How to Set Your New Sales Manager Up for Success

When you’ve promoted one of your sales people to the role of Sales Manager, you need to ask yourself: is this person ready to “manage” or will they get caught in the trap of being a “Doer”?

In my role as a Fractional VP of Sales, a classic trap I see newly minted sales managers fall into is to assume their new job role is to be an amplified version of what they were doing as a salesperson. Meanwhile, business owners often assume that first-time sales managers are prepared for their new management role when in fact, they are not.

Doing vs. Managing

The situation I most commonly see play out is one in which an ambitious salesperson is identified as the next great sales manager. That person gets promoted amidst high expectations, but eventually begins to flounder and gets buried six, nine, and twelve months into the role while all parties are left scratching their heads as to why.

The job of a sales manager is to manage the numbers and lead the salespeople. This means devoting time to coaching their reports rather than doing their jobs for them. A sales manager who is a doer will quickly get buried in tasks that they are doing on behalf of their team. In other words, their time gets eaten up by doing the fishing rather than spending time teaching their reports how to fish for themselves. 

How to Help a New Sales Manager Succeed

Here’s how to avoid the common pitfall of having a sales manager who is a doer rather than a manager.

1. Give Your Sales Manager Leadership Training 

Most people are promoted to leadership positions without having a clue how to be effective leaders. It is just presumed that because they were a good salesperson they will automatically be a good leader.  This is often not the case because leading is an entirely different skill set.

Look externally to find someone who can offer leadership and management training to your sales manager within their first couple of months in the role. If you google “leadership or management training” you’ll have more local options at your fingertips than you ever believed could exist. Another option is to find a paid leadership coach or mentor for your new hire. 

The reason for hiring someone external to your business is that they can provide an objective learning experience  to a new manager. They will guide this person in a way that teaches them leadership and management with a fresh perspective not beholden to anything in the organization.

 2. Establish Relevant KPIs for the New Sales Manager 

The first KPI to set would be the number of coaching sessions held with direct reports. You want to know the frequency, duration, and content of those sessions. This is the simplest way to know whether your manager is actually managing as they should be, or if they are guilty of doing.

If they are managing, they will be devoting regular time and energy in the form of 30-to-60-minute one-on-ones with their direct reports. The content of these coaching sessions should make sense to the business owner relative to what the salespeople should be doing on a daily basis.

If there’s no coaching happening, it’s not happening frequently enough, or when it is happening it’s focused on the wrong things, then you can be sure that your sales manager is not teaching their people how to fish. A new sales manager should be having meaningful one-on-ones with their team by their second month in their role.

3. Task the Sales Manager With Creating a Professional Development Plan for Each Salesperson

If a sales manager doesn’t have this documented, they probably haven’t considered the development of their people. When combined with not having coaching sessions that should be devoted to developing each member of their team the path is set for the manager to be doing rather than managing.

4. Assess Your Manager’s Approach to Problem Resolution

Ask your new sales manager what role their salespeople are playing in fixing problems that arise. If your manager is using language that has a lot of “I’s” (ex. I did x, I solved y, I took z over…etc.) then the manager is likely taking matters into their own hands rather than encouraging their people to find solutions.

Of course, there are natural points of escalation when a manager needs to get involved. But a manager’s role is to provide guidance to all their people and follow up as needed. Their reports should be the ones in there with their sleeves rolled up and fixing issues.

5. Structure Your Manager’s Role to Allow Them to Manage

You need to free up your manager to manage. If you want them selling, then their title should be a salesperson. If your sales manager has dual roles that require them to both sell and manage others, they’ll be challenged to succeed. 

It’s simply too much work for one person to sell and maintain accounts and lead others. When someone is tasked with both things, at least one of those two things will not be done satisfactorily. Or worse, neither of those things will be done well!

6. Talk to Direct Reports of Your Sales Manager to Assess How They are Doing

It’s a good idea to check in with the salespeople to see how they are doing working with their new manager. Of course, you need to keep in mind that people are generally reluctant to throw someone under the bus, so you need to ask questions carefully and read between the lines to interpret not only what they’re saying but also how they’re saying it.

As a business owner, you want your manager to succeed. So be sure to listen for things you may not want to hear. The sooner you have a real insight into how your new manager is doing, the sooner you can course-correct to help them improve.

By following these steps, you’ll give your new sales manager the tools they need to succeed and prevent them from getting burnt out. If you have questions about any of these steps or are looking for help with getting a new sales manager ready for their position, get in touch.

How to Create Part-Time Roles for Sales Reps on Parental Leave

Every sales manager or business owner will eventually encounter a situation in which an employee goes on maternity or paternity leave. In some cases, after a period of time the employee may express a desire to get back to work on a part-time basis before their parental is finished.

Of course, before setting up any kind of work arrangement with an employee currently on parental leave, be sure to check all the required governmental rules and regulations in your area before doing so.

Though there are certainly some precautions that need to be taken, if managed correctly, this is a great opportunity for both the company and the employee in question. The employee has the opportunity to feel fulfilled by contributing at work, and the business can benefit from a positively contributing resource.

