Short Sales Leadership Tenures

A reader writes, "In the last five years I have had three different sales leadership positions at three different companies. I was laid off from the first position, resigned from the second to accept a job at the third and got laid off again. This experience has been stressful and damaged my confidence. More than anything, I want to stop this from happening again. What steps should I take?"

Let's start with some simple math. Five years equals 60 months. With three different jobs, you've averaged 20 months per stay. Regrettably, you're right on track. Sales leaders last, on average, less than two years in the job. Sometimes, it helps (a little, anyway) to know you have company. Sales leaders (sales managers, directors of sales, VP's of sales) rarely enjoy long tenures.

Take an Assessment

Before you accept another position, make sure you have the necessary competencies and skills. Talented reps (of which you were probably one) don't necessarily make talented sales leaders. If you haven't already, take an assessment specifically geared toward the sales profession. Avoid general personality assessments or deals that seem to good to be true.
Should the assessment show you not to be a strong candidate to manage others, take that seriously. You'll have to work hard to succeed.

If it shows you have the capabilities to manager others but shows some areas of weakness, pay close attention. Hone in on those and get some training or coaching to help you address any problem areas.

Conduct Your Own 360°

Go back two jobs, contacting your direct supervisor and a few reps you managed. People sometimes speak more freely when enough time has passed. Ask them for a candid evaluation of you management abilities. 

Be brave. Include a rep you suspect didn't enjoy working for you. We're talking about your career here and you need to understand what's happening. Explain why you need this information. Not everyone will agree to participate, but some will, especially if enough time has passed.

Once you've completed this exercise, look at the notes you took when speaking to the different individuals. What did you learn? Were there any "Aha!" moments and patterns?

Break Down Past Interviews

Think about the interview processes you went through for you prior positions.

  • What questions were you asked?  
  • Which ones did you find to be the most effective and thought provoking?
  • What questions did you ask?
  • What did you not ask that you should have?  
  • Did you get the answers you were looking for?
  • Who interviewed you and how many times?  
  • Did you meet a wide range of employees or remain almost entirely in the sales department?  

If you kept notes from past interviews, look them over. Be aware of inconsistencies or red flags.


When you formally accepted these three jobs, did the responsibilities you took on bare any resemblance to what you learned in the interview process? What came as the biggest surprises (negatives and positives)?  Did you experience any significant let downs? Think about any "If I had known this beforehand" moments.  

Create columns on a spreadsheet for the three past sales leadership jobs. List the various pros and cons for each one. Again, look for patterns.

Final Thoughts

The four exercises I recommend should help you develop a better understanding of yourself as a sales leader as well as what might have gone wrong with past jobs. It's important work.

In next month's newsletter, I will address the job interview itself, making specific recommendations about questions you should ask throughout the process.

Qualifying Questions - A Sales Manager's Best Friend

A reader writes, "One of my reps gets really excited after meeting with a potential new customer. He then puts in a request for a sales engineer to accompany him on the next visit to this prospect. Unfortunately, he usually gets very incomplete information from the decision maker. It's costly for me to send the SE out to speak with poorly qualified possible buyers.

"Having accompanied him on several unproductive visits, the SEs have lost trust in this rep, pushing back about visiting clients with him. I can't blame them. How do I make this rep understand the importance of getting certain information from prospects before I commit additional company resources?"

Many of my clients struggle with a lack of proper qualifying information from their reps. These suggestions should help.

The Root Cause

This goes back to the fear of rejection. First, reps worry about asking too many questions - the potential client might get annoyed and refuse to answer some of them or shut down altogether. Then, if they do answer the questions, reps fear discovering the prospect might not really need their product or service. That's one less prospect to put in the pipeline.

What Do You Need to Know?

Before speaking to the rep, make a list of the questions you need answered before authorizing a sales engineer visit. Of those questions, determine which two or three are absolutely essential.   

Stay flexible, though. Sometimes prospects can't or won't answer every single question. With other prospects it might take multiple contacts from the rep to qualify them. Don't always expect a "one and done" to get the required information.

