Tag Archives: Pipeline

Detecting and Eliminating the Rolling Hairballs in your Sales Pipeline

Quick:  what’s the biggest deal in this quarter’s sales pipeline?  Was that the biggest deal in last quarter’s pipeline?  How about the quarter before?  Do you have deals in your pipeline older than your children?

If you’re answering yes to these questions, then you’re probably dealing with “rolling hairballs” in your pipeline.  Rolling hairballs are bad:

  • They exaggerate the size of the pipeline.
  • They distort coverage and conversion ratios.
  • They mess up expected-value forecasts, like a forecast-category or stage-weighted sales forecast.

Maybe they’re real deals; maybe they’re figments of a rep’s imagination.  But, if you’re not careful, they pollute your pipeline and your metrics.

Let’s define a rolling hairball

A rolling hairball is a typically large opportunity that sits in your current-quarter pipeline every quarter, with a close date that slips every quarter.  At 2 quarters it’s a suspected rolling hairball; at 3 or more quarters it’s a confirmed one.

Rolling Hairball Detection

The first thing you need to do is find rolling hairballs.  They’re tricky because salesreps always swear they’re real deals that are supposed to finally close this quarter.  What makes rolling hairballs obvious is their ever-sliding close dates.  What makes them dangerous is their size (including an accumulation of them that aggregate to a material fraction of the pipeline).

If you want to find rolling hairballs, look for opportunities in the current-quarter pipeline that were also in last-quarter’s pipeline.  That will find numerous bona fide slipped deals, but it will also light-up potential rolling hairballs.  To determine if an opportunity is  a rolling hairball, for sure, you can do one of two things:

  • See if it also appeared in the current-quarter pipeline in any quarters prior to the previous one.
  • Look at its stage or forecast category.  If either of those suggest it won’t be closing this quarter, it’s another big hairball indicator.

The more sophisticated way to find them is to examine “stuck opportunity” reports that light-up deals that are moving through pipeline stages too slowly compared to your norms.

But typically, the hairball is a big opportunity hiding in plain sight.  You know it was in last quarter’s pipeline and the quarter before that.  You’ve just been deluded into believing it’s not a hairball.

Fixing Rolling Hairballs

There are two ways to fix rolling hairballs:

  • Fix the close date.  Reps are subtly incented to put deals in the current quarter (e.g., to show they’re working on something, to show they might bring in some big sales this quarter). The manager needs to get on the phone with the customer and, after having verified it’s a real opportunity, get the real timeframe in which it might close.  Assigning a realistic close date to the opportunity makes your pipeline more real and reminds the rep that they need to be working on other shorter-term opportunities as well.  (There is no mid-term if you fail enough in the short term.)  The deal will still remain in the all-quarters pipeline, but it won’t always be in the current-quarter pipeline, ever-sliding, and distorting metrics and ratios.

 

  • Fix the size. While a realistic close date is the best solution, what makes rolling hairballs dangerous is their size.  So, if the salesrep really believes it’s a current-quarter opportunity, you can either reduce its size or split it into two opportunities (particularly if that’s a possible outcome), a small one in the current quarter along with an upsell in the future.  Note that this approach can be dangerous, with lots of little hairball-lets flying below radar, so you should only try if it you’re sure your salesops team can produce the reports to find them and if you believe it reflects real customer buying patterns.

Don’t let rolling hairballs pollute your pipeline metrics and ratios.  Admit they exist, find them, and fix them.  Your sales and sales forecasting will be more consistent as a result.

How to Train Your VP of Sales to Think About the Forecast

Imagine a board meeting.

Director:  What’s the forecast for new ARR this quarter?

Sales VP:  $4.3M, with a best case of $5.0M.

Director:  So what’s the most likely outcome?

Sales VP:  $4.3M.

Director:  What are you really going to do?  (The classic newb trap question.)

Sales VP:  I think we can come in North of that.

Director:  What’s the worst case?

Sales VP:  $3.5M.

Director:  What are the odds of coming in at or above the forecast? 

Sales VP:  I always make my forecast.

Director:   What do you mean by worst case?

Sales VP:  You know, well, if the stars align in a bad way – a lot of stuff would have to go wrong – but if that happened, then we could end up at $3.5M.

Director:  So, let’s say a 10% chance of being at/below the worst case?

