- February 23, 2026
- Posted by: Dave Kurlan
- Category: Understanding the Sales Force
A Steely Dan tune came on the radio and it got me thinking about them as a band. In my opinion, they tried to be all things to all people. They integrated jazz chord changes (Deacon Blues), recorded some pure rock songs (Reelin’ in the Years), and even had some easy listening tunes (FM). They were a commercial success but not as respected as they could have been — or should have been — if they had catered to a single audience. Lack of targeting.
George Benson was a jazz guitarist who dared to cross over to popular music with his 1970s hit, “This Masquerade.” The jazz world crucified him for selling out. He was scarred for life. Al Jarreau had the same experience, and the scarring was so bad that when he played concerts he refused to sing his commercially successful songs.
Benson and Jarreau were both scarred for life.
Scarred for Actual Life
February 18, 2026 was the first anniversary of my being scarred for life from my quadruple bypass surgery. One year out, the only reminder I have is the scar down the middle of my chest — which reminds me to follow my dietary restrictions.
Scarred for Sales
There are a few ways we get scarred in sales.
Targeting How many times does the combination of ego and ideal customer profile have to bite us in the ass before we learn this lesson? Ego causes us to chase opportunities that are bigger than our target. I’ve made this mistake personally and by allowing the guys on my team to make it too. We’ve invested months and crazy amounts of time working to win 7-figure deals despite the fact that we never win 7-figure deals.
It happens when ego and hope meet at the crossroads of stupid and history. It’s especially stupid when you consider that the ideal Kurlan client has a 5-6 figure spend. It even happens with startups where ego prevents the team from walking away from 4-figure deals in the hope it will become a 5, 6, or 7-figure deal.
In my opinion, it’s just more of the same stupidity. Granted, our clients do include startups and multi-billion dollar corporations, but it’s the deal size that predicts whether it’s worth investing the time. When you come out on the losing side of those opportunities enough times, you are scarred for life and it won’t happen again.
Pipelines How many times do you need to be staring into an empty pipeline before you are scarred for life and won’t let it happen again? I remember my first time, sitting on the top step of an office building staircase, sobbing and feeling sorry for myself because I didn’t have any opportunities in the pipeline and had to return to cold-calling. How could I have let that happen? It happened again in 2001 during the internet bubble. Scarred for life. Can’t happen ever again.
Facilitating How many times must you show your prospect how willing you are to help them? You jump through hoops, do what it takes, revise your proposal and lower your price multiple times, only to lose the business. I haven’t done that but guys on my team have. My clients have. How many times must it happen before you are scarred for life?
Alignment This one might not apply to a lot of you but it applies to me, my team, my competitors, and my colleagues in the sales development space. How many times can you enter an agreement with a Sales Leader, only to learn that the sales leader’s priorities (and the work you were hired to do) are not in alignment with the priorities of the executive who signs the check? Surprise! Scarred for life.
The great thing about being scarred for life is that if you are smart, the things that caused you to get there will never, ever, happen again. Ever.
When companies keep their pipelines full of opportunities with companies that are in their sweet spot, and stop facilitating, their win rates improve, they increase their average sale or account size, improve their margin, and their sales cycle gets shorter.
Doesn’t that sound great?
But How?
That kind of sales transformation comes down to several factors:
- A staged, properly sequenced, milestone-centric, buyer-focused sales process that is appropriate for what they sell and who they sell it to
- Vastly improved ability to have great discovery calls with decision makers, where salespeople effectively uncover compelling reasons to buy
- Effective differentiation
- Thorough qualification
- Consistent, effective coaching from sales managers
- Accountability for change, KPI achievement, and quota achievement
If your sales team excels in those 6 areas, congratulations!
If there is room for improvement, that’s exactly where we come in. My team and I have helped hundreds of companies get properly scarred for life (in the best way possible) so they never make those painful mistakes again.
Want to see what that looks like for your team? Shoot me a note and we can have a conversation — no charge, no pitch, just straight talk.
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