Sales Team Challenges

26 Feb 2021

Amy Wunderlich Remote Leadership, Sales Team Challenges, Team Engagement + Culture, Sales Leadership Insight

3 Challenges Facing Every Remote Team (And How to Combat Them)

Many of the same challenges we faced when we worked on-site carry over to this new reality of working remotely. Other, more recent obstacles are specific to virtual teams.

One advantage we have at our disposal today that was absent for the last generation is an abundance of high-end technology. Instant communication and remote workflows have become essentially mandatory worldwide as a result of COVID-19. Fortunately, there are a lot of really great ways you can use technology to make remote work more efficient and tolerable.

Here are 3 challenges technology can help solve while you and your team continue to work remotely.

Effective Communication

Working from home can be a blessing and a curse. When you were on-site, you were able to see your coworkers at their stations, in meetings, or while completing tasks as a team. How do you reconnect while maintaining high productivity?

Video communication software, like Zoom, allows you to participate in video and audio conferences, chats, and more from your computer or phone. You can share your screen, documents or other files and links amongst your team members to help overall comprehension and productivity.

Group chats are also essential for remote teams. These chat apps are useful for instant contact with colleagues, collaborators and even clients to discuss important tasks that may not require a meeting. Not sure what group chat software is best for you? Check out this comparison article to weigh your pros and cons to help you decide between two of the top contenders: Slack and GroupMe.

Sometimes too much communication can be more of a hindrance. We’ve tried a “no meeting Monday” to optimize the workweek. You could make this a “no Slack chat Monday” to allow you to focus more and limit distractions, while still leaving other communication open in case of urgency.

Time Management

A great way to better manage your time is to stay organized. Leave yourself reminders or clear notes of upcoming tasks. Label all of your important files and documents for ease of reference. This will save you from having to search when you need it now.

Another important factor for time management is your work-life balance. It can be easy to get so focused on your job that you aren’t taking time to take care of yourself. Take short breaks when you can to give your eyes, mind, and body some time away from your computer screen. Try these apps for harboring a healthy work-life balance.

Similarly, a challenge teams face while working from home is not having or taking the time to run out and shop for whatever supplies you need while working from home. This could be anything from migraine and allergy relief to office cleaning supplies. For those hectic, busy days, consider trying the convenience of a home essentials delivery service to get the household items you need without leaving your home. Use that time you just saved to make some coffee, do a quick workout, or plan for your upcoming meetings.

Remote Collaboration

It’s great that we can communicate with one another to make sure we’re all on the same page and have maintained our comradery, but in what way can technology help our teams get the job done more efficiently than ever? Try using some collaborative, coworking tools like Google Suite to help your coworkers.

What’s great about this service, and ones like it is that once the link to the document is shared, everyone with access is able to make real-time edits––no more waiting for an email response before you can proceed. Hop on a chat or video call and communicate while you edit. By utilizing this collaborative workspace, you’ll find that your team feels more apt to participate. This can cause your teammates to feel fulfilled and that their ideas and voices have been heard.

Staying connected during a global pandemic can be as challenging as it is important. By taking a look at your team’s priorities, you will be able to develop the correct solutions. Modern technology has made working remotely more user-friendly and efficient than ever before.

Share these solutions with your team and see what works best for you. At the very least, do your best to help your colleagues stay connected during these difficult times. You’ll be glad you did.

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30 Jun 2020

Factor 8

Having Difficult Conversations With Ease [Webinar Recording]

Having Difficult Conversations With Ease

[Webinar Recording]

TIPS TO HAVE DIFFICULT CONVERSATIONS AT WORK

Is there a magic formula for delivering bad news? How do we have the tough talks and make sure that we not only get results but leave the other party intact?

If you dread (or find yourself even putting off) the difficult conversations with employees, bosses, friends, or clients, please join us to learn:

A simple model for delivery
Tips on planning the conversation
Pitfalls to avoid
Steps to be sure you maintain everyone’s esteem
Incredible tips and stories from top leaders

Sometimes the kindest thing we can do is deliver bad news quickly, efficiently, and compassionately. So stop avoiding confrontations and start inviting authentic exchanges.

Get ready to learn insight, stories, and advice from four amazing panelists below.

