Dear Mike,

Sorry, Robert Frost fans. I'm not taking the road less traveled in 2024, I'm taking the road less stupid.

How so? Read on...

Avoid the Dumb Tax

One of my favorite business books is "The Road Less Stupid", by Keith Cunningham. It talks about the many dumb mistakes we make as business owners, and how to prevent them.

I see sales organizations make three preventable mistakes year after year. Here's what they are, and more importantly, how to prevent them.

#1: Not Expecting Employee Turnover

Turnover in the technology industry is brutal yet predictable. Sales turnover across our industry is over 30% per year. It's worse for new hires. Some surveys show over 70% of newly hired salespeople quit or are fired in less than 12 months. Turnover of engineering is more variable, spiking higher or lower than 30% depending on the year and economy.

Stupid:

• Not planning for 30% sales turnover and 20% tech turnover

Less Stupid:

• Planning for turnover in talent
• Planning for significant investments in recruiting & on-boarding
• Planning to have "bench" of new hires in the pipeline at all times

#2: Underestimating Your Competition

If you ask a salesperson why they lose a sale, they will invariably say their prices were too high. Balderdash. As my former boss Charlie Nichols used to say "There's only two reasons you lose: you got outsold, or you shouldn't have been there in the first place."

Stupid:

• Underestimating your competition
• Not qualifying your opportunity carefully enough

Less Stupid:

• Expecting tough competition in terms of both skill and price
• Creating a "Pre-Mortem" evaluation process - anticipating all the things that can go wrong and creating a strong game plan to win

#3 Under-preparing for Big Opportunities

If you are fortunate, you'll get a couple "whale" opportunities a year. Ones that are truly game-changing in size and impact on your business. Most sales organizations have no idea how to properly prepare for these rare opportunities.

Stupid:

• Not involving high level vendor and company executives
• Not creating a SWAT team to plan and prepare a winning strategy
• Not conducting at least one full dress rehearsal before each presentation

Less Stupid:

• Creating a team to conduct in-depth account and oppo research
• Researching the relevant hard and soft dollar impacts of your solution
• Anticipating and preparing counters to your competitive weaknesses
• Outworking - Outsmarting - Outselling the competition