Remote Leadership
How to Improve the Relationship Between Sales Reps and Managers
With all the economic uncertainty out there, it’s tough to find and keep good reps right now. Data from HubSpot indicates that sales rep turnover is around 35% (even in an economic downturn, attrition is shockingly high).
So how do you keep your star players around? Well, according to our Sales Team Retention Research Project study, the top reason both reps and managers stay with a company is ongoing training and development opportunities to help them succeed in their roles.
In my opinion, the key to a solid rep-manager is: both sides support each other to develop and grow. Here are some tips to put it into action to improve the sales rep-manager relationship.
What should managers do to retain their reps?
READ: How to Hire and Retain Sales Reps
1. Create coaching opportunities outside the normal flow
A lot of managers wait until the pipeline call or the forecast call to coach. While those meetings add value, they focus on specific outcomes. Where reps often struggle is investing in skills that they can apply to a variety of situations, like negotiation and price anchoring. Spend 30-60 minutes with your reps to work on these skills, and you’ll start seeing more engagement from them. As a general rule, newer or underperforming reps should be coached once per week and tenured or high-performing reps should be coached once per month.
2. Create an explicit growth template
Reps can’t grow if they don’t know what their growth path is supposed to look like. This means you need to actually document the basic competencies and objectives you expect. Then monitor rep improvement on a weekly, monthly, and quarterly basis—not just during an annual 360-review.
READ: Increase Sales Coaching Frequency
3. Don’t be hypocritical
People have a strong B.S.-meter. They know when you’re faking them out. So if you’re going to expect things from them, you better make sure you’re holding yourself to the same standards.
This doesn’t mean you need to be “macho” or push bravado all the time. You’re going to make mistakes, just like anyone. But set the example of always striving to be better, holding yourself to a high standard, and fixing problems when they arise.
4. Drive deeper engagement
The more engaged your reps are at work, the more they’ll stick around. So make sure their work stretches them and helps them grow. Provide opportunities for them to push themselves without setting them up to fail.
When appropriate, let them provide input on the direction and growth of the product and company. They have valuable insights that you can use. Plus, it helps them feel included.
5. Stay hungry and humble
Even though you’re in a management position, there’s always the opportunity to learn more. Don’t rest on your laurels. Stay hungry, and always look for ways to learn, grow, and improve.
DOWNLOAD: Tips for Retaining The New Generation of Sales
6. Don’t expect your people to always copy you
Don’t fall for “mini-me” syndrome. Just because you have a great process for selling doesn’t mean it’s the best for everyone. Instead, think about how effective reps are in driving results and meeting quotas, and focus on helping them close gaps and reach those goals faster. There can be an openness in process and style, while at the same time consistency in results.
7. Seize on little opportunities to build human connections
Managers can do a lot to show reps that they care about them not only as sales machines, but as individuals. And these don’t take a lot of extra time.
Especially in virtual environments, reps hear from their managers only to discuss forecasts, or when there’s a problem. Find other ways to connect with them as well, even if it’s just to talk about how they’re doing on a personal level.
What can reps do to build a better relationship with their managers?
1. Be solution-oriented
Don’t come with problems and no solutions. Be a solution-oriented thinker. It helps show the manager that you’re taking ownership of a problem, rather than force them to handle every little thing that comes up.
2. Be coachable
The opposite of coachability is “I already know everything.” Know what you know, but also know what you don’t know. And be open to learning and growing. It’s really hard for a manager to support a rep who thinks they know everything.
READ: 10 Tips for Sales Success from a High Performer
3. Don’t blame the leads
We all hear it all the time: If only the leads were better… Strike that phrase from your vocabulary! Stop blaming outside sources for your problems. Find a way to make the most of what you already have.
4. Get comfortable with ambiguity
Things aren’t always going to be straightforward, especially at different stages of companies. Can you execute when the answer isn’t fully defined? Are you willing to put the answer together yourself? If so, your manager will love you for it.
5. Always be curious
No one knows everything. There’s always a chance to learn, grow, and evolve. While your manager should be open to your own style, don’t assume that your way works best. Learn from others, and find a way to implement those learnings in your own unique way.

Final thoughts on the ultimate rep-manager relationship
The key to a good rep-manager relationship is this: support each other, hold each other accountable, and focus on growth. If you do that, you’ll build a solid foundation that makes both parties hesitant to leave the organization. Happy selling!
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5 Components of a Great Sales Onboarding Experience
What’s the most important component of a sales rep’s onboarding process? If we measure by time spent, most companies’ inadvertent answer would be company history, product, and systems. In an employee’s first few weeks, that’s where the majority of time is spent.
