
Difficult Conversations


5 Things to Do Immediately After Being Laid off in Sales
Layoffs, Recessions, and RIFs (Ooooooh, my)
It’s a crap situation folks, no way around that. But if you’re in a revenue role and you smell it coming, or just got your notice, here are our top 5 tips to help you recover from a sales layoff:
- Attitude is everything. I don’t mean to not FEEL angry, sad, betrayed, and revenge-fueled! I just mean don’t show it. You’re in a fishbowl right now and everyone you rant to may actually be a prospective employer or referrer. And let’s face it, they’re all wondering if it was the company or it was you. We’ve heard that companies use uncertain economies to trim the fat, and telling the story of your betrayal may tip things in the direction of you being the problem.
- Try a re-frame. Perhaps you were cut because you were the most expensive! It’s the most efficient way to cut costs, right? You may have not been as aligned with the new leadership or go-to-market strategy. It’s probably time to refresh your skills, sharpen the saw, and expand your horizons! What I’m talking about here is your internal self-talk AND your “packaging.” Are you a dejected, rejected, dime-a-dozen AE on the hunt? Or are you a senior-level, uber-expensive, in-demand revenue professional!? I thought so. 🙂
- Get clear on what you want. For decades I’ve made a hobby of helping great people find great companies, and every time I get an email requesting help, I reply asking them to detail their dream job. I don’t mean title and income (you DID think that didn’t you!?). I mean what industry, working with what kinds of customers? What will you be learning? What kind of product or service would make you proud? How will your boss treat you, how do sell, and how will you be led and fed? Go nuts on the wish list and ask questions about past peeves like work hours, development opportunities, bosses and mentors, facilities, friends at work, tools, and more! When we know exactly what we want, we can describe that for people and INSTANTLY get better referrals than a generic, “anything in SaaS.”
Try this: When I ask if you know someone who leads a new or growing sales team in the banking industry, runs an insurance house, or manages a team that sells into government, did your brain find someone? Could you feel it scanning deeper than, “Know anyone hiring?” When you help people picture someone they know, you’re more than halfway to a referral.I’m also a believer that putting it out there in the universe is necessary step #1 in bringing what we want to us!
- Brag a little. No, strike that. Brag a LOT. Your resume needs to be packed with results!
Numbers Are The Love Language Of All Sales Leaders!Get yours in order! What percent did you increase market share? Was there a spike in metrics under your leadership? How many quarters did you exceed quota? How about your team? Did you win any records? Awards? Listen, if the very best thing you did was reach quota consistently realize that is a WIN! If you’re still there, start running reports to shore up your data.
What else did you do? Customer satisfaction? Product development? Process documentation? Testimonial acquisition? New customer types? Lead with numbers and close with some voice of the customer. They’ll be lining up to talk to you!
- Call in the favors (by offering to help!) If you fear it’s coming but haven’t left yet, NOW is the time to work your network. Funny how our colleagues, customers, and friends lose our numbers when we leave (and listen, some actually do only know your work email). But a call from an employed friend calling to catch up and see how I am and how they can help me gets 10x the callbacks than my newly laid off buddy who wants to give me the Telenovela version of their unfair termination. So do as many favors as you can before you’re gone, so it’s easy to call up for the payback when you need it. Start your re-frame marketing campaign about where you’re headed and your desire to leave to move up or move on! Then find out how you can help THEM and do it. Reciprocity is real (and everyone will like you better.)
In short, approach this well-deserved break like the freaking diamond you are. There’s an international shortage of professional sellers – especially virtual sellers. Find an industry and company that’s thriving and package yourself as a FIND! I’m confident that YOU are something you can sell.
Good luck out there! If we can help you brush up on your selling skills at Factor 8 with free virtual sales BDR, AE, or Account Management training, please email us at info@factor8.com and mention this blog.
If you’re a woman in revenue leadership, please apply to join the #GirlsClub Sales Leadership Certification Program as a Protégé (new or aspiring manager) or Mentor (5+ years of leadership experience). Our amazing sponsors will help foot the bill.
