During the 25% of the time when things are good, are they "so good" that they make up for the slog through the other 75%?

If the answer is yes, you are in a good spot. If the answer is no, it's unlikely you will be happy in this role, and it’s probably time for a change.

Needing to love what you do at all moments is a myth. I have seen the most passionate people have awful days and want to quit. Anything worth doing is hard, and when something is hard, it usually comes with many failures to find small wins. Look at professional baseball players. You are considered great if you hit the ball 30% of the time. I have to imagine they don’t love the other 70% when they are striking out or otherwise.

You need to love what you do in the aggregate, not in the moment. The feeling you get from your wins, albeit fewer and farther between than your failures, is how you get there.

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Do: Leave customers, projects, and teams with next steps and action plans while out of the office.

Don't: Open slack or email while you are with friends, family, or in pajamas watching Home Alone.

Do: Budget time to get organized. Your pipeline, desktop, google drive, and calendar can probably use some housekeeping.

Don't: Ping people for things you can solve yourself. We all blended our work and personal lives and feel obligations to respond regardless of time or circumstance. Follow the golden rule and "ping unto others as you would have them ping unto you."

Do: Set goals. Professional, financial, personal, spiritual, relational, or physical. Come up with 4-6 things that are most important to you and write them down.

Don't: Get pushy with customers. If you are B2B, honesty is the best policy. Tell your customer it would mean a lot to get the deal done before the end of the year, but you would be happy to pick up conversations in January if that isn't possible. All SaaS companies are trying to close pipeline. They will understand.

Do: Share gratitude with people who have helped you along the way. These are strange times. We see each other less. When someone goes out of their way to help you or provide advice, it's more intentional than it used to be. Give this gift to yourself and send out some gratitude emails and texts.

Don't: Carry performance burden into your holiday time. What's done is done. The sun will rise, the moon will set, and all will be well in the universe whether or not that customer signs.

Do: Reconnect to the things that make you the most human version of yourself. Family, friends, hometown experiences, or pets - whatever that is for you. There's no sense in becoming professional powerhouses if we miss out on the things that make life worth living.

Thank you all for allowing me to share my stories with you in 2021. Wishing you all the best holiday season and new year. Onward!

Tommy

In the face of a labor shortage, sales professionals have more bargaining power than ever. If you haven’t initiated or been part of a compensation conversation already this year, you might want to have one soon.

I speak to many folks who get particularly anxious about these types of conversations. They are worried about how they are going to appear. But, any semi-decent manager respects an employee’s right to advocate for themselves. For that reason, it’s less about “can you ask” and more about “how you ask.”

The rational “how” for these conversations:

• Start from a position of logic, not feeling. Have reasons other than “wanting” that should inform someone’s decision to give it to you. Those can include:

  • The market rate has changed.

  • It’s been “x” amount of time since your last increase.

  • Switching costs for your role drastically exceed the increase you will get.

  • You have stellar performance.

  • Your OTE (base + commission) is less than 20% of your annual revenue.

• Respect that a decision can’t be made at the moment you ask. This process will have to go through a series of steps. Don’t get upset if your manager doesn’t give you the head nod or green light at the moment. It takes time.

• Be professional. Collaborate with your leaders in a non-antagonistic way. You want them to champion for you, and the easiest way to lose a champion is to present as immature or non-deserving.

• Don’t be greedy. Standard annual increases are 2.5-5% if you remain in the same role. In tech, that tends to skew higher to 7-10%. Ensure your expectations are set correctly on how far you can jump in one ask.

• Set expectations and be direct. If a 20k bump will make you happy, you are just wasting your and your managers’ time by making them think a 5k bump will do.

Lastly, if you’d like to know a well-kept secret: leaders go outside of company policy all the time for the right people. If you think you are one of them, it doesn’t hurt to ask.

If you need help planning for these, we are happy to support you free of charge. Just send an email to tommy@atlasone.com.