Tips for a Successful Part-Time Work Arrangement During Parental Leave From a Fractional VP of Sales

It’s easy to imagine what might go wrong when a member of your sales team is not officially back from leave yet contributing again. The danger is that tasks might be partially completed and left dangling for someone else to pick up, all at the risk of appearing disorganized or unprofessional to your customers.

Luckily, there are some steps you can take as a sales leader to minimize the chances of this happening.

1. Have the Employee Secure Regular, Committed Childcare

For any staff member to do their job well, they need focused time and attention. Without committed, reliable childcare, that just isn’t possible. If a staff member on mat leave plans to deliver on tasks, there is likely a co-worker downstream whose ability to do their next task depends on that thing being done. 

If a person on mat leave has committed to doing something by a certain time, but that gets prevented by insufficient child care planning, that disrupts the people downstream and everyone –  the sales rep, the customer, and the company – experiences frustration.

With reliable childcare, the employee can have some guaranteed closed-door time during which they can effectively do their job, and downstream parties can rest assured that they can plan their own tasks and days accordingly.

2.  Have Childcare Planned for the Right Time of Day

If the duties and tasks the employee wants to do must be done during business hours (such as customer-facing interactions), then their childcare needs to be available at the right time of the day to serve the needs of all parties. 

It may be that the tasks they’re doing can be done after hours, in which case, that’s great! Just keep in mind that tasks can carry over to the next day if there are questions about them that need to be answered. 

3. Establish Key Performance Indicators (KPIs)

The person on leave must commit to how much they will do of which duties and tasks. As the work they are doing is likely going to impact other people they’ll need to know what’s going to be done and when. This will help the leader manage the situation and prepare resources downstream from this person for whatever outputs will be coming their way.

The KPIs should include a weekly one-on-one meeting to assess how things are going and course-correct along the way if necessary. This of course means that the employee must be available once a week for a 30-minute meeting with their manager.

4. Communicate, Communicate, Communicate

When an employee is on leave, they may not present at all departmental meetings. This makes it important to establish clear, open, and frequent communication to ensure that all parties are consistently aligned. 

This will facilitate addressing any day-to-day challenges that might arise during a part-time work arrangement. 

5. Provide Appropriate Compensation According to Local Labour Laws

In Canada, it is possible for an employee to work up to ten days during maternity leave without losing maternity pay or benefits. This arrangement is referred to as ‘keeping in touch’ days. Before setting up any kind of part-time work arrangement, be sure that you and the employee on leave are both fully aware of the regulations around working during maternity leave and how that impacts benefits.

Returning to the workplace in some capacity during maternity leave can be a great opportunity for interested parties to remain fulfilled and “connected to the adult world”. It’s also a great opportunity for employers to help those employees remain fulfilled. By following the tips above, you can set the stage for this to be a win-win situation.

Feel free to Get in touch with Rob if you’d like to discuss this further.

The Benefits of an Outsourced Sales Manager

Ever wondered how hiring a Fractional Sales Manager could help your business and whether it’s worth it? This article is designed to help make your decision easier by exploring the factors you need to consider when hiring a Fractional Sales Manager.

What is Outsourced Sales Management?

As you probably know, sales management is the process of leading, directing, and controlling an organization’s sales force. The main objectives of sales management are to achieve your desired sales outcomes and, ultimately, to meet your organizational goals.

This includes developing sales plans, setting quotas, managing customer relationships, monitoring performance, and providing motivation and training for your sales reps. Depending on the size of your business, the task of recruiting, hiring, and evaluating salespeople may also rest with your sales managers.

Outsourced sales management, then, is when you outsource the responsibilities of a sales manager to an outside firm or individual. This can have several advantages for your business.

What are the Benefits of Outsourced Sales Management?

There are many pros of outsourcing your sales management, including access to specialized knowledge and expertise, improved efficiency, and cost savings. Let’s look at some benefits in more detail.

  1. Increased Sales: When you outsource your sales management, you are essentially hiring experts to help boost your sales. These experts have the know-how and experience necessary to help close more deals and increase your revenue.
  2. Cost-Effectiveness: Outsourcing your sales management can be very cost-effective, especially if you choose a reputable and experienced company or consultant. You will likely see a return on your investment (ROI) relatively quickly.
  3. Flexibility: Outsourcing gives you the flexibility to scale up or down as needed, without having to worry about managing a team of employees. This can be extremely helpful during busy times or periods of growth.
  4. Free Up Your Time: One of the biggest pros of outsourcing your sales management is that it frees up your time so that you can focus on other strategic aspects of your business. When you outsource, you no longer need to worry about day-to-day sales tasks or managing a team of salespeople.

When is the Right Time to Outsource Your Sales Management Needs?

There are several things to consider when deciding whether to outsource your sales management needs. The single most important factor is the size and complexity of your sales operation. If you have a large and sophisticated sales operation, it may save you time in the long run to outsource your sales management tasks so that you can focus on other aspects of your business that only you can do.