Outside of company orientation, there are five components of a great sales onboarding experience:
- Sales
- Acumen
- Systems
- Process
- Product
I’ve put these in priority order, let me tell you why I rank sales first and product last (you probably didn’t see that coming):
Sales
Sales tactics are the little skills that determine if an employee feels successful in their first 90 days. If you want them to stay, this is critical. Too often young reps quit sales because those first few months are full of calls, voicemails, and rejections. Product training will help them in a few months when they have sales conversations, but we need to focus first on getting them more of these conversations.
DOWNLOAD: Sales Team Retention Infographic
Focus on skills like how to prospect, how to make an outbound dial, how to write a valuable sales email, how to leave a good voicemail, and how to overcome initial brush-offs. When we focus on these skills with new hires, we see results like 200% more productivity than previous new hire classes (HPE, 2023).
Pro Tip: weave sales training and practice into the curriculum daily. Combine with product training to produce better questions, with acumen information to help identify ICPs and do better discovery. Daily practice builds better recall and confidence!
READ: Quick Sales Voicemail Tips to Build Phone Confidence
Yes! Outsourcing sales training in new hire onboarding can be very successful. License a vendor’s online content for a great virtual experience and then come together in live workshops to tailor messaging and role play. You’ll save time and help reps ramp faster.
Acumen
This is business, industry, and customer know-how. What do they care about, what are the challenges, what are the trends, and how do I have an intelligent conversation with them? Then, how do these relate to what I’m selling? New reps are afraid of conversations, and helping them get to know their customer and their customer’s business, lingo, questions, and challenges can fix this.
Use customer testimonials, old call recordings, and lingo bingo to get the voice of the customer.
Systems
I wish I could put systems last, but just like sales, it takes repetition to get good. Please resist the temptation to teach a system start to finish and start instead with the first 10 things they’ll do on the job.
Practice system drills DURING sales role plays. It’s not the individual skill that’s hard, it’s using them together. Systems finals should include multi-tasking and be timed.
Systems and sales are ripe for outsourcing by the way. Use your systems provider’s training – just re-organize it from the rep’s point of view. Using outsourced training helps mix it up, cover different learning styles, and infuse your program with expertise. Same with sales – some things need to be customized but don’t rely on professional training facilitators to coach selling tips.
READ: How to Build Sales Confidence During Onboarding
Process
Process is how to GSD (get stuff done). Try organizing this by the top ten questions managers get and customers ask. Teach reps how to use tools to answer their questions instead of giving them the answers. I like a good scavenger hunt for this and it’s easy to do remotely. Reps need to know how to get accounts assigned to them, do research, send info, answer customer questions – do a day-in-the-life study of your last newbies, and your curriculum is written!
Process training can also cross over into acumen practice. Role-play conversations with customers or use recordings with questions and challenge reps to find the answers.
Product
Finally product. Sure, I overcorrected a hair by putting it last, but there’s such a glut of product training in most programs I wanted to balance it a bit! When we give full-blown product training to new hires, we actually DECREASE their confidence. If you don’t expect a rep to have a conversation about the intricacies of what you provide in the first 2 months, then SKIP THIS. Focus instead on what problems it solves, the customer situations/profiles who love it, and the questions to ask to uncover this situation. Then provide resources just in case to look up answers. Slimming down the product features and functionality helps beef up the “how to sell it” portion.
Pro Tip: do product training daily just before sales training so you can incorporate the product situation questions into your sales questions and be teaching them how to do discovery right from the start.
We’re talking about unconscious incompetence and it’s important. We can’t have reps making outbound dials feel underprepared and afraid. So lop off half of the training you’re doing in the first month and instead drill the basics. If they don’t know the complexities of what they’re selling in month one it’s a win. We will only retain about 50% of what we’re taught in sales onboarding unless we drill it, practice it, and role-play it, so less info and more practice! Bonus: mix it all up and use it together like they will on the job.
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How to Build Sales Confidence During Onboarding
I’ve heard from many sales leaders lately that it’s tough getting the next generation of sellers to pick up the phone.
We all know that no one wants to make cold calls, but the endless email and InMail touches and cadences that your reps are using aren’t working.
And, with the new Gmail and Yahoo email restrictions that kicked in this year, it’s more important than ever to go back to basics and get new sellers to pick up the phone.
At Factor 8, we’re focused on teaching reps tactical phone sales skills to help them build sales confidence (so they’ll pick up the phone AND feel great about it!)
Today, I’m talking about new sales hire onboarding.
When you’re bringing on someone new – especially when they’re remote – one of the most important things you can do in new hire onboarding is use call recordings.
READ: Tips for Virtually Onboarding New Sales Reps
The game has changed over the past few years. When sellers are remote, they can’t just sit next to their peers, hear what’s happening, and learn the good, bad, and ugly.
