prisoners of hope      

"At the start of the quarter, each sales rep ‘committed’ several deals that they were hopeful to win this quarter. Some deals won, but too many didn’t. If we understood which deals were shaky earlier in the sales process – and why – we could likely influence many of those deals. We should win some of them. But we need to lose some of these faster and refill the funnel with strong prospects faster."

Agony of Defeat         

“Most of our reps from time to time are shocked when a big deal they were counting on fails to win. These losses can really distract the reps and our management team.  I am sure in many of these cases there were signals that a deal had challenges, but we spent a lot of time spinning our wheels. I am sure that they could have used that time on other deals that were not getting enough attention. This lack of focus is costing us money.”

Impossible Impartiality 

“Our reps tend to prioritize their sales activities based on their gut feelings about which deals in their pipelines are most promising. We need to understand what our sales data is telling us about the opportunities in our pipelines and rely less on our gut feelings. If we do this, our 1 – 1 pipeline reviews will be more efficient and our reps will be positioned to focus on the deals that should close.”


Forces of nature

"We don’t hire salespeople. We hire forces of nature. They are all unique individuals, but they are all driven, motivated, competitive and successful – and we compensate them very well. But because they all bring unique skill sets we have found that our investments in general coaching and training have not shown any real ROI."

The Kpi conundrum

"We designed our talent KPIs to help maximize the efficiency of our managers by giving them data-driven insights into their reps. We have found that our KPIs force us to see reps who have probably “checked out,” but they really don’t position us to support the majority of our reps who are giving it their all. And we have too many reps who miss certain KPIs, but crush their quota."

Time well spent?

"We have weekly one-on-one coaching sessions between managers and reps. We want our managers to help our reps navigate to their quota. However, we are finding that these sessions usually revert to gut feeling discussions about the largest deals in the pipeline. Managers and reps both question the value of these sessions."


Breakdown of the roll-up

"My regional directors give me a rolled up forecast every week. They are using old, outdated KPIs and then massaging the result based on certain reps who they think are overly optimistic or pessimistic. It takes them a lot of time. We usually hit the target, but when we miss, we waste a lot of time trying to figure out what went wrong…and then go right back to what we were doing.”

If not now, when?      

"There were a few big deals that we won and in retrospect we knew they were going to win. Timing of these deals? We had no idea. We waste time guessing when deals will close and debating the ramifications of those close dates. Ideally that time would be reinvested in learning what we should do to reduce the cycle times on all of our deals."

Didn't see that one coming 

"We have a good handle on our pipeline, but every quarter there are deals that weren’t in the pipeline on Day 1 that come into the pipeline and close in the same quarter. We know that some of this is a result of reps sandbagging deals, but some of our products and some of our buyers have naturally short cycle deals. That number varies every quarter and we have no method to project these sales."


this time will be different

"We have tried everything to get our sales team to use our CRM system yet we still struggle to get adoption. Every six months at our sales kickoff meeting we stress the importance of the CRM. We have tried using cash incentives to get people to use it. We have tried penalizing people who don’t. However, when we get busy we never seem to enforce our own policies."

the trick question

"On more than one occasion a rep has asked the question, ‘What do you want me to do: Close business or enter data?’ It’s an easy answer for a new rep or a rep who hasn’t been at the top of the leaderboard. Unfortunately, it always seems to be the good reps who ask the question. I need reps to see the CRM as a system that needs good data to be useful, but I don’t want it to divert their attention too much.”

consistently inconsistent

"We want to use AI to improve our sales, but our data is a mess. Data management was never part of our company’s culture. We experienced so much change in the last decade – growth, acquisitions, leadership changes. We need to start from scratch and just hope for a couple years of consistency."