I’ve talked before about how to assess your sales strategy and execution, and when it makes sense to hire a Fractional VP of Sales. When the organization and its sales team is small and the sales process is not complex, it may make more sense to hire a Fractional Sales Manager.

You may also find that you don’t have the internal resources or expertise to effectively manage your sales operation – especially if you’re growing faster than you can handle. In this case, outsourcing may be the best option.

Another important factor to consider is the cost of outsourcing versus the cost of maintaining an internal sales management team. In some cases, outsourcing can be more cost-effective. Of course, this will vary depending on the specific services you require and the provider you choose.

Finally, you should consider the level of service and support you need from a sales management team. If you require a high level of service and support, it may be more effective to outsource your sales management needs rather than trying to manage everything internally.

How to Find a Good Fractional Sales Manager

Before you hand the sales reins over to a Fractional Sales Manager, you want to be sure you’ve found one who is up to the task. Here are a few key tips:

  1. Do your research. It’s important to understand the different types of outsourcing options available and what they entail. This will help you narrow down your search and find the right fit for your business.
  2. Consider your needs. What type of sales assistance do you require? How much experience does your ideal candidate have with that? What skills should they possess? Answering these questions will help you create a job description and identify the best candidates.
  3. Check references. Once you’ve compiled a list of potential candidates, be sure to check their references. This will give you insights into their previous work experiences and performance levels.
  4. Interview multiple candidates. Once you’ve narrowed down your list, it’s time to start interviewing candidates. This is where you’ll get a better sense of who they are and whether they’ll fit within your company culture.
  5. Make an informed decision. After careful consideration, it’s time to hire the right Fractional Sales Manager and enjoy the perks.


It’s clear that there are some great advantages to outsourcing your sales manager. Just keep in mind there is no one-size-fits-all solution, so you should weigh the pros and cons carefully in the context of your specific business goals. If you need help thinking through whether a Fractional Sales Manager could help you, please contact me to discuss this further.


How to Test for Integrity When Hiring Sales Reps

Integrity matters in any business endeavour. But it’s especially important in sales. When it comes to the trust factor, no job role involves a higher degree of trust than sales. In my role as a Fractional VP of Sales, a mistake that I see business owners make during the hiring process is presuming sales candidate integrity instead of rigorously testing for it.

Why Should You Test Sales Candidates for Integrity?

Sales is a highly independent job role, especially in small businesses, which don’t typically have the enforcement mechanisms that large companies do to ensure all processes are being followed to the letter.

As a business owner or manager, you may only see your salespeople for a couple of hours per week – or even less, given today’s remote working options. Often, you’re taking everything your salespeople say as complete and accurate.

If you hire a salesperson who is prone to misrepresenting themselves, their sales productivity will be lower than their peers and they are likely to create a significant amount of pain and heartache for all other people they touch within the organization. So, how can you prevent this from happening?

How to Weed Out Sales Candidates With Questionable Integrity During the Hiring Process

Most business owners screen for personality traits like competitiveness and the ability to take initiative when hiring because these are known to be correlated with sales success. In the way you do this to hire sales overachievers, you should test for integrity during the hiring process. Here’s how.

Use Behavioural Interviewing Techniques for Sales Candidates

The best predictor of future behaviour is past behaviour. Behavioural interviewing is an interview technique based on this premise that is designed to help the interviewer understand how a candidate might perform in the job based on past performance.

For example, instead of asking, “Tell me how you would [insert the skill or task you’re looking for here]” a behavioural interview question would ask, “Tell me about a time in your past that you [insert the skill or task you’re looking for here]”. Instead of “how would you beat your sales quota”, ask “Tell me about a time in a past job when you beat your sales quota. How did you go about doing that?”.

Using this approach regarding integrity, you should ask the sales candidate questions about how they handled situations in which they had to make decisions using integrity. Some questions to include:

  • Tell me about a time when you observed some sort of injustice happen to a fellow employee that no one else knew about. What did you do?
  • Describe a time when you found it necessary to slightly bend or stretch the truth when talking to a customer in order to help with a sale. (for example, stretching the truth may look like a salesperson telling a potential buyer that clients experience great results in 3 to 6 months when in reality clients don’t typically see results for at least 6 months)
  • Tell me about a situation in which you had to choose between making the right decision and making an easy decision.

Be sure to sprinkle these questions related to integrity throughout the interview (ie. Don’t ask them back-to-back!) to get a more accurate view of the candidate across all the questions related to this theme.

Implement and Interpret Behavioural Interviews Properly

It’s great if you’ve decided to use behavioural interview questions, but you want to ensure you’re doing it correctly so that they yield useful information. There are three main things to keep in mind when asking behavioural interview questions:

  • Don’t lead the candidate in any way.

It’s all too easy to let on what the ‘right’ answer is if you’re not careful. Candidates may quickly understand what an interviewer wants to hear if the question is not presented neutrally.

  • Once you’ve asked the question, stop talking and actively listen to what they tell you.

