Notes From Scaling Sales With Confidence

ChatGPT Image Jan 27, 2026, 02_33_59 PM

There Are Four Areas You Need to Look at Your Sales Organization:

  • Talent: Do we have the right people in the right roles to get where we want to go?
  • Skill: Do they have the skills we need to sell to our buyer against our competition at our price point?
  • Leadership: Do our leaders know what they  need to do to get us where we need to go? Are they focused on the right things for this stage of our growth? Do they know what those are?
  • Infrastructure: Do we have the right infrastructure in place? Team structure; sales process; compensation and incentives; technology stack and tools; use of those tools and technology; hiring process; talent development program; accountability; metrics and tracking?

Most organizations wildly overindex in one area, leading to underperformance across the others and in sales numbers. 

Pipeline and forecasting

  • The pipeline should be the single most accurate predictor of future revenue
  • Most are staged inappropriately
  • Most are poorly managed
  • The information is inaccurate: close date, deal size, likelihood of close
  • You need criteria for each stage
  • The review of it should take 15 minutes
  • It needs to be visualized
  • Quality and quantity
    • Quantity: We need to mathematically know if we have enough deals by stage to hit our targets in 1, 3, 6, 12 months. There’s usually not enough in there. 
    • Quality: Do we have the right information in there?

Closing

  • Understand each rep’s conversion rates and their critical ratios: conversion by stage
  • We can build a plan for them to exceed their goals if we know their ratios
  • Core data points: Sales cycle, average deal size, closing rate and their monthly goal
  • If a 4 month sales cycle: February’s numbers were set in November
  • They need to be at the right level, having the right conversation, following the right steps in the right order

Sales Cycles

  • Math (critical ratios)
  • Process: Are they following the right process?
  • Skill: Are they able to move an opportunity along effectively?

Sales Process

  • Most organizations have every person following a different process – no one will admit it, though
  • This makes coaching and standardization and pipeline management impossible
  • Process needs to focus on achieving milestones, not just having meetings, holding calls, sending quotes/proposals or doing demos – those all mislead
  • Four key stages: getting the meeting; finding willingness to buy; qualifying ability to buy; closeable
  • The process needs to follow an advancing order where everything is sequenced appropriately
  • Most people skip from 1st to 3rd and have to recover everything between 1st and 2nd, and 2nd to 3rd

Scorecards

  • Resources are wasted on opportunities we cannot and will not win
  • Focus on the winnable deals
  • Identify 5-6 (no more) predictors of winning deals
  • These should be objective criteria
  • This information often lives in the minds of various people in the organization but it’s never been gathered appropriately
  • These predictors should be weighted according to various options
  • They should add up to 100
  • Test it against prior wins and losses to see if it would’ve predicted them
  • Refine until it does

Sales Talent

  • Myth of the star performer
    • We often believe the top performer is better than others. Often they’ve:
      • Got the best accounts
      • Got the best territory
      • Were handed relationships
    • Often they can’t reproduce their success if you took it away
    • There are hidden talents with others if you know where to look
  • 26% rule
    • 6% are elite
    • 20% are “very good”
    • 74% are mediocre performers or simply ineffective
  • 5 weaknesses, 4 core elements
    • Weaknesses are the desire to be liked, discomfort talking about money, how they personally make purchases (buy cycle), their inability to stay emotionally disconnected and be in the moment, and a collection of beliefs.
    • Core elements are desire to succeed in sales, a commitment to do what it takes to succeed in sales, outlook (how they feel about themselves, their career, your company and where they are in life), and responsibility – do they take ownership of results, or blame external factors? 

Hiring Process

  • Turnover is often too high – not getting or keeping the right people; or too low – tolerating mediocrity.
  • Problems with sales hiring:
    • We usually sell the candidate instead of vice versa
    • We don’t look for proof they can do what they said they did
    • We don’t test them enough in the interviews
    • We fall in love
    • We don’t have enough candidates, period
    • There’s not a clear view of what “good” looks like
    • Failure rate is one data point this isn’t working
  • Myths in hiring sales talent
    • Athletes!
    • Industry experience!
    • She worked at SomeBigCompany!
    • He has a network!
    • I know what a great performer looks like.
    • They were referred by my forum buddy.
    • They’re all competitive.
    • Need a closer.
    • 1 interview – I can tell if they’ll be great.
  • Process
    • Clear, appropriate job description to measure against
    • “Right” ad to attract the right candidates and discourage the wrong ones
    • Pre-hire assessment: know what you’re looking for
    • 5-10 minute phone screen that’s scored
    • Tough, scored, repeatable interview: audition
  • Assessments
    • Know what they measure and tell you
    • Right tool, right time
    • Not about IQ or personality 
    • Look for predictive of success in the role

Upskilling

  • It’s not a closing problem
  • Most reps are skilled at relationship building and presenting, and weak at selling consultatively, selling value, qualifying, reaching decision makers, and closing
  • “Closing” is the least important because if the prior elements are executed well, closing happens more naturally and easily
  • If there’s not an intentional effort to develop people, it won’t happen on its own
  • A sales leader needs to be involved in developing the people in the organization
  • Skills need to be developed along the following areas:
    • Hunting
    • Reaching decision makers
    • Building relationships
    • Selling consultatively
    • Selling value
    • Qualifying
    • How they present, when, to whom, and for what reasons
    • Closing
    • Questioning 
    • Listening 
    • Ability to find reasons to buy
    • Problem solving
    • Ability to poke holes
    • Ability to ID missing pieces
    • Analytical skills
    • Financial skills
    • Business understanding
    • Quantification
    • People skills
    • Posturing

Incentives and Motivation

  • Discuss comp multiple times per year to impact how it is viewed by reps
  • Contests that reward “Most sales” are counterproductive
  • Contests need to be short
  • Contests should reward multiple people
  • Let them pick the prizes
  • Things over money, and experiences over things
  • Something they won’t spend their own money on
  • Motivation: Find out for every person if they
    • Hate losing more than they love winning
    • Prefer to self manage or be closely managed
    • Put pressure on themselves, or need pressure put on them
    • Compete with others or with themselves
    • Spend to reward results or pressure themselves
    • Prefer recognition or satisfaction
  • All of these impact motivation
  • A sales leader needs to know if the reps are motivated daily, and thus able to effectively handle opportunities

Sales Tools

  • CRM is a must
  • It must be fully utilized
  • Most tools aren’t used, or are used poorly
  • Call recording tools are one of the  most valuable tools you can give people, but it must be used weekly at a minimum

Sales Managers

Manager – by role, not title (managing reps)

  • Coaching: 50% of their time, daily
  • Accountability
  • Recruiting
  • Motivating
  • Developing the people

Leader (Managing managers)

  • The above
  • Leadership
  • Strategic thinking
  • 360 degree relationships 

Most orgs promote the best rep, and get a lousy manager and lose their best seller

Some average sellers are great managers.

Adam Boyd