Category Archives: Management

Don’t Let Product Management Turn Into “The Roadmap Guys”

At many enterprise software companies product management (PM) ends up defaulting into a role that I can’t stand:  The Roadmap Guys*.

Like a restaurant with one item on the menu, the company defaults into ordering one thing from product management:  a roadmap pitch.

  • “The VP of PM is in Boston and Providence this week, can she visit some customers and do a few roadmap presentations?”
  • “Hey, there’s a local user group in NY this week; can PM do a roadmap pitch?”
  • “There’s a big customer in the executive briefing center today; can the PM do a roadmap?”
  • “As part of our sales cycle with prospect X, we’d love to get PM in to discuss the roadmap.”
  • “We’ve got a SAS day with Gartner next week, can PM come in a present the roadmap?”

You hear it all the time.  And I hate it.  Why?

From a sales perspective, roadmap presentations are the anti-sales pitch:  a well organized presentation of all the things your products don’t do.  Great, let’s spend lots of time talking about that.

From a competitive perspective, you’re broadcasting your plans.  If you’re presenting roadmap to every prospect who comes through the briefing center and at every local user group meeting, your competition is going to learn your roadmap, and fast.  Then they can copy it and/or blunt it.

But what irks me the most is what happens from a product management perspective:  you turn PM into “the talking guys” instead of “the listening guys.”  Given enough time, PM starts to view itself as the folks who show up and pitch roadmaps.

But that’s not their job.

PM should be the listening folks, not the talking folks.  Just like sales, PM should remember the adage:  we have two ears and one mouth; use them in proportion.

Wouldn’t the world be a better place if we changed the five previous bullets as follows?

  • “The VP of PM is in Boston and Providence this week, can she visit some customers and observe how people actually use the product?”
  • “Hey, there’s a local user group in NY this week; can PM break off a small focus group to ask customers about how they use the product?”
  • “There’s a big customer in the executive briefing center today; can PM come in and interview them about their impressions on evaluating the product?”
  • “As part of our sales cycle with prospect X, we’d love to get PM in to discuss what specifically they are trying to accomplish and how the product can do that?”
  • “We’ve got a SAS day with Gartner next week, can PM come in and hear from Gartner about what they’re seeing in the market and in their interactions with customers?”

So every time you hear the word “roadmap” in the same sentence as “product management,” stop, pause, and think of a better way to use the PM team.  Sure, there are certainly times when a roadmap presentation is in order.  But don’t default to it.  Keep your PM team listening instead of talking.

# # #

* I’m using “guys” here in a gender-neutral sense like “folks.”

Kellblog (Dave Kellogg) Featured on the Official SaaStr Podcast

Just a quick post to highlight the fact that last week I was the featured guest on Episode 142 of the Official SaaStr  podcast produced by the SaaStr organization run by Jason Lemkin and interviewed by a delightful young Englishman named Harry Stebbings (who also runs his own podcast entitled The Twenty Minute VC).

In the 31-minute episode — which Harry very nicely says was “probably one of his favorite interviews to record” — we cover a wide range of my favorite topics, including:

    • How I got introduced to SaaS, including my experience as an early customer of Salesforce in about 2003.
    • Challenges in scaling a software business, learned at BusinessObjects as we scaled from $30M to $1B in revenues, as well as at MarkLogic and Host Analytics.
    • My favorite SaaS metric.  If you had to pick one, I’d pick LTV/CAC.
    • Why simple churn is the best way to value the annuity of a SaaS business.
    • The loose coupling of customer satisfaction and renewal rates.
    • Why SaaS companies need to “chew gum and walk at the same time” when it comes to driving the mix of new and renewal business.
    • User-based vs. usage-based pricing in SaaS and how the latter can backfire in disincenting usage of the application.
    • My thoughts on bookings vs. ARR as a SaaS metric.  (Bookings is generally seen as a four-letter word!)
    • Why SaaS companies should make “the leaky bucket” the first four lines of their financial presentation.
    • Why I think it’s a win/win when a SaaS company gives a multi-year prepaid discount that’s less than its churn rate.
    • Why I view non-prepaid, multi-year deals as basically equivalent to renewals (just collected by finance/legal instead of customer success.)
    • Why it’s OK to “double compensate” sales and customer success on renewals and incidental upsells, and why it’s OK to pay sales on non-incidental upsells to existing customers (don’t put your farmer against someone else’s hunter).
    • Why you can’t analyze churn by analyzing churn and why you should have a rigorous taxonomy of churn.
    • My responses to Harry’s “quick fire” round questions.