Define the Term

Make sure the rep understands the definition of a qualifying question. Explain that these critically important inquiries determine whether or not a prospect can potentially use your product or service. The answers don't guarantee a customer will buy, just that they could buy.   

High performing reps use these valuable questions to decide if they should spend any more of their valuable time with a prospect.

Be Clear

Go over the list of qualifying questions you put together.  Say something to the rep like, "I need you to ask these questions to determine whether or not sending an SE out makes sense. You must get answers to a minimum of 7 out of 10 and numbers 1 and 2 are required. Without answers to those, I cannot justify a visit from a sales engineer."

Reinforce the Behavior

Ask this rep to pick out a book on early stage prospect qualification. Many excellent ones exist. Have them read and discuss it with you. 

Help the rep get comfortable through practice. During staff meetings, role play. Take turns having the salespeople play the part of the rep and the decision maker and ask each other qualifying questions. Discuss afterwards.

Do the Math

Determine the approximate cost of sending an SE out on a sales call. Include travel as well as pre-call preparation and post-call follow-ups. Share this information with the rep.  Demonstrate the expense involved in meeting with an inadequately qualified prospect.  

Make Necessary Changes

If after a period of time, the reps report consistently struggling to get certain questions answered, look into it.  Run the question by peers or a few trusted customers. Find out whether or not they would answer it. Why or why not?  The question might need to be re-worked, eliminated, or used further into the sales process.

Final Thoughts

Successful salespeople ask high value, insightful questions to develop solid rapport with prospects. The information they bring back helps the sales support staff and their direct supervisors prepare for productive meetings with potential new clients.

Advice from Sales Leaders

To continuously improve and grow in our chosen profession as sales leaders we:  listen to webinars, read books, follow other sales and business leaders on social media, attend training classes, join professional organizations and talk to industry and professional peers.  

Along the way, there's always that one piece of advice that stays with us. This year, I asked these six accomplished sales leaders to tell me about the best sales management advice they've ever received. Here were their responses.

"Sales leaders serve both customers and your sales team. Sales leaders must make every effort to stay as close as possible to the front line, facing and meeting with customers as well as the sales team. Sales leaders must constantly view the environment they are creating and the culture they are fostering from both the customers position and the sales person's view point. It is a delicate and ongoing balancing act. Bottom line... always be listening."


Frank Costanzo
SVP Sales and Business Development, Caliper
Objective, accurate employee assessment instruments.


"It's all about sales results. But if you just focus on sales results, you might not get there. Know what causes sales, what causes that order to happen. If I can understand that, then I can measure, monitor, and coach to raise the expectation of that behavior, in turn getting the sales result."


Ken Pfrommer
VP of Sales, Kenseal Construction Products, A Division of A.H. Harris
Innovative solutions in waterproofing, glass and glazing, restoration, and building envelope.


"Assuming you are aligned in your goals and objectives, whenever possible, have a collaborative relationship with your rep by working with them as opposed to dictating and mandating."


Mike Waldron
VP of Sales, Xactly Corporation
Cloud-based incentive compensation solutions for employee and sales performance management.


"You don't have all the answers. Always be seeking the advice of others. When possible incorporate the advice of others into your work, especially advice from the people actually doing the work. People never disagree with their own words."


Brian Donovan
North America Sales Trainer, HomeAway
Vacation rentals available to travelers through our online marketplace.


"One of my earliest mentors when I was taking on my first management role told me something that has always stuck with me. I know it's a pretty common saying but at the time I had never heard it.  He told me to, 'Always be a duck. Calm on the surface even when padding a million miles per hour under the water.'"


Christopher Rack
Chief Revenue Officer, PureB2B
Lead generation and data provider that connects marketers and buyers


"It is essential to listen to your salespeople and understand that each person is different. You need to manage each person according to their specific needs and personality in order to communicate your expectations effectively."


Matt Beirne
National Sales Manager, GIE Media, Inc.
Marketing and communications business-to-business media.


A big thank you to Frank, Ken, Mike, Brian, Christopher and Matt for giving my question serious thought and sharing your advice with my readers. I appreciate it very much.

Have a wonderful holiday season!