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5 Signs It’s Time to Fire a Sales Rep
Is it time to fire a sales rep? We’ve all made bad hires. And we’ve all made wrong assumptions about team members. So second-guessing ourselves on whether or not to cut bait on an underperforming rep is only natural – especially in today’s war for talent.
It’s only in hindsight we realize we should have done it long ago. When the team mood shoots up, other performance rises, or we hear a few nightmare stories we kick ourselves for not acting on sooner.
But on the reverse, we don’t lose that number when we lose the headcount. Is SOMEbody better than NObody?
I’ve got to go with no. Sure, calls are getting made and a few wins in the pipe, but what could a top-performing rep do with those leads or accounts? How many messes are being made below the surface with the leads, the existing customers, and especially the team. When I hear relief from the team members “left behind” is when I feel the worst about not cutting bait. After all, culture is created by the behavior we accept, not the goals we set or even the high performers.
Here are 5 signs that you’re prolonging the inevitable and need to fire a sales rep:
1. There’s more than a performance issue
When someone isn’t going to make it, there’s typically evidence in more than one place. Call volume is an issue, but they’ve also been late a few times. Close percent isn’t great, and neither is their attitude. Check for behavioral and cultural issues in addition to sales performance. They may not be a clear-cut write-up, but they’re your evidence to double down performance managing the quantifiable issues.
2. There’s a lack of ownership
A friend of mine recently cut bait and replaced someone on their team. When I asked how onboarding the new hire was going I heard, “Well, they’re an adult, so that helps.” This was a (possibly less than eloquent albeit true) summary of what many of us have felt before. If you could be replaced by a $15 /hour babysitter, it’s a sign. If it takes more than one conversation to get something fixed all the way to completion, you’re dealing with a lack of ownership. Could be on a deal, could be about getting to work on time. Maybe it will hit you when you hear your third, fourth, or fifth excuse. The key is to recognize it early, call it out, and get them on your list.
3. One stat rises and another falls
Talk time is up, but dials are down. Quotes are up, but penetration is down. They just can’t seem to get it all going in the right direction at the same time. It’s a great clue they’re either over-employed or don’t care the right amount to give this their full effort. Try to aggregate your performance management here so they can’t sneak by with a “different” offense. Your write-up (or whatever you use) should indicate ALL measures within goal, not one specifically. Don’t waste months chasing different tails!
4. Cover-ups
The very first time you find something in the gray area, something hidden, a half-truth or half-baked answer, you have your sign. Why? Because if you see one (or a half) now, I guarantee you’re going to find 5-10x more when they leave. Look for a customer complaint, a team member’s eye roll, a deal called back by finance, an unexplainable call time or a customer CRM note. If it raises a yellow flag, do yourself the favor of turning that flag red and saving time.
5. Hiding
Having trouble getting a meeting nailed down? See 1:1 meetings being rescheduled or long delays in getting back to you? You’ve got a hider! Hiders know something is wrong and they’re avoiding the conflict for as long as possible. Folks who are working hard and giving you their best are responsive. Employees carrying some guilt and shame don’t speak up, don’t make eye contact, and avoid 1:1 time with you. If your time together has been pushed more than once, there’s your sign (anyone else hearing Jeff Foxworthy every time I say that??). Please note that hiding may also mean going quiet. When Gallup studies engaged, disengaged, and actively disengaged employees, the ones that cost you the most (actively disengaged) are actually NOT the voice of discontent or detractors in meetings. They’re the quiet ones who have decided speaking up isn’t worth their effort. Look for voices you haven’t heard in a while and check in privately here.

In addition, see what you can do to coach them up or out sooner. Plenty of employees welcome the opportunity to admit they don’t love the job, but they don’t want to let you down. Together you can decide what might be a better fit and how you can help them get there. Just last month an employee I helped coach out (and helped land the next gig) came into town and stayed with my family. We continue to like and respect each other because we addressed the growing lack of fit, clear expectations on what we needed going forward, and mutually decided on a timeframe to part ways. That’s a win-win.
It probably doesn’t feel that easy right now, but I’m willing to bet it’s because you’re second-guessing yourself on taking action. Re-read my signs above, and if your yellow flag goes even halfway up on more than one, schedule a conversation. Ask how they’re liking their job, how they think they’re performing, and if they see themselves here long term. Share your feedback with specific examples and clear go-forward expectations. It doesn’t have to be contentious, instead, expect it to be a great air-clearing meeting of the minds where you both feel better afterward.
