Chris Pollot, Director of Sales Development at UpGuard, Discusses Coaching Secrets, Recruitment, and More.
Leading a sales team can often feel like putting out fires, mitigating disasters, and otherwise being “on call” 24/7. So when Chris Pollot (LinkedIn) began his professional life in sales, but took a career “aside” to pursue actual firefighting and paramedics, it seemed like a natural transition. But knee surgery put a kibosh on his EMT ambitions, and so the current Director of Sales Development at UpGuard found his way back to sales as a recruiter for software startups. But his eyes were soon set on SaaS—and on sales roles like the ones he spent years headhunting for. Once Chris set his sights on software sales there was no turning back. He worked his way up from AE to Head of Sales Development for SaaS startup ClearSlide, building out their SDR team from zero to thriving in just three short years. At Showpad, he was brought on to do the same for their SDR organization, first internationally and then in North America—in just eighteen months. In our interview, Chris imparts his passion for building successful sales teams, his wisdom around cultivating strong leadership, and how the secret to his record of high performance is rooted in getting off on the right foot, in recruiting.
What’s the secret to hiring for high performance? What are the most important characteristics you look for?
I just hire really good people and then make them happy to work for me. The rest kind of takes care of itself.
There are some universal characteristics of high performance, but I think it’s dependent on two overarching factors. One, what is the organization? What is the culture and values of the organization? What is the organization trying to accomplish?
Two, what is the role? There are very different pillars for each role that depend on the team and on every specific role or capability. But there are some pillars that always carry over: For example, a demonstrated track record of dealing with adversity and ambiguity, not just dealing with it, but actually actively succeeding.
“I think there’s a big difference between someone being able to talk a good game and being able to actually demonstrate that capability. That’s a trait that always carries over.”
I’m being particular to startups here because people who can’t operate with ambiguity shouldn’t be at a startup—especially in a sales or sales development role. Demonstrated work ethic, particularly in a team environment, is really big—as is seeking out someone with a “student” mentality. All of these things cross over, all are important characteristics.
There is a very specific process to look for the high performance pillars for a given role. They follow a very specific pattern, essentially every time.
Usually I’ll start with what seems like a very basic question: “Hey, could you tell me a story of when you demonstrated x, y, or z?” From there, I ask them to explain:
“What was the problem that you were having?”
“Can you walk me through the problem?”
“What are the specific steps you took to address the problem?”
“What were the outcomes?”
And finally, “What did you learn from that whole experience?”
Of course, your interview may not be quite that formulaic. But if you ask those five questions, then it gets you around a lot of those pre-prepared answers that people have when they come into interviews.
Oftentimes in sales and sales development, you’re hiring for potential and capability versus hard skills or hard metrics. But you’d be surprised how many kinds of “hard” skills crop up in people’s everyday lives—even outside of work—demonstrate those high performance pillars of your candidate profile.
For example, I love guys who have done fundraising for their college. That’s a brutal job where you get beat up and hung up on. Generally, if you’re really good at it, then you have some kind of accolades that you can show—things that you’re proud of or can speak to. Excelling in sports, obviously, is another example, though maybe a bit of an overused one. In general, however, people who tend to excel at things, take pride in them, and actively participate in them tend to rack up accolades.
“Call me old school, but I’m a big believer that if you’re going for an interview, then you should have what I call a ‘brag book.’ You should have a record of your accomplishments.”
I also look for people who know their numbers off the top of their head. Whenever a candidate gives you a percentage of something they increased (“I think it increased about x percentage”) they’re usually full of it, to be honest with you. Good salespeople know their numbers.
I do something that’s relatively unique in that I alternate the cadence and the process of my one-on-ones on a weekly basis.
Every SDR who works with me has some one-on-one time at least once a week, generally half an hour because they don’t need much that much time. For sales reps, depending on where they are on the maturity curve, it’s between forty-five and sixty minutes.
Then, I alternate weeks where I own the agenda for the one-on-one and then they own the agenda for the one-on-one.
“I call one-on-ones ‘alignment conversations,’ because the one-on-ones that I run are intended to get us aligned on expectations and what it takes to meet those expectations.”
