Guest Column | November 15, 2021

Finding Keepers: How To Find, Build, And Keep Top Sales Reps

By Dr. Richard L. Chambers, America’s Return Inc.


The “Great Resignation” trend has people voluntarily leaving jobs in unheard-of numbers, their sensing a gap between the life they seek and the path they were on. Addressing your Sales Rep staffing due to the pandemic presents an opportunity to upend recruiting as a front-end transaction, putting in its place a method to manage the life cycle of a long-term Rep. IT Solution Providers’ top needs include 1) increasing sales and 2) finding/keeping top people. I help you achieve the first by building a team of the second, via a system that has pulled in over 11,000 candidates through ads, efficiently vetted the best candidates and placed hundreds of Sales Reps. Those Reps along with their managers became my sales training audience over many years. I share below the lessons I learned to keep the top reps and, in turn, find more.

If your goal is to poach competitors’ experienced Reps to hit the ground running, stop reading now. If your belief is “I just need someone,” prepare to repeat that mantra for years. If you are willing to “build a bench” or have a “farm system” where you invest in the Reps’ personal life plan, you will realize the following paradoxical benefit: the more you equip your people to leave and pursue their dreams, the longer they stick around because other firms are not helping them do that. My tracking shows the average tenure of a Rep hired through this process is 4-to-7-years, rather than the 6-month wheelspin many firms experience. With our 6-step process, your Reps will prefer being coached to being poached.

  1. The Ad. Most of your ad response comes from the headline.

You know that ad headlines and text promoting the reader’s benefit will get you a good response. But since you do not want to lose time on resumes and interviews with unqualified people, perhaps you dilute the appeal with highly restrictive qualifications. What you do not know is how many otherwise extraordinary job seekers fail to respond because they self-select out of the running, believing themselves to be unworthy of your standards. At least a third of my placements come from this surprising audience – the “maybes” – which I suggest you include in interviews using a unique group hiring process (see Step 2 below).

Good ad headlines and text stress becoming someone rather than being someone. An ad that emphasizes a development path yields applicants who are eager to learn and willing to trade away up-front rewards for long-term growth. Experienced Reps also reply because these vets want the same outcome. My two biggest pulling ads had the following headlines:

  • “Join a 12-year-old tech start-up,” invoking the vision of unlimited opportunity balanced with the lower risk of an established company.
  • “Get on board the technology train.” Corny, but the ad triggers the imagination of people committed to changing their lives, not just job hopping. This ad placed sixty call center Reps, many of whom went on to become HP managers.

The ad and text should invoke a fantasy about the Reps’ future (see Exhibit One), one in which your firm is seen as a potential route to achieving it.

Exhibit One. The candidates’ vision for themselves.

  • Tip: Along with dedicated sites for jobs (Indeed, ZipRecruiter, etc.) do not overlook, which gives an immediate measure of your ad headline quality and zeroes in on specific cities. With a group process, you can manage the higher share of “maybes.”
  • Tip: Use the same appealing headline whether the ad is on a job site or your website. The headline will become the theme of your presentation.
  1. The Resumes and Interviews. A group process saves time and turns up more good people.

The resumes. With a more energizing, less restrictive ad, you will activate more responses. Sort resumes into three piles: Yes, No, and Maybe. Invite back all the Yes and Maybe candidates to one or more group sessions.

The presentation. Tell a 45-minute exciting story once to multiple people rather than a 10-minute intro you must otherwise race through on a back-to-back interview schedule. The presentation can be done in-person or remotely, followed by a string of one-on-one 5-10-minute interviews held in a breakout room immediately after.

The first interview. The questions are goal-oriented, not resume-focused. You will know in those few minutes if you want to talk further in a later interview. A hiring manager can hold at least six brief sessions in an hour. A colleague can host the waiting candidates with informal chatting, which often reveals as much as an interview. If the audience is large, multiple breakout rooms can be working concurrently. Our tracking shows that only about four out of twenty attendees will be called back for a full interview. You would save hours reaching the same judgment about the “Yes” applicants in a traditional first interview while discovering some “Maybes” that also move forward. Our surveys also find that even those that were declined express that they had a positive experience because of the presentation quality.