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Communicating through stories has been ingrained in us since our earliest years - storytime at school, at bedtime with parents or caregivers, etc. Therefore, listening to stories allows us to hear information in a non-threatening and non-judgemental way. The very best stories are personal, and when that wisdom is delivered it's more likely to be heard and remembered. This is a must-have skill for any great salesperson or leader.

Why does storytelling work?

• Communicates values, not just information.

• Reduces teaching time.

• Ignites more regions of the brain than fact sharing.

• Helps us organize and make sense of someone else’s world.

• Provides a dependable way for people to remember, retrieve, and retell a meaningful message.

Qualities of a great story

1. Simple: Tell your story in a way that's easy to follow, simple to understand, and free of jargon. Tell a story the way you'd talk to a friend over coffee or lunch. In other words: talk like you talk.

2. Emotional: The stakes are higher when you share an emotion. That journey you are sharing will have more meaning for your audience.

3. Authentic: Audiences are savvy. They'll smell the “realness" and truth in your story. If you know you're making something up, wild exaggerating, holding something back, or otherwise, there's a pretty good chance the audience will know it too.

Strategies for a great story

1. Start strong: Assume you have very little time to earn your audience's attention. How can you open your story in a way that says: tell me more.

2. Show conflict. A good story takes the listener on a journey or narrative arc. We start at A and get to Z, and along the way, we overcome B. Conflict signals to the listener that something is at stake - and they'll have to stick around to find out what happens.

3. Tell your story with clarity and details. We've all been taught for as long as we've been writing and sharing stories to "show," not "tell.”

4. End strong. Finish your story with a few words that offer some conclusion.

5. Have a presence. Your body language sends signals not only to the audience but also to your brain. Your mind will ride that same train if your physical body looks confident.

Give it a shot the next time you’re trying to convey a point to a customer, you may be surprised at how quickly you can get to a resonating point.

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With any matrix, the bottom left equals bad, and the upper right equals good. You can probably look at this and immediately think of a who’s who amongst your peers:

• The coaster is on their way out.

• The politician is weirdly involved in random things at the company.

• The doer is in the upper middle of the leaderboard.

• The dynamo is at the top of the leaderboard. 

• The artisan is telling everyone the customized and uniquely clever things they did to win a deal that took 3x as long as it should have. 

The owner is the one who stands out from the crowd. Owners have parts of other personas like excellent performance or craftsmanship but display two key differences. First, they problem solve and get better at things on their own. Second, they ensure solutions are made available to the broader org and don’t remain well-kept secrets. To sum it plainly, they figure things out and share what they learn. 

Now, you may be thinking, “why would I want to help other reps I’m competing with?”. A few years back, I would probably say the same thing. However, that mentality is precisely why so many top AEs get pegged as dynamos who shouldn’t be doing anything besides closing certain types of deals in their career. 

Whether it’s moving to larger deals, management, or just more compensation, the path forward is to create and show impact, not just execution.

It’s hard to stress how important this is if you plan on moving up the ladder at your company. As Warren Buffet says, “it can take 20 years to build a reputation, and 20 seconds to tear it down”. Sales is stressful, but you need to create space between the day-to-day tension and how you are perceived across your organization. Here are some tips:

Keep your promises. There are two parts to keeping your promises. First, do what you said you would do. It creates trust with others and within yourself. Second, be careful what you say yes to. Your job is not to be a hero. It is to stay focused on your role and to work to your strengths. For example, falsely forecasting things you know won't close will lead to more stress later on.

Align to the right level of engagement. Appropriate engagement varies from the executive table to individual contributors. There is a continuum from strategy to execution that moves from “why” to “what” to “how.” Keep your focus on the right point for your role. For example, as a middle manager, your job is to translate the “why” of strategy into the “what” of discreet projects. At the AE level, it's about translating the "what" of discreet projects to the "how" we get it to customers. Try not to get too caught up outside of your engagement areas.

Focus on what you can control. No matter how good the plan we make, we are not in control of or responsible for everything that happens around us. What we are in control of is how we respond to the impact of these circumstances. Sometimes we lose deals, and there isn't a damned thing we can do about it, regardless of how good we are!

