12 Questions to Ask Your Sales Reps Before Building your First Competitive Enablement function

Dejan Gajsek
Dejan Gajsek
November 10, 2023

12 Questions to Ask Your Sales Reps Before Building your First Competitive Enablement function

Gathering Information

To be completely honest, you have a bucket of knowledge captured in-house. It’s in the heads of your internal teams - marketing department, customer success, product, but especially - your salespeople. 

They are the only ones who actually talk to prospects and potential customers every single day. 

But because the company is fast-paced and there’s always a rush, there’s rarely a time for someone to capture all the knowledge locked inside their heads (or scattered in CRM notes and recordings). 

I shouldn’t say every company because 90% of Fortune 500 companies are using competitive intelligence and I’m sure that includes gathering primary data - the data you have inside your company. 

However, chances are you’re tasked with building a competitive intelligence function and you’re looking for ways to start collecting that sweet sweet data. 

The best way to start is with your colleagues. 

Limitations of Secondary Research

Now, there's a lot of information out there. Blogs, market studies, webinars, social media, and my personal favorites - Reddit and X/Twitter - the list goes on. It’s a joy to get lost sleuthing for pieces of information across the Internet. 

However, this secondary data is great for confirmation of what you’ve already discovered in the primary research. It’s a cross-check. Your customer success and sales reps hear about the nitty-gritty of what’s going on with prospects and customers, and if there’s ever a need for a detailed narrative there’s always a win/loss opportunity.

Contify and Fletcher/CSI conducted research back in 2020, on where companies gather information. 

This is the breakdown of their findings on how to consolidate your data:

Source: FletcherCSI

Here’s the fact - if you want fresh information you should go to the “source” - your sales team.  They're out there, in the field, talking to actual users and soon-to-be customers. That’s information you can’t find anywhere else.

The 30-for-30 Framework

Tracy Berry, Director of Intelligence at Freshworks (and previously a competitive strategy manager at ServiceMax and Automation Anywhere) uses a “30-in-30” framework.

What is that?

It’s scheduling 30 meetings with different stakeholders for 30 minutes. 

The goal is to see the situation of competitive intelligence in the company and see how you can help. 

These are the questions she asks:

  • What is your history of CI in the context of your role?
  • What’s working?
  • What is confusing?
  • What is broken?
  • What is missing/wishlist?
  • Off the record: If you had a magic wand, where would you wave it?
  • Consumption preferences and frequency of deliverables.

But that’s if your team already has a competitive intelligence function. A lot of mid-market tech companies are just establishing it and you need to get the information from your sales heads as fast and unfiltered as possible 

Questions for Sales Reps - The Dirty Dozen 

If your competitive intelligence department is still somewhat lacking - then you should rely on your sales teams for a constant flow of fresh intel. 

In-person or video interviews are the best to start with, but later on, you can switch to email surveys if you’d like. You don’t want to waste anyone’s time unless it’s important. 

And this definitely is important. 

Here are the questions we suggest at Grow + Scale — the dirty dozen - 12 questions to ask your sales teams to learn what they wish, what they need, and how you can best support them. 

Warning! It’s important to say to your interviewee that you’re looking for raw and unbiased answers. The interview is a safe space but you can only help them if they give you the whole truth and nothing but the truth. 

Feel free to adapt and edit these for your context!

  • Q1: Which competitors do you encounter most frequently in deals?
    This identifies primary competitors and refines focus.

  • Q2: What are the top objections or pushbacks you hear related to our competitors?
    Helps in crafting precise battlecards to counter objections.
  • Q3: What information about competitors do you wish you had during sales conversations?
    It shows exactly the gaping knowledge holes at the current situation. 
  • Q4: Do you feel our current competitive intelligence is accurate and up-to-date?
    You’re asking them to check the pain temperature of current conditions. If there’s no program yet, this is a good way to collect the ideas and wishes before building the program.
  • Q5: What type of content format do you prefer for competitive insights? (e.g., cheat sheets, slide decks, videos)
    Ensures delivery of competitive intelligence in easily digestible formats.
  • Q6: Can you share a time when a deal was won or lost because of competitive positioning?
    Gives you a look into real-world examples to base enablement materials on. You should also attend the sales meetings or listen to the recordings yourself.
  • Q7: What training or resources would help you confidently position against competitors?
    Find out what type would be the most useful for structuring effective training sessions and building better content for them. 
  • Q8: How often do you want updates on competitor movements or changes?
    Ask about the frequency wishes. You don’t want to bombard them every day but also you want to make sure your team gets fresh intel on the regular. This question will set expectations for how often you'll refresh and communicate updates.
  • Q9: What barriers do you face when trying to use competitive insights during a sale?
    Find out potential friction points when building your collateral. No matter how good your enablement content is - if it’s not going to be used it’s worse than nothing.
  • Q10: How do you currently track and share insights about competitors with the team?
    Slack messages back and forth or water cooler salty sessions? We need to change that - understand the existing communication channels and potential silos.

  • Q11: Which parts of the sales process do you feel are most impacted by competition?
    In most cases, those would be at the end stages of the deal but if your team is stacked against a competition at the start, then you should address it fast. This question will help you determine the critical stages in the sales cycle where competitive enablement can make a difference.
  • Q12: Are there specific tools or technologies you wish you had access to for better competitive positioning?
    Using the tools that are familiar is the easiest way to get the adoption from sales teams but they might be yearning for a tool that would make them easier as well. 

Treat these questions as open-ended sales questions - almost like you're the sales person on a discovery call. Let your sales rep speak and don't interrupt them when they go deep into their pain points. Ask follow-up questions to and note if there's genuine interest in what you're doing.

You might notice that new sales members are more incline in working with you than seasoned veterans. Based on enthusiasm you can build your first specialized "Yes Team" who will use your suggestions faster.

Even when you have a competitive intelligence program running, there's a huge value in a follow-up with your team members. As a CI professional, you're there to support them and make their job easier after all.

What’s Next?

Once you have your questions and answers, you’re sitting on a treasure chest of in-house collective knowledge. You’ve gathered and collected thoughts, objections, and impressions from your customer-facing teams. 

The next step is to consolidate it with your secondary research — the data you’ve found available on public pages - i.e. your competition websites, social media, and review aggregator pages. 

All this data is enough to kickstart the production of collateral your sales teams and other departments crave. Conduct a plan, prioritize the most glaring holes in your program, and figure out what’s the best way to measure the effectiveness (win/loss rates, sales confidence, or usage of CI materials are some suggestions). 

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