve dimensions. You won't answer all of them every time; you answer the ones that fit the moment.

Two rules before you start:

• Answer against baseline. The question isn't "is this good," it's "is this different from how it used to be."
• An honest "I don't know" is data. If you can't answer a question about a client, that gap is itself a signal worth noticing.

Trust — do they trust you to do your job?

• Are approvals getting faster because they trust me, or because they've stopped engaging?
• Am I being asked to justify decisions I wasn't asked to justify three months ago?
• When I make a judgment call, do they back it or relitigate it?
• Has anything happened recently that would have dented their trust, even if neither of us named it?

Loyalty — are they looking at other options?

• Have they mentioned a competitor, a price they saw elsewhere, or "exploring options"?
• If a cheaper alternative pitched them tomorrow, would they take the call?
• Do they talk about our work as a long-term thing, or one cycle at a time?
• Are they comparing me to a previous provider in a way that suggests they haven't fully committed?

Expectations — are their expectations realistic?

• Is there a gap between what they expect and what this engagement can actually produce?
• Did I make a promise early on that's quietly becoming a liability?
• Have we explicitly aligned on what success looks like, or are we each assuming?
• Is any unrealistic expectation widening week over week without being addressed?

Grace — how do they react when something goes wrong?

• The last time something slipped, did they give benefit of the doubt or treat it as a referendum?
• Am I operating with margin for error, or does every detail have to be perfect?
• Do they judge me on the recovery, or on the stumble?

Budget Commitment — will money be the reason they leave?

• Is there budget pressure on their side, even if it has nothing to do with my work?
• Have invoices, scope, or spend conversations changed tone recently?
• If their budget got cut 20%, would my line item survive the conversation?

Relationship Depth — is there a real relationship beyond the work?

• Is there a genuine connection here, or is it purely transactional?
• Has the personal warmth changed in either direction recently?
• Am I relying on one human bond that could vanish if that person left?

Replaceability — how embedded am I?

• How hard would it actually be for them to replace me?
• Is my work woven into how they operate, or is it a discrete deliverable anyone could pick up?
• Have I become more essential over the last six months, or less?

Communication Tone — warm and direct, or cold and clipped?

• Has the tone of their messages cooled, even slightly?
• Are replies shorter, later, or more formal than they used to be?
• Is there warmth that's gone missing without an obvious reason?

Decision-Making Authority — can my contact actually say yes?

• Does my main contact have the authority to keep me, or are they a relay?
• Has decision-making quietly moved to someone I don't have a relationship with?
• Do I know who, besides my contact, could decide my fate here?

Communication Frequency — the rhythm (U-shaped: both extremes are risk)

• Has our contact gone from a steady rhythm to radio silence, where I always initiate?
• Or has it spiked into constant, anxious back-and-forth?
• Does the current frequency match what this client actually wants, or what's convenient for me?

Stress Response — how do I find out when something's wrong? (U-shaped)

• When something goes wrong on their end, do they tell me, or go quiet and handle it internally?
• Do they escalate loudly in a way that destabilizes the work?
• Am I finding out about problems too late because they don't surface them?

Reporting Need — how much do they want to hear from me? (U-shaped)

• Is the current reporting cadence sustainable, or is it drifting toward "don't bother me" or "send me everything"?
• Have they asked for more detail recently, and if so, why now?
• Could a sudden request for a comprehensive summary mean someone above them is asking "is this worth it?"

Cross-cutting questions worth asking every time

• What's my honest gut feeling about this relationship right now, and what evidence would confirm or kill it?
• What's changed since the last check, in either direction?
• If this client left in 90 days, what would the reason most likely be?
• Where would the next hour of my attention produce the most relationship value, here or somewhere else in my book?

How to run it

1. Cadence by health, not calendar. Monthly for critical accounts, quarterly for stable ones, yearly for thriving. Don't get pinged on a schedule that makes you rush through to clear the queue.
2. Answer honestly, including the blanks. The questions you can't answer are telling you where you've stopped paying attention.
3. Read the lowest dimensions together. The combination is the diagnosis.
4. Update the profile. A health check only sharpens your reads if the answers actually go back into the system.

Retayned chooses the right questions for each client based on what's already shifting, so a check-in stays short and pointed instead of becoming a 47-question form you fill out to get it off your plate.