5 Sales Leadership #worstpractices When Times Get Tough

Jun 21, 2023 | Blog

5 Sales Leadership #WorstPractices When Times Get Tough

“The importance of sales management depends upon the importance of the field selling job.”

“Prior to 1907, most personal salesmen sold barehanded. it was comparatively easy to sell merchandise in the field. Sales management was haphazard and hit-or-miss, because field selling was generally smooth-sailing.”

– Quotes from 1909’s book, Sales Management

Now, replace “Prior to 1907” with “Between the Fall of 2020 and mid-2022” and read this again.

I’m not much of a pot-stirrer, but I do have a spoon.

So many of the issues we’re blaming the field for – and I’m hearing on the daily – are actually leadership issues. Tasked with doing “more with less”, are we actually executing strategies that result in doing “much less with less”? We’re asking the field to be more productive and effective, but we tend to be doing things that are actually making that harder!

1) Casting a wider net:

If on a given day a rep is calling on ten different industries and five different buyer personas, there’s zero chance of them being more effective.

Do the opposite! Do firmographic sprints

Pick a vertical where you’re seeing some success. Focus on it for a few weeks. Bring in industry experts and/or customers from that verticle for a session with the team. Ask them (a) what’s top of mind right now in their business & role, (b) how they’re measured and how it’s going, (c) where they go to get smarter about their industry, business and role, and (d) ask them if you can see their inbox…what stands out and what doesn’t. 

You’ll find their confidence goes up…and confidence is contagious. Their empathy to outcomes will go up, too, which leads to short-term and long-term revenue growth. They’ll be seen as advisors and consultants instead of a necessary evil. Win rates will go up. Cycle lengths will shorten. Time to loss will go down, too…as qualification in and out will become more efficient. Try it! Then, expand out slowly. 

2) Cutting investments in enablement & training:

In so many cases I’m seeing & hearing, we’re placing the burden of skill & process optimization on the leaders themselves..whatever is in their head is what we’re going with. My business has experienced a palpable shift…small companies have stopped investing. However, larger companies are investing MORE! 

  • Sales Melon LLC revenue from companies under $100M in revenue: First 6 months of 2022 = 51% | First 6 months of 2023 = 20%
  • Sales Melon LLC revenue from companies over $1B in revenue: First 6 months of 2022 = 26% | First 6 months of 2023 = 59%
  • Number of clients: First 6 months of 2022 = 22 | First 6 months of 2023 = 11%
  • Revenue? Almost flat year-over-year

Go get a Sales Assembly membership for your team and take advantage of everything! Call me…or one of the many people who study revenue optimization as a life focus.

3) “The beatings will continue until morale improves” cultures:

If your team is concerned about their jobs, they’re not sleeping as well. When they don’t sleep as well, they don’t perform as well, they’re less creative, and at least part of their time is CYA keeping their eyes out for their next job.

Invest time in understanding the science of intrinsic inspiration – what actually drives your teams to stay, do their best, thirst for learning, perform, and advocate for you, your company and your customers!

4) Top Grading

“Our sales team isn’t cutting it – and there are many salespeople on the market. Let’s top-grade!”

Let’s think about this one for a minute. You’re missing short-term targets. You believe a large portion of the team is the problem. You begin to invest the time, resources, and opportunity cost in recruiting in hopes you can find “better” salespeople. How long does it take to find, hire, on-board, and see the fruits of that labor? Six months? A year? Or, are you just looking for an excuse to tell your boss and the board? 

If your team has said “thirst for learning”, you’re 95% of the way there! Invest in that learning. If they don’t have that thirst, find it…create it…and if it doesn’t come up, then consider tactical flips. But only then! Water those seeds! 

5) “Clear ROI or Bust” Thinking

I commented on a LinkedIn post this morning from Jeff Rosset saying that CEO’s prevailing thought on everything right now is,

“I am not willing to pay for anything that doesn’t drive clear ROI.”

Smart growth…yes! However…

I’m seeing leaders take this point to an extreme. When they say, “I am not willing to pay for anything that doesn’t drive clear ROI“, they’re eliminating the investments in enablement…teams, training, etc. CEOs (I had one I had to convince was incorrect once) and boards tend to see the line between what they often consider “overhead” and optimization as too squishy (versus “clear”) to the ROI.

Throughout history, the tighter the market, the more important every element of your revenue engine is optimized. With every opportunity that your team is working on finding, developing, cultivating and/or closing right now, it will never be any earlier than right now.

There are so many more…injecting automatic price increases into contracts, cutting travel budgets entirely (when the competitors are still seeing their prospects and your customers), etc.

So, I’ve now stirred the pot a little. What do you think?

At the very least, be careful out there! And remember, there are so many incredible resources out there to help. If you need some help – even if that just means talking to your CFO about this, happy to provide some ideas!


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I speak and teach revenue organizations on how to leverage transparency and decision science to maximize their revenue capacity. It’s what I do…teach sellers, their leaders, and really entire revenue organizations the how we as human beings make decisions, then how to use that knowledge for good (not evil) in their messaging (informal and formal), negotiations and revenue leadership. I wrote a 3x award-winning book (𝘛𝘩𝘦 𝘛𝘳𝘢𝘯𝘴𝘱𝘢𝘳𝘦𝘯𝘤𝘺 𝘚𝘢𝘭𝘦), and have a newish book out (𝘛𝘩𝘦 𝘛𝘳𝘢𝘯𝘴𝘱𝘢𝘳𝘦𝘯𝘵 𝘚𝘢𝘭𝘦𝘴 𝘓𝘦𝘢𝘥𝘦𝘳) now that just won its first award!

Reach out if you want to discuss The Transparency Sale sales methodology, or really…anything else (sales kickoffs, workshopskeynotes, the economy, history, etc.)! Email info@toddcaponi.com or call 847-999-0420.

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