Generally, they focus on specific activities—whether that’s positive stage changes in their pipeline, the number of new meetings, or an increase in average opportunity or average deal size. All of that can vary depending on what stage they’re at and what the needs of the business and the individual are. But generally those are the types of leading indicators I’m looking for.
When it’s my week, we can talk about very specific business outcomes that need to happen that they may not even be aware of. For the alternating week, where I allow them to own the agenda, that’s where I have them come to me with specifically what they need help on. I ask them, “What are the things you’re struggling with? What are the things you need my support on?”
This allows them to feel a lot more heard, and it decreases wasted one-on-ones where, if I ran the agenda the whole time, I won’t get to the difficult things that they need that I may not have on my radar. It’s really good for morale.
The first thing is you have to bribe them a little bit because they have to earn resources! And the best way to earn resources is to stay on top of stuff. That’s the number one way to keep me off your behind: to keep me from constantly asking, “How many calls have you made? How many meetings have you set?” It’s to put stuff in Salesforce and keep me abreast of what’s going on. Communicate with me. That way I don’t have to bribe you and bug you!
If you keep me in the loop of what’s going on, keep me in the loop of what’s working and what’s not, then I can support you as a manager and I can fight for resources to make your job easier.
The second thing is that I have one-on-ones and team meetings with very specific agendas, and I stick to them. I don’t reschedule on my team, and I don’t disrespect their time at all.
The third thing is a constant and genuine focus on my team’s individual development and on overall team development. I think my team very much feels that I’m invested in their success—that I don’t just give lip service to it. I actually deliver on it. I show them that I make it a focus.
“In general, organizations do a bad job of communicating why things are or aren’t valuable to their reps. As a leader, always make your communication focused on how it benefits the rep, not how it benefits the business.”
In short, if you’re able to manage your deals, then you’re able to keep me off your back. When you need me to jump on the call, because the deal’s not going to close and you need someone to come and negotiate, I have all my notes right there so I can best represent you and the company. As a leader, always make your communication focused on how it benefits the rep not how it benefits the business.
Individuals need to set the goals themselves. If they’re way off base, then I’ll bring them back in.
“Individuals don’t care about the goal you set out for them. They care about the goals they set out for themselves. It’s leading them to water versus making them drink.”
For me, individual goals start with making employees see the light. Make individuals reverse engineer what their goals should be, but then truly let them set their goals themselves—and only step in if they’re way off base or they’re completely unaligned with what it will take to be successful.
I don’t think there’s any more of an advanced answer than that. Reps need to be focused on the right things for the business and for their business. I’ve asked each person on my team to be an entrepreneur.
“I’m a big believer in aligning your team goals as an aggregate of your individual goals.”
For example, I want my compensation to be an aggregation of my team’s compensation. My goal should be an aggregation of what my team’s goals should be. I think that ultimately they should be directed by the business’ needs. But the team goals should, as long as all goals will meet that sort of outcome, be completely aligned with individual goals.
What are the aspects of qualitative performance that you like to pay attention to which are hard to instrument?
“Quality customer interaction for sure. And stakeholder coverage: how many people within the account or opportunity are we actually getting involved?”
If there are 5.7 or 5.9 decision makers per business decision or per purchasing decision nowadays, then what percentage of those are we actively engaged with?
And I’d probably say the quality of messaging, too. Gauging how well your messages are representing your value is almost impossible unless you’re sitting on every call, which no manager I know has time to do nowadays.
Maybe this seems like a no-brainer, but I think live observation are something that is absolutely crucial. I don’t think managers do this enough. They either don’t join calls, or they don’t have their team record their calls. Generally, they hear snippets of calls and assume they know what’s “wrong” with a rep or what a rep is “doing right.”
I know a lot of leaders who don’t understand what good work looks like. Not only that, but they don’t communicate with their team. Every meeting ends up being a subjective—instead of actionable—feedback session, which is a waste of everyone’s time. They say, “Oh, I noticed you did this,” or “You did that wrong!” or “You did this great!” All that means is that they don’t have an organized, well-thought-out sales process or review process—and it’s all too common.
“Something I see on my high performing teams is a very mapped-out sales process.”
We know what the steps are, what things we need to get out of the conversation, what questions we need answers to, and what key things have to be communicated at each stage of the sales process. Then we analyze activities or behaviors or work against an objective scoring system, so that when we’re done reviewing the rep’s work we have something you can hand to the rep that’s tangible that they can learn from.