Sales VP:  I’d say more like 5%.

Director:  What do you mean by best case?

Sales VP:  Well, if we really struck it rich and everything lined up just the way I wanted, that would be best case.

Director:  You mean if all the deals came in — so best case basically equals pipeline?

Sales VP:  No, that never happens, I’ve made about 10 scenarios of different deal closing combinations and in 2 of them I can get to the best case.

You see the problem?  Does it sound familiar?  Do you realize how much time we spend talking in board meetings about “forecast,” “best case,” and “worst case” without every discussing what we mean by those terms?

Do you see how this is compounded by the sales VP’s natural, intuitive view of the outcomes?  Do you see the obvious mathematical contradictions?  “I always make my forecast” says it’s a 100% number, but then the VP says it’s the “most likely” number which implies 50%.  Then the VP says there’s a 5% chance of coming in at/less than worst case (which is much lower) and then kind of implies that there’s a 20% chance of beating best case – but the 2 out of 10 is meaningless because it’s not a probability, it’s just a count of scenarios.  Nothing adds up.

The result is, if you’re not careful, the board ends up counting angels on pinheads.  What can we do to fix this?  It’s simple:  teach (and if need be, force) your sales VP to think probabilistically.  Ask him/her how often:

  • It is reasonable to miss the forecast.  A typical answer might be 10%.
  • It is likely to come in at/below the worst case? Typical answer, 5%.
  • It is likely to meet/beat the best case? Typical answer, 20%.

So, with those three questions, we’ve now established that we want the sales VP to give us:

  • A 90% number on being at/above the forecast
  • A 20% number on being at/above the best case
  • A 5% number on being at/below the worst case

Put differently, when the sales VP decides what number to forecast that they should be thinking:

  • I should come in under my forecast once every 2.5 years (10 quarters).
  • I should hit/beat the best case about once every 5 quarters (a bit less than once a year).
  • I should come in/under the worst case once every 20 quarters (once every 5 years, or for most minds, basically never).

The beauty here is that when you work at a company a long time you can get enough quarters under your belt, to start really seeing how you’re doing relative to these frequencies.  What’s more, by converting the probabilities into frequencies (e.g., once every 10 quarters) you make it more intuitive for the sales VP and the organization to think this way.

In addition, you have a basis for conversations like this one which, among other things, is about overconfidence:

CEO:  You need to work on your forecasting.

Sales VP:  You know it’s hard out there, very competitive, and we don’t have much deal flow.  Back when I was at { Salesforce | Oracle | SAP }, I was much better at forecasting because we had more volume.

CEO:  But we agreed your forecast should be a 90% number and you’ve missed it 2 out of the past 4 quarters.

Sales VP:  Yes, but as I’ve said it’s tough to forecast in this market.

CEO:  Then forecast a lower number so you can beat it 90% of the time.  I’m asking you for a 90% number and empirically you’re giving me a 50% number. 

Sales VP:  OK.

CEO:  Plus, when those two big deals slipped last quarter you didn’t drop your forecast, why?

Sales VP:  Because where I grew up, you don’t cut the forecast.  You try like crazy to hold it.  Do you know the morale problems it causes when I cut the forecast – especially if it’s below plan? So, yes, when those two deals slipped it added more risk to the forecast – and I told you and the board that — but I didn’t cut forecast, no. 

CEO:  But “adding risk” here is meaningless.  In reality, “adding risk” means it’s not a 90% number anymore.  You’ve taken what was a 90% number and it’s now more like a 60% or 70% number.  So I want you to forget what they taught you growing up in sales and always – every week – give me a number that based on all available information you are 90% sure you can beat.  If that means dropping the forecast so be it.

sales forecast

This also helps with the board and the inevitable sandbagger issue.  In my experience (and with a bit of exaggeration) you always seem to be in one of two situations:  (1) intermittently missing plan and in trouble or (2) consistently making plan and a “sandbagger” – it feels like there’s nothing in between.

Well, if you establish with the board that your company forecast is a 90% number it means you are supposed to beat it 9 times out of 10 so you can only really be labelled a sandbagger when you’re 15 for 15 or 20 for 20.  It also reminds them that you’re supposed to arrive at the forecast so that you miss once every 10 quarters so they shouldn’t freak out if once every 2.5 years if that happens — it’s supposed to happen in this system.  (Just don’t let a once-in-ten-quarter event happen twice in a row.)

