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

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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.