Active listening includes making eye contact, letting the person know you hear them, and asking follow-up questions at the appropriate times to elicit more relevant information.

  • Take their response at face value and then reassess that answer after the interview.

A lot is going on during an interview since you are interpreting body language and tone along with what the candidate is saying. Reassessing their responses after the interview can help you identify things such as the use of evasive language. A candidate may give their true answer first and then backpedal to try and minimize it, or they may gloss things over their initial response and give a more accurate answer in the second half.

Have a Sales Candidate Do Multiple Interviews With Different People Within the Business

It’s important to have a multi-interview process to ensure that the sales candidate is interacting with several different people within the company. By having the candidate speak to multiple people, you’ll gain more insight into whether they’re the right fit for your team. Of course, you need your team to have their radar up for integrity and be clear on the techniques discussed above.

Before getting too far along the hiring process, you should also do a social media check to actively look for any signs of a disconnect between how the candidate portrays themselves in interviews and their day-to-day life.

How to Assess the Integrity of a Sales Rep You’ve Already Hired

We’ve seen how to test for integrity during the hiring process, but what if you have concerns about the integrity of someone you already have on staff? Many things can raise a red flag, but some of the most common issues I’ve seen with questionable sales reps are:

  • Promising sales results that don’t materialize
  • Stating actions and activities as completed (when they’re not) or not completed (when they are)
  • Saying different and conflicting things to management vs. other staff
  • More obvious things like inaccurate expense reports etc.

Every business owner or manager has had experience with one of these people. If the dots don’t seem to be connecting, take the time to dig into the details. It’s tedious work, but it has to be done to avoid any further damage to your productivity or team morale.

This means going through reports to make sure numbers add up or to check whether the person in question is misrepresenting information. If you do find discrepancies, meet with the salesperson with an open mind instead of jumping to conclusions. Be candid and ask them to help you understand what you’ve found. Of course, if it turns out they are cutting corners, then you need to decide what to do (but that’s a whole other topic)!

The truth of the matter is, if you have a job to offer that someone wants, they will be highly motivated to successfully navigate an interview, maybe to the point of telling you what you want to hear. Meanwhile, a hiring manager also wants to screen someone in rather than out because they’re motivated to get the position filled. This is why integrity can sometimes fall by the wayside and should be intentionally assessed.

The tips here are not completely failproof, but actively testing for integrity will help reduce your chances of hiring a dishonest person who is likely to make your business and team suffer. If you’d like to chat further about how to judge the integrity of sales candidates through behavioural interviewing, please get in touch.


How to Deal with Underperforming Sales Reps

On any sales team, there are top, mid-level, and bottom performers. It’s easy to know what to do with the first two – keep paying them to produce results! Sales leaders often have more trouble dealing with underperformers.

When I consult as a Fractional VP of Sales, I typically see two problems with underperforming reps: 1) they are left on the team to dwindle or; 2) they have a high level of staff turnover. So, what is the right way to handle your underperformers? Hint: the answer is not to immediately fire them!

How to Assess Your Bottom Performers

As a sales leader or business owner, you need to approach unsatisfactory sales performance from a place of curiosity. In other words, you should be asking why your bottom performers are struggling to get results. Here are three questions you can ask to get to the bottom of poor sales performance:

  • Why is the person in question producing at that level?
  • Why is that person going about their sales job in the present manner?
  • What is motivating this salesperson to chronically underperform?

An astute manager will flip this hierarchy of questions around and start by asking about motivation. It’s something that I don’t see managers consider very often, but it is absolutely the most effective way to get to the crux of the problem. That’s because there are two main drivers for success as a salesperson: competence and motivation.

How Competence Influences Success as a Salesperson

If we consider competence to mean knowledge and the skill needed to apply that knowledge, then it’s possible to teach salespeople things to empower them to improve their performance.

If someone is performing poorly in sales, it could be that…

  • you’re not giving them what they need to succeed
  • they don’t know what tools to ask for
  • they know what they need but are afraid to speak up
  • they don’t know how to use the tools they already have

For example, the CRM provided to a sales team may be either insufficient or too complex for some salespeople. Or perhaps they are expected to use technology platforms they’re not adequately trained on, which negatively affects their interactions with potential customers.

Whatever the specific issue may be, you can ensure that competence is not the problem by providing all the tools and training necessary for a person to improve their performance.

How Motivation Influences Success as a Salesperson

If you understand a person’s motivators when it comes to their job, you can feed them those motivators to set the stage for success. To know what motivates someone, you as a leader need to get to know your people.

Whether you choose to do that in a direct or roundabout way, you need to understand exactly what drives a bottom performer. Is it achievement? Do they enjoy competition? Do they prefer to work as part of a team? Do they shy away from public recognition, or thrive on it? Perhaps they’re motivated by a mix of money and an innate desire to help people.

Every person has a different mix of motivators that drive them to perform. Note that not every salesperson has money as their number one motivator. With that being said, if money is not in their top three motivators, they’re likely in the wrong job.

