How To Develop Your Sales Team Like You’re Saving For Retirement


Develop your sales team by borrowing these two powerful tactics from retirement saving.

Previously, we explored why sales team development is a critical variable in your future success—much like saving for retirement. We discussed the cognitive biases working against sales managers in developing their teams and how to think about that investment the same way we are taught to plan for retirement. But thinking is not doing. So, in this blog, we are going to show you how you can develop your sales team by applying retirement savings tactics.

Isolating the problem is the first step to solving it. But let’s not be naïve and suggest that self-awareness by itself is enough. Developing your sales team on an ongoing basis in the current operationally-driven sales environment is a tough problem for several reasons:

  1. Finding the time to focus on coaching competes with your core operational responsibilities.
  2. Good coaching requires knowing what to coach on, and that requires regular observation of your people and a keen ability to diagnose problems.
  3. Even if you could get past the first two, the pressure to deliver sales right now can be overwhelming.

To counteract these challenges, let’s apply a couple tactics that work for retirement planning to developing your sales team.

Develop your sales team using “automatic investment”

In the financial world, the automatic investment plan allows you to put aside a set amount of money each month. This tactic is proven to significantly increase retirement savings and keep participants on-track toward their retirement goal.The concept can work in the same way for developing your sales team.

Start by identifying a development area that you would like to see your sales team improve on within the next quarter. For example, you might say, “This quarter we’re going to focus on the discovery call. Next quarter it will be delivering an accurate, on-time forecast.” The key principle here is to focus each quarter on getting better at one thing.

Once you have a development area identified, run the development loop.

Step 1: Baseline
Use the first 30 days of the development loop to observe your sales team’s behavior in the specific development area you are focusing on to get a baseline for your team’s strengths and weaknesses. Resist the temptation to try and fix problems as you see them. Just focus on understanding the current state.

Step 2: Group & Coach
Once you have a feel for where your team’s skill levels are currently, take the next 30 days to group and coach. Based on your assessment, how can you most efficiently allocate your time and energy toward developing your sales team to have maximum impact? This will take some practice, but getting good at it will save you a lot of time.

Step 3: Progression
During the final 30 days of the development loop, look for progression. Can you see evidence that your team is improving? Celebrate progress on the skill the same way you would celebrate hitting quota and you will be on your way toward creating an environment for your people to get better.

Make this simple process automatic by running it quarterly and scheduling regular time on the calendar. For example, you will need to agree on the development focus each quarter, schedule dedicated time for observation and assessment, and share the baseline and progression results with the team. I also generally recommend taking one quarter off as needed, which should correspond with your “busy season”.

Develop your sales team using a “manager match” program

One of the tried and true tactics to get people to contribute to their 401K is a company match. This is where an employer typically matches up to 50% of employee contributions for the first 6% of salary that an employee contributes.

develop your sales team ecosystemWhether you are a secondline or frontline manager, you can pitch your own “manager match” program down or up. Here’s how it works:

Frontline managers agree to make an automatic development investment in improving their sales reps prospect-facing interactions. In return, the secondline manager will match that investment with an automatic development investment in their frontline managers’ team-facing interactions, thus the concept of a “manager match”.

For prospect-facing interactions, look at common interactions within your sales process like the discovery call, a solutions demo or delivering a proposal. For manager-team interactions, look at recurring meetings like a forecast review, deal review or quarterly business review. Note that these interactions may go by different names, such as one-on-one or team meeting, which is actually part of the problem. By clarifying the agenda and driving formality into these interactions, the team will become more effective. Standardizing what an effective prospect-facing or team-facing interaction looks like will raise the bar for your entire team and is one of the few levers a manager actually has to drive performance.


To run the manager matching plan over a year, alternate between one quarter focused on interactions led by the seller and the next for interactions led by the manager. If you are a secondline manager who wants your frontline managers to develop their sellers, what better way than to create your own automatic investment in your management team? All parties have equal skin in the game, creating a healthy environment for sales team development.

Both of these tactics that we’ve borrowed from retirement planning are powerful tools for developing your sales team. However, what I’ve profiled will simply be too much to process for many sales managers. The weight of trying to make the number, day in and day out, will continue to weigh them down. But if you are the type of manager who is passionate about sales team development and is looking to buck the status quo, these battle-tested tactics will help you put a system in place that allows you to not only build an environment for sales team development but also creates a long-term sustainable revenue generating machine. Talk about standing out from the crowd.


Your Demo May Stink if it’s Only Focused on You


How a Leading Fortune 500 Company Successfully Shifted their Demo Focus

There is a legend in the sales world about four finalists in an RFP process that were invited to give a two-hour demo of their solution. Each company’s sales representative was given the same basic agenda —you have two hours, show us these 10 things.

Sellers from companies A, B, and C — all dressed to the nines — showed up and did what they were told. They each presented two-hour demos that highlighted each and every feature.

Then in walked the Seller from Company D. Seller D approached the conference table and offered the buyer not one, but two options for the demo. Option 1 was the same two-hour demo that Sellers A, B, and C presented, but Option 2 was a 20-minute version that only touched on the features that specifically addressed their pain points. Which do you think the buyer chose? Yeah, Option 2. Do you think Seller D won the deal? Of course they did!

Differentiation is Key

So what is it about differentiation that is so essential not only in the sales process, but even more importantly at the demo phase? The enemy of differentiation is “sameness.” The human brain craves contrast, and sameness will cripple the buyer into a state of no decision.

While the greatest sellers and sales engineers understand its impact, the element of differentiation is still absent from many demos. While it sounds simple, too many demos are the same old show up and throw up feature dump that we all dread.

