GUIDE 2024

Shadowing Your Sales Team

As product managers, we only succeed if our products are adopted. That means that we need to know both how to build amazing products as well as how to sell amazing products.

And what better way to know how to sell your product than to join your sales team on their calls?

When you join your sales team on calls, you’ll learn a couple of eye-opening insights. You’ll learn how prospects make decisions, how your salespeople position your product, and where the key gaps are in your product versus the competitive landscape.

These learnings are critical, because they drive tangible next steps on how to strengthen your product offering.
You can get involved with your sales team at varying levels of commitment. Generally speaking, there are three levels of commitment, starting from easiest to hardest:

  1. Shadowing
  2. Partnering
  3. Driving

I’ve broken these up into three separate articles, one for each level of commitment.

In each, I share best practices on how to be involved and tangible examples of how joining my sales team enabled me to build better products.

Then, in a fourth article, I provide a framework to enable you to decide whether you should join your sales team on calls, and what level of commitment to devote.

So, let’s kick off this series of articles, starting with shadowing!

Definition of Shadowing

First, what is shadowing? BusinessDictionary defines shadowing as “accompanying an experienced worker as they perform the targeted job.”

When you shadow, you play a supporting role, which gives you the opportunity to ask questions and to learn through experience.

I’ve personally found that the best way to shadow a sales call is to jointly prepare for the call, then to silently observe and take notes during the call, and finally to jointly debrief after the call.

Preparing for Shadowing

Start by asking one of your salespeople whether she would be comfortable with letting you shadow her.

Let her know why this is important to you. You want to strengthen the product by understanding how prospects think about your product, and you want to learn where the key product gaps are.

In my personal experience, I’ve found that salespeople are usually incredibly excited to have product managers join them on calls. If she’s not comfortable, ask her who she would recommend, then try asking that salesperson.

Once you’ve found a willing salesperson to work with, talk her through how you’re looking to participate.

Sit down with her to prepare for the call together. Ask her what she needs to make the call a success, and help her with her preparation by conducting research and gathering materials on her behalf.

In my experience, I’ve seen that preparing for a call involves the following:

  1. Gain context about the prospect
  2. Identify the prospect’s interests
  3. Determine relevant competitors
  4. Craft an agenda for the call

First, you need to understand the background of your prospect. Are they working at a large company or a small company? How do they make decisions? Are they actively looking for a new solution, or is this a cold lead? Ask your salesperson about what other attributes you should discover.

Then, you need to identify the prospect’s interests. Are they looking to save on costs? Grow their user base? Consolidate vendors? Strengthen their marketing presence? Compete against others in their market? Try to dig up more information about the prospect through Google searches and through publicly available research reports.

Next, you need to know what other products they are already using or are already considering, so that when you speak with the prospect, you can position your product in a favorable light.

Finally, you need to have a clear agenda for the call. What is your objective? Are you seeking to close them on this particular call, or just to open a conversation for them to consider a new product?

Join PMHQ’s community of product professionals to learn how others shadow their sales teams.

Joining the Call

When it’s time for the call, join your salesperson in person if possible. You’d be surprised at how much you can learn through observing body language!

Throughout the call, take notes. Here are a handful of questions that you should try to address in your notes.

  • What are the prospect’s goals? How does your salesperson conduct discovery?
  • Do competitors come up in conversation? If so, how does the prospect view competitors – favorably, neutrally, or unfavorably? How does the prospect bring up competitors in the first place?
  • How is the salesperson positioning the product? How do prospects perceive the product?
  • Where are prospects challenging the product? What existing objection handling is there? Does it seem to be effective?
  • How often does the product roadmap come up in sales calls?
  • Where does your salesperson seem to feel the most confident?
  • What kinds of questions make your salesperson tense up or feel uncomfortable?
  • How does your salesperson get to the next step with the prospect?
  • What kinds of commitments are being made by the prospect for next steps? What kinds of commitments are being made by your salesperson?
  • How does sales escalate issues to product? Where are issues being recorded?

Debriefing on the Call

Right after the call, debrief with one another – in other words, conduct a retrospective.

What does your salesperson feel went well, and where does she feel the call could have gone better?

How could the product team have better supported her in the call?

Did she feel that she was missing any collateral, key statistics, or talk tracks that the product team could have provided upfront?

Analyze how information from the sales team flows to the product team. What is the existing process? Are you getting all of the right information with the right context? If not, what sort of enhancements need to be made to the process?

What I Learned When Shadowing

When I was an associate product manager, I shadowed my sales team on their calls.

I gained incredible insight from these calls, because I was able to get a crystal-clear understanding of how our sales team defined our target audience.

I learned that particular kinds of leads were considered poor fits by the sales team and therefore were deprioritized, whereas other leads were considered strong fits.

I noticed that these lead definitions were more specific than what our product team had at the time, so I relayed that information back to our product team so that we could further narrow down our product focus.

On top of that, I could hear prospects talking through their concerns and their decision-making process. I noticed that they made decisions not based on which products had the best technical performance, but rather which one had the stronger brand name.

That insight enabled me to go back to my product team to push for stronger brand marketing efforts.

Furthermore, I found that we hadn’t equipped our sales team to handle product-oriented objections. Each salesperson came up with her own objection handling script, none of which were aligned with one another – which caused confusion for prospects, especially when they with multiple salespeople.

So, I started creating objection handling guides for the most common product objections that came up, and worked with sales managers to ensure that all of our salespeople had the same narrative.


Set aside time to shadow your sales team. It’s one of the fastest ways you’ll learn about your product, your competitors, and your customers.

Furthermore, your sales department is one of your strongest champions and one of your most critical stakeholders. Gaining empathy for them by working alongside them is a fantastic way to build better products.

In our next article in this series, we’ll talk through how to build off of your experiences in shadowing, and how to level up as a product partner on sales calls.

Have thoughts that you’d like to contribute around shadowing or around how to work with sales? Chat with other product managers around the world in our PMHQ Community!

Clement Kao
Clement Kao
Clement Kao is Co-Founder of Product Manager HQ. He was previously a Principal Product Manager at Blend, an enterprise technology company that is inventing a simpler and more transparent consumer lending experience while ensuring broader access for all types of borrowers.