You can listen to the podcast via iTunes, here.  Enjoy!

 

Are You a “Challenging” or Simply a “Difficult” Direct Report?

Most managers, save for true sycophants, want to challenge their boss.  Few managers want to be puppet yes-people to the boss.  They’ve worked hard to get where they are.  They bring years of wisdom and experience.  They want to push and challenge.  But many don’t know when or how.  More importantly, they don’t know what they don’t know.

How often do you think you’re challenging the boss when he/she thinks you’re just being plain difficult?  Challenging direct reports keep their positions and rise with the organization.  Difficult ones get jettisoned along the way.

There are two great ways you can figure out how often you’re being which:

  • Think of things from the boss’s perspective
  • Ask the boss

Think from the Boss’s Perspective

Bosses want to get things done.  Things generally fall into two buckets:  easy and hard.  Easy things may still entail a lot of work and planning, but there’s nothing really conceptually difficult or unknown about them.

Running the company’s presence at a tradeshow you attend every year might be a lot of work, but I’ll consider it easy for this conversation because that work is known.

Deciding to terminate a problem employee is easy.  (Note inclusion of word “problem.”)  If you see a problem, the adage goes, everyone else has probably already seen it for months and the damage done is more than you know.  This decision is hard from a personal perspective — I’ve never met anyone who enjoys terminating people.  But firing someone who routinely misses deadlines, training sessions, and team meetings isn’t hard in this context.

Launching the new version of a product is easy.  Yes, the positioning may be hard, but managing the overall launch process is easy.   It’s hopefully done a few times per year.  Yes, it’s a lot of work and planning, but there’s nothing conceptually difficult about running the process.

Difficult direct reports make easy things hard.  How?

  • Complexification.  When you ask someone the time you discover that there are three types of people in the world:  those who tell you the time, those who tell you how to build a watch, and those who tell you how to build a Swiss village.  Simplifiers go far in organizations, complexifiers get stuck.
  • Lack of follow through.  Bosses want to talk once about a project, agree to it, and then have it get executed.  As my friend Lance Walter always said bosses want “set it and forget it” direct reports.  If you have a question, come ask.  But otherwise I assume you are tracking our agreed-to objectives and they’re going to happen without me having to check and re-check.  Ditto for feedback given along the way.
  • Drama.  Difficult directs tend to take things personally.  They turn criticism of work into criticism of them.  They view a heavy workload as dramatic sacrifice and not a prioritization problem.  They are sensitive to criticism, defensive when questioned or given feedback, and often unable to separate bad performance from bad intent.

The result is that over time the boss starts to loathe the idea of meeting with the direct report which results in a downward spiral of communication and relationship.

Challenging direct reports keep easy things easy.  They get shit done without a lot of supervision, complexification, or drama.  On the flip side, challengers don’t just go along for the ride when it comes to inherently hard things like fixing a break in the sales pipeline, selecting company or product strategies, or working on a competitive campaign strategy.  They weigh in, sometimes challenging the majority or consensus view.  They provide good arguments for why what everyone else is thinking could be wrong.  Their selective Devil’s advocacy helps the company avoid groupthink and the organization make better decisions.  And they do this without going overboard and positioning themselves as the resident contrarian.

Simply put, when you say something to the boss or in a meeting, imagine how the boss will react and then count the ratio between the following two reactions

  • God, what a pain in the ass.
  • Wow, I hadn’t thought of that.

Ratios above 1.0 indicate you are a net difficult direct report.  Ratios below 1.0 indicate you are a net challenger.

Ask the Boss

Since knowing is always superior to guessing, I’ll give you a set of good questions that can help you figure out where you stand.