The Influence of the Interpersonal

As a business leader, you need to know how your people are doing as human beings in general. What’s going on in someone’s life outside of work can have a profound impact on how they show up in their job. In fact, one of the top indicators of job performance is the direct relationship between an employee and their superiors.

If you have no idea how they are doing as people, you’ll likely be at a loss for how to help them succeed. How you choose to get to know your people is up to what is appropriate for you and your style. Take whichever path you’d like, as long as you get there – or else, risk high turnover.

How to Deal with Bottom Performers Based on Your Assessment

So, now you have your diagnostic checklist for assessing a poor performer:

  • Are they competent (have you given them the tools they need to succeed)?
  • Are their motivators the type that will position them for success as a seller?
  • What’s going on in their life outside of work?

With all this information, you can figure out whether you’ve got what Jim Collins would call ‘the right person on the bus’.

You may find that with the right training and motivators, a bottom performer is in fact in the right seat on the bus and can get results when given the right tools. But not all salespeople are cut out for the role.

Someone may be an amazing fit for a different role in your company. For instance, you may find you have a bottom performer on a sales team who doesn’t have a competitive streak and doesn’t like asking for business. In that case, they’re not right for a sales role, but may be amazing in a customer service or account management role. In other words, they’re in the wrong seat on the right bus. Now it’s a matter of moving that person to a different seat on the company bus where they can excel.

If you’ve been through the diagnostic list and determined that someone is not capable of performing well in any role in the company, then they’re not a fit for your business. They’re on the wrong bus altogether, and it’s time to exit them (in a respectful way that allows them to succeed in the future of course- but that’s a topic for another post)!

If you’d like to talk through how to approach bottom-tier salespeople on your team, reach out to me and I’d be happy to help.

Top Three Sales KPIs to Ensure Steady Revenue Generation

When things are going well and your sales are up, you can sit back and relax, right? Wrong! Business leaders tend to sound the alarm when sales are already down – but if you’ve waited until your revenue has dipped, it’s already too late.

Find out why the best time to question your approach to revenue generation is when your sales are up, and the three leading indicators you should consider when doing so.

Why You Shouldn’t Wait for a Dip in Sales to Optimize Your Sales Process

Imagine you’re walking along in the mountains and you take a path going down toward a valley. If you go too far in that direction without being sure that’s the way you want to go, it’ll be a long hike back up.

If you’re already at the bottom of a sales valley when you realize you need to do something about it and ring the alarm, you’ve clued in much later than you need to and have made climbing back up the mountain very difficult.

Typically, sales are measured at the end of a quarter. When sales are trending down, business owners often don’t sound the alarm because they assume it’s just a temporary dip. The next thing they know, another 90 days have gone by and they’re in the valley of despair, sounding the alarm that something needs to be fixed. 

Unfortunately, two quarters have gone by and now there are only another two left to get sales back up. In other words, an entire calendar year can be negatively affected if course corrections aren’t made in the first quarter or two.

So, what can you do to make sure you’re not too far down the valley before you realize sales are going to dip? What you need is a map that can help you continue your journey without losing elevation. This is where leading indicators (KPIs) come in.

The Top 3 Indicators for Assessing Sales Performance from a Fractional VP of Sales

If you’re a business owner and you want to significantly decrease the number of times you find yourself in a sales valley, you need leading indicators in place that you and your team follow diligently to understand if and why your sales are going to go down. These are the top three sets of indicators to consider.

Leading Indicator 1: Sales Activity Levels

 This category of indicators looks at crucial activities that lead to revenue down the road. If two or three weeks go by and sales activity levels are below where they should be, it is virtually guaranteed that it will lead to a low-revenue month.

There are many specific indicators you could choose from, but the top three must-haves are:

  • On a per-sales rep basis, how many sales calls or meetings with potential buyers are happening per week?
  • How many proposals are being sent out weekly?
  • How many hours per week does the team spend prospecting?

In my role as Fractional VP Sales, I often encounter sales leaders in small to medium enterprises who are not comfortable checking in with their salespeople about these indicators because they don’t want to be perceived as micromanaging. If you want a clear picture of whether your sales are on track or not, you need to keep track of these metrics.

Leading Indicator 2: Top-of-Funnel Health Check

The next set of crucial indicators for assessing and optimizing your sales process relates to the top and middle of your sales funnel. Bearing in mind your conversion rate from proposals issued to deals won…

  • At the top of the funnel, you should have at least three times the revenue opportunities that you need to meet your target for a given period. For example, if your monthly target is 100k in revenue, you should have 300k worth of opportunities at the top of the funnel. This is because typically, two-thirds of your opportunities won’t convert into paying customers.
  • In the middle of the funnel, you should have at least two times your target revenue forecasted to close in the next 30 days (if you’re measuring monthly) or 60 days to close (if you’re measuring quarterly).

If at any time you’re not meeting one of these minimums, a month or quarter down the road, you won’t meet your revenue goals. Based on these metrics, it will be obvious what you need to do to course correct depending on where you’re stuck.