Acting on Assessment Results

A reader writes, "Earlier this year, I had my reps take a sales assessment. I reviewed the results with each of them, finding the information provided to be accurate and eye-opening. The problem - I haven't done anything with or about the assessments since. What do you recommend?"

This happens often. Sales leaders go through the assessment with the rep and then neglect to re-visit this powerful, career enhancing document.

Look At It Again

Sales leaders taking a second look at the reps' assessments tell me they get even more good information the second time around. They don't have the pressure of telling the rep some things they might not want to hear. They've also had time to consider the results, which they see validated when they monitor or accompany reps on calls.

Most conclude the assessment captured the salesperson's strengths and challenges very accurately.

Responses Vary

Salespeople have different reactions to the information provided, especially if they've never taken a sales assessment before.

  • Some focus only on the areas needing improvement and ignore any positives. They require some time to process the critiques and take a more balanced view of the results.
  • Others have no idea what their areas of strength are.  They just get out there every day and sell. Having the test point out and validate their talents serves as great motivation.  
  • Ambitious reps see it as a vehicle for increasing their income. If they can address a few of the weaknesses, they can earn more money.

Though rare, sometimes reps shut down. They consider the information nonsense and want little to do with discussing the results.  

Most reps, after thinking it over, see the comments and critiques as valid.  


Prior to the next regularly scheduled monthly or quarterly one-on-one meeting with the rep, tell them you want to discuss their assessment again. Ask them to review the document before the two of you talk.

Start the conversation by asking them open-ended questions like:

  • Now that you've had some time to consider the results, what are your thoughts?
  • What surprised you the most?
  • Have you changed anything about your sales approach based on some of the comments?
  • What findings did you disagree with?

Let them talk. Let a little silence fall while they process their thoughts. Resist jumping in or arguing with any conclusion they've come to.  

Moving Forward

Together, look at the suggested areas of improvement and discuss only one or two specifically. Continue to ask questions such as:

  • Have you become more aware of this since we first looked at the assessment?
  • How do you think it affects your sales performance?

Create a plan for reading a book on the topic, participating in targeted on-line training, and observing other reps who excel in this area. Attach dates, goals and outcomes. When working together, discuss the particular issue right after a sales call or appointment.


Many companies provide guides or workbooks to accompany the assessments. If available, I recommend purchasing them for each rep. These documents use the same terminology as the assessment and help to focus coaching sessions.

Casual Check-ins

Look for other opportunities, besides one-on-one meetings, to coach reps on areas for improvement. Email or pick up your cell phone frequently. Say to the rep, "I saw you called on LHS Associates this morning. How did it go? Were you able to try the response we came up with to the configuration objection?"

These calls remind salespeople that you want to see them succeed. It also reinforces the new behaviors the two of you are working so hard to make part of their regular routine.

Final Thoughts

Assessments aren't a one-and-done event. As a sales leader you want to turn it into a working document that you refer to throughout the rep's tenure with your organization.

Keeping a Star Rep

A reader writes, "Recently, one of my best sales reps expressed interest in becoming a sales manager. While I think he has the qualities to succeed as a leader, I have no plans to create a sales management position. I supervise the sales staff and plan to do so until I retire or sell the company - both events are many years away. An excellent rep, I would like him to remain with the company for as long as possible.  How do I handle this situation?"

Support him in every way possible.  

Education as a Benefit

Companies of all sizes offer full or partial tuition reimbursement programs for a reason. They know those who learn and grow make better employees. People capitalizing on these programs tend to have longer tenures with their organizations.

Offer to pay for all or part of a sales management training program. Be clear about the maximum the company will spend and any other conditions attached - like achievement of a minimum grade.

Provide Some Experience

Put this rep in charge of a project. It doesn't necessarily need to involve direct management of others. You might be considering changing CRM vendors, starting an inside sales group, purchasing new lead tracking software, or improving communications between marketing and sales.

See if he has any interest in creating or heading up a committee to begin looking into any one of these initiatives.

Act as a Mentor

Share your management know-how and wisdom. Agree to have lunch with this rep once a month to discuss your experiences supervising people. Talk about what you find challenging and what you enjoy. Recommend books or tapes that have positively influenced your career.

