CEO Sales Guide | Intelligent Conversations

Before You Invest in Your Sales Team, Answer These 5 Questions

Written by Mike Carroll | Mon, Aug 3, 2026 @ 16:08 PM

How do you know whether your next sales investment will actually produce a return?

Most sales investments fail not because the program was bad but because the problem wasn't diagnosed before the solution was purchased. Training gets bought when the issue is belief. Coaching engagements start when the issue was hiring. Technology gets deployed when the issue is management. Before spending another dollar on the sales team, five questions need clear answers. Most CEOs can't answer all five. That diagnostic gap is where investments go to die.

Key Takeaways

  • Most sales investments fail because the diagnosis came after the purchase, not before it.
  • Five questions determine whether your next investment will produce a return.
  • If you cannot answer all five clearly, the risk of misdiagnosis is high enough to run a diagnostic process before committing the budget.
  • The Sales Effectiveness and Improvement Analysis (SEIA) is built to answer these questions at the organizational level.
  • The CEO who can answer all five before spending is the CEO who gets real return on that investment.

Why Do Sales Investments Keep Producing Disappointing Returns?

Leadership identifies underperformance. Someone recommends a solution. The solution gets purchased.

It might be a training program, a new CRM, sales technology, additional headcount, or a coaching engagement. Whatever it is, it gets implemented with the expectation that performance will follow.

Twelve months later, the number hasn't moved meaningfully.

Leadership reviews what happened. The conclusion is usually that execution was poor, timing was off, the team wasn't ready, or the vendor underdelivered. Another solution gets considered.

In most cases, the real cause is simpler. The wrong problem was diagnosed.

Sales performance problems cluster around a small number of root causes. Investing in the wrong one produces a plausible explanation for failure and another year of flat results. The cycle repeats because the diagnosis step keeps getting skipped.

According to Objective Management Group, only 7% of sales managers are effective at sales coaching. Yet, most organizations keep investing in coaching programs without first assessing whether their managers can actually deliver them.

Question 1: Can Your Underperformers Actually Be Coached?

Before spending anything on development, answer this question for each underperforming rep specifically: does this person have the self-awareness, openness to feedback, and willingness to change behavior required for coaching to land?

Coachability is measurable. OMG's evaluations identify it directly. A rep who scores low on coachability will sit through every coaching session, agree with every piece of feedback, and return to their prior behavior immediately after. The coaching investment gets absorbed without producing results. The manager interprets this as a coaching failure. Coachability was the variable, and no one measured it.

A rep with strong Sales DNA and a mediocre resume will outperform a rep with a polished background and low coachability in almost every case. The coaching investment compounds on the first rep. On the second, it evaporates.

 

Coachability Level

What Happens to Your Coaching Investment

High coachability

Coaching sticks. Rep improves and sustains it. Investment compounds over time.

Low coachability

Rep complies in sessions and reverts afterward. Investment is absorbed without return.

Unknown

Every coaching dollar is a bet. Some pay off, most do not, and you cannot tell the difference in advance.

Question 2: Do You Know What Your Managers Are Actually Coaching?

Most CEOs know their managers are running one-on-ones. Very few know what those conversations actually cover.

If the manager spends those sessions reviewing pipeline and tracking activity, that's management. The visible layer gets addressed. The beliefs, mindset, and Sales DNA gaps underneath stay untouched. Nothing at the skill or belief level changes because nothing at the skill or belief level gets coached.

There's also the question of whether the manager has the capacity to coach what the team needs. As covered in B-Level Managers Produce B-Level Teams, a manager's own Sales DNA gaps become blind spots. A manager who's uncomfortable discussing money will steer coaching conversations away from budget qualification. A manager with a non-supportive buy cycle won't push back on discounting. The team inherits the manager's limits.

What you need to know is whether your managers' coaching is capable of producing the results you need from this team at this level of competition.

Question 3: Do You Know Whether Your Sales Process Is Being Followed?

Every sales team has a defined process. Most teams have a defined process that gets followed selectively.

Process inconsistency produces forecast unpredictability. When different reps treat the same stage differently, the pipeline data is unreliable. Leadership makes resource decisions based on a picture that does not reflect what is actually happening in deals.

But the more important question is not whether the process is being followed. It is why it is not followed when it breaks down.

Reps skip steps they find uncomfortable. The rep with a high Need for Approval skips the closing sequence because pressing for commitment risks the relationship they have built. The rep who is uncomfortable discussing money skips or delays the budget qualification step. The rep with a non-supportive buy cycle stops driving urgency when a prospect stalls because stalling feels reasonable to them personally.