Leading Indicator 3: Revenue Closed

Although this is classically a lagging indicator that shows what you’ve done, it can also be a leading indicator of what your team is capable of doing. It helps you understand your conversion rate and forecast the results you can get if you continue to do what you’re doing. Thus, it’s another opportunity to gain some insight to inform course correction to achieve the targets you want.

When you’re at the top of a sales peak, your valleys can be anticipated by looking at these leading indicators. The pitfall for most business leaders is to be happy when things are going well and then focus their attention elsewhere. Instead, you should be asking what will happen to sales in 30, 60, and 90 days based on your assessment of these indicators.

There’s a lot to think about when it comes to applying these high-level tips to your business, and far more detail than can be covered in a blog. I’m always happy to have a conversation about how this applies to you, so please contact me for more information.



How to Assess Your Sales Strategy and Execution

Even if a business is well established, the sales strategy should be assessed at least once every six months. A good leader will pause to assess the sales results, then course correct on strategy and execution to ensure the company stays on track to hit its goals. As the old saying goes “if you do what you always did, you will get what you always got”.


  1. Assess the Sales Execution

As a business owner, you can take many approaches when assessing your sales strategy and results.  The approach below starts from sales execution and works its way up to the overarching strategy.

Here are the core questions you should ask related to sales execution…

  • How well do we conduct thorough, professional sales meetings with buyers?
  • How well do we currently navigate our buyers’ decision-making processes?
  • How well do we sell the value of our solutions versus their features?

If your answer to any of the questions above is “not very”, take steps to get your team the resources and education they need allow them to be successful in the sales arena. If your team lacks the skill or knowledgebase to execute, even the best strategy will never work.


  1. Evaluate the Supporting People and Systems

Once you’ve assessed the ability of your team to execute on the strategy then look inward to determine how well the organization has been doing in providing the team the necessary tools to facilitate their selling.

Here are some questions you can ask yourself (on a looking forward basis) about how the organization can support the ongoing sales effort…

  • What new or different marketing support will your sales team need to help them attract buyers that match your ICP (ideal customer profile) and execute on their daily sales activities?
  • What new or different after admin support will your sales team need to free them up to execute on more of their daily sales activities?
  • What new or different products/pricing [if any] will your sales team need to help them improve their results?
  • Will the CRM (customer relationship management software) configuration need to be adjusted to support the sales approach?
  • How will the weekly team and one-on-one sales coaching need to be structured to support sales success?
  • Is the staff compensation plan structured to incentivize the sales behaviours that will act in support of the strategy?
  1. Review the Sales Strategy

Strategy is a broad topic in business. So, to assess your sales strategy start by considering the following questions…


Are our Ideal Customer Profile and Buyer Personas accurate?

It might be that the people the team used to sell to are now in fact the wrong people to sell to. Double check that your team are having conversations with the right buying influences.


Is the business we are winning the business that we want to win?

Sometimes the sales path of least resistance leads sales to say yes to opportunities that are in fact outside of the strategy. Has this been happening to you? Is your team in fact applying sales efforts to the wrong type of prospect client?


How is our profitability?

Sometimes we aim for business of the type we believe we would like, but over time determine that it is problematic business (unprofitable, unwieldy to service, difficult to retain etc).  Such a revelation may in fact take you back to the start of your strategy planning and result in significant course correction interventions. In my experience as a fractional VP sales I’ve seen that companies unwilling to “rip off the Band-Aid” and re-strategize suffer greater in the long run than they would have by addressing the situation in the short run.


Plan-Do-Assess & Course Correct-Repeat

I recommend to business-to-business sellers as well as business to consumer sellers the simple approach of Plan-Do-Assess & Course Correct-Repeat.  The Plan piece is blue sky time and fun. The Do part is exhilarating and rewarding. The Assess & Course Correct component however is the heavy lifting element. The team needs to pause the exhilarating Doing and be ready to face the reality that they may have been marching in the wrong direction or climbing the wrong hill.


  1. Hire a Fractional VP of Sales

As always, there is a great deal nuance in applying the principles I’ve outlined above. And it takes time which not every leader has in abundance. My role as a fractional VP of sales allows me to facilitate this process and much more. I’m happy to speak with you if you would like to learn more [email protected].


The Top 5 Traits of Successful Salespeople

Show me a salesperson who works 60-hour weeks and I’ll show you someone who is inefficient, ineffective, frustrated and likely to leave you sometime soon.  They appear committed and passionate, then they’ve quit and you have a hole to fill.

It’s been my experience that the best sellers don’t log a ton of overtime.  They may work late here and there (prepping for that big presentation) but otherwise they show up on time and leave on time. 

If the path to sales excellence isn’t paved with copious hours worked, then what’s the secret?

As with excellence in any endeavor, overachievement in sales is not due to any one trait, but several.

Here are the top 5 traits of successful salespeople.


The best sales representatives are organized.  Their calendars are full of meetings, often color coded by type.  Their Task list is ever present with only a few overdue items.  When there is a big presentation scheduled, there is corresponding prep time scheduled too.  When something is due from them, it’s on time.



