How to run proposal software customer interviews that produce useful answers

What to take away

Proposal software customer interviews are structured research conversations with buyers and users of quoting tools, run to test what people do rather than what a vendor assumes.

Start by writing down who counts as a customer

An interview programme depends on its sample definition. Before recruiting, agree job title, company size, sector and tool each person uses. For an England-focused study, say if you mean businesses registered in England or teams based here.

State exclusions: agencies quoting clients, teams sending only PDFs. Our audience research guide for England covers the sampling choices behind this step.

Write the criteria down and keep them. Widen the net halfway through and the early interviews stop being comparable with the later ones.

Recruit from three places, not one

Draw participants from at least three sources: existing customers, people who signed up but never bought, and people who left. Lapsed users often explain the moment a tool stopped fitting the job. Ask account managers for two introductions each and keep a short waiting list so one cancellation does not stall the schedule.

The Office for National Statistics business demography bulletin shows how often UK firms start, stop and survive, a reminder that your pool of former users keeps refilling. Treat churn as a source of interviewees, not a dashboard number.

Ask about the last document, not about software

Generic questions produce generic answers. Ask the participant to open the most recent quote or proposal they sent and talk you through it. You learn which fields they fill in, where they pause, and what they copy from an earlier job.

Follow the document, not your feature list. If they mention a spreadsheet, ask to see it. If a colleague checks pricing, ask what that person changes. Photograph or screenshot the document only with permission.

Cover the rules that shape what they can send

The Information Commissioner's Office guidance on direct marketing and privacy explains how consent rules apply when a business contacts people. That matters when a proposal doubles as a marketing message.

Quality processes are worth probing too. BSI's quality management standards explain why organisations build consistency into documents and approvals, so ask who signs off a quote before it leaves.

Run the session to a fixed script

Book 30 to 45 minutes and keep the same question order every time. Open with role and process, move to the last document, close with what they would change. Do not pitch, and do not defend your product if they criticise it.

Where possible, two people attend: one asks, one takes notes. Otherwise record the call with permission and write up notes the same day. Write notes under fixed headings: role, trigger, document, blockers, workaround. Aim for six to ten interviews per segment before drawing conclusions.

Compare assumptions before and after

Build a simple table at the start and fill the right-hand column as evidence arrives. The examples below are illustrative, not measured, so replace every figure with your own findings.

One row per assumption is enough. Review the table with the people who will act on it, not on your own.

Turn findings into a target list

Group participants by the problem they described rather than by company size. That grouping feeds your target audience in England, which explains how to segment buyers of quoting and proposal tools.

Share a one-page summary with sales and product within a week. Three or four findings are usually enough to move a roadmap item or a demo script. Give each change an owner, otherwise the findings sit in a document nobody revisits.

Common questions

How many interviews are enough?

Six to ten per segment is a practical starting point for a small B2B team. Stop when new sessions stop producing new themes.

Should I pay participants?

For business buyers, a modest voucher or a charitable donation is common. Existing customers who want the product improved rarely need one.

Can I run interviews remotely?

Yes. Remote sessions make recording easier and reach teams outside your own region, so ask for permission before you record.

What if a participant asks about pricing?

Say you are gathering feedback first and will follow up separately. Mixing research with a sales conversation changes the answers you get.