Watch the video replay!

TIPS TO HAVE DIFFICULT CONVERSATIONS AT WORK

Is there a magic formula for delivering bad news? How do we have the tough talks and make sure that we not only get results but leave the other party intact?

If you dread (or find yourself even putting off) the difficult conversations with employees, bosses, friends, or clients, please join us to learn:

A simple model for delivery
Tips on planning the conversation
Pitfalls to avoid
Steps to be sure you maintain everyone’s esteem
Incredible tips and stories from top leaders

Sometimes the kindest thing we can do is deliver bad news quickly, efficiently, and compassionately. So stop avoiding confrontations and start inviting authentic exchanges.

Get ready to learn insight, stories, and advice from four amazing panelists below.

Watch the video replay!

Meet the Panelists

Natalie Severino
VP, Marketing | Chorus.ai

Natalie is the VP of Marketing for Chorus.ai. Passionate about elevating the craft of Sales and helping B2B sales professionals win more, Natalie enjoys writing and speaking about sales technologies and trends. Natalie loves technology – she started her career at leading technology companies like Intuit, Logitech, and Trend Micro and then found a passion for building technology start-ups at ClearSlide, getTalent, and now Chorus. She oversees all marketing and sales development for Chorus, including product marketing, demand generation, and communications.

Brenda Roper
VP, Global Sales Enablement | Thomson Reuters

Brenda is currently the VP, Global Sales Enablement at Thomson Reuters based in Minneapolis, MN. In addition to sales enablement positions, she has also held various sales roles throughout her career including VP Sales and Business Development and Master Principal Sales Consultant. Brenda has trained over 15,000 salespeople and has a wealth of experience creating successful sales and presales training programs. Her passion is to see behavior change as a result of training, to create successful sales teams, and to drive revenue!

Wendy Mitchell-Covington
National Vice President, Sales Success | TriNet

Wendy Mitchell-Covington, National Vice President of Sales Success at TriNet, is a high-energy, driven sales executive who possesses a proven track record of outstanding results. She is a strategist who has successfully built and scaled sales organizations. Throughout an extensive sales and leadership career, she has been committed to attracting, developing and retaining top talent. She believes top-performing sales professionals are the engine that drives every flourishing company.

Wendy has spent the last 20 years in the HR outsourcing space funneling her expertise into helping America’s businesses improve and thrive.

Shianne Sampson
VP of Sales & Customer Experience | PetDesk

Since 2009, Shianne has been working with great startups and technology companies across the U.S. to help build out world-class sales teams. With her M.A. in Organizational Leadership and over 20 years in sales, she founded Yelp University and the Yelp Sales Development Program and has trained over 4000+ salespeople and hundreds of sales leaders. Shianne has worked with several great companies such as Yelp, Zenefits & Varsity Tutors in San Francisco, Seattle, St. Louis, and Scottsdale, Arizona. Shianne is currently the VP of Sales & Customer Experience at PetDesk in San Diego as well as a freelance consultant that specializes in helping SaaS companies turn their sales teams around, increase revenue, and train their sales leaders to be the best in the business. She is also the author of the published book Broken to Badass and a proud single mother of six.

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4 Jun 2020

Lauren Bailey Sales Team Challenges, Sales Leadership Insight, Team Engagement + Culture

What I’ve Learned (So Far) & Actions Leaders Can Take

It’s a crazy time to be an American right now, but a great time to lead a team. I’ve learned a LOT in the past few days. My goal is to share my learning (so far) and add value by helping other leaders have conversations about today’s current events.

First, a fear-based disclaimer: I’m a privileged white woman. I’ve known a little discrimination in a male-dominated industry and I’ve taken action to help fix it with #GirlsClub. I’m unimpacted by riots, and I do not have solutions to share (yet).

So who am I to say something?

So I didn’t. Until a few days ago, a brave (and rightfully angry) black female on my team called me out. Truth: I thought I’d offend her more by saying something. I’m uneducated and inexperienced with racism. It was an uncomfortable exchange, but she handled it beautifully. I love that she called me out and taught me some things.

I’ll share first what I’ve learned from my team and end with some advice (if you want to scroll, but I hope you’ll soak in some learning first. There are some wicked-cool perspectives I’m about to post).