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Should You Step Down from Sales Management?
Not sure you did the right thing pulling the trigger for the promotion? Miss your old customers? Not getting done working until dark? Losing your mind babysitting? Have you calculated what you make an hour now vs. when you sold for a living?
We get you. You aren’t alone!
In fact, over 50% of new sales managers don’t stay in their role. Some opt to take a step down from sales management, some are asked to leave due to poor performance. The sad part is that you LOVED selling, right?! Most awesome sellers are ambitious and competitive by nature like you. Of COURSE you investigated moving up! And yes, you probably should be a VP someday soon, but this interim gig of front-line sales supervision stinks.
Nobody cares as much as you do. Not a single week goes by with everyone actually showing up and working a full week. You’re saying the same things over and over. You spend your days fighting fires. It’s impossible to know where to spend your time. Useless meetings crowd your calendar. Remember the days where your own hard work determined your destiny and your paycheck? Where you could carry the number over the line AND win a great trip or bonus? Those were the days…
Now you’re thinking of leaving the company – throwing away all the product and service knowledge and years of experience…not to mention relationships and street cred! AHH!!
So, how do you know if you should stay or you should go (if you’re singing it in your head, you get it)? Only you have the ultimate answer, but in the meantime, I’ve created a fun little quiz to help.
Take the Quiz Below!
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How to Have Difficult Conversations at Work
Difficult conversations are often dreaded and sometimes even avoided, but hey, let’s be honest, these are conversations that we need to have. Before I became Lauren’s sidekick (AKA Executive Assistant), I was in sales. I’ll be honest, I would find myself occasionally avoiding difficult conversations, sometimes at all costs, but that’s not going to help us grow and get results. LB was joined by four amazing ladies on a panel talking about how to overcome the temptation to avoid a conversation, how to prepare for the talk, and what to expect.
Our panelists included:
Shianne Sampson who has been working with great startups and technology companies across the U.S. to help build out world-class sales teams. She’s currently the VP of Sales & Customer Experience at PetDesk in San Diego as well as a freelance consultant.
Wendy Mitchell-Covington, National Vice President of Sales Success at TriNet, who is a high-energy, polished strategist who builds and scales sales organizations. Wendy has spent the last 20 years in the HR outsourcing space funneling her expertise into helping America’s businesses improve and thrive.
Brenda Roper who is the VP, Global Sales Enablement at Thomson Reuters based in Minneapolis. She’s also held many sales leadership roles but her passion is seeing behavior change as a result of training – and she’s trained over 15K sales people!
Natalie Servino who is the VP of Marketing for Chorus.ai. where everyday she gets to help B2B sales professionals win more. She oversees all marketing and sales development for Chorus, including product marketing, demand generation, and communications.
What Mistakes Are You Making When Having These Conversations?
- People don’t address the situation or the problem – they address the person and sometimes it feels like a personal attack. Our job is to help them understand how to do it right the next time.
- Delaying the conversation – this is never going to help the situation as it can continue to spiral and get worse.
- Not setting clear expectations up front on what you are asking of them.
- Managers should not have the conversation on the fly – instead think about what you want to say, plan the conversation, and the desired outcome.
Lauren used the Factor 8 COACHN℠ Model framework as a guide. This model is used for all sales manager meetings to help leaders provide consistency and embody coaching best practices. For difficult conversations, it’s called the E-COACHN℠ Model.
The “E” reminds us to maintain an employee’s self-esteem. It also reminds us there are four legs of research to do:
- A private location
- Ample time (double your best guess)
- Data or examples
- Desired goal
Once prep is done, we can follow the COACHN℠ Model to guide the conversation:
- Clarify Expectations: one sentence intro for the meeting – the “problem statement”.
- Observations: Talk about behavior you have observed, data you’ve seen. Not hearsay.
- Asking questions: can the employee explain what’s going on?
- Committing to action items – this is where the employee decides and commits to fixes.
- How can I help? Great managers offer to get involved where appropriate.
- Next steps – nailing down when we check back and what will be done.