Always keep in mind, this person still works for you, and use good judgment in considering what subjects get covered.  Speak in general terms. Never talk about current employees specifically. When discussing an experience with a past employee, don't name names.  

Make Introductions

Ask professional contacts currently managing employees if they would be willing to meet the salesperson for coffee to discuss their experiences. Hearing from people outside of the company helps provide a fuller perspective.

Why Do Any of This?

Those interested in pursuing a management position eventually find a way. Sometimes reps leave a job where they're perfectly happy to accept a sales position with a company offering management opportunities.

If this salesperson starts down that path, you now manage a distracted job-hunter as opposed to a focused sales representative. Instead, embrace and encourage their ambition. Grateful for the opportunity to learn and grow, they'll likely remain productive and on the job for some time to come.

The Flip Side

Most sales reps at some point in their career consider the possibility of becoming a sales manager. When you support the rep as they take a course and speak to other managers, they may come to the realization they either don't want or aren't ready to manage others. It happens.

While it looks glamorous from the outside, anyone managing people knows it to be anything but.

Final Thoughts

If this rep remains serious about pursuing a management position, and you have none, he will eventually go elsewhere. It's inevitable.  Having been supported and encouraged by you, he'll likely leave on very good terms, express gratitude for your help, and remain a great business contact. He may be in a position to do you a good turn at some future point.

Is Your Sales Rep Moonlighting?

A reader writes, "My company hired a sales representative for a territory far from headquarters. Shortly thereafter, I started to get the uneasy feeling she had two jobs. Sometimes, she missed our weekly staff conference calls. Other times, she was unreachable during certain hours of the day, or days of the week. She was achieving her sales goals, but not by much.

"A few weeks ago, she resigned. I would like to hire a rep for that territory again.  How do I protect against an employee holding a second job?"

Reps like this are salaried employees with your company. They should be singularly focused on your customers as well as developing extensive product knowledge over time. 

Technology allows most every company to place reps in territories all over the world. With this ability comes risk, such as not knowing where they are, or what they're doing with all of their time. Sometimes, these reps have another job.

David Sawyer, an expert with over 35 years in the private security industry and President of Safer Places, Inc., a background screening firm, offers the following advice:

Employment Contracts

Act preemptively. Your employment contract should clearly prohibit sales representatives from working a second job in sales.

Background Check

Require a background check as part of the hiring process. The release form most new hires sign gives permission for this check as long as they remain an employee. (This varies state-by-state.)  

Credit Reports

Ask your background screening company to run a credit report. Often, employers are listed near the top of this document.

Database Search

Many background screening firms outsource their employment verification to companies such as The Work Number ( A search of this database may show title and dates of employment. If the dates are current, you'll know they have a second job.  


This agency is an excellent source for verifying salary and employers. However, they require a special release form to be signed for each search. Include this in your initial background check. Then, consider making it a policy to run an annual background check and include the IRS search every year.

Private Investigators

"I list this last," says David, "as it is the most expensive option. Investigators charge by the hour. If you're acting on a hunch, it could take quite a while keeping your employee under surveillance before you'll become satisfied that your hunch may be unfounded."

Final Thoughts

Clients with remote sales forces often worry about the sales reps having two jobs. I suggest adding specifics to the employment contract including:

  • Starting / ending times of the workday
  • Availability to be reached during the workday
  • Dates / times of staff meetings
  • Dates / times of quarterly or annual offsite sales meetings
  • Lead times for taking vacation / personal days

Most remote reps have considerable respect for their employers and work hard at their jobs. Only a small number "work the system." Don't let those few inhibit you from hiring a remote rep. Just make sure you have the safety net in place to help if you suspect the rep isn't on the up and up.

What to Do When a Rep Makes a Big Mistake

A client asks, "One of my better reps made a significant mistake with a major account.  She told me what happened and admitted it was her fault. Before this, no problems existed with the customer. I called two executives she deals with regularly and visited them in person. Promises were made, apologies accepted. We retained their business.  