A good salesperson will spot things that need (or will need) doing to move their deals forward and they do them.  They actively look for ways to wow buyers, and they make them happen.  They invite the right internal stakeholders to meetings, grabbing a piece of their calendar with ample notice.



Your best salespeople have a burning desire to bring people (aka. buyers) to their way of thinking.  They enjoy turning a No into a Yes if they believe doing so will help the customer.  They want to earn an above average income.  They are competitive in a positive way and aren’t shy about it.



A top seller will regularly read books and articles, attend workshops and seminars as well as other learning opportunities related to their craft.  If asked, at any given time they’ll have at least one business book on the go.  They’ll also read in other disciplines to inform their approach to their craft (yes, they view sales as a craft).



The best athletes on earth need a good coach to help them excel, as do your top sales reps. The cream of the crop will be salespeople that embody all of these traits while still being humble enough to receive feedback from their (fractional) VP of sales or sales manager.

In my role as a Fractional VP of Sales, I’ve had the pleasure to work with many sellers.  Some great, many very good and a few that were miscast.  The myth that the Gift of the Gab = Great Salesperson is just that, a myth.  Meet with your best and my guess is they’ll display most of the foundational traits and characteristics listed above.  Encourage the rest of your team to follow suit and watch results improve. 

As always, there is lots of nuance to the application of the concepts I’ve noted.  I’m happy to chat further about them with you [email protected].


5 Tips to Optimize Your Sales Funnel and Avoid Stagnant Revenue

For business owners, it’s not uncommon for stagnant levels of revenue generation to creep up on you. Most often, this is because of a problem with one or more stages of the sales funnel.

Unfortunately, it typically takes one to three months to realize that your revenue is stagnant. By the time you become aware of flat revenue and start addressing your sales funnel, another quarter has gone by. It may even be that you realize there’s a problem halfway through the year, and it’s too late to fix it.

By not identifying problems with your sales funnel early, you risk setting the stage for an entire fiscal year of flat revenue. So, what can you do to prevent this?

Top 5 Tips for Addressing Stagnant Revenue from a Fractional VP Sales

To avoid a long stretch of stagnant revenue, it’s crucial to put in tangible fixes on time and at the right time. Here’s how you do that.

1.      Assess Your Revenue Generation Levels Monthly

To address a problem, you must understand what it is. By looking carefully at your numbers each month, you can identify flat revenue and then ask yourself what the reason behind it may be. You need to dig deep and search for the “why” behind the “what”.

Consider three different levels to find out why your revenue is flat:

  • Are you not getting enough deals into the top of your sales funnel?
  • Are the leads in the middle of your sales funnel not moving to closing fast enough?
  • Are you not closing enough of the later-stage leads at the bottom of your sales funnel?

Once you’ve identified which of these (or which combination of these) is the problem, you can do something about it.

2.     Fix the Top of the Sales Funnel

You may find that you’re not getting enough prospects into the top of your sales funnel. If this is the case, you need to assess how your sales team is doing with business development and ensure they are addressing the correct customer profile to increase their likelihood of finding prospects who are a good fit.

To determine whether your sales teams are doing enough outreach, you need to examine your activity-based metrics. If you don’t have any, there’s your first problem! If you do have them, are they at the right level? If you have goals for business development, determine whether your team is hitting them and consider whether the goals are the right ones.

3.     Fix the Middle of the Sales Funnel

If you’ve determined that the main reason behind stagnant revenue is a clog in the middle of your sales funnel, then you know you’re dealing with a lack of sales velocity. In other words, your deals are taking too long to close (and note that “too long” here depends on your product in your particular industry and market).

Once you’ve determined that your sales are taking too long to close, you need to drill down one level deeper and ask your sales team why – they have the answers. Next, you need to examine the reasons they identified and figure out which of those you can control or influence so that you can improve your process and nudge your deals forward.

4.     Fix the Bottom of the Sales Funnel

If your sales team is not closing enough, it’s a sign that something is amiss in the process that precedes asking for the sale. Again, speaking with your sales team should give you the valuable insight you need to course correct.

Walk through the sales process with your team and double-check how effectively and efficiently they are executing those steps. If they are ineffective or inefficient on some of those steps, you know where to make improvements.

5.     Map Out Your Sales and Business Development Processes

As you’ve seen from tips 1 through 4, it’s crucial to have your sales and business development processes mapped out so that you can easily assess where things are going off the rails. If you don’t have your processes clearly mapped out, then you can’t do any of the preceding steps.

This involves sitting down with your team and asking them exactly how they go about moving a customer from being a prospect to being a paying customer, writing it all down, and then determining how you can make the process more efficient and effective.

This comes full circle right back to the first tip, which is to assess your teams’ performance and processes regularly. That way you’ll identify where the problems are, put the fixes in place, and deal with stagnant revenue effectively.

What If These Fixes Don’t Improve Your Revenue?