There used to be an old, common, belief with feedback called, and pardon my language, “a shit sandwich,” where you give positive feedback, negative feedback, then positive feedback. I think that method sends very mixed messages.
Sales professionals and sales leaders generally hear the things that they want to hear and they tune out the things that they don’t; negative people will only hear the bad stuff, and the people who think they’re God’s gift to selling will only hear the positive things.
First of all, don’t mix the two types of feedback. You should have separate questions with separate focuses, and an objective method to deliver feedback where’s there’s a system of recognition and very specific action items that have to be done to improve.
For example, in the discovery phase of our sales process there are about five questions that must be answered in order to move a deal forward—then, there’s a bunch of context questions. Understanding the buying process is a good question; understanding every stakeholder in the process is not necessarily a must-have, but I do evaluate whether they’ve accomplished that level of understanding or not. Again, having something tangible to rate individuals on is important.
“I also believe that positive feedback needs to be delivered more regularly than negative or constructive feedback—I would say in a three-to-one ratio.”
Another key to effective feedback is this: any time you give positive feedback you should ask the recipient to pay it forward or find a way to communicate what they’ve done well to others so that everyone else can get better and foster a culture of best practice sharing.
“I’m a huge believer in using leading indicators and sales-customer interaction data to diagnose sales problems.”
This is something that I’m the most well-known for in the organizations I’ve worked in, only because, frankly, I’ve sold sales enablement and sales engagement data tools for the last six years.
So I can tell what’s happening based on the number of phone calls, your connect rate, your email, how many emails you have, your open rate, your reply rate, your meetings set, and meetings converted into real opportunities. I can literally pinpoint exactly where you’re screwing up in your process. On top of that, I use live observation as a way to figure out even more granular areas where you’re screwing up your sales process and what you’re doing to screw things up. But I’m also a big believer in using data to figure out what specific areas need improvement.
An important thing to remember is you have to be very granular and you have to give one piece of feedback at a time. If you overwhelm a rep with constructive feedback, then they won’t know what to focus on. Great managers only deliver one piece of feedback at a time, or at least per feedback session, that’s very granular and can be acted upon until the problem is solved.
Constructive feedback is so different from positive feedback because you can just keep piling positive feedback on and you can make it a lot more subjective. Negative or constructive feedback should be very narrow and very results oriented.
How do you do feedback where the answer is measurable (“fewer bugs in the code please”) versus less measurable (“You come off as aggressive, Bob.”)
That’s a really tough thing as well.
“One thing I’ve learned is that measurable things are often much better delivered by managers, and feedback on subjective things is better delivered by peers.”
So I will often enlist my senior reps—the ones that are interested in being a manager, who are very senior and very trusted—to give subjective feedback. When somebody you work with everyday at the same level tells you, “Hey man, that call was really aggressive. Why don’t you think about it like this?” the rep’s a lot more apt to act on that kind of feedback. When they hear it from a peer there’s less inclination to internalize subjective feedback and shrug it off.
Now, you can give subjective feedback, but you also have to enable the recipient to witness it themselves. Here’s what I mean:
You know how when you hear your voice recorded, it sounds terrible? I think my voice is terrible whenever I hear it out of the speaker, but I think I sound like an angel when I talk in my head. It’s very similar with subjective feedback. I’ll give reps subjective feedback, but then I’ll frame it in a way that puts the ball in their court; I literally make them listen to themselves.
So I might say something like, “Hey, maybe you don’t believe me, but on your next three calls I’d like you to use Talkdesk to record yourself. Then I want you to listen to those and let me know what you think.”
That tactic uses the methodology I’ve talked about before: observe, diagnose, prescribe. I’ll observe them and say, “All right, that was too aggressive.” Very subjective feedback. I will diagnose it and say something like, “Hey man, you’re really aggressive; you really turned this guy off. Here are some different things you can do.” My prescription is then, “I want you to record the next three calls in this scenario and record yourself, then listen to those recordings. Then come back and report to me on what you’ve found and what you thought.”
If I just gave them that subjective feedback that they’re too aggressive and end there, then it’s easy for them to shrug it off or get defensive: “Whatever, it was just an off day,” or something. But using this method four out of five times they come back with an epiphany: “Holy shit, I really was aggressive. You were right!”