Be a player, not a victim. If you begin to feel things like “this isn’t fair,” you are likely seeing yourself as a victim. How can you move from victim to player? A player works with intention rather than being controlled by external events. They can often find themselves engaged more productively by evoking a coaching stance, being creative to propose solutions, or respectfully challenging the status quo.

Know who you are (and who you aren’t). Keep an inventory of your strengths in mind, and as you plan your work, assign yourself work that fits these strengths. The corollary here is that you also know what you aren’t good at, which means finding others who are. For example, I’m aware that I am not great at navigating tense conversations with customers, so I avoid letting conversations escalate, where some sellers might use this as a tactic.

Check-in with yourself. Make time for yourself to stay on plan. At a minimum, set time aside for a one-hour weekly meeting where you take stock of pipeline, catalog problems, notice opportunities, and update your calendars and plans for the next week, month, or quarter. You might do this daily to “zero out” of the day, so you know where to pick up in the morning.

Avoid “coveting.” Coveting is defined as a yearning to possess or have something. When we do this, we attach our happiness to future outcomes, which can provoke feelings of stress in the present about achieving those outcomes. Keep your energy in the present, knowing that good work now leads to good results later. We often see coveting manifest in sales through the lens of upcoming promotions.

Nurture yourself. You can’t do your best if you aren’t at your best. Know that you will be most effective if you eat well, focus on physical wellbeing, and get at least seven hours of sleep daily. Also, know when it's okay to deviate from routine for the sake of letting off some steam. Nurturing yourself isn't about being regimented 100% of the time. If you can do this 50% of the time, you are winning.

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• Our peer/friend is now managing us.

• A random person is now managing us.

• Our manager has changed 2/3/4 times in a matter of months.

• Our manager is overwhelmed and dropping the ball on requests. 

It's important to remember that it's rarely a deliberate decision to make your life more difficult. Starting from a place of empathy can go a long way, not just in your mental peace but also in how you eventually deliver constructive feedback. Externally hired managers didn't decide not to promote internally, managers with 10+ reports didn't decide to skimp on leadership hiring, and if our peer is managing us, we might very well find ourselves in their shoes one day wishing we had an advocate to help make the transition easier. This isn't to say we shouldn't have high expectations of the people chosen to lead us, just that we should try and appreciate decisions through every lens before coming to a conclusion. 

Nip it in the bud: Nothing festers worse on a sales team than an issue with your manager. It quickly spirals from an action they took that displeases you, to a named deficiency of the person, to a larger hypothesis about why they will be unable to ever help you succeed. We can accomplish quite a bit by being prepared, open, and direct about an issue with another person. 

• Being prepared: Documenting, with evidence, precisely what is happening that is causing you frustration. If nothing else, this exercise helps formulate your thoughts on naming and communicating the challenge you are having with the other person. It's hard for anyone to digest or solve general problems like "I don't feel supported." It's a lot easier to get your point across in the format of "when I did this," "you did this," and "I felt this." 

• Being open: It's impossible to find solutions if you are unwilling to share your problems. Assuming you've done the work to be prepared, you need to have the courage to enter into what will probably be a difficult conversation. Regardless of how uncomfortable it feels, this is a necessary step to rectify a problem.

• Being direct: The worst thing that can happen is you do the work to prepare, muster up the courage to have the conversation, and the person on the receiving end perceives something different than what you wanted to get across. It's essential not to use too much fluff or shy away from the point you need to get across. I've found it easier to be direct in a less formal setting than a conference room table, such as a walking 1/1 or coffee meeting. That may be difficult with remote work, but just something to consider. 

Know your last line of defense: If after some time of giving someone the benefit of the doubt and working to communicate your challenges in a productive way, you are still not getting the results you need, it's essential to know who or what your last line of defense is and how to activate it. This will vary by company but can take the form of a skip-level conversation, HR discussion, or anonymous feedback and ratings during a review cycle. Like the point on being prepared, whenever you choose to have this conversation, you will need to bring that next person along for the ride on what has been happening, so having a detailed and documented chain of events to share can get you to a resolution much faster than communicating an issue more generally.