The next interviews. Rather than calling the semi-finalists back for a broad round-robin first-impression by colleagues, drill down instead with tasks that reveal the applicant’s will, skill, and true wishes. By having three or more successive exercises for candidates to engage in over a week or two, you can measure how well they work (writing ability, speaking poise, technical knowledge). More indicative of their potential long-term tenure is that “jumping through hoops” tells the firm who wants the job the most.

Turn the tables on the interview process, determining how the company fits the candidate’s goals rather than just the reverse. If you detect they have a better path, urge them to take it. And if they do not have a convincing story for you, they will not have a compelling one for themselves when they get out of bed. You and the finalists should agree that Your Company Way is the best path available to achieve the Employee’s Personal Life Plan (see Exhibit Two):

Exhibit Two – Unity of goals between company and Rep.

  • Tip: During enrollment, describe the group meeting as “an individual interview with a manager following a group presentation,” not an open house or job fair.
  • Tip: the best presentations follow this flow: The customer; The competition; The unmet need; Our unique solution; The opportunity for you.
  • Tip: Involve current Sales Reps in the presentation. The exposure rekindles their passion for having joined.
  • Tip: Best first question to start the interview: “What excited you about the presentation?” The best answer includes “learning” or “becoming.”
  • Tip: you may choose to circumvent the group to meet one-on-one with a clear “Yes” candidate but recognize that you trade away the psychological leverage of having the candidate feel the competition.
  1. The Hire. Hire the finalist who wants the position the most.

Sales candidates can be persuasive, so check your excitement against the maxim: “people vote with their feet.” Evaluate them. Their persistence in reading white papers and passing sample certification tests suggests IQ. The completeness of a narrative describing their personal goals suggests EQ. Repeated screening visits at different hours reveal their time management. More importantly, these measures are proxies for their will and true enthusiasm to pursue “The Company Way.”

Your path needs to be a credible route to the Employee’s Personal Life Plan. By framing compensation in terms of long-term pay-off, both parties are forced to assess the hiring decision at the start of a relationship. Consider the candidate’s unique life plan to structure a ramp-up that fulfills dimensions other than money. Rather than just demanding a 30/60/90-day plan for how the Reps intend to get up to speed, also have the Rep outline a multi-year plan of their aspirations so that you may respond with non-monetary rewards the Rep finds fulfilling. For example, a candidate may wish to become a more effective public speaker, be involved with customers in the healthcare industry, travel internationally, transition to a business consulting role, or get certified in NextGen technology. Build those benchmarks in their development plan. The Rep should agree that if they want to make more money, they merely need to create more customer value, a share of which they capture for themselves.

The Reps need to feel in their gut they are in the right place as they sit at Point X (see Exhibit Three):

Exhibit Three – Getting a start on Your Company Way.

  • Tip: Share the Risk. Rather than the firm bearing the responsibility to assure the Reps will be financially safe during the first year, probe for the applicants’ liquidity to make sure they can survive a ramp-up.
  • Tip: Share the Reward: In some small and medium private corporations, having an equity-ownership path to a “fraction of the action” after a certain number of years helps not only with the “Hiring” but also the “Keeping.”
  1. The Training. Lay down a track.

Imagine never having to ask in an interview, “What can you do for us?” because you already know what they can do: faithfully execute the documented systems you train on. This capability is what allows you to skip the heavy-hitter expensive Reps who want to be their own boss, in favor of a smart bet who is attracted to order and eager to learn.

Your training should lay down tracks for these sequences:

Sales stages of an opportunity. The building blocks of your sales process are usually labeled in your CRM system as the steps from prospecting to meetings, proposals, and closes. The training should model the behavior at each stage, with all collaborating positions engaging together in role-played training. A common language limits fumbling on hand-offs from, say, an Account Manager teaming with a technical Sales Engineer. Written training materials should cover meeting guidelines, FAQs, and customer objections.