One more point of perspective first: My team has 2 black women, 1 police officer’s wife, and 1 man who got the fright of his life walking unsuspectingly into a riot. We have people in NJ, ATL, DC, DFW, ORD, MSP and PHX, (look up the airport codes if I lost you). We are a family that doesn’t always agree, but who cares deeply about each other, the work we do, and our own families. We are male, female, black, white, and Hispanic. This is my Factor 8 family.

OK, mind-blowing insights I learned this week by asking, “What do you need?”:

1. The fear some of us have felt during the riots (for ourselves, our spouses in the front lines, for our families, for our communities…) is new to us and it’s scary. Counterpoint: “Black people feel this all the time.”

Bam. I don’t know that fear. I’ve never been scared by a cop outside of getting a ticket. Period. We’re getting a glimpse, folks. And if you want to think now about downplaying it, nitpicking at it, disproving it, there’s your learning. We can’t judge other peoples’ fear. She has it. She’s grown up with it. She fears for her family like the cop’s wife fears for hers.

2. Your black employees feel a pull to protest. Mind blown. My SDR shared this. Get this: she’s personally survived COVID, her husband just got out of the hospital, she’s homeschooling and has WAY too many people living in a small space. She’s still making calls. She’s keeping her ship afloat right now but feels a pressure, a GUILT about not getting out and adding her voice.

Holy crap, of COURSE she does! She’s let herself off the hook right now because she has higher responsibilities. But she may want this in the near future, and it’s my job to give it to her. She asked for a mental health day (and got it no questions asked), but your team members may want a protest day. This could actually be (I hope it is) a turning point in history. If you could have marched with MLK on Washington, wouldn’t you have? I would. Be open to helping them do their duty and be part of history.

3. The connection between a murder and a riot is “disruption.” I started out not understanding this. “What the hell did a Target store do to African Americans?” I asked. Now I get it. EVERY MAJOR CHANGE in America started with disruption. You’ve got to check out this article I found on the subject. Folks, this country was BUILT on protest, disruption, and yes, violence.

So I now hold some space for this. I am sorry for the small business owners. I’m fearful of loss of life. I’m completely inspired by the non-violent disruptions happening, but I get the need for disruption. Would I be talking about this right now if there weren’t riots? Ask yourself that toughie.

Again, check your response right now. Are you proving me wrong? Railing against the idiots causing damage and harm? Yeah, that’s OK. Me too. I’m saying make room for the need for protest. Remember the white people who’ve protested, rioted, fought, and hurt merchants to make their point (soaking wet tea anyone?)

4. We can all be right together. Truth: I avoid politics like the plague. It’s because I hate the pandering tactics that have to make the other side wrong for their side to be right. This is a critical time in our country right now because for the first time in recent history, people see both sides. NOBODY is arguing for Derek Chauvin who murdered George Floyd. We can hate the violence of riots and understand the why of it. We can fear for the police and for the black community at the same time.

This kind of tolerance and understanding is a brand-spanking-new muscle for a lot of people. You may see people on your team lash out with some anger against the “other side.” It’s OK. That’s what society has taught them to do. They may lash out at you (Yup, I took some heat). That’s OK too. They’re ANGRY, and dammit they have a right to be.

5. We have more to learn. Start here. The woman who called me out for not using my voice to take a stand accused me of having some blind-spot racism. God, I don’t THINK I do, but could that be why I hesitated? I have more to learn. My team recommended two resources so far:

These are my revelations and insights so far. And because they asked for it, here’s my company’s stand:

Factor 8 and #GirlsClub are appalled by the recent and far too frequent acts by the police against black people. This. Must. Stop. We recognize that the vast majority of officers are not aligned with the bad apples. We respect and appreciate their service.

We are supportive and proud of the thousands of Americans using their voice to promote change. We are inspired by the brave law enforcement leaders who have deterred riots to protect their people, but even more by those who are helping protesters use their voice while protecting people and businesses with plain-clothes officers keeping people safe vs. the riot-gear and tear gas. Most inspiring is seeing all shades and colors of humans joining in unity and using their voices to incite and inspire change. We prefer non-violence but we respect that it’s working. We love both the people in the black community and the law enforcement community.