There are great managers and not-so-great managers. What is usually most in our control is how we respond to a situation, and although not guaranteed to provide the desired outcome, you'll know you took the high road. 

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Salespeople do a tremendous amount of amazing work over the course of their careers. Winning complex deals, providing great customer experiences, soliciting feedback for product iteration, coaching others, winning quarters, and piloting new sales methods are just some examples. Unfortunately, we often do a poor job of keeping track of these accomplishments & we very rarely have an artifact we can show as “proof-of-work.” As an interviewer, especially in sales which tends to hire at a high frequency, having something tangible and relevant to show can immediately move you ahead of the pack. This type of online portfolio already exists for most other professions. Just look at this Angellist sign up form:

If it works for engineers, designers, influencers, & content creators, why can’t it work for those who drive revenue at these same companies? Let’s go through a few examples of what a good sales portfolio would include:

Verified performance & accomplishments: Are you a consistent above quota performer? Have you ever won a month, quarter, or year? Have you ever been acknowledged at a town hall or SKO? If you have, here are things you can do:

• If your company has your performance managed in a report in SFDC or Hubspot, export it as a CSV or take a screenshot.

• If you get commission emails that show your percent to goal, always forward them to your personal email.

• If you win an award, always ask for the deck and/or to take a photo with your manager showing the award.

• Take a screenshot of yourself at the top or near the top of the dashboard.

Customer testimonials: If you have customers you have a great rapport with, always ask them to leave a review mentioning you by name on Trustpilot or whatever review site is used. Those are public & live forever on the internet, so you can go back and pull them to show future employers at any time.

Communication samples: I am a HUGE fan of writing samples you can show or link to. Whether it’s an article, community contribution, short post, marketing material you created, a script or training deck you made, etc. This helps show your thoughtfulness & ability to convey complicated ideas. Rule of thumb, whenever you create something for your company, always send it to your personal email.

In addition to the above, you should be able to speak to the top end of the sales motions you’ve managed. What ICPs or large customers do you have experience with? What is the high end of the ACVs you’ve worked on? What was the frequency of deal closings in the environments you’ve worked in?

None of these will be silver bullets but having some or all of these will certainly help you stand out in your next round of sales interviews.

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Whenever passing information from one to another, we have to consider the receiving end & their ability to process it. In the sales world, bugs or lack of functionality can lead to severe outcomes like a lost commission or poor customer experience. In turn, the feedback provided can be severe and difficult to receive. As a salesperson, you may have been experiencing this problem and its severity and have a clear, visceral understanding of why it needs to be fixed. However, when you provide this feedback to a product manager, it may be the first time they hear about it and therefore require time and information to understand the potential impact. To provide great feedback, sales must shepherd the process and ensure that information is packaged so that it can be received and understood, understanding that it could take time for a resolution. The communication breakdown in this direction usually takes one or multiple of these forms: fire-drill feedback, recency feedback, or no-evidence feedback.

Fire-drill feedback is when we skip right to ringing an emergency bell. In some instances, it's warranted, like being unable to do your job because an API is down or having all customers locked out of their accounts. However, crises like these are usually few and far between, and in most situations, problems feel more urgent than they are. This manifests for a product manager as an attempt to decipher the problem while trying to solve it simultaneously. To use an analogy, imagine waking someone up in the middle of the night whose house is on fire, but instead of asking them to escape, you ask them to figure out where the fire started, how to put it out, and how to save the household members - tough gig! The stakes are not nearly as high in business, but everyone requires orientation to solve a problem. The heavy hyperbolic and emotional tinge that usually accompanies this feedback can make it more difficult.

