*First-Line Sales Management:* How to Empower Your Reps With the Ability to Systematically Win More Business
First-line sales management isnât for the faint of heart as it requires the management of all kinds of different personalities who all have their own unique ways they prospect, forecast, view the health of a deal, view partners, view the sales process, etc. Basically, everyone has their own unique style of selling. The first-line sales manager is responsible for bringing together a team of professionals, with varying personalities and past experiences, and somehow get them to semi-conform to a unified selling process.
In fact, the most advanced sales organizations have established a Level 4 Dynamic Process which means that reps are trained on a well-defined methodology thatâs regularly measured, enforced, and optimized.
A big part of getting your sales org to that level of sales process maturity is ensuring your first-line managers are trained on a structured and disciplined methodology for systematically coaching their reps through each fiscal period and thatâs what weâre covering in this write-up.
What is the One Metric That all First-Line Managers Are Ultimately Responsible For?
The answer is âQuota Attainmentâ. At the end of the day, a first-line manager (FLM) has a bookings number that needs to be attained. If the FLM hits it consistently, the career path red carpet gets rolled out and life is good. If itâs missed consistently: well, we all know where that road leads and itâs not a fun one.
You need your reps to account plan and get their targets into highly-personalized outbound cadences as quickly as possible; preferably in the first two weeks of the year because the faster you start this process, the sooner a sales cycle starts, which means the sooner deals start closing, which maximizes the time you have available in the year for selling. Wow…mouthful, but true. We covered best practices around that topic in this guide: Proper Account Planning: Winning the Outbound Cadence Personalization War
From this point on, thereâs only two key metrics you need to pay attention to as youâre evaluating your repsâ performance:
- Pipeline: Is my rep generating enough pipeline to hit the bookings target Iâve set for him or her? Every organization has different pipeline targets, which are traditionally multiples of what your bookings number is. So, if your rep has a target of $1.25MM, and you know, based on historical performance, that you need to have 3.5X pipeline in order to hit your number, then there should be $4.375MM worth of opportunities in the repâs pipeline. If this isnât the case, then you know you need to make sure youâre coaching the rep on how to drive more pipeline through various prospecting activities
- Win Rate (Bookings): Is my rep winning deals? If youâre seeing an overabundance of losses, slipped deals, or excuses for why things are not closing on time, this is an indication that you have a sales cycle control issue on your hands. There are two types of sales cycle control issues:
-
- Deal Strategy: Basically, in this situation, the rep may have the wrong strategy in place (selling something thatâs not meeting the customerâs requirements). Has the rep documented the prospectâs evaluation considerations? Ensure the rep is paying attention to the customerâs needs and is providing a personalized and meaningful experience thatâs helping the customer solve the challenges theyâre looking to solve. This seems like a no-brainer, but I can assure you itâs a problem that I see quite often thatâs very easily solved for with coaching and discipline.
-
-
-
- Deal Process: Is the rep systematically driving deals to a close by using buyer maps and close plans? If not, then you likely have a deal process challenge on your hands, which is an opportunity for coaching. We all know that most reps donât do these because itâs too time consuming. FYI – Forecastable takes away this objection and makes it easy for reps to build and maintain these.
- Deal Process: Is the rep systematically driving deals to a close by using buyer maps and close plans? If not, then you likely have a deal process challenge on your hands, which is an opportunity for coaching. We all know that most reps donât do these because itâs too time consuming. FYI – Forecastable takes away this objection and makes it easy for reps to build and maintain these.
-
As a Manager, How Should I Structure My Weekly One-On-Ones With My Sales Reps to Maximize the Value Iâm Delivering?
Below is what we believe is the most effective sales one-on-one structure. This could also be done bi-monthly if weekly is too often for you and your team.Â
For the first weekly one-on-one of each month, spend 15 minutes going over the numbers. Itâs important that everyone is on the same page about what the targets are and where gaps need to be filled. This looks like a lot of information, but all of this data is easily available and can be prepared in just a few minutes of work, immediately prior to the one-on-one meeting.
