Processes that Make or Break Your Win-Loss Program

Braydon Anderson

So you just got the go ahead to start a win-loss interview program. Depending on a few factors, either you or a third party vendor is now going to conduct the interviews.

What’s next?

Much more goes into a win-loss interview than the actual interview. After developing a set of interview questions to ask (the interview guide), actually carrying out the interviews can take a fair amount of work - both before and after each conversation. Here’s a brief outline of what goes into the process:

  • Prepare a list of qualified contacts to reach out to
  • Email or call each contact to schedule the interview
  • Conduct the interview
  • Record the interview
  • Transcribe the interview
  • Analyze the interview (tag themes, highlight quotes, compose a summary, etc.)
  • Share what you’ve learned
Much more goes into a win-loss interview than the actual interview. Conducting each interview takes a fair amount of work both before and after the conversation.

Understanding and then optimizing each step of the process can make or break your program. In my time at Clozd, I have heard many business leaders lament failed win-loss implementations because they neglected, underestimated, or mismanaged parts of the process.

If you choose to hire a vendor to run your program, don’t just vet the resumes of their interviewers, the prices they charge, or the look and feel of their deliverables. Take time to vet how they will execute the entire win-loss process, knowing that their execution of each step will directly influence the success of your program. Efficient scheduling and transcript output means higher participation rates, a better interviewee experience, quicker interview turnaround times, cleaner transcripts, etc.

A mastery of the following tasks is key to any successful, on-schedule, and on-budget win-loss program:


It may come as a surprise, but for most companies the biggest hurdle for scheduling interviews is compiling and approving a list of interview candidates. Expect to consult your client or CRM at least once a quarter, if not monthly, to get the freshest contacts. Minimizing this bottleneck is instrumental in getting names on a continual basis. Waiting on a slow drip to fill your cup is both frustrating and expensive.

Once you have names, automate where possible to simplify scheduling. A few tips:

  • Use an email service — Your initial list of contacts will likely be large. Find a service where you can upload a CSV file of contacts and send in bulk, rather than one at a time.
  • Follow-up — People need reminders. How many automated emails you send and at which cadence is up to you, but you’ll want to balance persistence with professionalism. We typically attempt around five emails over a two-three week time period.
  • Use a scheduling service —  Make it easy for people to sign up for interviews using a scheduling link (don’t make them email or call you back). Even simple, free tools like Calendly, Doodle, or TimeTap can work well. Let your interviewees pick a time slot that’s easy to coordinate, reference, and reschedule if necessary.

Note that enlisting the help of a third-party for interviews doesn’t just save you time, it’s often more inviting to contacts. People are more likely to speak with (and speak candidly with) a neutral third party than with the company they just told “No.”


Furiously taking notes during an interview is not only distracting and imprecise, but also off-putting to an interviewee. Don’t miss a thing. Record each interview whenever possible. Most modern online meeting solutions — like Zoom, GoToMeeting, WebEx, etc. — make it easy to record meetings or interviews.

Transcription & Cleaning

Record and transcribe EVERY interview if possible. If you don’t have the time or resources to transcribe the interviews yourself, consider outsourcing to a qualified third-party. Use a service or partner you trust who will protect your company’s privacy and confidentiality. You may consider services such as Scribie, Rev, or Otter. In our experience, human transcription services still far outperform automated ones. Regardless of which method or service you use, make sure to carefully proofread your transcripts before sharing them.

Analysis & Sharing

To make your win-loss interview findings actionable, you should analyze the themes and trends that you’re hearing across interviews. Develop a methodology for tagging meaningful quotes and themes from each interview transcript. Then, develop a system to track and compare the themes from across all the interviews you conduct. This will help you identify real areas for improvement that are worth acting on. Throughout the program, freely share the individual transcripts and the analysis of interview themes with colleagues and leaders across your business. For even more tips and best practices for sharing win-loss findings effectively, check out this previous blog post.


At Clozd we have the opportunity to work with great clients. Before hiring us, some clients are more diligent than others in vetting the processes of the various win-loss vendors they are evaluating. In certain cases, prospective clients pilot our services alongside competitor services. In one such “bake off” last Fall, a prospective client worked with us and another vendor simultaneously to conduct 10 total interviews (5 per vendor). Ultimately, Clozd published seven interviews in the time it took our competitor to schedule two. The hands-on experiment confirmed to this particular client that not all vendors approach the win-loss process the same. It was easy for them to make a final decision to move forward with Clozd. Had they selected the other vendor it is likely the program would have sputtered and the interviews they paid for might never have been completed.

Great ideas — like win-loss analysis — often crash in execution. Don’t let that happen. Invest adequate time and resources into developing effective processes for scheduling, interviewing, transcription, and analysis. They can make or break your program.

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