"I always enjoyed a collegial, respectful business relationship with this rep. Since the incident, we have polite but awkward interactions. She seems upset.  Did I handle this situation correctly?"

You did what comes naturally - jumped in to save the day.  From her point of view, you showed little faith in her ability to right the wrong. Worse, you probably diminished her standing with this account.

In terms of client relations and her career development, consider handling things a little differently next time.

Acknowledge Her Candor

Whenever a rep approaches you about a potential screw-up, start with, "I appreciate you coming to me directly. Take a deep breath. Start from the beginning. Tell me what happened."

This acknowledges the rep has done the right thing by bringing the situation to your attention. It leads to a more productive conversation.

Hear the Rep Out

Just listen. Don't interrupt. Resist jumping in with suggestions or criticisms. Ask questions only to gain clarity.

Getting the facts gives you a clearer picture of the issue. Take a moment to gather your thoughts on how to proceed.


The company has the final say on client matters. But the rep handles this account. For their professional growth and future relationship with this client, make them part of the solution.  

Solicit their suggestions for fixing the problem. Formulate a plan together.

Call in Tandem

Depending on the severity of the situation, a face-to-face visit could be necessary or, a phone call or Skype might be sufficient. Either way, you need to be present during the conversation. Have the rep set-up the meeting.  

Prior to the meeting, tell the rep that they lead the discussion, offer solutions, and issue apologies where appropriate. When questions or comments get directed towards you, let the rep know you'll be turning the conversation back their way.  

Say to the rep, "I'll make a comment like, 'That's a fair question. Julie and I discussed this issue. She'll talk about the potential solution.'"

Julie takes it from there. If she stumbles or the call begins to go badly, you step in only when absolutely necessary. Redirect towards her as soon as possible.


Company leaders in this situation worry about how they'll come across if they let the rep steer the meeting. Many feel the customer will perceive them as:

  • Unaware of the details
  • Abdicating responsibility
  • Not taking the problem seriously

Your presence in the meeting speaks volumes. You're listening, taking notes, participating where appropriate - and most of all - supporting a salesperson you hired and entrusted with this account. You're not running away from anything.


Post-meeting, talk about what went on. Let the rep speak first.  Make your first comments positive. Be candid about areas needing some improvement. Help with any internal follow-up necessary to fix this problem.

Mentoring Employees

Leaders recognize, acknowledge, and develop talent. Any rep tasked with addressing and fixing a problem experiences a real learning moment. You earn their respect and loyalty.  Likely, they'll work harder for you and the organization going forward.

These rules apply when the company makes a mistake, not just the rep. If an order gets messed up, the rep should work to make it right, so as to maintain their customer relationship.

Explainer: Role of Sales Manager vs Sales VP

A reader writes, "I'm considering promoting my current sales manager to VP of sales. In the past, you've written newsletters about the risks of promoting a top salesperson to sales manager.  Are there risks in offering the VP job to a top performing sales manager? If so, what are they?"

Kudos to you for giving this potential promotion serious thought. So many times business leaders neglect to think it through. 

The two jobs differ. Just like transitioning from salesperson to sales manager alters what an individual does on a daily basis, the promotion requires the new VP to leave some aspects of their old job behind. They assume many new responsibilities.

To get his perspective, I spoke to Stan Davis of Standish Executive Search, who has placed many senior executives over his 11 years in the executive search business, and who previously served as a corporate resources executive and in-house organizational development leader for over 30 years.

Function versus Leadership

"A sales manager has direct supervisory responsibilities - problem solving, running meetings, disciplinary issues," Stan says. "But a VP of Sales takes part in the leadership of the company - influencing people, enacting change, developing and deploying talent."


Sales managers manage to the sales plan by accompanying reps on calls, tracking the rep's progress and holding them accountable for achieving quota.   

Stan adds, "Vice Presidents of Sales no longer plan just for themselves and the sales team. The sales plan is a component of the company plan.  They participate in planning for the whole organization now, and monitor the progress of sales through the sales managers."


Sales VP's, along with others on the executive team, work 12 - 18 months into the future on company-wide initiatives. They don't sell the product directly to customers anymore.  When considering someone for a VP role, Stan asks himself, "Can they build relationships with others to make sure the product works for the company financially, technically, and operationally?"