We are all Americans and we want change.

This all boils down to the following advice for my fellow leaders:

1. Start the conversation with your team. I recommend 1:1 or small groups. I sent an email saying, “What do you need?” I got 6 VERY different answers and some with no replies… I’m choosing not to do a group meeting right now because it’s volatile and not everyone is ready with tolerance and understanding and point #4 that we can all be right at once.

2. Increase your understanding. Assume you have blind spots and find resources to fill them.

3. Use your voice. Yes, I’m going to piss some people off and get some things wrong with this blog and advice, but the alternative is to say nothing and be a coward. My employees wanted me to give them a voice because mine is louder than theirs right now. If you lead a team, a company, an association, an HOA… you have an opportunity right now to speak up. Remember:

The only thing necessary for the triumph of evil is for good men to do nothing. ―Edmund Burke

4. Look for solutions. I don’t know what they are yet, but I’m really eager to hear from more experts (not politicians) who have some and do my part in helping implement them. Who has ideas for reform? For education? For screening? What can help fix this? Let’s get quickly past blame and into solutions. Like you, I want something tangible to do.

I hope this helped you. It’s why I wrote it. If you’d like to share a solution or an insight or a criticism, I’m ready to learn. My email address is . You may not get an immediate response, but I am listening.

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27 May 2020

Lauren Bailey Sales Leadership Insight, Team Engagement + Culture, Sales Team Challenges

Where Are We Now? And What’s Next?

In an informal survey of top Factor 8 clients and friends, our community reported and shared the following:

100% reported sales as down overall
Most are at the “how can we help” stage of sales.
Deals are getting stuck at the close

Let me fill in a little background on what I learned and why this is critical for you to share.
Although some of our leaders reported early and significant pivots in sales strategy that have helped refill the pipeline, nearly everyone reported that the existing pipeline as of March 15th, 2020 died.

Most successful pivots included at least one of three things:

A look to new industries (e.g. traditional field-focused)
Focus on growing industries (e.g. healthcare segments)
Sales playbook change (selling to finance w/ ROI vs. targeting discretionary marketing spend)

Brilliant moves by brilliant leaders whose fast reaction is keeping their company and workforce afloat. But they too, are down.

Activity? Up on average.

Connects and Conversations? Up on average.

Sales? Down.

Here’s why you need to share this with your community:

Smart leaders have already adjusted quotas and metrics and contests – beautifully aligned today toward deep profile conversations and fuller pipelines
Step-behind leaders are still hoping for old KPIs and quotas and inadvertently spreading fear down the line

I spoke with a young sales leader this week whose team of Account Managers serves small business owners. They sell a subscription service + multiple up and cross-sells, and they are coming in about 35% to quota. As the news reports up to 40% of small businesses may close forever (in the neighborhood of 7.5 million at risk of permanent closure) and this segment was one of the hardest hit, it feels a bit like hope as the strategy, right?

This #GirlsClub superstar manager is now afraid for her job.

That’s. Just. Wrong.

It’s time to adjust, my fellow leaders. Adjust your Q2 number and your Q3 number. Consider strongly adjusting your Q4 and Q1 2021 numbers as well. Find new markets, new strategies, new revenue streams to help you get there and translate these into new expectations for your teams.

Here’s where I’ve seen us at (and where I see us going) in roughly 2-week steps since mid-March:

Step one was focusing on connectivity (WFH)

Step two was focusing on morale and connections (Zoom happy hour anyone?)

Step three was focusing on messaging (leading with empathy)

Step four is about re-aligning sales metrics, KPIs, milestones and goals

Step five is about closing new sales with finance

Step six is about going back to work / back to normal

Where are you?

Where are your sales?

Share this list with your fellow leaders. Share that others are down. Share what “public opinion” expects and how you can react and prepare for next steps.

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1 Apr 2020

Lauren Bailey Sales Leadership Insight, Sales Training + Development, Inside/Virtual Sales Training Tips, Sales Team Challenges

Is It Time For Sales Training?

Should we be doing more or less sales training right now?

Let’s talk about why some companies are doubling down on training right now (and some aren’t).