Again, objective data should always be delivered by a leader. It should be very actionable. You should never deliver measurable feedback without actionable behaviors they can implement right away. The feedback should be documented and, when you follow up, you should note the level of progression or regression that they’ve made against that hard number.
I know there are a lot of things I’ve said that I’m really passionate about, but personality management and employee management are my biggest passions.
For professional development, there are a couple of key things. I won’t hire somebody for a role unless I have a career plan already in place, and I won’t build an SDR team without first building a career path for it.
If you don’t have a career plan mapped out, you shouldn’t even start hiring for the role because you’re not going to keep people, you’re not going to attract top talent, and you’re not going to keep people on their feet long enough to pay for themselves before you have to promote them or before they’re looking for a new job.
Now, that career path must come with very hard goals to make them eligible for promotion. For example, my SDR team has to hit 100% of their quota for twelve months to even be considered for promotion. Now, maybe they can do that in six months. If they hit 200% they could be technically ready for a promotion after six months in terms of the metrics they need to hit. I weave some other things in there to make it so they can’t just get promoted because they hit their number.
Professional development is something that is constant and never ending. I’m a firm believer that you should dedicate ninety minutes, at a minimum, every two weeks for one-on-one development, then two hours a month for team professional development. At least half of that development time should be focused on the job they do today, and the other half of that time should be focused on teaching them skills for the next level, something outside of the scope of their day-to-day jobs. That could involve bringing in other parties to educate them, sales training, or having a CMO of another company present to the team.
But having their career path in place, and giving them the skills they need to learn along the way so they can earn a promotion are key.
“It’s very wide-ranging, but that’s how I think about professional development. It never stops. You have to dedicate the proper amount of time, or people just don’t feel invested in the company.”
You have to manage them out quickly. It’s not that hard to pinpoint those people early on. But so many managers are either afraid to fire them because they’re under pressures to keep their head count up or to give the impression that things are working really well and everybody’s happy. Or, frankly, they are just weak managers.
I’m the exact opposite. If I know that someone is not going to work out from the beginning, then I’ll either manage them up or manage them out very quickly. I think the liberal use of performance improvement plans or coaching plans—or whatever you want to call them—is super important and I will apply those pretty quickly, too.
I will give a rep or an SDR a grace period that I define when I hire them because I’m a big believer that improvement plans should be done in a very specific way.
“Most organizations just hand you a performance improvement plan that says something like, ‘Hit your number or you gotta go.’ That’s garbage.”
That doesn’t help anybody perform. A performance plan needs to diagnose.
I’ve already observed that there’s an issue, so the diagnosis should be a combination of hard metrics like, “You’re not hitting your number of meetings,” or “You’re not hitting your number of opportunities,” or “Your average opportunity is too small,” and subjective things, too, like, “Here is what I’ve observed that you’re doing wrong in your sales process or in your management process.”
I have one page of what they need to improve and then two pages, sometimes even three pages, of what resources they’re going to get to support them—whether that’s more time with their manager, more meetings, or more checkups or marketing support. It’s never ever just, “Hit your number or you’re gone.” It’s always, “Hey, you need to fix these things and here’s how I’m going to help you.”
Present the plan with the idea that this is actually a good thing. Start by saying, “You are underperforming, and I don’t want to fire you because you have potential, but you’re going to have to show me what you can do.” If you have a real sales person, a real SDR, or a real manager on the payroll that you’re delivering this to, then they’re going to buckle down. It’s going to light a fire under their ass, and they’re going to get it done. If it’s the wrong person for the company, then they’re going to wither and fail very quickly, and then you can manage them out.
“Drive is tough. I think you weed lot of that out in the hiring process. Otherwise, I think you start with the carrot, and later, you switch to the stick.”
There’s a really good course called SLII, Situational Leadership II, that talks about two different axis: One axis is motivation—simply, people are either motivated or demotivated. The other axis is competency—either people are very competent or they’re not very competent. I’m paraphrasing, but that’s the gist of it.
As you go along this curve of competency versus motivation, then people start off not very competent but extremely motivated. Those people are like, “Let me at ‘em! I want to tackle this task!” For someone at that stage, you want to be very directive. You want to give them very specific expectations and directions on how to do things.