Recency feedback is when we react to a recent, isolated incident to prove a larger hypothesis that something is broken or needs updating. This frequently happens on sales floors and will usually come from a customer request. Salespeople live and die by each deal, and although these requests are one-off and non-recurring, if they are the cause of a lost deal, it will create the feeling that the issue at hand is the most important thing for a company to solve. In this case, product managers have to spend time trying to recreate the problem and research whether it's something that, if solved, solves for everyone or just for one customer or sales rep.

No-evidence feedback is exactly what it implies, providing feedback without any supporting data. This will often look like a bug duty or feedback request that comes in without a customer link, description, or any supporting material on what happened. It's difficult to solve a problem without a full story. In this case, rightfully so, product managers will generally de-prioritize the request as the lift of piecing together the full picture may be too high.

The next time you’re giving feedback to your product team, keep the above in mind. Present information that is thoughtful, calm, & collected with evidence on what happened and the impact a fix might have. You don’t want to be known as the salesperson who cried bug.

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Let’s say it is your first quarter on the job, and you are asked to make 50 calls a day. No problem - you blaze through it. The following quarter, expectations are then set at 55 calls a day. What was no problem three months ago is now tedious & tiresome. We deem the repetitious practice as something that is not helpful, fun, or interesting.

In sales, practice is important, and the way to practice effectively is through repetition of your process: prospecting, pitching, following up, etc. If you want to be good, you will have to do these things over and over again. The decision to become frustrated is our own, and shifting how we approach repetition as part of the process towards mastery and away from something that causes boredom and grief will allow us to develop skills AND patience. Not all the “old stuff” has to be tedious. Just look at the Olympians. Most are spending time perfecting the basics of their craft.

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Rising tides lift all ships, and for any group to be successful, they must transition from single-player mode to a low-threshold multiplayer mode. In other words, looping in others to help with your problems is generally the only thing separating you from solving them. And, for this to be truly low-threshold, we must be comfortable being both supply & demand for information on our teams and be willing to step in to help when needed.

Every salesperson is a node on an information network, with a unique set of experiences from a unique set of customers. Unlocking the power of that information isn’t just the right thing to do; it’s the easiest thing to do! Why solve a problem yourself when it’s already been solved? Not asking for help is like sitting next to a human calculator during a math test, but instead of using it, you choose to do large integer long division on your own. (maybe some of you like math, but this wouldn’t have worked for me)

Whether it’s deals, pipeline, career, work relationships, or office snack choices, the simplest, fastest, & most effective way to solve a problem is to take yourself out of single-player mode immediately. And in return, pay it forward by being the easiest person on the team to ask questions to. The worst case is you help someone out. The best case is you become a self-educating machine by learning through teaching.

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Habits become habits because once we start to cut a groove, we return to it again and again, which makes the groove deeper and deeper. Somewhere in the process, the groove becomes the most comfortable and familiar approach. This presents the major challenge in achieving performance breakthroughs in sales as it requires breaking old habits and walking away from the tracks we’ve mentally carved out over the years.

Rewiring our instincts is no easy feat. It requires effort and support. You constantly need to form habits, break habits, and fill in the groove to flexibly update your approach. You can start by modeling a new habit, usually with something small that you can pick up and work with right away. From there, it becomes easier to commit to doing something entirely new, expanding your skillset and broadening your capabilities. In the relational example above, a mini-habit might be to start asking for a credit card after the first or second call and eventually working into building urgency across your communication map.

Good performers can form & maintain strong habits. Great performers, the best, can just as easily break them.

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The Salesperson

“It has been said that salespeople are big problems to their bosses, their customers, their husbands/wives, to conservative credit managers, and sometimes to each other.

Individually and collectively, they are cussed and discussed at corporate meetings, conventions, behind closed doors, as well as in bathrooms, and from as many angles and with about as much fervor as the daily headlines.

They make more noises and mistakes, create more cheer, explain more discrepancies, hear more grievances, pacify more belligerents, and waste less time under pressure without losing their tempers than any other group we know.