We’re all in brand new situations today, but our companies, our people, and ourselves are affected differently. Some of us are:

Facing layoffs and massive business downturns
Ramping up amidst high demand
Slowing down but staying the course

And many of us are moving between these three as situations change daily and we plan for the best (and the worst). At Factor 8, we’re seeing some companies decide it’s time for more sales training and others are pausing. Here’s why:

Most of what we’re hearing is #3 – we’ve slowed down. Smart leaders here are focusing the teams on what is in our control and on positive production. It may NOT mean calling the list/book for the fourth time. It might mean writing case studies, cleaning out the pipeline, and spending time developing the team.

Not only are there some obvious team development needs right now, but we’re seeing some companies push beyond “WFH” topics to really improving call quality and efficiencies in preparation for the turnaround. Some no-brainer topics to consider starting with are:

Sales Managers:

Remote management – our front line managers may have it toughest right now
Remote call coaching – now is the time to better engage through coaching
Essential meetings – they can’t be ad-hoc anymore
Developing your team – do’s and don’ts of team development
Pipeline fundamentals – hey, we’re cleaning out the garage at home…you get it

Sales Reps:

Weaving empathy into messaging – we all wish every vendor was teaching this! 😉
Voicemails that get returned – now’s the time to leave better messages
Conducting remote meetings – enough said
Engaging customers – ditching the script and getting human
Pipeline fundamentals – yup.

What gets me excited are companies that are digging in even further. Working with teams on how to attack their books and leads when we’re back online. Capturing new decision makers, getting strategic, practicing messaging for their introductions, writing better questions, using stories, overcoming objections, asking for referrals…you get the idea. The blocking and tackling needs we all have skill gaps in but never have time to address.

Here’s the strange but apt analogy. Factor 8 does training inside women’s prisons for the hundred of women doing outsourced calls on behalf of clients who hire Televerde. Really amazing program that meets a business need while changing lives. In talking with these women we’ve learned that the women who make it when they are out are the ones who spend their time inside preparing for the outside. School, studying, physical and mental fitness. Quarantine is starting to feel a little like the inside, right?

Like sports, when we’re off the game field, we go straight to the practice field. Are college basketball teams all sitting on the couch right now because playoffs were canceled? Hell no. They’re doing drills. They’re staying fit. They’re doing all they can to come back stronger and their coaches are doing all they can to keep the team operating as a team and spirits high.

Leaders! Get your teams off the couch and focused on sales drills! Let’s prepare for the comeback and stay positively focused!!

OK, now the other side. We’re NOT training teams right now if:

We’re planning layoffs or cutbacks
Leadership is still heads-down on the transition (connectivity, remote management, etc.)
We don’t have a rally strategy to get behind yet
All budgets are frozen and time is allocated in bridging the situation

All valid reasons my friends. But if you’re swamped, I invite you to investigate ways your team can still rally and drill without you. Delegate to a hopeful team lead. There are free resources, self-study, and programs available (we’ve offered shorter terms, discounts, and delayed payments at Factor 8). Employees stick with leaders and companies that help them develop, and now may be a critical time to engage our people (and may also offer us more time to do so).

And if you’re ramping up, it’s tempting to get them a log-on or a script, but I hope that you too will find time eventually to train these folks if you want to keep them. This rapid-ramp model works for a short period only. Can you weave in a schedule where they’re on the phones for a few weeks and then digging into skills training? Your customer experience and your employee retention numbers will thank you.

If you’re using the free webinars and resources on the web, check out my next post to help you get more out of these and better engage your team during training. And if you wish you had access to awesome sales and manager skill drills but your budget is frozen, we’ve got your back with assistance programs. Let us know you want to learn more and we’ll show you in a no-pressure meeting (info@factor 8.com).

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8 Aug 2017

Factor 8 Hiring + Retention, Sales Team Challenges, Sales Leadership Insight

The Top 5 Ways Companies Fail Their Salespeople

In my line of work, I spend a lot of time on sales floors around the world watching Reps, Managers, Directors, and VP’s try to drive the number. I see well intentioned organizations and leaders spend countless hours and dollars trying to unlock the secret that will bring in more customers and keep them coming back for more. The problem is that they are trying to run before they can walk.