Then people go from not being very competent, but very energetic and motivated, to a little bit more competent and a little bit less motivated. They’ve been at the job for a while, so you have to start becoming less directive and more supportive. By “less directive” I mean to stop telling them exactly what to do. By “more supportive” I mean to ask them more how they think things should be done. Steer them right, and if they go off base give them an opportunity to come up with the answer themselves and maybe deliver on it.
The next step in that curve is when they’re competent, but they have very low motivation because they start thinking, “I’m way better at this than anybody else. I know what I’m doing. Stop telling me what to do!” At that point, as a manager, you have to go even further along that curve and become even more supportive and even less directive. If you do this well then, eventually and hopefully, they get to be very competent and very motivated. Because you’ve been supportive of them and not directive they feel some ownership, they feel like they’re contributing, like their opinion matters, and they feel like they can make a difference. When they reach that part of the curve—competent and motivated—that’s when they’re ready for promotion.
Then, I take those two curves—competency and motivation—and I teach that language to my team. The beauty of that is if they speak the same language and you use data to track things and you have good metrics, then you can often point to metrics and have frank conversations with them about performance. For example, you might say, “You might think you’re competent, but you’re only performing at a fifty percent level. So, let’s give you more support to become more competent.” Of course, I wouldn’t say it exactly like that, but that’s the idea.
“Ultimately, I think what you have to do is to give unmotivated people challenges that you know they can’t overcome.”
For example, if someone’s very motivated but not very driven or not able to accomplish something, I’ll actually give them more responsibility—as long as it doesn’t harm the business. Then when they fail it’s okay; it allows you to demonstrate both that they need to level up and your willingness to support them.
I have a guy right now that I’m working with who fits this mold. He read some article and did some research, and now all of a sudden he thinks he’s God’s gift to sales. He is literally saying he needs to be the president of the company because he had a revelation. But he was actually fifty eight percent of his number last quarter. I gave him a few big tasks and he wasn’t able to accomplish them, and it’s knocked him down a peg. Now he is asking for my support, which I gladly give him.
Promotion is a huge problem in startup culture and for millennials in general; they think they’re ready way before they actually are. Have you heard the term “the Peter Principle” before? Where people are promoted to the level of their incompetence?
It’s a huge organizational problem in the United States and the world in general, and it happens really fast in startups. I’ve joked that being a leader in startups is like being a general in the Army—there are only two reasons you get promoted: someone retires or someone dies. This happens in startups a lot. People go get new jobs, they go on to the next thing, and the people that stick around often just get promoted by default.
As far as knowing when someone’s ready for promotion, there are couple of things that I look for. First, however, I almost never look for A+ players to promote. It sounds really weird, but often the best sales people make terrible managers because, frankly, they’re wolves. Being A+ comes naturally to them. When something comes really naturally to you you’re usually a bad teacher. “You should do it the way that I do it,” doesn’t work.
So I look for someone who may not be an A+ player, but has gotten to the point where their job doesn’t challenge them anymore. They juggle all the extra tasks that I delegate to them, still crush their number, and still go golfing on the weekends; they aren’t super stressed out about everything at work.
“That’s the number one test for a manager when you’re looking to promote someone: Can they crush their number, can you pile on a bunch of other responsibilities, and do they still come in with a smile every day?”
The next thing is operational thinking. They need to be able to think operationally about the business. They have to be able to tell you the levers that need to be pulled to make whatever role they’re currently in successful—as a team and not just as an individual. They need to be able to tell you, “Here are the things we can move and shake to be successful.”
The third thing is training, making sure they’ve had training and have been certified on the training that will enable them to be successful at the next level. The way that I design the career plans for my teams is so that people can actually start the next level of job training once I’ve identified that they’re going to be ready for promotion in six to nine months. They have to juggle the training and the extra responsibilities I give them, hitting their number at the same time. Once they get through training—and the whole time they’ve juggled their additional responsibilities and their number—then they’re ready.
The hard metrics are: revenue, performance, pipelines generated, and the “soft” metric—or KPI, or whatever you want to call it—“number of additional tasks performed.”