If your company doesn’t record calls, or you’re worried about not having a specific rep’s call recordings, toss that – it doesn’t matter. You can learn so much from any call recording.
In fact, at Factor 8 in our Sales Bar, our online sales training platform, we have thousands of user-submitted recorded sales calls from all different industries, organized by skill (i.e. call intro, overcoming objections, call bridging, closing, etc.)
READ: 7 Hacks to Improve New Sales Rep Onboarding
During onboarding, break down the call and let reps listen to what it sounds like, even if it’s not a good call, because what we’re scared of is what the customer is going to say to us (and the inability to think on our feet to respond to them intelligently).
When reps hear different scenarios on sales calls 20 or 30 times, they begin to feel comfortable and that fear starts to go away and the confidence rises.
And that’s the name of the game, folks: confidence. You’ve got to have it to succeed in sales, and building it begins at onboarding.
Need help building sales confidence in your sales reps? Email me at LB@factor8.com. I’m happy to help!
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Sales Enablement Secrets: Actionable Sales Training Tips, Trends, and Advice [Webinar Recording]
Sales Enablement Secrets: Actionable Sales Training Tips, Trends, and Advice
[Video Recording]
Strategies to Improve Your Remote Leadership Capabilities
The concept of work-from-home isn’t new, but in recent years this mode of work has quickly become the norm. The pandemic restricted everybody’s mobility, and adjustments had to be made in order to compensate for the physical limitations.
Studies show that the increasing benefits that many have experienced with remote work — such as flexibility and productivity — have given birth to a new culture. More companies continue to consider making permanent work-from-home arrangements to reduce office space. An example of this is Morgan Stanley. Around 90% of their employees worked from home during the pandemic, leading to Morgan Stanley CEO James Gorman noting that the company now needed much less real estate. Companies, like Morgan Stanley, are now trying to strike a balance to minimize the risks and maximize the gains.
Finding balance can be tricky, however, which is why a remote team requires strong leadership. Top executive leadership plays several roles in an organization, including effectively delegating tasks, as well as managing relations among different individuals (which is why the median wage is far above the average at $103,950). Executive leadership is particularly important for designing programs and setting standards so that organizations can meet their goals.
Improving remote leadership capabilities means executive leadership can do their work. Fortunately, this can be easily developed with consistent practice. Read on to know the tips for effective leadership in a remote team.
Keep track of your goals
It is easy to feel disconnected when your work environment all lies within a screen. This is where designing programs and setting standards come into play. It helps to establish clear and measurable goals with quantitative objectives, key performance indicators (KPIs), and a set schedule. This sets a direction for the team.
Above all, these goals must be consultative with your team members. Business development goals usually go through multiple phases before completion, so keeping track of everyone’s progress allows leaders to adjust accordingly.
Pay attention to your team
Transparency and consultation are key to ensuring that your goals are realistic. This is where checking in with your team and remembering their needs come in. Our previous post discusses the different ways leaders can engage their remote team, which surprisingly means strategies like fewer calls – Zoom fatigue is real, after all.
The important thing to remember throughout is that numbers and performance are important, but teams are composed of individuals. Only a healthy, collaborative team can produce great outcomes in the long run.
Trust in your team
The fear of a dip in effort and production can be overpowering. Some leaders may find themselves micromanaging their teammates to compensate for the distance.
However, it is actually the lack of trust that causes a breakdown around employee autonomy, perceived competence, and respect, and that ultimately affects productivity in your team. Remember that your goals are their goals as well, so what’s left is to guide and lead the way.
Focusing on improving communication skills
To build trust, open channels to discuss company goals aren’t enough. Leaders need to cultivate a workplace culture of clear communication. Sharing every little detail about your life isn’t necessary — a level of independence in working is essential after all — but transparency allows your team to understand one another and fosters empathy. It also encourages asking questions, which minimizes the chance for misunderstandings.
The physical distance of remote work is hard enough to manage without knowing what your members are going through in their homes. Having a clearer picture of this allows you to adjust accordingly and provide a safety net for the entire team.
To lead is to be responsible for others, and this weight is never easy. However, under effective and collaborative remote leadership, not only will you be watching out for your team, but they’ll also be watching out for you.
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3 Sales Leadership Challenges (and How to Fix Them)
Being a leader is hard. When faced with a new sales leadership challenge, it can often feel like you are alone on an island. Turns out, finding a group of peers that both grasp your issue and can provide valuable insight into how they have handled a similar situation is like finding a needle in a haystack. Enter Factor 8’s Executive Open Bar, a place where we can speak openly about the challenges that often accompany a C-level position. Whether we are talking about the big picture or the daily struggle, we have created a safe space to share our challenges.