By The Numbers:Â
Current Year:
-
-
- Annual Quota: $1,200,000
- Target Pace: $256,000Â
- YTD Closed/Won Bookings: $273,000
- Annual Bookings Gap: $927,000
- Remaining Open Pipeline (through end of current fiscal): $2.1MM
- Target Pipeline Multiplier: 3.5X
- Actual Pipeline Multiplier (Remaining Open Pipeline/YTD Bookings Gap): 2.26
- Pipeline Deficit:Â $1.15MM
-
Current Quarter:
-
-
- Quarterly Target: $275,000
- QTD Closed/Won Bookings: $26k
- Quarterly Bookings Gap: $249k
- Actual In-Quarter Open Pipeline: $1.256MM
- In-Quarter Open Pipeline/QTD Bookings Gap (Pipeline Multiplier): 5.04
-
Here are the comments and coaching opportunities I would bring up based on these numbers:
-
- Youâre ahead of the target pace, but not by much, so letâs keep an eye on that.
- You have 5X pipe in the current quarter, but just a little over 2X for the year. With such a healthy in-quarter pipeline, youâre in store for a great quarter, but youâre going to need to increase prospecting activities to fix the current pipeline deficit of $1.15MM for the rest of the year, otherwise youâre likely to fall short at the end of the year. Whatâs your plan for filling that gap?
If reps know this line of questioning is coming every month, they should be presenting these numbers to you as their manager. They should be able to self-identify their challenge areas and self-prescribe resolutions. Getting to this stage is a big accomplishment for any FLM. Once achieved, the FLM can then begin spending more time on deal specifics instead of top-of-funnel activities, which is a much better use of time.
For the rest of your one-on-one, you should be focused on deal specifics. To help hone in on which deals you should focus on first, use your Forecastable evaluation plan dashboard. This will help you quickly identify deals that are potentially at risk. We recommend focusing on those first, then moving on to the rest.
Sales execution is hard.
We can help.
For every opportunity you discuss, you should have its corresponding buyer map and evaluation plan on the screen to help facilitate the discussion. Itâs difficult to provide truly meaningful advice as a manager when youâre not staring at the entire picture. You have so many deals on your plate, across your entire team, itâs impossible to keep up with each deal in your head. Use these tools to your advantage as itâll allow you to add significantly more value as a manager. Challenge your repâs buyer map, timeline, support status of each stakeholder. This effort will strengthen your repâs discipline for this and all future deals.
There are three types of deals you need to focus on:
Current Month: Every deal should be in later stages (legal/procurement/pricing negotiations, etc.).Â
-
-
- Are there any deals with a low evaluation completion percentage?Â
- If itâs the beginning of the month, we recommend flagging anything thatâs less than 50% complete. Once flagged, see what you can do to expedite the completion of those items and if thatâs not possible, you should dig deeper. If thereâs not a clear path to get the timing of the deal back on track, you may consider kicking the deal out of the current monthâs forecast.Â
-
Current Quarter: Deals can be in a wide variety of stages, so the evaluation plan completion percentage metric isnât necessarily a flag.
-
-
- Are there any deals above a certain opportunity amount that are missing evaluation plans completely?
- Are there any deals where the evaluation plans were not accepted by the prospect?
- Are there any deals where executive alignment is missing?
- Are there any deals that donât have buyer maps at all or deals where your rep is single threaded?
- Is there anyone in my partner network that I should be inviting to the table to collaborate with me on my buyer map or my deal strategy?
-
Large and Strategic Long-Term Deals
-
-
- There should be lots of focus on buyer maps for these, ensuring youâre establishing and nurturing the right relationships throughout the organization. On large, strategic deals, your buyer map will be deep and complex, so it must be maintained and leveraged often.
- Executive alignment, possibly at multiple levels throughout the organization, will be essential.
- Partner collaboration could also be an important aspect to winning these deals. Invite partners to the table that have existing relationships in the account or who bring a unique offering to the table that your competitors canât match.