I like this quantitative basis for sales forecasting and I carry it down to the salesrep and pipeline level.  I believe that each “forecast category” should have a probability associated with it.  For example, at the opportunity level, you should link probabilities to categories, such as:

  • Commit = 90%
  • Forecast = 70%
  • Upside = 30%

This, in turn, means that over time, a given salesrep should close 90% of their committed deals, 70% of their forecast deals, and 30% of their upside.  Deviations from this over time indicate that the rep is mis-categorizing the deals because the probability should be the basis for the forecast category assignment [1].

Finally, I do believe that salesreps should give quarterly forecasts [2] that reflect their sense for how things will come in given all the odd things that can happen to deals (e.g., size changes, acceleration, slippage).  I believe those forecasts should be a 70% number because the sales manager will be managing across a  portfolio of them and while there is little room for a company to miss at the VP of Sales level, there is more room for and more variance in performance across salesreps.

While I know this will not necessarily come naturally to all sales VPs — and some may push-back hard — this is a simple, practical, and rigorous way to think about the forecast.

# # #

[1] Some people do this through an independent (orthogonal) field in the CRM system called probability.  I think that’s unnecessary because in my mind forecast category should effectively equal probability and your options for picking a probability should be bucketed.  No one can say a deal is 43% vs. 52% and forecast category doesn’t indicate some probability of closing, then … what use is it and on what basis should you classify something as forecast vs. upside?

[2] Some people believe that only managers should make forecasts, but I believe both reps and managers should forecast for two reasons:  (1) provided it’s left independent and not “managed” by the managers, the aggregated salesrep-level forecast provides another, Wisdom of Crowds-y, view into the sales forecast and (2) it’s never too early to teach salesreps how to forecast which is best learned through the experience of trial and error over many quarters.

The Evolution of Marketing Thanks to SaaS

I was talking with my friend Tracy Eiler, author of Aligned to Achieve, the other day and she showed me a chart that they were using at InsideView to segment customers.  The chart was a quadrant that mapped customers on two dimensions:  renewal rate and retention rate.  The idea was to use the chart to plot customers and then identify patterns (e.g., industries) so marketing could identify the best overall customers in terms of lifetime value as the mechanism for deciding marketing segmentation and targeting.

Here’s what it looked like:

saas-strategic-value

While I think it’s a great chart, what really struck me was the thinking behind it and how that thinking reflects a dramatic evolution in the role of marketing across my career.

  • Back two decades ago when marketing was measured by leads, they focused on how to cost-effectively generate leads, looking at response rates for various campaigns.
  • Back a decade ago when marketing was measured by opportunities (or pipeline), they focused on how to cost-effectively generate opportunities, looking at response and opportunity conversion rates.
  • Today, as more and more marketers are measured by marketing-sourced New ARR, they are focused on cost-effectively generating not just opportunities, but opportunities-that-close, looking all the way through the funnel to close rates.
  • Tomorrow, as more marketers will be measured on the health of the overall ARR pool, they will be focused on cost-effectively generating not just opportunities-that-close but opportunities that turn into the best long-term customers. (This quadrant helps you do just that.)

As a company makes this progression, marketing becomes increasingly strategic, evolving in mentality with each step.

  • Starting with, “what sign will attract the most people?” (Including “Free Beer Here” which has been used at more than one conference.)
  • To “what messages aimed at which targets will attract the kind of people who end up evaluating?”
  • To “who are we really looking to sell to — which people end up buying the most and the most easily – and what messages aimed at which targets will attract them?”
  • To “what are the characteristics of our most successful customers and how can we find more people like them?”

The whole pattern reminds me of the famous Hubspot story where the marketing team was a key part forcing the company to focus on either “Owner Ollie” (the owner of a <10 person business) or “Manager Mary” (a marketer at a 10 to 1000 person business).  For years they had been serving both masters poorly and by focusing on Manager Mary they were able to drive a huge increase in their numbers that enabled cost-effectively scaling the business and propelling them onto a successful IPO.

hubspot

What kind of CMO does any CEO want on their team?  That kind.  The kind worried about the whole business and looking at it holistically and analytically.