Account development stages. Posit a proactive implementation path in which a customer adopts a deeper and wider engagement. Define the sequence of projects or services leading from initial purchasing agents’ requests through infrastructure projects and up to fiscal-year planning in the customer board room. Train your Reps to understand a customer’s digital transformation journey, identify the gaps in their processes, and become their guide.

Your track defines the skills that Reps will master as they proceed on “Your Company Way” (see Exhibit Four):

Exhibit Four – The track

  • Tip: Major hardware and software vendors have adopted detailed sales training methodologies. Map your sales training to the process of your major vendor(s), and benefit from their materials and common language for account planning.
  • Tip: Commit to vendor-certify Reps in exchange for marketing leads.
  1. Evaluation and Motivation. The path of progress.

Your company’s track gives you the groundwork for an evaluation of the Reps’ performance. You should define clear pipeline metrics beyond just the sales quota: the number of events in a week to perform; the expected amount of time on the phones; conversion rates from one stage to the next; revenue or gross margin expectations. Your evaluation should also include qualitative feedback:

  • Prospecting. Assess how Reps are dealing with voicemail.
  • Defining business needs. Determine if Reps are eliciting desired business outcomes.
  • Gathering detailed technical requirements. Confirm that tech probing is coordinated with business needs.
  • Getting commitments to proposals. Note how the Reps handle objections.
  • Implementation review. Check the Reps’ ability to secure testimonials, referrals, or new projects.

Equally important is the Reps’ feeling of progress toward their own goals (see Exhibit Five):

  • Reconfirm the unity between the Reps’ Personal Life Plan and the company path to help take them there.
  • Note the progress (X) they have made along that path since starting, the feeling of advancement itself being a major motivator.
  • Direct the Reps’ attention to the distance remaining to their goals, stoking energy to take specific steps to move forward with you.

Exhibit Five – The motivating evaluation.

  1. Retention. If you don’t have a track, you can’t get back on track.

All the steps to this point have prepared a manager and a Rep to reconfirm the relationship that may come under question at some point. For many people, this event is uncomfortable and ends in separation, partly because the relationship was based on a hiring transaction, not a career plan.

In Exhibit 6 of our model, the Rep’s drift off the path co-occurs with low-performance numbers and a negative attitude. The typical manager’s response is to shame Reps to improve to hit the firm’s needs. In my process, the emphasis is captured in the following sample coaching:

 “You are off track from the standards we discussed. When you started, your aim was in the same direction as my path. Lately, you seem to be taking a different route. Have you redefined your goals and want a path elsewhere? If so, let me help usher you to your new goals. However, if you still hold your original goals, you need to get back on track for your own sake because right now you are headed to disappointment. So, I need you to get back on track for both our sakes. Can I get that commitment from you?”

If you had not exercised steps 1-5, this would be a much harder conversation. Many managers want to avoid personal discussions. However, most traits that send Reps off track arrived with that Rep on Day 1. Treating hiring more as a revelation than a transaction reduces the surprise resignations. All the efforts up to this point have been to assess who really wants to be on your track because they make it their track. The ads trigger emotions from a wide audience. The interview sequence shakes out who most wants the opportunity for the long term. The training is tied to step-by-step metrics, with detailed qualitative underpinnings that allow a specific evaluation and the opportunity to motivate for longevity. Knowing the Reps’ goals, the manager is equipped with the ability to coach the Reps through the natural stress of the Sales career.

Exhibit Six – Getting back on track.

  • Tip: You may already have a Sales team whose goals you have not yet discovered. Fast forward to Step 5 as well as you can, before you need Step 6.
  • Tip: As a manager in someone’s firm, you are no different from the Reps in having Life Plans pursued along The Company Way. Share your story with the Reps and your boss. If you are the owner, have counsel with your key executives or advisors on implementing this system.
  • Tip: January and September are peak ad response months. Be ready for those moments.
  • Tip: Reach out to for a free sounding board on what you are doing and how we might help.

RichardAbout The Author

Dr. Richard L. Chambers is president of America’s Return Inc., provider of The S.A.L.E.S. System, an SMB channel sales development program helping OEMs, ISVs, distributors, VARs, and MSPs sell solutions with higher profit in less time.