Reinforcing process compliance without addressing what's driving the noncompliance produces short-term improvement and long-term reversion. The rep knows the process. Something inside them is overriding it. Coaching the process harder won't reach that.

Question 4: Does Your Team's Talent Match the Demands of Your Sales Environment?

Sales talent isn't generic. A rep who thrives in a high-volume, transactional environment often struggles in a complex, multi-stakeholder consultative sale. The competencies required are genuinely different, and a strong performer in one context can look like a weak performer in another without that being a talent problem at all.

If the team was assembled over time without a clear picture of what your specific sales environment demands, some of the underperformance is structural. No coaching investment will fix a mismatch at that level. The 2025 State of B2B report from Membrain found that fewer than half of reps in companies actively seeking help were hitting quota — a figure that points directly to structural talent mismatch, not just coaching gaps.

OMG evaluations assess whether individual rep profiles match the demands of your specific selling environment. That question is answerable before the next coaching or development decision gets made.

Question 5: What Does Your Data Say About the Root Cause?

The first four questions can be answered with the right assessment data. Most CEOs are making investment decisions without any of it.

This is common. Gathering competency data across a full sales team and management layer without a structured process is difficult. Most organizations rely on manager observation, performance reviews, quota attainment history, and gut judgment. All of these have value. None of them identify root causes reliably at scale.

The result: investments get made on symptoms. Training gets bought because reps aren't closing at the expected rate, but the closing problem is rooted in Need for Approval and training won't touch that. Coaching gets engaged because deals are stalling, but the stalling is driven by a non-supportive buy cycle the manager shares, so the coaching conversation never goes deep enough to address it.

What a Diagnostic Process Changes

The Sales Effectiveness and Improvement Analysis is an organizational diagnostic built to answer all five of these questions before the investment decision is made. It evaluates the full sales team and management layer using OMG's competency framework, identifies the specific root causes of underperformance across the organization, and produces a prioritized picture of where investment will generate the highest return.

The SEIA surfaces the actual problem. The right solution follows from that. And when it does, the investment lands where it can produce results.

The Five Questions

What the SEIA Reveals

Can your underperformers be coached?

Coachability score and development potential for each rep assessed

What are your managers actually coaching?

Manager DNA profile and coaching effectiveness evaluation

Is your sales process being followed, and why not?

Competency gaps that predict where and why process breaks down

Does your talent match your sales environment?

Rep profiles measured against your specific selling environment requirements

What does the data say about root causes?

Organizational-level diagnostic with prioritized findings by team and role

CEOs who complete the SEIA before their next sales investment know exactly what they are buying and why. The ROI conversation changes entirely when the diagnosis comes first.

If you cannot answer all five of the questions above with confidence, the SEIA is the right next step before the next spending decision.

Frequently Asked Questions

What is a Sales Effectiveness and Improvement Analysis?

A Sales Effectiveness and Improvement Analysis, or SEIA, is an organizational diagnostic that evaluates a company's full sales team and sales management layer using OMG's competency assessment framework. It identifies the root causes of underperformance, surfaces gaps in coaching quality and hiring practices, and produces a prioritized picture of where investment will produce the highest return. The SEIA answers the question that most sales investments skip: what is actually limiting our results, and what should we fix first?

How do you calculate the ROI on a sales training or coaching investment?

Real ROI measurement requires a baseline: how each rep was performing, on which specific competencies, before the investment was made. Without assessment data taken before the program begins, you can measure outcome changes but cannot attribute them reliably to the investment. Teams that assess before spending can track specific competency shifts, connect those shifts to performance improvements, and calculate actual return. Teams that skip the assessment measure activity changes and call it success.

What should a CEO do before investing in sales training?

Before any training investment, a CEO should be able to answer three questions: can the underperformers actually be coached, do the current managers have the capacity to reinforce training in their one-on-ones, and is the underperformance rooted in skill gaps or belief gaps. Training addresses skill gaps. Coaching addresses belief gaps. Investing in training for a belief problem produces no return and a set of explanations that sound reasonable but do not explain the actual failure.

How long does a sales effectiveness diagnostic take?

Timeline depends on team size and scope. An individual OMG evaluation takes under an hour to complete. A full team assessment and analysis across salespeople and managers can typically be completed and reviewed within a few weeks. The time investment is modest compared to the cost of a misdiagnosed solution and a quarter of lost momentum. Reach out to IC to discuss what a diagnostic process looks like for your team size and situation.

Related: Why Sales Coaching Fails (And What Data-Driven Managers Do Differently)