If you assess your revenue every month, make fixes, and then reassess at the end of the quarter to see how effective your fixes were at getting your sales unstuck, you should be able to make up ground on declining or stagnant sales. Then all you need to do is continue with this cycle and optimize.

If, however, you find that none of the fixes worked, it could be that you don’t have a sales problem. You may have a product problem, meaning it’s the wrong product fit for the market or customer. Or, you may have a service delivery issue in which you’re not meeting client expectations, preventing them from coming back to buy from you a second time.

In my role as a Fractional VP Sales with a manufacturing client, I’ve optimized a client’s sales process to be effective and efficient only to find that production couldn’t keep up with sales. Interestingly, in this case, sales were a part of the fix because the way they were communicating with production was insufficient to have production be successful and meet demand. Internal collaboration turned out to be the fix, but if we hadn’t optimized the sales process first, we wouldn’t have identified this issue.

The bottom line is that in sales the opportunity cost of time is very high. If your salespeople squander their time doing the wrong things, they won’t have enough time to do the right things, and your revenue will suffer. By following the steps above, you can ensure your sales team is effectively and efficiently executing each step of the sales process so that you can make the fixes necessary to keep your revenue growing. Get in touch with me if you’d like to discuss this further.

How to Retain Your Top Sales Performers

As a business owner, retaining your top salespeople is important for consistently hitting your sales targets. After all, recruiting is a costly and time-consuming process, and when you hire someone, you want them to stick around for the long haul to minimize disruptions to productivity.

As a Fractional VP Sales, I’ve seen how common it is for the resumes of salespeople to show a pattern of job jumping. So, how can you ensure that you hold on to your top salespeople? If you’ve ever had salespeople jump ship and found yourself wondering why, or if you simply want to avoid this from happening in the future, keep reading.

How to Find the Right Management Mix to Keep Top Performers

Retaining your top talent needs to be a purposeful exercise, and you shouldn’t manage all people in the same way. If you try to take a one-size-fits-all approach to management, there are going to be people who don’t respond well and often they will speak with their feet by walking out the door. Here are four ways to ensure you’re finding the right balance to keep your top performers motivated.

1.     It All Starts With Your Company Values

To address employee retention, you first need to have a clear understanding of your company’s fundamental values and principles. A strong values-based management foundation is the toolset from which you, as the business owner, and your managers can draw from to help manage your employees.

It’s worth noting that it’s not a matter of completely different management styles for different employees. The magic lies in the nuance of how you apply your company values and principles to manage and lead your people from day to day.

2.     Recognize That Top Performers are Always Different

In any team, you have top performers, middle performers, and some at the bottom of the pack. Whatever makes your top performers different from the rest of your staff is typically what makes them successful in their roles. These differences are precisely the reason you need to take a different management approach with them than with other staff.

Understanding exactly how top performers are different will help managers and other leaders figure out which leadership style or approach to take to keep them motivated, and ultimately, loyal to your business.

3.     Understand What Motivates Your Top Performers

Different people are motivated by different things – that’s as true in business as it is in life. Top performers often value different things than your lowest performers. That’s why if you want to hold on to them, you need to be able to recognize what your top performers are motivated by, and to what degree.

When it comes to sales success, top performers are typically more motivated by money. If you set up a compensation plan that does not richly reward those who are motivated by money, they will go elsewhere to find a plan that does. For people motivated by money, financial incentives like commissions are important.

Another trait typical of top performers is a high degree of initiative. Top performers who value freedom and independence will not respond well to micromanaging. If you try to make them always stick to rules, they are likely to feel restricted and leave.

Similarly, you need to consider whether your top performers are motivated by teamwork before setting team-based sales goals. A top performer who is a team player and feeds off team motivation may prefer this, but someone who is more of a lone wolf motivated by independence won’t want their performance tied to someone else’s. If a top seller who prefers to work alone has their income tied to something they can’t control, they’ll leave.

4.     Inventory the Traits and Characteristics Needed for Success

Just like there’s no one-size-fits-all solution for how to manage top performers, there is no blanket solution for retaining talent across industries. As a business owner, a manager, or another leader, it’s necessary to inventory the traits and characteristics needed when it comes to success in sales for your industry, with your products or services, and in your market.

Then, you need to provide those motivators for your top performers to keep them happy so that they can be as successful as they want to be. This may involve doing it in a slightly different way for different salespeople – as mentioned above, the magic is in the nuance of the day-to-day application of your values to how you manage your people.

After reading this, the steps for holding on to your high-achieving staff may seem fairly obvious. Yet, the loss of key talent is something I see business owners struggling with all the time in my role as a Fractional VP Sales. Maintaining a stable, productive team depends on your ability as a leader to identify, understand, and apply different motivators in your management of top performers.

Once you can successfully do so, you’ll not only be able to hit sales targets and reduce staff turnover but also create a more appealing environment for recruiting new hires. I’ve given you a lot of ideas here, and there are a lot of layers to consider. I’d be happy to help you think through how to apply these tips to keep your top performers. Contact me today to start a conversation.