  1. If you had to rank your direct reports from top to bottom in terms of difficultly, would I fall above or below the median and why?
  2. Can you please list 3-5 things I do that make it difficult to manage me so I can work on them?
  3. To what extent do you find me difficult/contrarian for difficulty’s sake vs. genuinely challenging ideas and helping the company reach better decisions?
  4. When it comes to strategic debates do you feel that I sit on the sidelines too much, participate too much, or strike a good balance?
  5. If there is a pattern of skipped/cancelled 1-1’s (a sign of avoidance) or higher frequency 1-1’s with other directs, then ask why?

Sycophants know they are sycophants.  Challengers usually know they are challengers.  The risk is that you are a difficult when you think you’re a challenger — and that rarely ends well.  So think about, ask, and take appropriate measures to correct the situation.  Before your boss doesn’t want to talk to you anymore.

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 be Passionate without Being Self-Righteous

I can easily think of a dozen cringe-worthy times in my career when I look back and say, “wow, I must have appeared to be a self-righteous idiot when I said thing X.”  Let me thank anyone on the receiving end of those statements for their patience.  I now get it; I understand.

Look, I’m all for passion in business.  I’m all for speaking up.  One day I’ll write a book called “Management by 1970s Bumper Stickers” and the first chapter will be on this sticker:

questionauthority

I enjoy questioning authority — ask any of my old bosses. As CEO, I like being questioned.  Good CEOs don’t fear questioning because you typically end up in one of two cases:

  • The point raised has already been considered in making the decision, and explaining the rationale behind that helps the organization understand the decision and increase buy-in to it.
  • The point raised has not already been considering in making the decision and results in either changing or not changing the decision. Either way, the decision is better because we either find a better decision or another reason to support the existing one.  (As long as you beware confirmation bias.)

As CEO, your job is to get the right answer and make the best decisions, not to think everything up yourself.  Pride of authorship should have no place in CEO decision making.

Most people get questioning correctly.  They don’t assume things.  They’re not accusatory.  The simply ask the question that’s on their mind without a whole lot of overtone.  Every once in a while, however, I find someone who gets it all wrong and appears, as I did back in the day, to be self-righteous and dumb.

Let’s start with an example from one of my favorite old sci-fi movies, Soylent Green.

 

What a great scene.  But imagine if everyone knew that already.  Imagine how stupid you’d sound if you were delivering all those messages with all that same drama.

Imagine Hatcher saying, “Yes, yes, Detective Thorn, everybody knows that.  And boy are they tasty.”

You’d look pretty self-righteous.  And you’d look pretty dumb.  What rock did he crawl from under?  Everybody knows that Soylent Green is made out of people.

So what’s the best way to question authority?  Here are some tips.

  • Assume there is information that you can’t be told.  “We need to buy company X, why can’t anyone else see how critical that is, why won’t anyone listen to me?”  Now imagine the company tried to buy company X last quarter and they wanted 3x more than we could pay.  But no one can tell you that because the whole thing is under non-disclosure agreement.  Should you raise the point?  Sure.  Ask the question respectfully and lose the assumption (and overtone) that you are being ignored.

 

  • Assume there is personnel information that you don’t know.  “The HR department is failing and nobody over there can get the job done — why isn’t anyone doing anything about this, and why won’t anyone listen to me.”  Now imagine that the HR manager is already on a performance plan and 30 days from being terminated.  No one could ever tell you that.

 

  • Assume there is a bigger picture conversation that you’re not privy to.  “Why are we giving the new head of Engineering control over Product Management and making the job EVP of Products instead of SVP of Engineering?  Product Management was working fine, we don’t need to make this change, why won’t anyone listen to me.”  Now imagine the company has been struggling to hire a new head of engineering, the CEO is under big pressure to do so, and an extremely well qualified Engineering candidate won’t join unless he also gets Product Management.  No one’s going to tell you that in a Q&A forum.

 

  • Don’t ignore constraints.   Some of the most self-righteous rants I’ve heard completely ignore practical constraints on the business like a lack of talent, a lack of money, the need to keep paying customers happy, or product constraints related to compatibility.  Now, yes, sometimes great breakthroughs happen when people challenge constraints — but never pretend they don’t exist.  It’s not a great strategy for our company if we can’t execute it.  Maybe it’s a great strategy for some other company, maybe not.