Download the E-COACHN℠ Model here.
Tips & Tricks For Having Difficult Conversations
The panel shared so many awesome tips and stories. Here were a few that stood out:
- Make sure that you are ending the conversation helping them come up with a solution for the problem. We can show our faith in them and be encouraging. This helps maintain esteem.
- Follow-through is critical. Get next steps on the calendar and be accountable for your own actions AND measuring their progress and actions.
- The most difficult conversations that you encounter aren’t just performance conversations. When we enter them with the intent to help and learn, they will turn out OK – even the really embarrassing ones!
- Don’t expect to have all the answers. It’s smart to ask HR, a mentor, or a boss for guidance and to practice before having the difficult conversation.
Now for some GREAT Q&A between the audience and our panel:
1. How do you give feedback up the ladder? To superiors, leadership, or your boss.
Always start with your end in mind. What outcome are you seeking? Prepare, have an outline, have someone you trust review and practice. Ask your boss if you can have an open conversation to help propel the business, relationship or whatever it is further. Tell her or him that you have been hesitant to bring this up (if that is true) and that you are seeking to improve whatever it is you are going to discuss AND then go for it!
Remember, your boss can’t read your mind. Everyone is human and makes mistakes. Be prepared to hear feedback that you may not want. How will you react? Do your best to take the feedback as a gift, even if it is something that doesn’t make you feel good.
“Feedback is a gift” – This came up many times during the webinar. What an amazing perspective to help all parties navigate giving and receiving feedback.
2. How can you use difficult conversations with clients as an opportunity to strengthen the relationship?
Many difficult conversations with clients occur because the company that you work for can’t or won’t fulfill something the client wants or needs. Sometimes these occur because expectations were not met.
Honesty and timely communication will actually strengthen a relationship, versus harm it. The worst thing anyone can do is avoid the crucial conversation.
3. What is the best way to have these conversations with your boss. For example if you disagree with an approach or need to “manage up”.
This one is tricky because it really depends on what type of boss you have, you’ll need to gauge your boss’s openness to feedback and these types of conversations. That being said, start with clear expectations. I use a simple format of expectation setting which is: Here is what you should expect from me, and what should I expect of you? They will almost always say the right things: support, transparency, accountability, etc. If not make sure they cover what you need by asking the right questions. Then, once expectations are clear you can use those expectations to align on feedback, similar to the roleplay we did in the webinar. Let them know where expectations aren’t being met and be specific with examples, then provide actionable solutions. The most important part of managing up is for YOU to come with solutions, don’t just come with issues and expect them to solve. If you disagree with their approach it means you are not aligned on what protocol/expectations should be, so start there.
4. Do you have any tips on having difficult conversations remotely, e.g. via Zoom?
Eliminate distractions and make sure you plan as you would for face-to-face. Then always make sure that your video is eye-level and that you maintain eye contact. The rest conveys just as well through video as it does in person. If this is a conversation that is HR-related or could end in termination, you should have HR present or record the session for documentation.
5. How do you acknowledge a counter argument and listen without agreeing?
Depending on the situation, you might not have to agree, but you likely need to address the disagreement and how to move forward. So to start, you need to be OK with disagreement. If the disagreement is done the right way it can actually be productive and build trust! There is a time and place for rude and blunt disagreement, for example at political rallies and debates, however, for business professionals, the polite and respectful approach is always the right way to go. Here are some tips to make this type of difficult conversation productive:
- First, you need to understand that your argument is stronger when you acknowledge an opposing side! It shows that you have thought deeply about your argument or position.
- Be respectful and listen intently. Before you disagree make sure you listen and ask clarifying questions. Sometimes the idea being discussed is good, but the articulation of the idea is not good. Either way, you must actively listen to the other person, don’t just be thinking about your response. Note: it is important to be aware that active listening can give the other person the impression that you agree with them even if you don’t.
- Mirror the person who is disagreeing. A technique you can use is to respond by repeating what he or she has said. word for word. “Correct me if I’m wrong, but what you are saying is…” This helps people feel as though you have heard and understood them. This puts them in a position to listen more carefully to what you have to say.