Salespeople typically receive a base salary and commission or bonus based on their individual performance. Sales managers most often get paid with base salary and commission or bonus commensurate with their group's performance. Sales VPs usually get compensated on overall company performance.  

Who Does Each Role Serve?

Sales reps call on customers. Sales managers serve the salespeople. Stan says, "Vice Presidents of Sales align themselves more directly with the shareholders, concerning themselves with earnings." 

Think Before You Begin

Many companies have a VP of Sales by title but not by actions. Sometimes this occurs because they think they should have one. On occasion companies fear looking small or unsophisticated if they lack someone carrying that title on their website. What does your organization really need?

Sales Manager
VP of Sales

Develop and implement company's sales plan
Responsible for quota attainment for a region or segment
Responsible for revenue production for the company
Hire and train new salespeople
Deploy sales force and sales managers as needed to achieve company plan
Check and manage daily / weekly sales activity and results by each rep
Monitor regional or segment activity and results by teams or sales units
Monitor CRM reporting / accuracy in support of VP and others
C- and Board- level reporting on revenue production
Coach / motivate reps
Coach managers / motivate managers and reps
Strategize with reps
Strategize on key accounts with managers and reps
Reassign / outplace underperforming reps
Reassign / outplace underperforming managers
Visit customers frequently
Visit customers occasionally

Final Thoughts

Hiring from within has its benefits. The candidate knows the company culture, customers, products and services. Other employees see promotions as real possibilities. Take the time needed to ensure you make the right decision for the employee and the company.

This article outlines the process a leader goes through when thinking about promoting a candidate from within. Next month I will write the questions leaders should ask before hiring for this position.

Lecture Less, Help More

Busy company leaders often lecture, pressure, or intimidate salespeople as a way to get them to achieve quota. They say things like, "I'm baffled by the fact that we don't do more business with software companies.  There are a million of them just in this area. You'll face consequences if you don't bring in a couple of those companies this year.  I'm very serious about this."

For 2014, set a goal to become more of a helping / coaching manager than a lecturing / intimidating manager.  Partner with the sales representatives as you ask them to improve their performance in a given area. Work with them to accomplish sales goals.

As an example, let's look at an exchange between president (manager) and salesperson regarding cold calling:

Lecturing / Intimidating

"You've got to cold call.  You lost accounts in your territory last year and had no new business to replace that sales revenue.  I want to see a lot of new business this year and I mean it.  I can't afford to keep you on the team if you can't open new accounts."

Helping / Coaching

"This last year, you lost 10 customers in your territory - one large, three medium-sized and six smaller accounts.  Unfortunately, with little prospecting activity, you had no new business to replace those clients. This situation is serious. Companies lose market share and go into decline when salespeople don't bring in new accounts."

Ask Questions

  • How do you go about cold calling currently?
  • What percentage of your time is spent cold calling?
  • How do you determine who to call?
  • What about cold calling makes you feel uncomfortable?
  • How can I help you?

Lay Out a Plan

"It seems like you did very little prospecting this year.  I think Barbara does the best job of cold calling at our company.  I've spoken to her about this and I'd like you to work with her for at least two days this month. Sit with her and listen to her calls. Accompany her when she meets with or makes a presentation to a new prospect.  Ask her about what you observe. In addition, please research books on cold calling.  Pick out a few that look good to you."

Remain Involved

"Let's meet again in two weeks.  By that time you'll have worked with Barbara at least once and have a list of cold calling books for us to discuss.  When we talk, I'd like the two of us to work together to assemble a list of prospects as well as set cold calling and new business revenue goals for 2014."

Rep's Reaction

Presidents and owners worry that reps won't take them seriously if they don't make a speech, yell, shake their fist, coerce or browbeat them.  Remember, the reps have grown accustomed to the dramatics.  By handling the discussion as more of a mentor / coach, you demonstrate how serious you are.  You do that through asking questions, listening, making suggestions, giving your time and showing support. 

When you use this new style, reps pay more not less attention. Rest assured, the salesperson gets the message. To stay with the organization they must prospect for and close new business - end of story.

