Brennan WardDeal Desk

Interview questions

Seven questions interviewers ask

Every example answers a question interviewers ask Deal Desk and Deal Strategy candidates. Each follows the same shape: the question, the situation, what I did, the give/get logic, who I worked with, and the result.

Samples 1 to 5 use fictional customers, numbers, and policies, and the first four come from one recording of me working a made-up renewal. Sample 6 draws on real work at New Relic and Equifax; names are withheld. Sample 7 is my plan for a new team, with example details. Each sample's "Deal" line says which is which.

Most answers include short clips from a recording of me working a fictional renewal pricing request. Watch the full 53-minute walkthrough.

  1. Interview question“Walk me through a complex enterprise deal you structured.”A renewal with a laundry list of asksRenata sends me a renewal with eleven asks, a competitor bid, and a pricing drop hiding in the numbers. Here's how I read it, who I pull in, and where I changed my mind.Deal: Harborline Logistics. Fictional customer I built in my own Salesforce dev account. The way I work it is real.Read the sample
  2. Interview question“How do you do price analysis? Show me.”Pricing the ask against what they pay todayI price what the customer asks for next to what they pay today, check what the discounts really are, and say which margin check I would run next. Here it showed about $800K a year coming off a renewal.Deal: Harborline Logistics. Fictional customer and numbers from my demo Salesforce account.Read the sample
  3. Interview question“Tell me about give/get. How do you keep discounts from being free?”Ask what they value, then trade for itA customer asks for eleven things. I find out what they care about most, hold the line on the rest, and trade each give for something we want.Deal: Harborline Logistics. Fictional customer and terms from my demo Salesforce account.Read the sample
  4. Interview question“How do you communicate with Sales when the answer is no?”Say it plainly, once, so Sales can repeat itAsk what the jargon means, tell Sales which asks are a hard no without leaving the door open, and point to the contract so they can say it with confidence.Deal: Harborline Logistics. Fictional customer from my demo Salesforce account. The note to Renata is my example.Read the sample
  5. Interview question“How do you work with Legal, Finance, and Product?”Meeting each team in its own workflowI bring each team the request, a proposed answer, and the reason, in the channel that team prefers. A renewal-cap request shows why Legal hears it before the MSA is negotiated.Deal: Illustrative example: fictional request and routing preferencesRead the sample
  6. Interview question“How have you made the deal flow itself more efficient?”Making the deal flow itself fasterA revenue-leakage reconciliation, a 62-video training library, a Legal Playbook, rewritten CPQ approval rules, and a daily brief that reads the pipeline before Sales asks.Deal: New Relic and Equifax — real workRead the sample
  7. Interview question“What would you do in your first 90 days?”The first 90 daysMeet the sales leaders, learn the business, meet the partner teams, ship one visible improvement, then simplify approvals and standardize the recurring requests.Deal: My plan: coverage and team details are examplesRead the sample