- Be sure youâre covering everything in the prospectâs evaluation considerations first in your offerings. Donât miss checking one of those boxes. Once all checked, then, and only then, can you elaborate on other differentiators that they didnât include in their initial evaluation considerations list or just flat-out werenât taken into consideration initially.Â
-
Finally, I always like to ask something like this at the end of most of my one-on-ones: Is there anything else I can be doing to better support you or anything you feel I can work on to improve as a manager? Remember, at the end of the day, your job is to attain quota. The most effective way to attain quota is to help your team be as successful as they can through a well-defined sales process thatâs measured, enforced, and optimized.
Sales execution is hard.
We can help.
You need your reps to account plan and get their targets into highly-personalized outbound cadences as quickly as possible; preferably in the first two weeks of the year because the faster you start this process, the sooner a sales cycle starts, which means the sooner deals start closing, which maximizes the time you have available in the year for selling. Wow…mouthful, but true. We covered best practices around that topic in this guide: Proper Account Planning: Winning the Outbound Cadence Personalization War
From this point on, thereâs only two key metrics you need to pay attention to as youâre evaluating your repsâ performance:
- Pipeline: Is my rep generating enough pipeline to hit the bookings target Iâve set for him or her? Every organization has different pipeline targets, which are traditionally multiples of what your bookings number is. So, if your rep has a target of $1.25MM, and you know, based on historical performance, that you need to have 3.5X pipeline in order to hit your number, then there should be $4.375MM worth of opportunities in the repâs pipeline. If this isnât the case, then you know you need to make sure youâre coaching the rep on how to drive more pipeline through various prospecting activities
- Win Rate (Bookings): Is my rep winning deals? If youâre seeing an overabundance of losses, slipped deals, or excuses for why things are not closing on time, this is an indication that you have a sales cycle control issue on your hands. There are two types of sales cycle control issues:
-
- Deal Strategy: Basically, in this situation, the rep may have the wrong strategy in place (selling something thatâs not meeting the customerâs requirements). Has the rep documented the prospectâs evaluation considerations? Ensure the rep is paying attention to the customerâs needs and is providing a personalized and meaningful experience thatâs helping the customer solve the challenges theyâre looking to solve. This seems like a no-brainer, but I can assure you itâs a problem that I see quite often thatâs very easily solved for with coaching and discipline.
-
-
-
- Deal Process: Is the rep systematically driving deals to a close by using buyer maps and close plans? If not, then you likely have a deal process challenge on your hands, which is an opportunity for coaching. We all know that most reps donât do these because itâs too time consuming. FYI – Forecastable takes away this objection and makes it easy for reps to build and maintain these.
- Deal Process: Is the rep systematically driving deals to a close by using buyer maps and close plans? If not, then you likely have a deal process challenge on your hands, which is an opportunity for coaching. We all know that most reps donât do these because itâs too time consuming. FYI – Forecastable takes away this objection and makes it easy for reps to build and maintain these.
-
As a Manager, How Should I Structure My Weekly One-On-Ones With My Sales Reps to Maximize the Value Iâm Delivering?
Below is what we believe is the most effective sales one-on-one structure. This could also be done bi-monthly if weekly is too often for you and your team.Â
For the first weekly one-on-one of each month, spend 15 minutes going over the numbers. Itâs important that everyone is on the same page about what the targets are and where gaps need to be filled. This looks like a lot of information, but all of this data is easily available and can be prepared in just a few minutes of work, immediately prior to the one-on-one meeting.
By The Numbers:Â
Current Year:
-
-
- Annual Quota: $1,200,000
- Target Pace: $256,000Â
- YTD Closed/Won Bookings: $273,000
- Annual Bookings Gap: $927,000
- Remaining Open Pipeline (through end of current fiscal): $2.1MM
- Target Pipeline Multiplier: 3.5X
- Actual Pipeline Multiplier (Remaining Open Pipeline/YTD Bookings Gap): 2.26
- Pipeline Deficit:Â $1.15MM
-
Current Quarter:
-
-
- Quarterly Target: $275,000
- QTD Closed/Won Bookings: $26k
- Quarterly Bookings Gap: $249k
- Actual In-Quarter Open Pipeline: $1.256MM
- In-Quarter Open Pipeline/QTD Bookings Gap (Pipeline Multiplier): 5.04
-
Here are the comments and coaching opportunities I would bring up based on these numbers:
-
- Youâre ahead of the target pace, but not by much, so letâs keep an eye on that.