When leaders manager by "getting tough" then waiting to see if the rep improves their performance, they tend to let reps remain with the company longer.  Ironically, most leaders discover when they've invested some time in a rep and things don't work out, they find it easier to put them on warning and eventually terminate them.

Going Forward

If this rep works hard and starts bringing in new business, you might want to send them to an advanced training course on prospecting.  You could set up a special contest that rewards their cold calling efforts.  Many possibilities exist, provided they put in the effort.  Meet with them regularly and hold them accountable to their goals. Compliment them on improvements they make.

You have a right to expect certain things from a rep (increasing business within existing accounts, opening up new vertical markets, selling the entire product line, and yes - opening new accounts).  Think about the salesperson you're most upset or disappointed with. Before you give up (or blow up) ask questions, offer assistance - be on their side.  See how it works out. 

My Blog

Earlier this year, I launched a blog to complement the longer articles I write in Sales Management Tips.  Check it out from the blog link on my website.

The Accidental Sales Manager Guide to Hiring

Available on my website, "The Accidental Sales Manager Guide to Hiring" summarizes the pre-hire process recommended in "The Accidental Sales Manager."

Managing Sales Efforts in Close Quarters

A client asks, "I am a sales manager at a small start-up company. Our office space is tight and we all sit in cubicles. No one has a private office. Because of this, there is a very casual style of communication. Virtually the entire office eats lunch together every day. I sometimes find it hard to feel like a sales manager or much of an authority figure at all. Any suggestions?"

You are wise to observe the problems that very small office accommodations can cause. Let's look at a few changes you can make to separate yourself a little bit from the people that you manage.

Hold Regular Meetings

Many of my clients who work in offices similar to the one that you describe forgo regular staff meetings because they don't have any place to hold them and "everyone hears what’s going on anyway." This leads to people misinterpreting what has been said or making their own rules. Either way, it isn't good.

Hold a regular weekly staff meeting with a formal agenda at a regular place and time. If there is no conference room, talk to your building manager and ask if there is a common conference room available for tenants or see if another company would let you borrow theirs for a nominal fee. If neither of these suggestions work, pull your chairs together in a corner. Somehow make it a separate and distinct event.

Find a Place for One-on-Ones

Similarly, there are many times a sales manager needs to have a one-on-one conversation with a salesperson. Find a location where you can have these talks when needed.

Curtail Cubicle Shouting

If someone shouts a question at you, resist the temptation to shout the answer back. Instead, ask them to come to your cubicle to discuss it. Say something like, "That's a great question. Come on over for a minute and let's chat about it." If possible, keep a chair or two by your desk to encourage this.

Set Policies and Procedures

Anxious to bring on new business and sometimes hesitant to foist too much of a stuffy corporate culture on the organization, many sales managers at start-ups resist having a policies and procedures manual for the sales organization. While a notebook-sized document may not be necessary, some guidelines are appropriate, especially when it comes to such topics as pricing, discounts, terms of payment, renewals, territories, leads, inbound calls, and commissions.

Having a "make it up as we go" culture undermines your authority by leading sales representatives to believe that if they present you with a compelling enough argument, anything can be negotiated.


If you managed 7 or 8 sales representatives, had lunch with only 2 or 3 of them on a regular basis, and other salespeople felt excluded from this activity, you would be perceived as showing favoritism. However, if the whole office eats together, the atmosphere is fairly collegial and the topics of conversation are appropriate, I wouldn't worry too much about it.

Working in close physical proximity to the employees you are charged with managing can have its complications. By following these suggestions, you will feel like you have created a little space (figuratively) and have regained your authority.

One Conversation Isn't Enough to Alter Behavior

A client asks, "Recently I had a discussion with one of my salespeople about a habit of theirs that was impacting productivity and making others in the office uncomfortable. After our talk, which went very well, there was a noticeable improvement in their behavior. In the past several weeks, much to my surprise, they are back to their old ways. I was very prepared for this discussion. Why did this happen? What did I do wrong? What can I do about it?"

