Pipeline Deep Dives

I wasn’t that slow. (Photo by Luca Ambrosi on Unsplash)

When I was about 8 years old, we used to play “Blind Man’s Bluff” in my house. This is “It” tag, with the person who is “It” wearing a blindfold.

This was an extremely fun game to play indoors. Especially for me, who was nicknamed Steven “Turtle” Ainslie by my older sister because I ran too slow to catch her in regular Chase Tag.

One day we were playing and my friend John was “It”.  After hearing us make a noise, he ran straight down the hall and into a wall, busting open his nose and bleeding all over the place. It was hilarious. We all fell down cracking up, even John. We iced him up and got back to the game.

Then I was “It”. I could hear everyone giggling in the dining room. I distinctly recall thinking,

“I’m not an idiot like John. I know exactly where the wall is and what I’m doing. I won’t run into it like he did.”

Then I ran full speed into the wall and split my head open.

When working to close their opportunities, our reps sometimes act like I did in Blind Man’s Bluff. They think they know the direction they’re going, but they’re about to veer off course and don’t even know it. 

This is where you can help them course correct with a Pipeline Deep Dive.

For an effective deep dive, it helps if you’ve already got a sales forecasting methodology, sales stages and a CRM in place.  If you don’t, I suggest you first read these posts: Perfect Forecasting and Is It Time to Move to a New CRM.

Dive Deep with Steven “Turtle”  Ainslie. (Photo by Jeremy Bishop on Unsplash)

The Inside Sales Dude Way to Do a Pipeline Deep Dive

I like to do these on sales floor, at each rep’s desk. That way other reps will overhear the conversation and will get their pipelines in order, before I get to them.

Just like with any coaching conversation, my goal here is to teach my reps what I expect, help them develop a process and then hold them accountable for the results.

  1. I’ll create a pipeline view for the rep that can be sorted by name, amount, stage, time in stage, last activity and age. It will look something like this:


2. We’ll start by looking at deals with a current QTR close date sorted by stage.

3. Then I’ll investigate each opportunity with the rep. I’ll ask questions like this:

  • Joe’s Hardware is new. Tell me about it. What’s the use case? How did you determine the budget is $5250? What are the next steps to move this forward to Eval? 
  • Home Depot  is your 2nd largest deal. They are notorious for dragging out the sales cycle. What’s their criteria and timeline for committing to a purchase? Who are you working with at HD? Is a partner involved? Have they agreed to do a pilot this quarter?  What is ur next step to move this forward?
  • Ace Hardware is in the EVAL stage? What do you think needs to happen to complete this successfully? Does the customer agree? What is your next action to take here?
  • Lowes will make or break your quarter. It’s your largest deal. But it’s been sitting at 60% for 2 months now and you haven’t spoken to them in 30 days. I’m concerned. What’s going on here?

For each opportunity, I’ll have the rep note in the CRM the next step and the date he will do it. That way he knows what to do when he looks at the Opp and in the next Deep Dive, we can see if anything was left undone. Sometimes, as we go through this investigation, we’ll move close dates, kill deals, or discuss additional info requirements so we can validate if this deal is still real.

4. I rarely will go through every deal with a rep. Instead, we’ll run through a few examples and then I’ll tell the rep “Now go through the rest of your pipeline and do this same process for all of your deals. Next week, I’ll want to see clear Next Steps with dates for each of these”. 

5. After 1 or 2 deep dives, every rep should have the hang of this. If someone is new to the team or is struggling, I’ll pair him with a senior rep to prepare for his next Deep Dive with me. This gives the senior rep the experience of coaching, bonds the team more, and gives the struggling rep a less intimidating coach than his boss. It always helps.

6. When we get rolling, every deep dive becomes a quick 15-30 minute discussion. We’ll cherry pick which deals to discuss. I’ll ask about large deals, key accounts, deals further along in the sales process etc. I’ll ask the rep if there are any deals he wants to discuss where he’s stuck or where he sees a bigger opportunity.

In the end, I am teaching each rep how to know his business and how to run his deals. Once he learns this, he can avoid running blindly into obstacles the way I did back when I was 8.

Teaching my reps how to do a Pipeline Deep Dive gives them a tool they can use throughout their sales career. It’s simple and effective. Just the way I like it.

For more on this, I recommend reading my post on Perfect Forecasting. It is a natural complement to the Deep Dive.

If you want my help building your sales team or improving sales, contact me here. I’d love to hear from you. 

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