 

  • Don’t trivialize execution.  Ideas are easy.  Execution is hard.  So when asking questions about ideas, don’t act as if they are free or if we could just get started with two people.  Yes, sometimes, great things start out with tiny investments — a $60K outsourced Twitter connector ended up serving as the genesis of Salesforce’s huge Social Enterprise strategy.   But often projects just end up dead because they were never properly resourced in the first place.  Execution is hard.

 

  • Don’t forget biases introduced by your personality type.  I stumbled into this great post the other day, What Everyone Desperately Wishes You’d Stop Doing, Based On Your Myers-Briggs Personality Type, and I just love the entry for ENFP — “Expecting everyone to be as excited as you are about today’s new BIG EXCITING PLAN when we all know you’ll have forgotten all about it by this time tomorrow.”  Look, some people are natural executors and others are natural idea generators.  Know which you are in assessing if you’re being ignored.  Is authority refusing to be questioned, or do you just have 10 ideas a day in a startup environment when the company needs to focus on one or two?

 

  • Don’t be naive.  Bob Waterman, co-author with Tom Peters of the legendary In Search of Excellence, was on our board at ASK, and one day he came down to hang out with the troops at the Friday beer bash.  I remember asking him (before I got my MBA) something akin to, “do you really believe all these green Harvard and Stanford MBAs should run companies or would businesses be better if everyone worked their way up.”  The man had an MBA from the Stanford and worked at McKinsey.  He must have thought I was the biggest idiot on Earth.  My spider-sense told me I’d done something wrong.  It was right.  He muttered something and walked away.   An opportunity wasted due to naivete.

I’m a big believer that the more someone knows about how a decision got made, the more they will agree it.  That’s why, as part of my management style, I spend a lot of explaining decisions to people.

That dumb corporate decision to prioritize X over Y might make more sense to you if you knew all the circumstances about how it got made.  Sometimes there’s a missing piece to the puzzle that makes everything make sense.  Sometimes you can be told about that missing piece.  Other times, you cannot.  But don’t assume it doesn’t exist, nor trivialize matters of focus and execution.

 

Blocking the End Run: Eleven Words to Reduce Politics in Your Organization

People are people.  Sometimes they’re conflict averse and just not comfortable saying certain things to their peers.  Sometimes they don’t like them and are actively trying to undermine them. Sometimes they’re in a completely functional relationship, but have been too darn busy to talk.

So when this happens, how do you — as a manager — respond?  What should you do?

“Hey Dave, I wanted to say that Sarah’s folks really messed up on the Acme call this morning.  They weren’t ready with the proposal and were completely not in line with my sales team.”

Do you pile on?

“Again?  Sarah’s folks are out of control, I’m going to go blast her.”  (The “Young Dave” response.)

Do you investigate?

“You know my friend Marcy always said there are three sides to every story:  yours, mine, and what actually happened.  So let me give Sarah a call and look into this.”

Do you defend?

“Well, that doesn’t sound like Sarah.  Her team’s usually buttoned up.”

In the first case, you’re going off half-cocked without sufficient information which, while emotionally satisfying in the short-term, often leads to a mess followed by several apologies in the mid-term.  In the second case, you’re being manipulated into investigating something when perhaps you were planning a better use of your time that day.  In the third case, you’re going off half-cocked again, but in the other direction.

In all three cases, you’re getting sucked into politics.  Politics?  Is it really politics?  Well, how do you think Sarah is going to feel in when you show up asking a dozen questions about the Acme call?  She’ll certainly consider it politics and, among other things, there’s about a 98% chance that she will say:

“Gosh, I wish Bill came and talked to me first.”

At which point, if you’re like me, you’re going to say:

“No, no, no.  I know what you’re thinking.  Don’t worry, this isn’t political.  It’s not like Bill was avoiding you on this one.  He just happened to be talking to me about another issue and he brought this up at the end.  It’s not political, no.”

But can you be sure?  Maybe it just did pop into Bill’s mind during the last minute of the other call.  Or maybe it didn’t.  Maybe the reason Bill called you was a masterfully political pretext.  Can you know the difference?

So what do you say to Bill when he drops the comment about Sarah’s team into your call?  The eleven words that reduce politics in any organization:

“What did Sarah say when you talked to her about this?”

[Mike Drop.]

# # #

(Props to Martin Cooke for teaching me the eleven words.)

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 noob 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.