When they notice a problem with a salesperson, many managers spend considerable time thinking about the situation, documenting offenses, discussing the issue with others, receiving counsel from Human Resources, and maybe even doing a little role playing before speaking with the offending employee. They are often pleasantly surprised at how well the discussion goes, and based on this result alone feel the matter is closed. After some time has passed, they are discouraged to discover that the matter is right back on their to do list.

Let's look at that initial conversation as well as some strategies that will ensure a better result the next time around.

Be realistic

Naturally the discussion with the salesperson went well. You are their boss, you were thoroughly prepared for the meeting, and you were armed with the facts. Of course they agreed to stop doing whatever it is you asked them to stop doing; what choice did they have?

Be practical

They have probably been spoken to about this issue before by other employers or colleagues. They might be practiced in agreeing that this is something that cannot continue.

Be sensible

This is a bad habit so it's unlikely that they will stop it completely. Look to significantly curtail or decrease the incidents.

Be specific

Let them know how frequently they do this and when it is the most annoying. Talk about patterns of behavior and brainstorm with them to come up with solutions to mitigate this issue.

Be proactive

Schedule a weekly meeting with them for the next six weeks in a row to talk about the progress they are making. This will signal to them that you are serious about solving this problem.

Be honest

Tell them what might happen if they cannot keep this issue under control.

By setting the expectation, during the meeting, that this will be an ongoing conversation until the matter is resolved, you will increase your chances for success. It is more work, but you will not be lulled into a false sense of security that this problem has been solved after the first conversation.

Friendship Impedes Decision-making

A client asks, "After a long period of poor sales performance, repeated discussions, and multiple attempts at helping him, I have decided to terminate the employment of one of my salespeople. The problem is that we are close personal friends, our wives are close friends, we socialize as couples, and our children know each other. My uncertainty about how to handle the friendship going forward is keeping me from following through on what I know to be the right decision for this salesperson and the company."

First, you seem to have done quite a lot for this individual to try and help him succeed on the job. For that you are to be commended. You also seem to realize the deleterious effect a poorly performing salesperson kept on the payroll will have on the rest of your sales staff. If you do not act, you relationship will be seen by the rest of the sales team as more important than the success of your business. Terminating your friend and colleague will be very difficult. Here are some suggestions for making this awkward situation a little more bearable.

Provide transitional support

Because this person is very important to you, provide the things that will genuinely help him through this painful transition period in his life. This could include: a generous severance package, health care coverage, commissions on unclosed business for a designated period, career counseling, and outplacement services.

Open your rolodex

If you know that this person is not appropriate for a sales position, don't risk your reputation or jeopardize his future by helping him to find another sales job. His stay at the next company will be brief and he will be out job hunting again. But do tell him that once he has some potential career paths in mind, perhaps after he has worked with a career counselor, that you will be happy to introduce him to anyone you know that can help him.

Take a break and then reach out

No matter how the person reacts to their termination, let some time pass before you initiate contact, but assure him that he should feel comfortable contacting you at any time. Once he's settled in to outplacement or you have heard that he is going on some interviews, give him a call. Be supportive and upbeat when you speak to him but don’t make social plans. Reiterate your offer to make introductions.

You might be surprised

Though some people struggle for quite some time to find themselves after a termination, many of my clients are shocked to find that their long-time employee immediately started a business they had been interested in for years or enthusiastically pursued a totally unrelated career path. They often wonder why this person didn't do it years before and realize that fear, inertia, or security kept him in a position that he was ill suited for.

Be prepared to say goodbye

Many people who form close friendships with colleagues are surprised to find that the relationships fade when they no longer work together. This happens even when they leave a job amicably under positive circumstances. Your friend may have formed a friendship with you to protect his job or the embarrassment of being let go may make it impossible for him to feel truly relaxed around you again. There is no way to predict what will happen.

Some of my clients find that once they no longer see the person daily, they have no interest in maintaining the friendship. Others find that they genuinely miss this individual and would like to resume the friendship. I advise them to have lunch with their former colleague and see if they really enjoy the other person’s company. If they do, they can start rebuilding the friendship. If it's strained, they can more easily accept that it is time to move on.