If you’re behind the number for 2017 or wondering how you will turn things around for next year, maybe you need to start with the basics. Are the steps you are taking going to provide a clearer path to success, or are you making changes for change’s sake? Here are five of the most common ways that I see companies fail their salespeople, and it’s killing their numbers.

Poor Compensation Plans – You’ve heard the phrase that salespeople are coin operated…so why do companies continue to design compensation plans that limit their reps ability to earn? Are you really going to punish your sales team for closing “too big” of a deal? Think through your comp plan enough to ensure that it can account for big wins. When someone on the sales team closes a huge deal there should be bells ringing, applause breaking out, and the leader on the floor slapping high fives, not in her office worrying about how that deal will push them beyond the commission budget. The second common failure related to compensation plans is the overly complex comp plan. You want to account for every contingency and every activity that you want to incent, and end up creating a 7 page document that requires four Excel sheets and an advanced degree in mathematics to calculate commissions. If you want compensation to drive behavior, make it simple enough so that your team can figure out on the fly how each deal/lead they close is going to impact their check.

Putting people with no sales experience in charge of sales – This one always shocks me. Would you make someone with no financial background your CFO? I’m not sure if companies don’t view sales as a “professional” department that requires experienced leadership, or if they think it’s a good way to round out an executive’s resume, but it can put your revenue generation machine in jeopardy. Fair or unfair, salespeople have a hard time following someone that’s never done the job. It’s also very difficult to make sound decisions around things like territory planning, sales process, compensation, and tools when you haven’t experienced the good and bad that sales has to offer.

Information overload – While it is usually done with the best of intentions, too much information can be paralyzing to a sales team. Resist the urge to jam every shiny new Salesforce plug-in down your team’s throat. Information without intelligence is useless to your sales team. Almost every salesperson I know would rather have one or two actionable nuggets of information than 100 potentially relevant pieces of data. I would also argue that, in many cases, the amount of data out there is making salespeople lazier. If a lead doesn’t come across with a bright flashing arrow showing the exact path to the sale, the process grinds to a halt. How can I possibly pitch this customer without knowing which direction his office desk chair faces? Your sales leadership team needs to be an advocate for the reps here. Establish a process for determining what information makes its way to the rep’s desks and why. Filter it hard. And when something does go through to the team, take the time to explain what it is and how they can use it to sell more effectively. If you can’t connect those dots, they don’t need it.

Lack of investment in rep development – When I hear reps tell me that their onboarding process consisted of 3-4 days of HR paperwork, systems training, and online selling modules, I wonder how the company expects anyone to succeed. There are too many organizations that strive to constantly reduce the time and money invested in onboarding salespeople because (a) the turnover is high so why waste the money, (b) an untrained rep is better than an empty seat, or (c) every day they spend in training is a day they’re not selling. I’ll tell you this, an untrained/poorly trained rep can do a ton of damage to your bottom line and your reputation….and they’ll still leave. Especially if you are hiring entry level salespeople, you need to provide them with sales training specific to your organization and customers. Show them what good looks like and give them a chance to sharpen those skills in a safe environment. If you don’t have the people internally to do it, bring someone in from the outside. You can’t afford to screw this one up. I won’t even get started on the lack of ongoing development…a rant for another day.

Spreading sales managers too thin – I can’t tell you the number of times that I walk on to a sales floor and see a flurry of rep activity and not a manager in sight. When I ask the reps what interaction they have with their manager, I get responses like: “we’re supposed to have weekly 1:1’s but they usually get postponed”, “she’s always in meetings”, or “I try not to bother him because he’s so busy.” The sad part is that when I ask the managers what they would do if they could change one thing, I almost always hear that they want to spend more time with their reps. Unfortunately, they are pulled in a hundred different directions by partners, bosses, and other departments, and their reps are usually the piece that slips through the cracks. Front line sales managers are some of the most impact people in your entire organization. They are responsible for translating senior leadership’s vision into daily action. They are the close enough to the customers to know what’s going on in the market, and high enough in the organization to do something about it. Take the administrative crap off of their plates and keep them on the floor!

If you caught yourself cringing while you read this list or a few (or all!) items hit a little too close to home, you’re not alone. The good news is that it’s not too late to make some changes and get things heading in the right direction. If you’re not sure where to start or what changes can make the biggest impact, I’d love to have that conversation with you.