- Validate the person who is disagreeing. Another approach is to express that you understand what they are saying (but not that you are agreeing). “It makes sense to me that…”. This approach helps to lower people’s defenses so that they are more open to what you have to say.
- Finally, be prepared to articulate how you can both “agree to disagree”. This shows that you are willing to recognize the other person’s point of view, but you do not agree.
6. How to disagree with your boss without getting fired.
We already know the complexities and tips to improve difficult conversations, but initiating one with your boss might be intimidating. However, it doesn’t have to be! If you have a good manager, disagreeing should not be an issue, it should just be another constructive conversation that you have. However, if you do not have a manager that is open to others’ opinions, here are a few additional tips.
- First, pick your battles wisely… you can’t and shouldn’t fight every battle!
- Carefully consider the time and place before you set up a meeting to discuss. If you believe your manager is not going to be receptive to your view, pick a time that is not stressful for him / her. Remember it is not just what you say, it is also about when you say it.
- Tread carefully and don’t make it personal. Stay positive, address the issue and focus on the facts.
- Use “I” statements. For example, “I see where you are coming from, but I am concerned about…”
- Ask questions! This will foster a collaborative discussion, rather than just your point of view. It is important that the conversation is not one sided. Questions are crucial for making your opinion more of a suggestion or request, rather than a mandate.
- Be prepared to confidently articulate the benefits of your position. You will likely be asked this so be prepared and be concise.
- No matter what, respect the final decision. Go into the conversation knowing that your boss does have the final say and be prepared to let it go and support the final decision if it does not go your way.
I hope you found these tips helpful!
If you’d like to watch the recording for our webinar on “Having Difficult Conversations With Ease”, just fill out the form below!
Having Difficult Conversations With Ease [Webinar Recording]
Having Difficult Conversations With Ease
[Webinar Recording]
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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Are You Having Race Discussions At Work?
Open Bars may be my new favorite thing. 😲
A new monthly feature for our “Friends of Factor 8” Community, this private executive-only forum is a place to learn from peers and share best practices. Last month we talked about COVID selling and back to work plans, this month we tackled race conversations.
So you know, light stuff.
Here’s the background: I had no plans to have these conversations nor make any statement. After talking with some brave black women on my team, I went the opposite direction. Sure enough, many leaders who joined us felt the same way.
“Who am I to say something?”
“My team actually isn’t that diverse, there’s no need.”
“It’s uncomfortable and I’ll be perceived as saying something just to say something… and what about the backlash?”
Most of us in our session were in or near this camp. Several, however, were doing more and shared what worked (and what didn’t) with the rest of us. Hope it’s helpful to you as well:
1. Ask what employees need (several wanted time to protest, process, heal)
2. Make a public team statement – you are giving your employees a voice. Get their input.
3. Do follow-up in private. People process differently and may want to talk.
4. Ask team members to share what they’ve done to take a stand or get involved.
5. Try cameras off during discussions (there are many different sides and everyone is entitled to their emotions without judgement).
6. Push for diversity in hiring – try an “HBCU = historically black colleges and universities”
7. Ask about diversity in the organization: “Why don’t we have any black / women / LGBTQ employees/leaders?”
8. Encourage education: “13th” on Netflix and read “White Fragility” by Robin DiAngelo
I’ve personally done most on this list and frankly I’m really enjoying the education. To be clear, most of the learning is hitting me right between the eyes, but the vulnerability and openness to get it wrong, be taught, and be ENCOURAGED by the black community is pretty awesome. I invite you to try the same. Just start with openness and the desire to learn with authenticity and you’ll be fine…
Final advice we received: This problem wasn’t created overnight and it won’t be solved overnight. Learning about our individual biases and unintentional racism (yeah, I said it. I found some I didn’t know I had) is how we make change in our own lives, families, companies, and communities.
I also find myself wanting to do more. If you could have walked with MLK, wouldn’t you have? If we all lean in two or three steps past comfortable we are joining another virtual march. Let’s make a bigger movement this time. I’m looking for leaders with suggestions. What else can we do? For now, I will keep self-educating.
Next Open Bar: Religion. JUST KIDDING! By popular demand we’re talking about virtual learning and coaching best practices. I have to admit looking forward to a trip back into my comfort zone. Email me personally at if you want an invite.