They live in hotels, automobiles, and reception rooms, on trains, buses, and park benches. They eat all kinds of foods, drink all kinds of liquids, good, bad, and indifferent, sleep before, during, and after business, working on schedules as inconsistent as the weather, with little effect on their or the public health.

And yet salespeople are the power in society and economy, and in many ways, they are a tribute to themselves. They draw more money with less effort than any other group in the business. They call at the most opportune times under the slightest pretext, stay longer under more opposition, ask more leading questions, make more comments, and put up with more inconveniences than any other breed of business person on payrolls today.

They introduce more new goods to the world, dispose of more old goods, load more freight cars, unload more ships, and keep more product lines rolling than any other people in the world.

With all their peculiarities and despite their adversities, a salesperson keeps the wheels of commerce turning and the currents of human emotion running. More cannot be said of any person”

Hope you enjoyed it as much as I do.

Have a wonderful weekend!

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Every sales floor has its own uke’s. The people who go out of their way to bring forward the next generation of great sellers. It’s easy to spot who these people are on your team, and it has little to do with the leaderboard. They are at reps’ desks with double wired-in headsets acting as the watchful guardian in case the call goes south. They are sending emails on behalf of new hires whose equipment isn’t working. They go on the walks after a new rep experiences their first hang-up, their first curse-out, or their first lost deal. They bridge the gap.

Unfortunately, most sales floors also have the anti-uke. The senior seller who sees to making new hires feel uncomfortable, unwelcome, or just plain silly. They exert their bravado in a way that causes the new seller to feel excluded, and are generally brash & harsh in their feedback.

If you are a tenured rep at your company, recognize which side of the fence you’re on. You’re VP of Sales already does and is weighing the behavior in who gets the next promotion. Creating more successful reps is not a zero-sum game. Be the uke, and help facilitate the environment that begets more success for all.

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Journalists, diarists, and anthropologists are good examples of people who are interested in the minutiae of life. Most keep heavy field notes on what they observe so they can review details, look for patterns, and eventually come to a conclusion on a perspective. In sales, your own notes don’t need to be this exhaustive, but just enough for you to learn what worked, what didn’t, and make adjustments next time.

Collect data, review your records, and be meticulous about pointing out where things went well, where they only got partway through, and where they fell apart. This requires discipline, but each week you will start to notice your changes, improvements, and when you might be falling back into a bad habit you were previously stuck in. The best part about this process is that failures become more exciting - they serve as natural, documented markers to change course.

Become the student of yourself.

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You can see both here:

Coinbase Demo Day Practice

Coinbase Investor Relations - 2021

You’ll notice many differences - the power of his statements, the fluidity of the story, & the confidence he brings. It’s like watching different people. My guess is this didn’t happen by one ah-ha moment, but through consistently practicing this story over the course of time.

There is no more relevant profession to this than sales. Anyone who has taken a new sales job is aware that it is nearly impossible to be good in your first couple of months, and if you are it probably has more to do with luck than skill. Engaging in deep practice & preparation, before you pitch, will give you the mental run-through required to be confident around every customer turn.

Figure out how you are going to engage in perfect pitch practice, examples include:

• Writing out your pitch as “acts” - opening, discovery, asking for the deal, etc

• Writing out potential customer objections & how you will handle them

• Doing a mock run-through with your peers

• Acquiring information & data on the customer you are going to be selling to

The way we all do this will be different, but if you can be disciplined about your perfect practice, you will be unstoppable.

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Walking this tightrope from sub-optimal to optimal requires moving from the known to the unknown. We have to try new things. Considering the consequentiality of the role, any normal person would find this highly uncomfortable, and when it doesn’t work, we are quick to retreat. However, there is a disciplined approach that is fairly simple to follow: curiosity before ideal state.

Our efforts will very rarely meet our standards initially - it’s why we are putting in effort in the first place! Our job as learners is to bring our efforts to a place where they match our standards while being able to find lessons in failure & discomfort. The best salespeople I have ever worked with consistently ask themselves the question - “what can I learn from this?”. They still make mistakes, but rarely the same ones twice. Reprogramming your mindset to embrace challenge in this way, pointing towards education and away from emotion, will help remove the fear of trying something new.