- You have 5X pipe in the current quarter, but just a little over 2X for the year. With such a healthy in-quarter pipeline, youâre in store for a great quarter, but youâre going to need to increase prospecting activities to fix the current pipeline deficit of $1.15MM for the rest of the year, otherwise youâre likely to fall short at the end of the year. Whatâs your plan for filling that gap?
If reps know this line of questioning is coming every month, they should be presenting these numbers to you as their manager. They should be able to self-identify their challenge areas and self-prescribe resolutions. Getting to this stage is a big accomplishment for any FLM. Once achieved, the FLM can then begin spending more time on deal specifics instead of top-of-funnel activities, which is a much better use of time.
For the rest of your one-on-one, you should be focused on deal specifics. To help hone in on which deals you should focus on first, use your Forecastable evaluation plan dashboard. This will help you quickly identify deals that are potentially at risk. We recommend focusing on those first, then moving on to the rest.
Sales execution is hard.
We can help.
For every opportunity you discuss, you should have its corresponding buyer map and evaluation plan on the screen to help facilitate the discussion. Itâs difficult to provide truly meaningful advice as a manager when youâre not staring at the entire picture. You have so many deals on your plate, across your entire team, itâs impossible to keep up with each deal in your head. Use these tools to your advantage as itâll allow you to add significantly more value as a manager. Challenge your repâs buyer map, timeline, support status of each stakeholder. This effort will strengthen your repâs discipline for this and all future deals.
There are three types of deals you need to focus on:
Current Month: Every deal should be in later stages (legal/procurement/pricing negotiations, etc.).Â
-
-
- Are there any deals with a low evaluation completion percentage?Â
- If itâs the beginning of the month, we recommend flagging anything thatâs less than 50% complete. Once flagged, see what you can do to expedite the completion of those items and if thatâs not possible, you should dig deeper. If thereâs not a clear path to get the timing of the deal back on track, you may consider kicking the deal out of the current monthâs forecast.Â
-
Current Quarter: Deals can be in a wide variety of stages, so the evaluation plan completion percentage metric isnât necessarily a flag.
-
-
- Are there any deals above a certain opportunity amount that are missing evaluation plans completely?
- Are there any deals where the evaluation plans were not accepted by the prospect?
- Are there any deals where executive alignment is missing?
- Are there any deals that donât have buyer maps at all or deals where your rep is single threaded?
- Is there anyone in my partner network that I should be inviting to the table to collaborate with me on my buyer map or my deal strategy?
-
Large and Strategic Long-Term Deals
-
-
- There should be lots of focus on buyer maps for these, ensuring youâre establishing and nurturing the right relationships throughout the organization. On large, strategic deals, your buyer map will be deep and complex, so it must be maintained and leveraged often.
- Executive alignment, possibly at multiple levels throughout the organization, will be essential.
- Partner collaboration could also be an important aspect to winning these deals. Invite partners to the table that have existing relationships in the account or who bring a unique offering to the table that your competitors canât match.
- Be sure youâre covering everything in the prospectâs evaluation considerations first in your offerings. Donât miss checking one of those boxes. Once all checked, then, and only then, can you elaborate on other differentiators that they didnât include in their initial evaluation considerations list or just flat-out werenât taken into consideration initially.Â
-
Finally, I always like to ask something like this at the end of most of my one-on-ones: Is there anything else I can be doing to better support you or anything you feel I can work on to improve as a manager? Remember, at the end of the day, your job is to attain quota. The most effective way to attain quota is to help your team be as successful as they can through a well-defined sales process thatâs measured, enforced, and optimized.
Sales execution is hard.
We can help.
How Does a First-Line Manager Achieve Quota?
Ideally, the FLM achieves quota by ensuring their direct reports (individual sellers) achieve their individual quotas. So, letâs say iâm an FLM and iâve got a $10MM number to hit for the year and I equally distribute quota to all eight of my reps, that means that each individual seller will have a $1.25MM number and my sole purpose in life is to ensure each of them hits it. When they all win, I win. Itâs a simple concept, but itâs easier said than done.