If I have a senior rep who I want to look at as a potential team lead or a manager, then I will generally give them some pre-managerial responsibilities. For example, I’ll tell them they’re going to be responsible for helping train all the new hires. I’ll look to see if they accomplish that task and if the new hires perform at a high level. I’ll often have them deliver a training. What I’m looking for is whether they can handle an extra project a week on top of their normal duties, whether they can execute on everything.
The other thing I look at is: do they complete the training module that I’ve asked them to go through in a timely manner? When I outline their training plan I ask them to deliver, or rather I ask them to own, the completion dates for their trainings.
“That’s a big one: Do they meet their due date? To become a manager or a leader, you don’t get to miss your dates because you were ‘busy.'”
Those are all about individual coaching moments. I think instead of beating them over the head with it, the answer is to help them post-mortem it, and to help them understand the failure or the setback. More importantly, actually give them actionable things that allow them to solve it.
“Two of the main motivators of human beings, in general, are pleasure and embarrassment. Most people are motivated by one of those two things.”
And so one of the most satisfying things you can deliver to somebody is a way to prevent them from embarrassing themselves. When you have a setback deliver good, thoughtful coaching in a way to help them avoid repeating the mistake.
I think the number one thing that you can look at for metrics are KPIs. Those are the very leading indicators. The main things that you see when motivation starts to wane are dips in the very leading indicators: things like calls, emails, and email open rates.
“The funny thing about sales leadership is that leaders often spend so much time looking at lagging indicators—like pipeline, deals closed, and opportunities—that they don’t catch the early warning signs.”
The number one thing that I’ve seen, and I’ve seen this data time and time again, is if a rep’s baseline for their highest level activities—calls, emails, appointments set, new meetings, that kind of stuff—dips by more than twenty-five or thirty percent (depending on the seasonality of the business) below baseline, then you can believe they’re checking out.
You need B+ players, generally.
I’ve turned five individual contributors to managers and a manager to a director. Actually, one of my managers was just recognized as one of the top fifty most influential sales development leaders in the Bay Area. That was pretty cool!
I think once you identify that someone has not only the individual contributor ability but also the managerial qualities (calm under pressure, the ability to translate very complex things into very simple answers or responses or action items, the ability to handle stress, excellent time management) once you identify all those things, and you need to identify those six to nine months in advance, then you have to put them through managerial training.
Managerial training involves situation training, which involves having them juggle additional team responsibilities. Potentially it even involves giving them a small aspect of their variable compensation based on key performance.
“More importantly, you have to have a training program that’s tied to a career path that has some certification aspects with it.”
For example, with my SDR managers, I’ve identified thirty-six skills that they need to know—which I need to feel comfortable that they can deliver on—in order to be a successful manager. The ICs have to agree to this plan, decide on a timeline when they’re going to accomplish it, and at the end, be certified in all thirty-six of those skills.
That certification may come in different formats, like “doing it live” or coaching or ramping new reps. Then there’s also some written certification and oral certification, for example, I’ll have them own and deliver a one-on-one. I’ll sit in on it, observe it, and give feedback on it. Ultimately, they need to go through the training and come out of it unscathed and still want to do the job.
Actually, that’s a much more simple answer than you think.
What I do with every employee in our first one-on-ones, and then every quarter I come back to it with them, is talk about five things:
- What are their short-term, mid-term, and long-term goals?
- What are the things that motivate them to be successful? For instance, personal motivation, work motivation, et cetera.
- What are the things that they want to work on as a professional and an employee?
- What are the things that I think they need to work on as a professional and an employee?
- What do they need from me, as a manager, to be successful?
You need to have that level of understanding about literally every employee on your team, inside and out. And you’ve got to be proactive about coming back to them every three months and asking, “How has this changed? How has this evolved? How am I doing as a manager to drive your goals? How have things changed, and how can I adjust to help you with those changes?”
“Coming back to help individuals accomplish their goals solves almost all the potential morale problems and keeps people motivated.”
That’s a very broad thing, though, because they all have competing interests and competing goals. But ultimately they all tie back to being invested in something, in some way or another—whether that’s time, training, money, support, or recognition. If you understand and genuinely care, if you revisit those documents yourself all the time, making sure that you’re always asking yourself, “Is what I’m doing serving those goals?”—then you’ll keep them motivated.
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