Having a pitch go south is not a good feeling, it never will be. The curious person turns the bad feeling into a lesson, creates their own path, and climbs the ladder consistently.

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1. Solving customer problems

   This is a proxy for the “meat” of what your company does. Is the industry interesting to you? Is the buyer a type of person you would be excited to help? Would you be proud to become an expert in the subject matter?

   When we sell, we live & breathe the industry we sell into. If you find it boring or uninteresting, you will probably miss the nuanced details that separate good from great. During my time at ZocDoc, it was always clear who the best reps on the floor were as they genuinely found the problem of patient access interesting & could speak to it at an expert level with doctors.

   Rule #1: If it’s not interesting to you, you probably won’t be good at it.

2. Engaging in the sales motion

   This is a proxy for how deals are done at the company. Is it transactional or consultative? Is it a two-week, two-month, or two-year deal cycle? Is it call heavy or email heavy?

   This is the work we will do every day and is where “fit” breaks down most often. Sales is unique company to company, and understanding the motion is key to understanding if you will have the will to do it. For example, if you enjoy small pipelines & building deep relationships, transactional is not for you. On the flip side, if you enjoy immediacy & lack of ambiguity in deal closings, it might be.

   Rule #2: If the motion makes you uncomfortable, you probably won’t be good at it.

3. Interacting with the team

   This is a proxy for your at-work community. Can you see yourself meshing with the people at the company? Does leadership’s communication style resonate with you? Would you be excited to have a coffee or lunch with someone from your interview panel?

   Contrary to popular belief, the number one source of sales burnout is not workload but breakdown in community. We are capable of remarkable outcomes when we feel supported, and are equally incapable when we are not. You have to enjoy the team.

   Rule #3: If you leave your interview unenthused about the people you met, you probably won’t be good at it

That concludes the series on evaluating your next sales role - I hope you enjoyed it! There is a lot of information jam-packed in these posts but to sum it all up: gather information, evaluate the team, evaluate the market, & evaluate your fit. If you need assistance, I’m happy to chat, just drop me a line at tommy@meetreps.com.

Lastly, shameless plug, but we are hoping to get to 500 subscribers soon. If you’ve found this information valuable, and think of others who might as well, it would mean the world to me if you could share it on LinkedIn or any of your social channels. There are 56M salespeople on planet earth, and 22.5M of them will not earn their full compensation this year. I am hoping to change that. In return for a share, I would be happy to provide a free hour-long coaching session where we can jam on deals, career stuff, or discuss the best slice of pizza in NYC - just drop me an email once you’ve posted!

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1. Ask for the calculation

   The most senior person in your interview process should know the potential market size of the business (if they don’t = red flag). Companies & founders will have different ways of calculating this, but this one is a simple equation, the bigger the better. Ideally, you are looking for a market opportunity north of 50B. I know it sounds ridiculous that something with a 25B opportunity is not interesting, but the truth is most businesses will only penetrate a small % of their total market. Companies in small markets will have moments of stalled growth, which can lead to career stagnation for folks in sales positions.

   Interview Qs: What is the total market opportunity for this business? How did you arrive at that number?

2. Find where the money is coming from

   Businesses will generally have revenue coming from new & existing customers. The best businesses have positive “net revenue retention” which means their customers spend more money with them year over year. When going through your interview process, understanding how residual revenue is growing is significantly more important than new bookings. The reason is that if residual revenue continues to grow, new bookings only have to grow linearly for the company to grow exponentially. Exponential growth = forward momentum = career opportunities.

   Interview Qs: What % of your revenue is from existing customers vs new customers? How has revenue from existing customers grown over the last 12 months? What % of customers churn annually?

3. Evaluate if technology can expand the market

   Last but not least, does the technology the business is developing have the potential to change the situation in the market. Uber is the perfect example of this. The ease of use and simplicity led many of its users to greatly increase the number of times they use an alternative car service, therefore increasing the size of the taxi market dramatically.