This quarter our participating executives shared some timely issues. We want to share the insights we discovered; in case you find yourself facing these same quandaries!
- Question 1: The company will be shifting a portion of the team from live selling to online bots. During the transition, we will need the live team to assist our customers in making the switch to digital. We are struggling with the strategy for keeping the live team members motivated when there is a foreseeable end to their position. What advice can you share about a change in strategy that results in job loss?
- Communicate, communicate, communicate! If we do not talk with our team members about the elephant in the room, the elephant only gets bigger.
- Town Meetings with the executive team can help ease employees’ anxiety. This will work best if relevant and specific information about the process is provided.
- Money talks. Offering a staying bonus to team members can be a great motivator.
- Question 2: With the weather getting nicer and the world reopening, we are seeing a drastic drop in staff engagement and performance. We are still 3-6 months from returning the full team to the office. What advice can you share for keeping people motivated?
- Change up your contests. Have the quantifier be the area that your team is struggling with. So, instead of awarding for the number of deals closed, maybe concentrate on the shortest deal closing window. Instead of just measuring the number of successful call connections, break it out into two games. Measure the number of successful connections both before and after lunch.
- Communicate! Have an all-team meeting. Acknowledge that you know the world is exciting again. You’ve let it slide for the last 2 weeks because we know the pandemic has been hard for everyone. However, it’s time to get back to work and crush those goals! We now have just 2 weeks to (insert goal here).
- Question 3: We’ve reached our end-of-year goal early. The CEO is saying “sell, sell, sell” while the supervisors are sharing that we need to ease off because the workload is not sustainable. How do I have the conversation with the CEO that selling more might not be in the company’s best interest?
- Do your research! Before speaking with the CEO, have hard numbers on hand.
- What is the expense to the company of burnout? How much does turnover cost the company?
- How much will it cost the company to hire/train new employees to execute additional sales?
- Come prepared with a better option. For example, “If you give the team a 30% break on the new goal, here is what we will be able to do with the time ______ (train to up our game, upsell current customers, prospect larger accounts, etc.)”
- Ask the CEO to help you find the best solution AFTER you’ve presented your research. Make finding the solution a collaborative effort. Often the CEO is looking at the big picture, not necessarily the daily details you are facing.
- Do your research! Before speaking with the CEO, have hard numbers on hand.
I always feel so invigorated after one of the Executive Open Bar sessions! I want to thank the leaders that joined us for their openness, insight, and assistance.
If our Executive Open Bar sessions would be helpful for you, please email us at info@factor8.com for an invitation!
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Top Challenges Inside and Virtual Sales Teams Are Facing Today
Is virtual sales here to stay? YES! (although your field sales teams sure hope not…)
The truth is, virtual sales is HARD. In fact, a recent Gartner research study cited that “An overwhelming 93% of sales reps are experiencing significant virtual sales challenges.”
We hear it all of the time. Reps aren’t being taught the tactical skills to help them sell in a virtual environment. There’s a massive disconnect between where reps are experiencing challenges vs. where leaders think their reps are struggling.
So, what are reps’ top virtual sales challenges? More specifically, where are they falling short when it comes to prospecting? And, do leaders really know what skills their reps need to succeed? We wanted to know all these things and more. So, we recently surveyed thousands of sales professionals (reps, team leads, managers, directors, VPs, C-suite – you name it!) in 50+ different industries across the world to learn the top virtual sales challenges their teams are facing today.
We began by asking what the most challenging aspects of the current sales market are. Then, we dug deeper to find out what makes those challenges, well, challenging. We asked about everything from prospecting to running sales demos to closing deals and more. Then, we compiled and condensed all of the results into our Factor 8 infographic of “The State of Virtual and Inside Sales: Top Virtual Sales Challenges”, putting the raw data right at your fingertips.
Spoiler alert! We found that reps and leaders are not always aligned when it comes to the challenges reps are facing on a daily basis. Let’s take ‘closing deals virtually’ for example, the majority of leaders that were surveyed reported that their reps struggle most with gaining referrals after a deal closes. When the truth is that most reps claim that knowing who is involved in the decision-making process was actually the hardest part of closing.
Have no fear, there were other areas where reps and leaders were seeing eye-to-eye! Namely, prospecting. Here, the majority of both reps and leaders found having a valuable message and enticing message to be the most challenging piece of the prospecting puzzle. We get it, crafting a short and enticing message isn’t easy.
Want more insight? Make sure you grab your free copy of our survey results below!
Download your copy of
“The State of Virtual and Inside Sales: Top Virtual Sales Challenges”
Learn where sales reps are experiencing the most virtual sales challenges.