“Companies that tie the demo back to specific pain points and articulate the value of the solution, are 35% more likely to be selected as the preferred vendor of choice.”

Sales Benchmark Index captured this perfectly, “Companies that tie back the demo to specific pain points and articulate the value of the solution, are 35% more likely to be selected as the preferred vendor of choice.”

How a Leading Fortune 500 Company Successfully Shifted their Demo Focus

There is something in our DNA that makes it difficult to shift the focus of our demos from us and to the buyer. World class sales organizations understand this challenge and are taking proactive steps to equip their sellers and sales engineers with a safe environment to practice and develop their skills.

One organization demonstrating this approach is is a leading financial management company. A division within this organization partnered with CommercialTribe to improve a specific sales stage where they noticed a drop in conversion rates. This particular sales stage involved a solution demo.

As a way to level-set the effectiveness of their consultants and measure progress, the Sales VP and team utilized CommercialTribe’s Seller Development Coaching Guide (sample below) to assess the team’s recorded demos against the key components of an effective and impactful demo. Having this visibility into exactly where the skill gaps were, the team was then able to develop targeted activities to improve skills and behaviors.

Over the course of three activities in the CommercialTribe platform, the consultants were able to practice, and receive coaching on:

  1. Effective agenda setting — Focus on audience and pain points
  2. Demo orientation — Position solutions that solve the customer’s specific challenges
  3. Solution differentiation — Create distinction by leading to unique strengths
  4. Connecting the dots — Help the customer see themselves using the solution

As a result of these activities, the Sales VP saw 57% of his team members grow in overall effectiveness.

The Sales VP saw 57% of his team members grow in overall effectiveness.

“Before Commercial Tribe, we focused on telling our buyers about the solution and what it does. Now, as a result of our practice initiative, we are back to what matters most—what it means and why our customers buy.” – Sales VP

When you think about how much is riding on each and every demo, the revenue lift in effective execution, and the time it takes to develop a seller or sales engineer, this investment in a development loop involving observation, assessment, practice and guided coaching following a framework like the Seller Development Coaching Guide, will yield dividends in a condensed timeframe. The proof is in the results!

Download our Sample Seller Development Coaching Guide and see how these guided coaching paths can not only improve and develop your reps, but also activate your frontline managers to be better coaches.


Why Sales Team Development Is Exactly Like Saving For Your Retirement


If long-term, sustained sales growth is part of your goal, you need to get serious about sales team development—before it’s too late.

Do you often wonder why you should be saving for retirement? Probably not. But how often do you wonder if you should be investing in your sales team’s development? Here are two commonly cited statistics that are meant to scare you:

What do these two statistics have in common? I will argue that the root cause is actually the exact same problem. Let me explain.

If you think retirement planning is your parent’s problem, I’ve got news for you. According to a recent study, nearly half of millennials have no retirement savings. The younger generation doesn’t see retirement as a priority, thinking first about student loans and financing the present instead. Getting people to save for retirement is an age-old problem, primarily because of “longevity disconnect bias”. People have a really hard time imagining what the future will be like, so they tend to ignore or de-prioritize it.

If you are a sales manager, you are faced with this same bias every day. Tell me if this sounds familiar:

You manage a sales team and your primary objective is to get your team to quota each month, every quarter. In the short-term, that naturally means inserting yourself into deals that are closest to closing, personally carrying any deal you need to, and riding your stars to try and make the number. In the short-run, that may indeed be the best plan to reach your goal.

But what sacrifices are you making when you prioritize short-term goals for long-term sales team development?

You are putting minimal attention on cultivating your early-stage pipeline for future quarters, you are creating dependencies within your team by trying to personally make up for deficiencies, and developing new sales stars gets lost in the chaos.

This pattern of putting short-term interests ahead of long-term sales team development may work for some time…but the music always stops. It’s the equivalent of waking up at 65 and realizing you have nothing saved, so you better keep working because retirement ain’t gonna happen anytime soon.

Make sales team development your priority

One of the investment products that may make sense for retirement is an annuity. An annuity is basically an insurance contract in which you pay a financial institution a lump sum or series of payments to be invested. Your long-term investment ultimately provides you with a guaranteed regular income in the future.

To get past “longevity disconnect bias” think in these terms when it comes to your sales team development. Ask yourself: “Are each of my salespeople paying me today?”

If not, what investments do you need to develop a future revenue stream? Delivering on your quota becomes more sustainable when you have more sellers on your team who are paying you.

Imagine your future self. How does it feel to have an entire team of sellers paying you?

Sellers do come and go, so it’s true that unlike annuities, they won’t be paying you forever. But there is actually another form of payment that—to some sales managers—is just as important. It is your reputation as a coach and your own development as a sales leader. When you commit to your sales team’s development, you become recognized as a multiplier of talent. You become someone that top talent wants to work for, and someone that people in your organization want to work with.

Continuing to look into the future, imagine what this would mean for your career. Sustainable, recurring “income” takes away the stress of just getting by day-to-day. And it allows you to strategically focus on the real challenges confronting you and your team in delivering sales objectives.

This future you’re imagining is not for everyone. Despite society’s best efforts, some of us are simply not going to save for retirement. Sales managers who recognize the long-term benefits of sales team development and are passionate about making it a priority are far more successful in generating revenue. If you are one of those rare sales managers who believe that the development of your team may be the single most important variable in your future success, you may be interested in learning about a proven sales team development framework, which we recently presented during BrightTalk’s Sales Training & Leadership Summit.