   Interview Qs: How does the product serve customers better than what exists today? How does it make accessing the service easier?

Market size is important in determining the forward trajectory of the company. The forward trajectory of the company is important in determining the forward trajectory of your career. The one caveat to all of this is to understand if a large market is already controlled by hard to displace players. For example, “advertising” is a massive market, but so strongly controlled by Google & Facebook that it will be difficult for any company to disintermediate even with a large TAM.

Choose the most senior person on your interview panel, and dig into the market. It’s the best proxy for what “up” looks like, and “up” is the best proxy for what your career can look like.

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We’ve been getting great feedback that some of this content is spurring additional thoughts & that folks wished there was a place to discuss further. For that reason, we’ve launched SaleBite, an exclusive community for the best sellers & leaders out there. RepSushi subscribers can get access to the community Here! We are capping at 50 members, for now, so sign up soon if you’re interested!

Now onto today’s programming…

“We are the average of the five people we spend the most time with” - Jim Rohn

There are few social circles we will spend as much time with as our direct managers & peers. After your significant other, children, or parents, your manager & teammates are probably the people you speak to most in the world. Yet oftentimes we don’t do the most basic diligence here even though these are going to be our highest frequency interactions in the workplace (and potentially in life). It’s really quite basic across both: can we learn from them & do we like them?

Manager

As best you can, you should try and meet your direct manager before starting at a company. Sales teams, unfortunately, shuffle around more than other departments and therefore this might not be possible, but it’s always worth a shot. When evaluating a new boss I’ve always thought of myself as a sponge and them as a well - if I suck up everything the well has to offer, am I better for it? or am I unchanged? This is going to sound cold, but not everyone is fit to lead, and even fewer are fit to lead real performers. We can save ourselves a lot of agony by determining upfront if we are going to be capable of respecting the person managing us, and this respect will generally come from trust & utility - can I trust this person & will they be useful to me? Plain & simple.

Evaluating your ability to build trust with someone might sound abstract, but there is a formula you can use, called the *drumroll*….trust equation

Credibility represents how much someone knows or has done. Reliability focuses on whether this person has a history of doing what they say they are going to do. Intimacy is whether or not you’d enjoy having coffee or lunch with this person. Self-Orientation represents individualism and whether they are more focused on themselves vs you (see a previous article here for more thoughts on that). So, credibility, reliability, intimacy = good, and self-orientation = bad. Rule of thumb if you want to be quantitative, assign each of these a number 1-3, and if the equation spits out anything less than a 4 there might be a problem. It’s not perfect, and it may be hard to suss this all out in the interview process, but I urge you to try and dig deep into whether or not you will be able to build a healthy relationship with your manager - not having it accentuates the worst part of the job.

Utility is a little more straightforward and I would define it as how much you will be able to learn from someone, about the job & the world in general. The learnings you get from a great manager will extend well beyond your roles & responsibilities on the job. Here you can look for this person’s experience - what have they done? how did they do it? And if the experience is limited, how are they going about getting better every day so that they will pass those learnings onto you?

Peer Group

If it’s not already part of your interview process, you must ask to spend time with at least three reps informally or do a “day in the life” shadow session. This is important to understand a) if you are going to jive with this team and more importantly b) what type of bar has leadership set for hiring salespeople. This should go without saying, but you want to be part of a team with an extremely high bar, as you will naturally get better through osmosis. Alternatively, if you join a team with a low bar, you may see your own habits become shells of their former selves as you integrate with your surroundings. I can’t stress this enough - there is no glory in being a giant fish in a small pond, eventually, you will drown.

So to sum it all up, teams have four components: 1) board & execs 2) department leaders 3) direct managers, and 4) peer groups - each requiring a different evaluation process. Nailing this part of the decision process is crucial - great teams make bad sales days great, and bad teams make great sales days awful.

The next post in the evaluation series will focus on evaluating the market your company is in, and how much runway up that gives you.

Have a great night

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